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15018—Chapter7—26/8/2006—22:01—SJAPPIYA
Second- and Third-Order Nonlinear
Optical Materials
Larry DaltonPhilip SullivanAlex K.-Y. Jen
7.1 Introduction............................................................................ 7-1
7.2 Second-Order Nonlinear Optical Materials ......................... 7-2
R—1501
Electro-Optic Materials † Optical Rectification Including
Terahertz Radiation and Detection
7.3 Third-Order Nonlinear Optical Materials.......................... 7-15
7.4 Summary ............................................................................... 7-16
Acknowledgments............................................................................. 7-16
References........................................................................................ 7-119
7.1 Introduction
Second- and third-order optical nonlinearity can perhaps be best understood as the coefficients of the
second and third terms in the power series expansion of molecular and macroscopic polarization in
terms of applied electric fields.
Pi Z aijEj CbijkEjEk CgijklEjEkEl C. ð7:1Þ
Pi Z cð1ÞijEj Ccð2Þ
ijkEjEk Ccð3ÞijklEjEkEl C. ð7:2aÞ
Pi Z cð1ÞijEjucosðutKkzÞC ð1=2Þcð2Þ
ijjEjju½1 Ccosð2utK2kzÞ�C. ð7:2bÞ
The terms b and g represent the first and second molecular hyperpolarizabilities, whereas the terms
c(2) and c(3) represent the first- and second-order nonlinear material (macroscopic) susceptibilities. Each
term arises from the nonlinear interaction of applied electric fields with the quasi-delocalized electron
distribution of molecules and materials. Moreover, each of these terms can give rise to a variety of
nonlinear responses reflecting different frequency dependences.1–13 Second-order terms give rise to
second harmonic generation (see Equation 7.2b), difference frequency (e.g., terahertz frequency)
generation, optical rectification (see Equation 7.2b), and electro-optic modulation (the Pockels effect).
Third-order optical nonlinearity gives rise to third harmonic generation, phase conjugation, optical
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limiting, optical parametric effects, and all-optical modulation (the Kerr effect). As is typical for power
series expansions, the second-order coefficients are larger than the third-order coefficients. Although
commercial applications have been realized for both second- and third-order inorganic materials, such as
lithium niobate electro-optic and titanium/sapphire optical parametric materials, organic nonlinear
optical materials are still struggling to obtain a beachhead on the commercial landscape. To the present
time, second-order nonlinear optical organic materials appear closer to commercial application and will
thus receive greater attention in this chapter.
It is very difficult to define a universal figure-of-merit (FOM) for either second- or third-order
nonlinear optical materials, as practical device performance will often depend on the details of device
design as well as intrinsic material properties. However, the most simplistic and yet somewhat realistic
figure-of-merit can be expressed as FOMZc(2 or 3) /ta, where t is the response time for the system
reacting to an electric field perturbation and t is the optical loss. For p-electron organic materials, the
response time, t is the phase relaxation time of the conjugated p-electrons, which is typically on the
order of tens of femtoseconds. If device bandwidths are determined by the intrinsic material response
time, bandwidths of tens of terahertz are possible. The optical loss, a, typically includes both absorption
and scattering contributions. Optical loss will, thus, be influenced by material heterogeneity as well as
molecular structure. Of course, practical device applications may also require many additional material
properties including stability (e.g., thermal and photochemical) and processability (e.g., solubility in
spin-casting solvent, appropriate sublimation temperatures for vapor deposition, appropriate glass
transition temperatures for nanoimprint lithography). The FOM defined above is most commonly used
in ranking third-order nonlinear optical materials. With second-order nonlinear optical materials, other
factors such as the resistivity of metal electrodes used in electro-optic modulator devices can limit
bandwidths, so the material FOM is commonly simplified to c(2)/a or as c(2)/a3, where 3 is the material
dielectric constant. For example, for electro-optic applications, it is important to match the velocity of
propagating optical and radiofrequency waves. Velocity matching is optimized when n2Z3, where n is
the material index of refraction.
Quantum mechanical calculations have proven useful in investigating the relationship of b and g to
molecular (chromophore) structure.14–24 For simple polyenes, the variation of molecular hyperpolariz-
ability with the length of the conjugated p-electron structure and with bond length alternation is
reasonably well predicted by theoretical calculations. Third-order nonlinear optical activity can be
observed for both isotropic and anisotropic materials. From the above polarization equations, it can be
seen that the symmetry requirement for second-order optical nonlinearity requires chromophores to
exhibit either dipolar23,24 or octupolar25–27 symmetry. For materials to exhibit second-order optical
nonlinearity, macroscopic dipolar or octupolar symmetry must exist; such symmetry is frequently
introduced by electric field poling or by sequential synthesis/self assembly from a functionalized surface.
Because of the additional symmetry requirement for second-order nonlinear optical materials, statistical
mechanical calculations have proven useful in guiding the optimization of desired nano- and
mesoscopic order.
In the following discussion, greater attention will be paid to second-order nonlinear optical organic
materials than for third-order materials. The reason for this disproportionate focus relates to the fact that
more commercial attention has been focused on second-order materials, whose design issues have
therefore received more intense research scrutiny. For example, very little attention has been given to the
optical loss and photostability of third-order nonlinear optical materials, whereas these properties have
been extensive studied for a number of second-order materials.
7.2 Second-Order Nonlinear Optical Materials
The primary applications of second-order nonlinear optical organic materials include electro-optic
modulation, second harmonic generation, optical rectification, and terahertz radiation generation and
detection. With recent success in the development of visible wavelength lasers and light emitting diodes,
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second harmonic generation has received less attention. Also, absorption at visible wavelengths of second
harmonic light by organic materials is problematic and has inhibited the practical utilization of materials
for this application. An excellent review of second harmonic generation, including an extensive
discussion of the concept of phase-matching, has been given by Stegeman.28 This review remains
highly relevant.
The most common application of organic second-order nonlinear optical materials is electro-optic
modulation. Electro-optic modulation involves the application of a low (relative to optical frequencies)
frequency electrical field to a material. This low frequency field is often referred to as a radiofrequency
field, although actual frequencies can range from DC to tens of terahertz. The applied field perturbs the
p-electron distribution of the material, which in turn alters the velocity of light propagating in the
material. Thus, electro-optic activity can be viewed as voltage control of the refraction index of a
material. The primary focus of this chapter will be a review of organic electro-optic materials and devices.
An increasingly popular application of second-order nonlinear optical materials is terahertz
generation and detection. This phenomenon is relevant to a variety of sensing applications, ranging
from homeland security to medical imaging. Organic materials also have potential for promoting the
development and increased utilization of terahertz spectroscopy. Terahertz generation is an example of
optical rectification or “difference frequency” phenomena. Like second harmonic generation, terahertz
generation involves the interaction of two optical fields with the charge density of the material.
7.2.1 Electro-Optic Materials
Organic electro-optic materials include single crystal materials such as 4 0-dimethylamino-N-methyl-4-
stibazolium tosylate (DAST),13,29 chromophore/polymer composite materials,30–33 polymeric materials
containing covalently incorporated chromophores (including heavily crosslinked materials),30,31,34–40
single-chromophore-containing dendrimers,24,41–44 multichromophore-containing dendrimers,44,45
chromophore-containing dendronized polymers,44,46–51 doped chromophore materials (including
binary chromophore systems),52 and materials prepared by sequential synthesis/self-assembly of
chromophores from a functionalized surface by Langmuir–Blodgett or modified Merrifield tech-
niques.13,53–57 The vast majority of systems studied involve dipolar chromophores; the reader is
referred elsewhere for an introduction to octupolar materials.25–27 In like manner, most devices are
currently prepared by electric field poling of polymeric or dendritic materials. For materials prepared by
electric field poling or by sequential synthesis/self-assembly, only two nonzero electro-optic tensor
elements (r33 and r13) exist. These are given approximately by:
r33 Z 2Nf ð0Þbzzz !cos3qO =ðn0eÞ4 ð7:3aÞ
r13 Z Nf ð0Þbzzz ! sin2q cos qO =ðn0oÞ2ðn0eÞ2; ð7:3bÞ
where N is the chromophore number density (molecules/cm3), f(u) are local field factors that account for
the dielectric nature of the media surrounding chromophores, n0o and n0e are the ordinary and
extraordinary linear refractive indices, and the order parameters, !cos3qO and !sin2q cosqO,
define the orientational distribution of chromophores. Equation 7.3 neglects the minor elements of
the molecular first hyperpolarizability tensor.
7.2.1.1 Optimizing Electro-Optic Activity
The process of optimizing electro-optic activity is typically a two-step process, in which quantum
mechanical calculations are used to guide the improvement of molecular first hyperpolarizability,bijk,
values14–24 and statistical mechanical calculations are employed to optimize the product of the
chromophore number density and the order parameter.58–64 Quantum mechanical calculations have
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guided the development of a number of chromophores, leading to dramatic improvements in molecular
first hyperpolarizability, i.e., to b0 values on the order of or greater than 1000!10K30 esu. The
tricyanovinylfuran (TCF) acceptor moiety shown in Scheme 7.1 has facilitated the development of
workhorse chromophores appropriate for prototype device development.65–72 In recent years, the
synthesis of chromophores has been greatly aided by the utilization of microwave-assisted synthesis
techniques.73,74 Of course, for a chromophore to be carried forward for development of device-
appropriate materials, it must exhibit appropriate thermal, chemical, and photochemical stability,
acceptably low levels of absorption at anticipated device operational wavelengths, and appropriate
processability (e.g., solubility in spin casting solvents, etc.). These features will be addressed later in this
chapter; note that the comments that apply for electro-optic materials also apply to other second-order
materials and, to some extent, to third-order materials.
The theoretically-inspired development of chromophores with improved molecular first hyperpolar-
izability can be divided into two categories: (1) variations of the fundamental donor, bridge, and acceptor
blocks of modular dipolar chromophores; and (2) investigation of novel chromophore architectures such
as “X-shaped”18,19,75,76 and “twisted”20,21 chromophores. The former strategy has proven to be very
effective in the past and significant future improvement may be possible following this strategy. The latter
strategy is much newer, but may afford dramatic improvements in molecular first hyperpolarizability,
while permitting desirable auxiliary properties such as high transparency at operating wavelengths.
Molecular first hyperpolarizability (b) values are commonly measured by hyper-Rayleigh scattering
(HRS).77–79 Such measurements are complicated by two-photon fluorescence and by molecular
aggregation. A variety of modifications have been made to he HRS technique in efforts to circumvent
these problems, including the use of femtosecond pulse techniques, measurements at a number of
wavelengths (using laser wavelength agility afforded by optical parametric devices), and measurements as
a function of concentration with measured b values determined exploiting extrapolations to zero
concentration.77–79 Moreover, HRS measurements are normally carried out to determine relative (to a
standard solvent such as chloroform) b values. Absolute values are most frequently defined using an
OS
OTBDMS
OTBDMS
N S
HONCNC
CN
O
R1R2
NO KO(t-bu)
N
OTBDMS
SEt2O
67%–78°C
OTBDMS
OTBDMS
N S
O
ON S
HO
Br
n-Buli(1-equiv.)DMF
THF95%
Br
HOS
Br
CIS S
Br
OO
OP
Br
HCI(conc)
quant.
NaBH4
NaOH
MeOH00C-RT
quant.
P(OEt)3
heat 3daysquant.
4)
4)
NaBH4
NaOHMeOH/THF
00C-RTquant.
ETOHRT 12h62%
n-BuliDMF
THF–78°C - RT70%
OTBDMS
N S
NC NC
CN
OR1R2
HO
SCHEME 7.1 The synthesis of a chromophore containing the tricyanofuran (TCF) acceptor.
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integrating sphere approach. A problem arises in the comparison of b values between theory and
experiment. Theoretical b values are calculated for isolated particles in the long wavelength or zero
frequency limit. On the other hand, experimental b values are measured in solutions of varying dielectric
constants and at finite infrared wavelengths such as 1.9 mm. To avoid comparing data corresponding to
different conditions, relative b values are frequently compared, e.g., both theoretical and experimental b
values referenced to a standard such as paranitroaniline.23
The product of dipole moment, m, and molecular first hyperpolarizability, b, is also a useful quantity,
particularly as the slope of the curve of r33 versus N in the low concentration limit is given by
2f(0)[mb]Ep/5kTn4, where for the sake of simplicity the subscripts on b and n have been dropped. The
product mb can be measured by electric field induced second harmonic generation (EFISH) techniques.
Like HRS measurements, many factors can complicate the measurements and great care must be
exercised to obtain meaningful data. If molecular first hyperpolarizability values relevant to electro-optic
response are to be extracted from EFISH data, then care must be exercised to avoid multiphoton
resonance contributions. Again, like HRS measurements, EFISH measurements should ideally be made at
a number of wavelengths.
The second aspect of optimizing electro-optic activity involves optimizing the product N!cos3qO. It
is now well-appreciated that intermolecular electrostatic (e.g., dipole–dipole) interactions involving
prolate ellipsoid-shaped p-electron chromophores can lead to serious attenuation of electro-optic
activity.58–64 The Monte Carlo calculations in Figure 7.1 illustrate this point. These calculations were
carried out with the restriction that the chromophores maintain a uniform lattice distribution. Different
results are obtained if a non-uniform chromophore distribution is permitted. This latter treatment
18
16
14
12
10
Load
ing
para
met
er
8
6
4
2
00 0.5 1 1.5 2 2.5
Number density (molecules/cc)
3 3.5 4 4.5 5
×1019
×1020
Loading parameter = N<cos3q> α r 33/b(constant)
Ising latticeRegion of enhancement
2:1 Oblate
Independentparticle lattice
Spherical
1:2 Prolate
FIGURE 7.1 Calculation (employing pseudo-atomistic Monte Carlo methods) of N!cos3qO vs. N for
chromophore shapes ranging from prolate to oblate ellipsoidal. Calculations are based on an “on-lattice”
approximation, which means that chromophores are restricted to uniform spacing among chromophores. Different
results, particularly at high loading, are obtained for “off-lattice” calculations, in which chromophores are permitted
to assume a non-uniform lattice distribution (e.g., to aggregate). For off-lattice calculations, results are much more
sensitive to the details of chromophore structure. Pseudo-atomistic calculations mean that p-conjugated segments
are treated in the united atom approximation whereas s-bonded molecular fragments are treated fully atomistically.
15018—Chapter7—26/8/2006—22:02—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
TBDMSO
TBDMSO
NS
NC
NC
CN
O
F3C
C45H55F3N4O3SSi2
C50H63F3N4O3Si2
Exact mass: 880.44
Exact mass: 844.35
C155H159F9N12O15S3Si3
Exact mass: 2779.04
C200H135F39N12O24S3
Exact mass: 3924.83
C, 61.16; H, 3.46; F, 18.87; N, 4.28; O, 9.78; S, 2.45
TBDMSO
TBDMSO
N
NC
NC
CN
F3C
O
NC NC
CN
CF3
S
O
O
OO
O
O
O
NC
CNCN
O
SN OTBDMS
F3C
OO
OS
CN
F
FF
F
F
F
F
FF
F
O
O
ON
S
NC
NC
OCF3
CF3
CN
O
OO
O
O
O
OF3C
O
SN O
O
OO
FF
F
FF
F
F
FF
F
CN
CN
NC
O
O
O
NO
O
O
O
FFF
F F
FF F
FF
S
CN
CN
CN
O
CN
O
CN
CF3
NOTBDMS
N
OTBDMS
CF3-FTC
YLD_124
PSLD_33
PSLD_41
FIG
UR
E7.
2F
ou
rch
rom
op
ho
rest
ruct
ure
sre
late
dto
the
dat
ap
rese
nte
din
Fig
ure
7.3.
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permits aggregation effects to be taken into account. The discussion of this latter treatment, which can be
critical for considering very large number densities (high chromophore loading), is sufficiently
complicated to be beyond the discussion presented here. In the present discussion, we restrict our
consideration to the more simplistic case of a uniform chromophore distribution. As shown in this
figure, intermolecular electrostatic interactions can also augment poling-induced noncentrosymmetric
order. It has been suggested in at least two studies that chromophore-polymer interactions can also
influence order.80,81 Indeed, in addition to chromophore shape effects illustrated in Figure 7.1, the spatial
and dynamical restrictions associated with covalent bonds impact poling-induced order. This is
illustrated in studies of multichromophore-containing dendrimers (MCCD), as depicted in Figure 7.2
and Figure 7.3. In Figure 7.3, a significant enhancement in electro-optic activity is observed for a MCCD,
relative to the behavior observed for the same chromophore in a polymer composite material. Indeed,
behavior for the MCCD lies between that expected for a chromophore in a spherically-symmetric
environment and the independent particle limit (see Figure 7.1). Even more intriguing behavior is
observed when a second chromophore is doped into the MCCD. The electro-optic activity, as shown in
Figure 7.3, increased nearly linearly with a slope more than twice the initial slope of the r33 versus N plot
for the same chromophore in an amorphous polycarbonate (APC) polymer host.32,33 A simplistic
analysis suggests that such behavior may reflect intermolecular electrostatic interactions, acting to
increase N!cos3qO in a manner analogous to that seen in Figure 7.1. However, unlike the case for
chromophore/polymer composite and undoped dendrimer materials, this behavior has not yet been
quantitatively reproduced by theoretical calculations. Moreover, all necessary control experiments to rule
out other potential contributions to the unusual behavior shown in Figure 7.3 have not yet been
completed. Nevertheless, the realization of electro-optic activities greater than 300 pm/V for doped
single-chromophore-containing dendrimers, MCCDs, and dendronized polymers is an important
milestone and provides the potential (providing further improvement in molecular first hyperpolariz-
ability is forthcoming) of realizing electro-optic activity on the order of 1000 pm/V. Of course, for large
electro-optic activity to be meaningful, it must be accompanied by acceptable optical transparency,
5
4
3
r 33
/ E
p
2
1
00 1 2 3 4
N × 1020 (molec/cc)
5 6 7 8
YLD-124 / PSLD-41
Dendrimer only
CF3-FTC / APC
FIGURE 7.3 Data for the four chromophore structures of Figure 7.2. Since a linear dependence of electro-optic
activity, r33, on electric poling field strength is observed in all cases, r33/Ep vs. N is plotted to facilitate comparison
among data sets. Data for composite materials consisting of the chromophore CF3-FTC in amorphous polycarbonate
(APC, Aldrich Chemicals) are indicated by triangles. Data for the two dendrimer materials PSLD 33 and 41 are
indicated by squares. Data for samples of YLD 124 doped into PSLD 41 are indicated by diamonds.
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thermal stability and photostability. We now turn attention to discussion of these issues, after a few
comments about the measurement of electro-optic tensor components.
Electro-optic activity of thin film samples is most commonly measured by the following techniques:
Teng-Man simple reflection82–84 attenuated total reflection (ATR),85–87 Fabry–Perot interferometry,
FPI,81,88,89 and two-slit interference.90 Electro-optic activity can also be measured in a variety of
waveguide (e.g., Mach Zehnder interferometry, MZI),91–93 ring microresonator,66,72 and etalon
devices. Each technique has its particular advantages and limitations, and in general it is desirable to
obtain electro-optic tensor components from multiple measurements using different techniques. It can
also be important to define the dispersion of tensor components. A variety of techniques, such as ATR,
FPI, and MZI devices permit both r33 and r13 to be determined. Such complete tensor determination
permits a more definitive characterization of chromophore orientational order. These various
characterization techniques can also be adapted by the introduction of temperature control and DC
voltage application stages to provide in situ monitoring of the introduction of noncentrosymmetric
order by electric field poling and the subsequent relaxation of that order.45
7.2.1.2 Minimizing Optical Loss
This discussion will first focus on “material” loss. Throughout the 1990s, most of the chromophores
being investigated had a charge transfer absorption maxima, lmax, of less than 600 nm. For such
materials, optical absorption loss at 1.3 and 1.55 micron telecommunication operating wavelengths was
most frequently dominated by hydrogen vibrational overtone absorptions. For dendrimer materials,
optical loss values as low as 0.2 dB/cm have been observed.94 When optical loss of greater than 2 dB/cm
was observed, it was normally indicative of light scattering arising from material heterogeneity associated
with various processing conditions.35 More recently, chromophores with interband absorption maxima
approaching 800 nm have come into use. For these materials, and even for some earlier materials,32,33
absorption loss at telecommunication wavelengths is dominated by electronic charge transfer absorption.
Thus, increasing c(2) may not lead to an improvement in FOM, because it is accompanied by a
corresponding increase in a. The appearance of exciton bands may even lead to a decrease in FOM. In
designing new chromophores for improved optical nonlinearity, it is critical to consider optical loss.
Optical loss due to electronic absorptions (both interband charge transfer and excitonic absorptions
associated with aggregation) is strongly influenced by solvatochromic and line broadening effects,
particularly as these effects influence the long wavelength tails of absorptions. Line broadening is
frequently defined by the heterogeneity of the chromophore environment and thus can be influenced by
chromophore order and by the mode of attachment of the chromophore to its surrounding matrix. The
dielectric properties of the surrounding matrix will, of course, have a profound effect on solvatochromic
shifts. Researchers at Lockheed Martin32,33 appear to be the first to focus on an effort to control
absorption contributions to optical loss by a systematic consideration of the roles played by the structure
of the chromophore and of the surrounding matrix.
Quite different effects on absorption loss can be observed for different types of materials at
telecommunication wavelengths. In this regard, dendritic materials may afford significant advantages
relative to chromophore/polymer composite materials due to the fact that they permit control of the local
chromophore environment and chromophore solubility in the surrounding matrix. For example,
chromophores incorporated in fluorinated dendrimers typically exhibit blue (hypsochromic) shifted
absorption maxima relative to the same chromophore in a polymer such as amorphous polycarbonate
(APC, Aldrich Chemical). Moreover, the “solubility” of the chromophore in dendrimers is controlled by
covalent bond attachment. Of course, comments made regarding dendrimers can also apply to
chromophores covalently incorporated into polymers, provided that access of chromophores to each
other is inhibited by the covalent incorporation. A high concentration of chromophores does not
necessarily imply disastrous optical loss, as illustrated in Figure 7.4, which shows the same chromophore
in a covalent-bonding-defined chromophore “bundle” and in APC.95 The absorption maximum of the
chromophore in the bundle is shifted to higher energy and no detectable line broadening is observed. The
molecular hyperpolarizability of the chromophore bundle is nearly three times that of the isolated
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1105
8104
6104
4104
2104
Extinction coefficient / M–1
cm–1
Wav
e nu
mbe
r / c
m-1
–210
4 1104
1510
421
0425
104
3104
3510
441
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chromophore. The experimental results shown here are in good agreement with theoretical calculations
carried out for the respective structures. Care should be exercised with respect to extrapolating the results
of Figure 7.4 to other materials; in general, the exact optical behavior will be determined by the precise
translational and orientational positioning of chromophores, which will vary from structure to structure.
Optical loss is also influenced by scattering losses. These frequently arise from material heterogeneities
introduced by spin casting, electric-field poling, crosslinking (lattice hardening), and by various device
processing steps (e.g., reactive ion etching of waveguides and deposition of cladding layers). The problem
is typically worse (ignoring for the moment issues associated with crosslinking or lattice hardening) for
chromophore/polymer composites than for chromophores covalently incorporated into dendrimers or
polymers. Again, the major issue is control of chromophore “solubility.” For chromophore/polymer
composites, problems include: the differential solubility of the chromophore and polymer host in spin
casting solvents; sublimation of chromophores during baking (to drive off residual spin casting solvents);
sublimation of chromophores during electric field poling; and “electrophoretic” phase separation during
poling. “Covalent-tailoring” of chromophores and their incorporation into host materials is a very
attractive means of controlling chromophore solubility and packing (void volumes) in the final material.
As we shall see shortly, crosslinking (or lattice hardening) is typically necessary to achieve adequate
thermal stability. Some crosslinking chemistries can lead to phase separation and lattice strain and thus
dramatic increases in optical loss due to light scattering. New cycloaddition crosslinking chemistries
involving the “soft” free-radical chemistry of the fluorovinyl ether group or the Diels-Alder/retro-Diels-
Alder reaction lead not only to lattice hardening without attenuation of poling efficiency, but also to
materials with low optical loss.
Optical loss can also arise from the process of fabricating buried channel waveguides. When this is
done by techniques such as reactive ion etching, care must be exercise to avoid pitting (waveguide wall
roughness) due to reactive ions with excess kinetic energy (i.e., a physical rather than chemical etch).
When care is employed, the excess waveguide loss can be 0.01 dB/cm or less.96 Loss can also be
introduced in deposition of cladding layers if the solvent used to deposit the cladding layer attacks the
electro-optic material. For both reactive ion etching and deposition of cladding layers, the lowest loss is
typically observed when very hard electro-optic materials are used. Loss can also arise from material
damage (dielectric breakdown) during electric field poling.
Optical loss can be influenced by the structure of the device, e.g., bending loss for ring
microresonators. Of course, one of the greatest contributions to total device insertion loss is coupling
loss. With organic electro-optic materials, the dominant contribution to coupling loss arises from a
mismatch in mode size and shape between light propagating in silica transmission fibers and that in the
organic EO waveguides. The solution to this problem is typically to employ a “mode transformer”
structure.97–101 Mode transformers permit per facet coupling losses to be kept to a few tenths of a dB. The
overall objective is typically to achieve a total insertion loss of less than 5 dB (the current standard for
lithium niobate devices). Thus, if device lengths of 2 cm or less are to be used, then material loss must be
kept to less than 2 dB/cm. Short device lengths, of course, have the advantage of permitting greater
operational bandwidths by minimizing loss occurring in metal drive electrodes. The calculated
performance of a Mach Zehnder device for typical EO, cladding, and electrode material conditions is
shown in Figure 7.5.
7.2.1.3 Maximizing Thermal Stability
The stability of electro-optic activity following the cessation of electric field poling is critical for device
applications. In the simplest sense, thermal stability relates to the temperature difference between the
operating temperature and the material glass transition temperature, Tg. With composite materials,
incorporation of chromophores results in plasticization and a corresponding reduction of glass transition
temperature with increasing dopant (chromophore) concentration. Thus, to realize sufficient thermal
stability to satisfy Telcordia standards, it is necessary to use a host polymer material with an initial glass
transition temperature on the order of 1508C or greater. Polycarbonates, polyquinolines, and polyimides
have been the most commonly employed polymers for producing composite materials appropriate for
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ts)
3
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4
0.1 0.2 0.3 0.4 0.5Interaction length, L(cm)
Interaction length, L(cm)
0.6 0.7 0.8 0.9 1
Material parameters:R33 = 300 pm/V
D(thickness) = 8 mmµWave loss = 0.75 dB(GHz)1/2/cmFiber coupling = 0.8 dB/coupling
Material loss = 2 dB/cm
Example L = 5 mm
BW(3dBe) = 90 GHzVp = 0.75V
Insert. Loss = 2.6 dB
Electrode dimensions
L
2µm
FIGURE 7.5 The variation of critical Mach Zehnder device parameters (bandwidth, drive voltage, fiber-to-fiber
insertion loss) with device (electrical/optical field interaction) length. An example of performance for a 5-mm length
Mach Zehnder electro-optic modulator expected with current materials is also shown.
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prototype device fabrication. One of the problems with very high-glass-transition-temperature
composite materials, such as polyimides, is that very high poling temperatures are required. Such
temperatures promote chromophore sublimation and the decomposition of chromophores, and can also
be incompatible with processing methodologies such as nanoimprint lithography. High glass transition
materials also commonly exhibit poor solubility in solvents used for spin casting. A convenient means of
avoiding this requirement for high temperature processing at intermediate stages of electro-optic
material production is to achieve thermal stability by crosslinking (lattice hardening) in the final
stages of electro-optic material production. With crosslinking, thermal stability will be defined by the
density of crosslinks and the flexibility of intervening segments. Throughout the 1990s, crosslinking
chemistries used to elevate final material glass transitions temperatures frequently involved condensation
(e.g., urethane and sol gel) chemistry.34,35 Such reactions give off water as an elimination product and are
influenced by atmospheric moisture. Moreover, the expulsion of gaseous elimination products can result
in lattice disruption and increased light scattering. As the condensation reaction proceeds, increased
lattice strain (e.g., lattice contraction) can also be a problem, which can be serious with sol-gel glasses.
Both thermal and photo-induced crosslinking chemistries have been explored.30,31 The latter has been
plagued by competition for light absorption involving the photo-initiator and the EO chromophore.
More recently, cycloaddition chemistries36–38,44,46–52,102 have become popular for realizing high glass
transition temperature (e.g., to 2008C) materials without the attenuation of electro-optic activity or an
increase in optical loss associated with earlier crosslinking reactions. These chemistries are pictorially
illustrated in Figure 7.6. The fluorovinyl ether crosslinking reaction illustrated in Figure 7.6a is a soft free
radical reaction that has the advantage of yielding high glass transition materials that are also
characterized by very low optical loss at telecommunication wavelengths due to low hydrogen content
in the final material. The Diels-Alder/retro-Diels-Alder reaction of Figure 7.6b has the added advantage
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O F
O
O
FF
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O
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FO
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O F
F F
O
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O O
O
N
O
O
N
R1
R2
R1
R2
O
NR
1
R2
cyclo-addition
∆
Concerted 4 + 2cycloaddition
"Diels-Alder"
RetroDiels-Alder Approx = 120°C
(a)
(b)
FIGURE 7.6 Fluorovinyl ether (6a) and Diels-Alder/-
retro-Diels-Alder (6b) cycloaddition crosslinking
reactions.
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(in some cases) of reversibility. That is, the
material is crosslinked below the glass transition
temperature but becomes uncrosslinked at the Tg,
permitting poling to be effected without being
attenuated by crosslinks. Choice of diene and
dienophile can permit systematic tuning of the
glass transition temperature, including for the
purpose of matching the poling temperature to
the thermal initiation temperature of the fluor-
ovinyl ether crosslinking reaction (when both
types of cycloaddition crosslinking are used
together). Obviously, for irreversible crosslinking
reactions such as reaction of the fluorovinyl ether
moiety, it is important to match poling tempera-
tures to the thermal initiation temperature of the
crosslinking reaction so that effective crosslinking
is achieved without unwanted attenuation of
poling-induced order. A final material glass tran-
sition temperature on the order of 2008C is more
than adequate for satisfying Telcordia standards
for thermal stability (long-term stability at an
operating temperature of 858C). Cycloaddition
crosslinking has been demonstrated to be effective
in providing such stability.
7.2.1.4 Maximizing Photostability
Photostability has been shown to be largely a matter of avoiding singlet oxygen chemistry.103–108
Stegeman and coworkers103–106 have demonstrated most of the critical features of photodecomposition
of organic electro-optic materials, including the absence of contributions from multiphoton absorption.
Indeed, they defined a single photostability figure-of-merit, B/s, where BK1 is the probability of
photodecay from the LUMO (lowest unoccupied molecular orbital) charge transfer state and s is the
interband (charge transfer) absorption coefficient. This definition has been used by subsequent
researchers, although the data analysis of Stegeman and coworkers may have been somewhat overly
simplistic, consequently over-estimating photo-instability. For example, more detailed analyses demon-
strate that the decay data cannot be fit with a single exponential and that “observer” power in the
Stegeman pump–probe experiment may lead to artificially fast decay. Moreover, Stegeman and coworkers
failed to carry out measurements at telecommunication wavelengths; this was addressed in subsequent
work by researchers at Corning.107,108 The Corning group demonstrated that the photostability FOM for
a given chromophore structure could vary over four orders of magnitude depending on conditions that
influence singlet oxygen chemistry. Even larger variation has been observed by other groups and
photostability has been shown to improve with the use of small quantities of singlet oxygen quenchers. In
addition to pump-probe experiments carried out by Stegeman and coworkers, researchers at Corning,
Gunter and coworkers, and Dalton and coworkers, photostability has also been investigated in operating
Mach Zehnder devices by Steier and coworkers69 and by Ashley and coworkers.109 Again, in these studies,
photo-instability could be attributed to singlet oxygen chemistry, with good photostability being
observed for materials and devices where this chemistry was partially inhibited.
In summary, it appears that good photostability can be achieved with appropriate materials
modification or with appropriate packaging of devices to minimize the presence of oxygen. In this
latter regard, the problems faced with organic electro-optic materials are analogous (but not quite
so severe) as those faced with organic light emitting device (OLED) materials. It should be noted
DEL CRC12a – pp. 1–126.
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that dense crystals such as DAST exhibit excellent photostability, again consistent with the role
played by oxygen.
7.2.1.5 Radiation Hardness
Very little work has been carried out examining the performance of organic electro-optic materials and
devices in the presence of high-energy gamma rays and protons associated with space environments. Part
of the problem of evaluating the impact of high-energy radiation on device performance is isolating
changes attributable to organic electro-optic materials from changes of performance induced by events
unrelated to the organic electro-optic materials (e.g., damage to silica input fibers). Nevertheless, the one
published report110 on this subject appears promising with respect to good stability exhibited by organic
electro-optic materials.
7.2.1.6 Fabrication of Prototype Devices
The most common prototype device fabrication involves stripline Mach Zehnder modulators; however,
ring microresonator, cascaded prism, and etalon structures have also been produced and evaluated. A
critical issue with the fabrication of prototype devices is how to deal with the properties of cladding and
electrode materials. Devices are typically multilayer structures consisting of bottom (ground) electro-
de/bottom cladding/electro-optic waveguide/top cladding/top (drive) electrode. If materials are poled
through cladding layers, the poling field can be attenuated due to the resistivity of the cladding layers. A
potential solution to this problem would be to identify cladding materials with significant conductivity.
Unfortunately, cladding materials with prerequisite conductivity have also exhibited, to the present time,
unacceptably high levels of optical loss. The presence of cladding layers thus makes it difficult to realize
the same electro-optic activity in device structures that have been achieved in thin films. Another issue in
the fabrication of prototype devices is the impact of electrode materials and device structure on
performance, including operational bandwidth. For stripline devices, such as Mach Zehnder inter-
ferometers, resistive losses in metal electrodes typically define operational bandwidths. Shorter electrode
structures (see Figure 7.5) lead to higher bandwidths, but at a price of increased drive voltage (Vp, the
voltage required to produce a p phase shift). As already noted, shorter devices afford the advantage of
reduced insertion loss and are more appropriate for high-density integration of many modulators on a
single chip. For resonated devices, such as ring microresonators and etalon devices, bandwidth is limited
by the optical lifetime in the resonated structure. This is defined by the quality factor, Q, of the resonant
device. High quality factors have the advantage of affording reduced drive voltage operation but limit
the bandwidth of the device. Very high center operational frequencies can still be obtained, but the
bandwidth about the center frequency is limited by the Q. Ring microresonators have the added
advantage of reduced size, which can facilitate high-density integration. In discussing bandwidth,
one needs to distinguish between digital and analog signals. This point will be illustrated in the
following simplified discussion of bandwidth and drive voltage requirement for resonant
device structures.
For a resonator, the 3-dB electrical modulation bandwidth (the detected voltage is down by 3 dB) is
given by
Df3dBe Z c = lQ Z DfFWHM; ð7:4Þ
where c is the speed of light, l is the wavelength of light, DfFWHM and is the full-width at half-maximum
of the bandpass of the resonant device. The case of digital modulation is considered first.
For a 10-dB contrast in the digital pulses, the voltage induced frequency shift of the bandpass must be
Df Z 3DFWHM = 2: ð7:5Þ
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The frequency shift with voltage is
ðDf =VÞ Z ðneff Þ2r33c = ð2dlÞ; ð7:6Þ
where d is the electrode spacing. Combining,
V10dB Z ð3dlDf3dBeÞ = ½ðneff Þ2r33c�: ð7:7Þ
In digital systems, the required bandwidth depends on the modulation format. Conservatively
assuming that Df3dBeZB (the bit rate), then
V10dB Z 3dlB = ½ðneff Þ2r33c�: ð7:8Þ
For example, if BZ10 Gb/s, nZ1.6, r33Z300 pm/V, dZ6 mm, lZ1.3 mm, and QZ5!103, then
V10dBZ1 V (with the result obviously scaling linearly with the bit rate).
Now consider analog signal modulation. The optical wavelength is set to the point of maximum slope
of the resonator transmission (bandpass) curve:
Dl Z DlFWHM = ð2ffiffiffi
3p
Þ ð7:9Þ
It is helpful to define a Vp equiv so that it corresponds to an equal Vp of a Mach Zehnder modulator:
ðV p equiv =Df3dBeÞ Z 4pdl = ½ð3ffiffiffi
3p
Þðneff Þ2r33c�: ð7:10Þ
For example, if nZ1.6, r33Z300 pm/V, dZ6 pm, and lZ1.3 pm, then (Vpequiv/Df3dBe)Z0.08 V/GHz. It is clear from the above analyses for digital and analog signal processing that the simplest
route to improving the performance of resonant devices is to increase the electro-optic coefficient, r, of
the material used to fabricate the device. The current performance of organic electro-optic materials
moves resonant devices close to practical application.
Device structures are most commonly fabricated using reactive ion etching, although ring micro-
resonator and Mach Zehnder devices structures have also been made by nanoimprint lithography.68
Nanoimprint lithography has the potential advantage of allowing complex electro-optic circuitry to be
mass-produced in a cost-effective manner.
The range of application of organic electro-optic materials has been recently broadened by the
incorporation of these materials into silicon photonic device structures.66 The small dimensions of these
structures and the obvious potential for convenient integration with silicon electronics is very attractive.
Moreover, the small (nanoscopic) dimensions of silicon photonic circuitry result in an optical field
concentration, which has recently been exploited to achieve optical rectification of light at mW optical
powers.66 Thus, the same device structure can be employed for electrical/optical and optical/electrical
signal transduction.
7.2.1.7 Applications
Applications of electro-optic materials and devices include electrical-to-optical signal transduction,
optical switching, optical beam steering, radiofrequency signal generation, phased array radar (radio-
frequency beam steering), optical gyroscopes, analog-digital conversion, frequency conversion (time
stretching), and sensing (of both physical and chemical phenomena). The term radiofrequency describes
frequencies in the range 0–30 THz. Electro-optic technology is at the heart of “RF Photonics,” or the
delivery of radiofrequency signals via optical transmission. Many applications of electro-optic materials
lie in the arena of defense and homeland security, but interest is growing in the areas of computer chip
manufacture, transportation, telecommunications (both fiber and wireless), civil engineering, and
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medicine. For example, in the development of next-generation computer chips, photonics may be used
to route high frequency information among various components of the chip, avoiding the problems of
signal loss and heating associated with moving electrons through metal connectors. The field of
embedded network sensing combines sensors, computer processors, and communication components
on a single chip. Electro-optic devices provide critical signal transduction and routing on embedded
network sensing platforms. Embedded network sensing is finding increasing applications in medicine
and infrastructure monitoring (civil engineering).
7.2.2 Optical Rectification Including Terahertz Radiation and Detection
Optical rectification is the difference frequency analog of second harmonic generation. Like second
harmonic generation, it will occur whenever the electric field component of the optical field is large
enough to produce a nonlinear perturbation of the charge distribution of the nonlinear optical material.
Normally, intense laser powers are required, but the nanoscopic dimensions of silicon photonic circuitry
can concentrate optical fields from milliwatt diode lasers to the point of producing optical rectification.66
Thus, organic EO/silicon hybrid devices can act as both electrical-to-optical signal transducers and
optical-to-electrical signal transducers. In other words, they have the potential to compete with
photodiodes as photodetectors, providing that sufficiently large material second-order optical nonli-
nearity can be obtained.
Another manifestation of optical rectification/difference frequency generation is terahertz signal
generation/detection. Recently, Hayden and coworkers,111,112 Gunter and coworkers,113 and researchers
in Japan114–116 have pioneered the use of organic electro-optic materials for terahertz applications
(imaging and spectroscopy). An advantage of organic materials is that optical and terahertz waves
propagate with comparable velocities in organic materials, permitting phase matching of the optical and
terahertz radiation. Also, the second-order optical nonlinearity of organic materials is orders of
magnitude greater than inorganic crystalline materials such as zinc telluride (ZnTe). A problem
encountered with poled organic (polymer) materials is that it is difficult to effectively pole thick
(millimeter) films. Such film thickness would be ideal for terahertz applications.
Among the promising sensor applications of terahertz radiation is the ability to image plastic weapons.
It is an attractive alternative to magnetic (metal detector) sensing in the arena of homeland security. The
possible applications in biomedical imaging are also attractive.
7.3 Third-Order Nonlinear Optical Materials
Third-order organic nonlinear optical materials have very little in common with second-order nonlinear
optical materials, other than the fact that both involve significant p-conjugation. Since no symmetry
requirement exists for third-order activity, a much broader range of materials can give rise to third-order
optical nonlinearity, c(3). Indeed, third-order materials range from conjugated polymers such as
polyacetylene, to molecules such as C60 and C70, to metallomacrocyclic complexes. When charge transfer
molecules are investigated, molecules with quadrupolar117 symmetry (e.g., donor–acceptor–donor or
acceptor–donor–acceptor) frequently exhibit larger optical nonlinearity than corresponding dipolar
(donor–acceptor) molecules. Dendritic materials containing connected p-electron segments have also
been observed to give rise to large third-order optical nonlinearities.
Although the third-order optical nonlinearity for organic materials has been increased over the past
two decades, values are still too low for practical applications. A possible exception may be for materials
incorporated into silicon photonic circuitry. Scherer and coworkers120 have demonstrated all-optical
modulation to greater than 5 THz with mW pump powers derived from a diode laser operating at
telecommunication wavelengths. The concentration of optical power in waveguides of nanometer
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dimensions results in an amplification of optical field intensities by orders of magnitude, permitting
much smaller c(3) values to be utilized effectively.
Recently, interest in c(3) materials has increased because of potential applications of materials with
large two-photon absorption coefficients. These applications range from sensor protection to biomedical
imaging, photodynamic therapy, and two-photon photolithography.
Because no symmetry requirement exists for nonzero third-order optical nonlinearity, lattice hardness
is a less serious problem than for second-order materials, although little research has been conducted on
this feature of third-order materials. Optical loss is as important for third-order materials as it is for
second-order materials, but very little research attention has been paid to this topic. Third-order
materials should afford comparable advantages in processability compared to second-order organic
nonlinear optical materials; however, it is unlikely that auxiliary properties will receive much attention
unless significant improvement in c(3) can be achieved.
7.4 Summary
Extensive p-conjugation of organic materials leads to significant second- and third-order optical
nonlinearities. However, until the present decade, values of c(2) and c(3) have been too small to
promote significant commercial application. Currently, electro-optic coefficients in the range 300–
400 pm/V are observed for a variety of dendrimer and dendronized polymer materials containing
chromophores with large first hyperopolarizabilities. Such values are an order of magnitude greater than
values for the commercial standard lithium niobate. New organic electro-optic materials afford the
possibility of more compact and lightweight devices operating with bandwidths of 100 GHz or greater
and with drive voltages of less than one volt. Realization of gain in RF photonics becomes a possibility for
the first time. Many issues remain to be addressed before significant commercialization is likely,
including the systematic control of optical loss, thermal stability, and photochemical stability. Moreover,
better utilization needs to be made of the processing advantages of organic electro-optic materials,
including for the production of integrated electronic/photonic circuitry exploiting a high density of
organic electro-optic devices on a single chip. The integration of organic electro-optic materials with
silicon photonic circuitry appears to afford some impressive new opportunities not only for high
bandwidth electro-optic modulation and optical switching but also for optical rectification. One distinct
advantage of organic electro-optic materials is that their processability may permit new device structures
and applications to be considered. For example, new sensor technologies appear possible, e.g., by
exploiting ring microresonators positioned on side-polished optical fibers.
The prognosis for third-order organic nonlinear optical materials is somewhat less optimistic, as c(3)
values still need to be increased by one to two orders of magnitude for many applications. Incorporating
third-order organic nonlinear optical materials into resonant structures (e.g., ring microresonators) and
into silicon photonic waveguides may help reduce the performance demands on c(3) materials. At any
rate, the development of third-order organic nonlinear optical materials is in a more immature stage than
the development of second-order materials, as very little attention is given to auxiliary properties such as
optical loss, stability, and processability. The most promising application of third-order organic materials
appears to involve materials with large two-photon cross-sections for applications such as biomedical
imaging, photodynamic therapy, two-photon photolithography, and ultrafast-responding sensor
protection (Table 7.1 through Table 7.3).
Acknowledgments
Support from the National Science Foundation, the Air Force Office of Scientific Research, and the
Defense Advanced Research Projects Agency is gratefully acknowledged. The authors thank their
colleagues, particularly Professors William Steier and Bruce Robinson, for many helpful discussions.
15018—Chapter7—26/8/2006—22:05—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
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15018—Chapter7—26/8/2006—22:06—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-17
Article in Press
817
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15018—Chapter7—26/8/2006—22:07—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-18 Handbook of Photonics
Article in Press
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15018—Chapter7—26/8/2006—22:07—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-19
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15018—Chapter7—26/8/2006—22:07—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-20 Handbook of Photonics
Article in Press
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NO
2
DM
SO45
8m
bZ
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47
(1.3
6)2
31
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:07—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-21
Article in Press
1021
1022
1023
1024
1025
1026
1027
1028
1029
1030
1031
1032
1033
1034
1035
1036
1037
1038
1039
1040
1041
1042
1043
1044
1045
1046
1047
1048
1049
1050
1051
1052
1053
1054
1055
1056
1057
1058
1059
1060
1061
1062
1063
1064
1065
1066
1067
1068
1069
1070
1071
TA
BL
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1(C
on
tin
ued
)
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15018—Chapter7—26/8/2006—22:08—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-22 Handbook of Photonics
Article in Press
1072
1073
1074
1075
1076
1077
1078
1079
1080
1081
1082
1083
1084
1085
1086
1087
1088
1089
1090
1091
1092
1093
1094
1095
1096
1097
1098
1099
1100
1101
1102
1103
1104
1105
1106
1107
1108
1109
1110
1111
1112
1113
1114
1115
1116
1117
1118
1119
1120
1121
1122
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tin
ued
)
15018—Chapter7—26/8/2006—22:08—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-23
Article in Press
1123
1124
1125
1126
1127
1128
1129
1130
1131
1132
1133
1134
1135
1136
1137
1138
1139
1140
1141
1142
1143
1144
1145
1146
1147
1148
1149
1150
1151
1152
1153
1154
1155
1156
1157
1158
1159
1160
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1165
1166
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1169
1170
1171
1172
1173
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ued
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)46
15018—Chapter7—26/8/2006—22:08—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-24 Handbook of Photonics
Article in Press
1174
1175
1176
1177
1178
1179
1180
1181
1182
1183
1184
1185
1186
1187
1188
1189
1190
1191
1192
1193
1194
1195
1196
1197
1198
1199
1200
1201
1202
1203
1204
1205
1206
1207
1208
1209
1210
1211
1212
1213
1214
1215
1216
1217
1218
1219
1220
1221
1222
1223
1224
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(con
tin
ued
)
15018—Chapter7—26/8/2006—22:08—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-25
Article in Press
1225
1226
1227
1228
1229
1230
1231
1232
1233
1234
1235
1236
1237
1238
1239
1240
1241
1242
1243
1244
1245
1246
1247
1248
1249
1250
1251
1252
1253
1254
1255
1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266
1267
1268
1269
1270
1271
1272
1273
1274
1275
TA
BL
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1(C
on
tin
ued
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ctu
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6)1
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5
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5
15018—Chapter7—26/8/2006—22:09—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-26 Handbook of Photonics
Article in Press
1276
1277
1278
1279
1280
1281
1282
1283
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294
1295
1296
1297
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308
1309
1310
1311
1312
1313
1314
1315
1316
1317
1318
1319
1320
1321
1322
1323
1324
1325
1326
XZ
CO
CH
3Y
ZH
p-D
ioxa
ne
280
3.1
2.0
(1.9
)45
XZ
NO
2Y
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p-D
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ne
304
3.8
4.1
(1.9
)45
XZ
SO2C
H3
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Ch
loro
form
340
6.0
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.9)4
5
XZ
CN
YZ
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ne
292
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tin
ued
)
15018—Chapter7—26/8/2006—22:09—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-27
Article in Press
1327
1328
1329
1330
1331
1332
1333
1334
1335
1336
1337
1338
1339
1340
1341
1342
1343
1344
1345
1346
1347
1348
1349
1350
1351
1352
1353
1354
1355
1356
1357
1358
1359
1360
1361
1362
1363
1364
1365
1366
1367
1368
1369
1370
1371
1372
1373
1374
1375
1376
1377
TA
BL
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15018—Chapter7—26/8/2006—22:09—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-28 Handbook of Photonics
Article in Press
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1379
1380
1381
1382
1383
1384
1385
1386
1387
1388
1389
1390
1391
1392
1393
1394
1395
1396
1397
1398
1399
1400
1401
1402
1403
1404
1405
1406
1407
1408
1409
1410
1411
1412
1413
1414
1415
1416
1417
1418
1419
1420
1421
1422
1423
1424
1425
1426
1427
1428
NS
i
n
CN
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rm33
34.
015
(1.9
)45
XZ
CN
YZ
NH
2C
hlo
rofo
rm34
25.
220
(1.9
)45
XZ
CN
YZ
NH
CH
3C
hlo
rofo
rm35
85.
727
(1.9
)45
XZ
CN
YZ
N(C
H3) 2
Ch
loro
form
372
6.1
29(1
.9)4
5
XZ
NO
2Y
ZH
p-D
ioxa
ne
326
4.6
16(1
.06)
32
XZ
NO
2Y
ZB
rC
hlo
rofo
rm33
53.
010
(1.9
)45
XZ
NO
2Y
ZO
CH
3p-
Dio
xan
e35
64.
414
(1.9
)45
XZ
NO
2Y
ZSC
H3
Ch
loro
form
362
4.0
20(1
.9)4
5
XZ
NO
2Y
ZN
H2
Ch
loro
form
380
5.5
24(1
.9)4
5
NM
P41
05.
540
(1.9
)45
XZ
NO
2Y
ZN
HC
H3
Ch
loro
form
400
5.7
46(1
.9)4
5
XZ
NO
2Y
ZN
(CH
3) 2
Ch
loro
form
415
6.1
46(1
.9)4
5
p-D
ioxa
ne
402
7.1
102
(1.0
6)3
2
Ch
loro
form
416
6.6
33(b
0)1
77
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:09—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-29
Article in Press
1429
1430
1431
1432
1433
1434
1435
1436
1437
1438
1439
1440
1441
1442
1443
1444
1445
1446
1447
1448
1449
1450
1451
1452
1453
1454
1455
1456
1457
1458
1459
1460
1461
1462
1463
1464
1465
1466
1467
1468
1469
1470
1471
1472
1473
1474
1475
1476
1477
1478
1479
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
XZ
NO
2Y
ZN
(C6H
5) 2
Ch
loro
form
418
4.8
28(b
0)1
77
Stil
ben
ed
eriv
ativ
es
XY
XZ
HY
ZO
CH
332
02.
86.
1(1
.06)
17
5
XZ
HY
ZN
H2
Ben
zen
e2.
112
(1.0
6)1
89
p-D
ioxa
ne
332
2.2
7.4
(1.9
)46
XZ
HY
ZN
(CH
3) 2
Ben
zen
e2.
429
(1.0
6)1
89
p-D
ioxa
ne
340
2.1
10(1
.9)4
6
XZ
Cl
YZ
HB
enze
ne
1.5
3.6
(1.0
6)1
89
XZ
Cl
YZ
N(C
H3) 2
Ch
loro
form
4.0
42(1
.06)
18
9
XZ
CF
3Y
ZO
CH
3p-
Dio
xan
e32
34.
312
(1.0
6)2
44
326
4.2
16(1
.06)
17
5
XZ
CF
3Y
ZO
Hp-
Dio
xan
e32
74.
712
(1.0
6)2
44
XZ
SO2C
H3
YZ
Hp-
Dio
xan
e36
44.
458
(1.0
6)3
2
XZ
SO2C
H3
YZ
OC
H3
Ch
loro
form
336
6.5
10(1
.9)4
6
p-D
ioxa
ne
335
6.1
9.1
(1.0
6)3
2
XZ
SO2C
H3
YZ
SC6H
5p-
Dio
xan
e34
44.
419
(1.0
6)3
2
XZ
SO2C
H3
YZ
N(C
H3) 2
p-D
ioxa
ne
376
6.9
66(1
.06)
32
XZ
SO2C
H3
YZ
N(C
H2C
2H
3) 2
Ch
loro
form
391
mb
Z57
!10
K4
7(1
.9)2
64
XZ
SO2C
F3
YZ
OC
H3
p-D
ioxa
ne
347
7.8
14(1
.9)4
6
p-D
ioxa
ne
350
6.6
34(1
.06)
32
XZ
SO2C
6F
13
YZ
N(C
H3) 2
Ch
loro
form
8.0
59(1
.9)4
3
XZ
CO
CF
3Y
ZO
CH
3p-
Dio
xan
e36
84.
216
(1.9
)46
XZ
CO
HY
ZN
(CH
3) 2
Ch
loro
form
360
3.5
24(1
.9)2
54
XZ
CN
YZ
OH
p-D
ioxa
ne
344
4.5
13(1
.9)4
6
XZ
CN
YZ
OC
H3
DM
SO34
2m
bZ
82!
10K
47
(1.9
)55
Ch
loro
form
340
3.8
19(1
.9)4
6
XZ
CN
YZ
N(C
H3) 2
DM
SO39
0m
bZ
98!
10K
48
(1.9
)55
Ch
loro
form
382
5.7
36(1
.9)4
6
XZ
NO
2Y
ZH
Ben
zen
e4.
629
(1.0
6)1
89
p-D
ioxa
ne
345
4.2
11(1
.9)4
6
XZ
NO
2Y
ZC
H3
DM
SO36
8m
bZ
20!
10K
48
(1.9
)55
p-D
ioxa
ne
351
4.7
15(1
.9)4
6
15018—Chapter7—26/8/2006—22:10—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-30 Handbook of Photonics
Article in Press
1480
1481
1482
1483
1484
1485
1486
1487
1488
1489
1490
1491
1492
1493
1494
1495
1496
1497
1498
1499
1500
1501
1502
1503
1504
1505
1506
1507
1508
1509
1510
1511
1512
1513
1514
1515
1516
1517
1518
1519
1520
1521
1522
1523
1524
1525
1526
1527
1528
1529
1530
XZ
NO
2Y
ZC
lC
hlo
rofo
rm3.
139
(1.0
6)1
89
XZ
NO
2Y
ZB
rp-
Dio
xan
e34
43.
214
(1.9
)46
Ch
loro
form
356
3.4
18(1
.9)4
6
XZ
NO
2Y
ZO
HC
hlo
rofo
rm93
(1.0
6HR
)48
p-D
ioxa
ne
370
5.5
17(1
.9)4
6
XZ
NO
2Y
ZO
C6H
5p-
Dio
xan
e35
04.
618
(1.9
)46
XZ
NO
2Y
ZO
CH
3p-
Dio
xan
e5.
781
(1.0
6)9
8
Ch
loro
form
105
(1.0
6HR
)48
p-D
ioxa
ne
364
4.5
28(1
.9)4
6
Ch
loro
form
370
4.5
34(1
.9)4
6
p-D
ioxa
ne
364
4.5
60(1
.06)
32
XZ
NO
2Y
ZSC
H3
p-D
ioxa
ne
374
4.3
26(1
.9)4
6
Ch
loro
form
380
4.3
34(1
.9)4
6
p-D
ioxa
ne
378
5.1
68(1
.06)
32
XZ
NO
2Y
ZN
H2
Ace
ton
e7.
526
0(1
.06)
18
9
Ch
loro
form
402
5.1
40(1
.9)4
6
XZ
NO
2Y
ZN
(CH
3) 2
Ace
ton
e7.
445
0(1.
06)1
93
DM
SO44
7m
bZ
42!
10K
46
(1.9
)55
DM
SO45
3m
bZ
76!
10K
47
(1.3
6)2
31
7.1
323
(1.0
6S)1
95
Ch
loro
form
427
6.6
73(1
.9)4
6
NM
P7.
270
(1.9
)46
p-D
ioxa
ne
mb
Z58
!10
K4
7(1
.9)1
07
Ch
loro
form
438
6.7
42(b
0)1
77
XZ
NO
2Y
ZN
(CH
2C
2H
3) 2
Ch
loro
form
452
mb
Z57
!10
K4
7(1
.9)2
64
XZ
NO
2Y
ZN
(C6H
5) 2
Ch
loro
form
436
4.8
37(b
0)1
77
XZ
NO
2Y
ZC
OO
CH
3C
H2C
l 235
04.
04
(1.9
)46
XZ
NO
2Y
ZC
OH
p-D
ioxa
ne
352
4.1
6(1
.9)4
6
XZ
CH
C(C
N) 2
YZ
N(C
H3) 2
Ch
loro
form
7.8
210
(1.9
)43
XZ
CH
C(C
N) 2
YZ
N(C
2H
5) 2
CH
2C
l 248
58.
218
0(1
.58)
54
p-D
ioxa
ne
468
mb
Z11
!10
K4
6(1
.9)1
06
XZ
Br
YZ
OC
H3
p-D
ioxa
ne
325
4.0
25(1
.9)4
6
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:10—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-31
Article in Press
1531
1532
1533
1534
1535
1536
1537
1538
1539
1540
1541
1542
1543
1544
1545
1546
1547
1548
1549
1550
1551
1552
1553
1554
1555
1556
1557
1558
1559
1560
1561
1562
1563
1564
1565
1566
1567
1568
1569
1570
1571
1572
1573
1574
1575
1576
1577
1578
1579
1580
1581
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
NN
O2
Ch
loro
form
438
796
(1.9
)46
NO
2
OC
H3
Ch
loro
form
360
3.8
4.4
(1.9
)46
NO
2
OC
H3
Ch
loro
form
370
3.7
1.6
(1.9
)46
NO
2
H3C
OC
hlo
rofo
rm39
03.
53.
8(1
.9)4
6
NO
2
OC
H3
Ch
loro
form
320
4.4
5.5
(1.9
)46
NO
2
OC
H3
Ch
loro
form
292
3.9
4.5
(1.9
)46
15018—Chapter7—26/8/2006—22:10—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-32 Handbook of Photonics
Article in Press
1582
1583
1584
1585
1586
1587
1588
1589
1590
1591
1592
1593
1594
1595
1596
1597
1598
1599
1600
1601
1602
1603
1604
1605
1606
1607
1608
1609
1610
1611
1612
1613
1614
1615
1616
1617
1618
1619
1620
1621
1622
1623
1624
1625
1626
1627
1628
1629
1630
1631
1632
NO
2
H3C
Op-
Dio
xan
e31
83.
95.
3(1
.9)4
6
NO
2
OC
H3
Ch
loro
form
362
5.0
22(1
.9)4
6
NO
2
OC
H3
Ch
loro
form
352
4.0
21(1
.9)4
6
NO
2
Br
Ch
loro
form
346
4.6
12(1
.9)4
6
NO
2
Br
Ch
loro
form
346
3.4
14(1
.9)4
6
H3C
O
F F
322
3.1
9.2
(1.0
6)1
75
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:10—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-33
Article in Press
1633
1634
1635
1636
1637
1638
1639
1640
1641
1642
1643
1644
1645
1646
1647
1648
1649
1650
1651
1652
1653
1654
1655
1656
1657
1658
1659
1660
1661
1662
1663
1664
1665
1666
1667
1668
1669
1670
1671
1672
1673
1674
1675
1676
1677
1678
1679
1680
1681
1682
1683
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
H3C
O
F
F
F
320
4.6
6.8
(1.0
6)1
75
H3C
O
FF
F
322
3.4
10(1
.06)
17
5
H3C
O
F
F
F
F
324
3.5
12(1
.06)
17
5
H3C
O
F
F
F
FF
322
3.3
16(1
.06)
17
5
H3C
O
F
CF
3
F
FF
334
4.0
23(1
.06)
17
5
15018—Chapter7—26/8/2006—22:11—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-34 Handbook of Photonics
Article in Press
1684
1685
1686
1687
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1689
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1691
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1693
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1700
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1704
1705
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1707
1708
1709
1710
1711
1712
1713
1714
1715
1716
1717
1718
1719
1720
1721
1722
1723
1724
1725
1726
1727
1728
1729
1730
1731
1732
1733
1734
CF
3
CF
3
H3C
O
326
4.2
11(1
.06)
17
5
CF
3
X
CN
XZ
Hp-
Dio
xan
e31
44.
74.
5(1
.06)
24
4
XZ
Cl
p-D
ioxa
ne
318
4.2
5.1
(1.0
6)2
44
XZ
Br
p-D
ioxa
ne
320
4.6
8.1
(1.0
6)2
44
XZ
CH
3p-
Dio
xan
e32
34.
87.
4(1
.06)
24
4
XZ
OC
H3
p-D
ioxa
ne
340
5.3
15(1
.06)
24
4
XZ
OH
p-D
ioxa
ne
348
5.5
16(1
.06)
24
4
XZ
SCH
3p-
Dio
xan
e36
25.
016
(1.0
6)2
44
XZ
N(C
H3) 2
p-D
ioxa
ne
410
6.4
29(1
.06)
24
4
NO
2
H3C
Op-
Dio
xan
e36
65.
226
(1.9
)46
NO
2
H3C
O
OC
H3
p-D
ioxa
ne
380
4.7
23(1
.9)4
6
NO
2
H3C
O
F
p-D
ioxa
ne
363
4.1
18(1
.9)4
6
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:11—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-35
Article in Press
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1751
1752
1753
1754
1755
1756
1757
1758
1759
1760
1761
1762
1763
1764
1765
1766
1767
1768
1769
1770
1771
1772
1773
1774
1775
1776
1777
1778
1779
1780
1781
1782
1783
1784
1785
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
NO
2
H3C
O
OC
H3
p-D
ioxa
ne
395
4.8
32(1
.9)4
6
NO
2
H3C
O
CN
p-D
ioxa
ne
361
5.3
21(1
.9)4
6
NO
2
Br
CN
p-D
ioxa
ne
340
4.6
8(1
.9)4
6
NO
2B
r
CN
Np-
Dio
xan
e38
24.
12.
1(1
.9)4
6
NO
2
NO
2
p-D
ioxa
ne
355
410
(1.9
)46
NO
2
NO
2
NO
2
p-D
ioxa
ne
354
25
(1.9
)46
15018—Chapter7—26/8/2006—22:11—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-36 Handbook of Photonics
Article in Press
1786
1787
1788
1789
1790
1791
1792
1793
1794
1795
1796
1797
1798
1799
1800
1801
1802
1803
1804
1805
1806
1807
1808
1809
1810
1811
1812
1813
1814
1815
1816
1817
1818
1819
1820
1821
1822
1823
1824
1825
1826
1827
1828
1829
1830
1831
1832
1833
1834
1835
1836
NO
2
NO
2
OC
H3
p-D
ioxa
ne
378
5.0
12(1
.9)2
55
NO
2
NO
2
H3C
Op-
Dio
xan
e38
44.
722
(1.9
)46
NO
2
NO
2
Np-
Dio
xan
e46
67.
057
(1.9
)25
5
p-D
ioxa
ne
mb
Z66
!10
K4
7(1
.9)1
07
NO
2
NO
2
H3C
OC
hlo
rofo
rm4.
115
(1.9
)43
NO
2
NO
2
NC
hlo
rofo
rm6.
245
(1.9
)43
NO
2
NO
2
H3C
O
OC
H3
p-D
ioxa
ne
404
5.6
25(1
.9)4
6
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:12—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-37
Article in Press
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1841
1842
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1845
1846
1847
1848
1849
1850
1851
1852
1853
1854
1855
1856
1857
1858
1859
1860
1861
1862
1863
1864
1865
1866
1867
1868
1869
1870
1871
1872
1873
1874
1875
1876
1877
1878
1879
1880
1881
1882
1883
1884
1885
1886
1887
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
NO
2
NO
2
H3C
O
OC
H3
OC
H3
p-D
ioxa
ne
390
3.1
11(1
.9)4
6
NO
2
Np-
Dio
xan
e34
64.
44.
9(1
.9)4
6
NO
2
Np-
Dio
xan
e35
14.
715
(1.9
)46
H3C
ON
O2
Np-
Dio
xan
e37
64.
414
(1.9
)46
NN
O2
ND
MSO
458
mb
Z50
!10
K4
7(1
.36)
23
1
H3C
ON
O2
Np-
Dio
xan
e34
95.
46.
6(1
.9)4
6
YN
XN
15018—Chapter7—26/8/2006—22:12—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-38 Handbook of Photonics
Article in Press
1888
1889
1890
1891
1892
1893
1894
1895
1896
1897
1898
1899
1900
1901
1902
1903
1904
1905
1906
1907
1908
1909
1910
1911
1912
1913
1914
1915
1916
1917
1918
1919
1920
1921
1922
1923
1924
1925
1926
1927
1928
1929
1930
1931
1932
1933
1934
1935
1936
1937
1938
XZ
SO2C
H3
YZ
N(C
4H
9) 2
Ch
loro
form
461
mb
Z51
!10
K4
7(1
.9)2
64
XZ
NO
2Y
ZN
H2
p-D
ioxa
ne
420
5.8
29(1
.9)4
6
DM
SO47
0m
bZ
77!
10K
47
(1.3
6)2
31
XZ
NO
2Y
ZN
(CH
3) 2
Ch
loro
form
498
mb
Z13
!10
K4
6(1
.9)2
64
Ch
loro
form
480
7.7
40(b
0)1
77
XZ
NO
2Y
ZN
(C2H
5) 2
Ch
loro
form
494
8.0
50(b
0)1
77
XZ
N0 2
YZ
N(C
2H
5)C
2H
4)O
HC
H2C
l 248
08.
990
(1.5
7)5
4
p-D
ioxa
ne
455
7.0
49(1
.9)4
6
DM
SO50
8m
bZ
11!
10K
46
(1.3
6)2
31
XZ
NO
2Y
ZN
(C6H
5) 2
Ch
loro
form
486
5.9
54(b
0)1
77
XZ
CH
C(C
N) 2
YZ
N(C
H3) 2
DM
SO49
2m
bZ
27!
10K
46
(1.3
6)2
31
XZ
C2(C
N) 3
YZ
N(C
2H
5) 2
DM
SOm
bZ
41!
10K
46
(1.5
8)2
64
XZ
C2(C
N) 3
YZ
N(C
2H
5)(
C2H
4)O
HC
H2C
l 251
310
190
(1.5
7)5
4
Pyr
idin
ed
eriv
ativ
es NO
2H
2N
NA
ceto
ne
6.5
3.7
(1.9
)46
NO
2N
OHN
p-D
ioxa
ne
376
7.2
18(1
.06)
25
p-D
ioxa
ne
11(1
.32)
25
p-D
ioxa
ne
11(1
.91)
25
p-D
ioxa
ne
5.5
17(1
.06)
26
2
H45
C22
NO
2N
Np-
Dio
xan
e35
76.
713
(1.0
6)2
5
p-D
ioxa
ne
9.3
(1.3
2)2
5
p-D
ioxa
ne
6.0
(1.9
1)2
5
NO
2N
N
p-D
ioxa
ne
361
6.8
22(1
.06)
25
p-D
ioxa
ne
12(1
.32)
25
p-D
ioxa
ne
11(1
.91)
25
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:12—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-39
Article in Press
1939
1940
1941
1942
1943
1944
1945
1946
1947
1948
1949
1950
1951
1952
1953
1954
1955
1956
1957
1958
1959
1960
1961
1962
1963
1964
1965
1966
1967
1968
1969
1970
1971
1972
1973
1974
1975
1976
1977
1978
1979
1980
1981
1982
1983
1984
1985
1986
1987
1988
1989
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
NO
2N
Np-
Dio
xan
e6.
115
(1.0
6)2
62
NO
2H
3CO
Np-
Dio
xan
e3.
52.
2(1
.9)4
6
H3C
ON
O2
Np-
Dio
xan
e3.
52.
2(1
.9)4
6
NB
rC
hlo
rofo
rm0.
910
(1.9
)46
NO
CH
3C
hlo
rofo
rm33
53.
816
(1.9
)43
NN
O2
Ch
loro
form
1.3
8(1
.9)4
6
15018—Chapter7—26/8/2006—22:12—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-40 Handbook of Photonics
Article in Press
1990
1991
1992
1993
1994
1995
1996
1997
1998
1999
2000
2001
2002
2003
2004
2005
2006
2007
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020
2021
2022
2023
2024
2025
2026
2027
2028
2029
2030
2031
2032
2033
2034
2035
2036
2037
2038
2039
2040
N
CN
CF
3p-
Dio
xan
e31
26.
24.
3(1
.06)
24
4
N
CN
CF
3p-
Dio
xan
e30
95.
54.
4(1
.06)
24
4
CN
NC
F3
p-D
ioxa
ne
307
5.1
4.2
(1.0
6)2
44
Cou
mar
ind
eriv
ativ
es
NO
O
Ch
loro
form
515
(1.9
)43
CH
3OO
OO
Ch
loro
form
58
(1.9
)43
ON
OO
Ch
loro
form
7.3
30(1
.9)4
3
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:13—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-41
Article in Press
2041
2042
2043
2044
2045
2046
2047
2048
2049
2050
2051
2052
2053
2054
2055
2056
2057
2058
2059
2060
2061
2062
2063
2064
2065
2066
2067
2068
2069
2070
2071
2072
2073
2074
2075
2076
2077
2078
2079
2080
2081
2082
2083
2084
2085
2086
2087
2088
2089
2090
2091
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
ON
NO
2OO
Ch
loro
form
8.8
50(1
.9)4
3
O
OC
H3
CH
3OOO
Ch
loro
form
5.8
9.5
(1.9
)43
O
OC
H3
CH
3OOO
CN
Ch
loro
form
7.3
15(1
.9)4
3
Oth
erpo
lycy
clic
arom
atic
der
ivat
ives
NX
N
XZ
Hp-
Dio
xan
e3.
6!
1(1
.9)4
3
XZ
SHp-
Dio
xan
e4
!1
(1.9
)43
XZ
CO
OH
p-D
ioxa
ne
2.6
!1
(1.9
)43
NO
2
N
N
p-D
ioxa
ne
X
SS
Y
XZ
HY
ZO
p-D
ioxa
ne
340
4.8
(1.3
4)2
8
XO
CH
3Y
ZO
p-D
ioxa
ne
312
13(1
.34)
28
15018—Chapter7—26/8/2006—22:13—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-42 Handbook of Photonics
Article in Press
2092
2093
2094
2095
2096
2097
2098
2099
2100
2101
2102
2103
2104
2105
2106
2107
2108
2109
2110
2111
2112
2113
2114
2115
2116
2117
2118
2119
2120
2121
2122
2123
2124
2125
2126
2127
2128
2129
2130
2131
2132
2133
2134
2135
2136
2137
2138
2139
2140
2141
2142
XZ
HY
ZS
p-D
ioxa
ne
438
11(1
.34)
28
XZ
OC
H3
YZ
Sp-
Dio
xan
e43
821
(1.3
4)2
8
OH
N33
34.
0b
0Z
12(S
)7
NO
H35
66.
2b
0Z
11(S
)7
NO
2
H2N
DM
SOm
bZ
23!
10K
47
(1.3
6)2
31
O2N
NN
NO
2
Ch
loro
form
7.6
36(1
.9)4
3
N
CN
CN
N
Ch
loro
form
7.3.
20(1
.9)4
3
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:13—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-43
Article in Press
2143
2144
2145
2146
2147
2148
2149
2150
2151
2152
2153
2154
2155
2156
2157
2158
2159
2160
2161
2162
2163
2164
2165
2166
2167
2168
2169
2170
2171
2172
2173
2174
2175
2176
2177
2178
2179
2180
2181
2182
2183
2184
2185
2186
2187
2188
2189
2190
2191
2192
2193
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
N
N C+
Cl−
N
CC
l 459
058
0(1
.06H
R)2
91
N
O
NC
hlo
rofo
rm4
10(1
.9)4
3
CN
NN
O
Ch
loro
form
400
6.7
31(1
.9)4
3
NO
2
N
O
NC
hlo
rofo
rm42
37
45(1
.9)4
3
NO
2
p-D
ioxa
ne
65
(1.9
)43
15018—Chapter7—26/8/2006—22:13—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-44 Handbook of Photonics
Article in Press
2194
2195
2196
2197
2198
2199
2200
2201
2202
2203
2204
2205
2206
2207
2208
2209
2210
2211
2212
2213
2214
2215
2216
2217
2218
2219
2220
2221
2222
2223
2224
2225
2226
2227
2228
2229
2230
2231
2232
2233
2234
2235
2236
2237
2238
2239
2240
2241
2242
2243
2244
NO
2
p-D
ioxa
ne
811
(1.9
)43
O
OO N
N N
NH
2p-
Dio
xan
e57
5m
bZ
30!
10K
47
(z2)
22
6
NO
2
NC
hlo
rofo
rm6.
535
(1.9
)43
NO
2
H3C
ON
MP
364
718
(1.9
)43
N
SO O
NM
P40
68
30(1
.9)4
3
H3C
O
NO
2
Ch
loro
form
394
852
(1.9
)43
NN
O2
NO
2
p-D
ioxa
ne
mb
Z13
!10
–4
6(1
.9)1
07
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:14—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-45
Article in Press
2245
2246
2247
2248
2249
2250
2251
2252
2253
2254
2255
2256
2257
2258
2259
2260
2261
2262
2263
2264
2265
2266
2267
2268
2269
2270
2271
2272
2273
2274
2275
2276
2277
2278
2279
2280
2281
2282
2283
2284
2285
2286
2287
2288
2289
2290
2291
2292
2293
2294
2295
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
Pol
yen
ed
eriv
ativ
es
CN
NC
N
Ch
loro
form
352
7.6
1(1
.9)1
56
S
X
nY
S
CO
HC
hlo
rofo
rm37
2m
bZ
30!
10K
48
(1.3
4)1
4
nZ
1X
ZC
OH
YZ
N(C
H3) 2
Ch
loro
form
284
6.3
3.3
(1.9
)15
6
nZ
2X
ZC
OH
YZ
N(C
2H
5) 2
Ch
loro
form
363
6.5
20(1
.9)1
56
nZ
3X
ZC
OH
YZ
N(C
H3) 2
Ch
loro
form
422
6.9
53(1
.9)1
56
nZ
1X
ZC
HC
(CN
) 2Y
ZN
(CH
3) 2
Ch
loro
form
374
8.9
6.1
(1.9
)15
6
nZ
2X
ZC
HC
(CN
) 2Y
ZN
(C2H
5) 2
Ch
loro
form
476
10.7
45(1
.9)1
56
nZ
3X
ZC
HC
(CN
) 2Y
ZN
(CH
3) 2
Ch
loro
form
550
9.9
211
(1.9
)15
6
nZ
1X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
6.3
4.8
(1.9
)43
nZ
2X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
6.7
21(1
.9)4
3
nZ
3X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
8.4
73(1
.9)4
3
nZ
3X
ZSO
2C
F3
YZ
N(C
H3) 2
Ch
loro
form
9.8
40(1
.9)4
3
CO
H
S
SC
hlo
rofo
rm45
6m
bZ
12!
10K
46
(1.3
4)1
4
CO
H
S
SC
hlo
rofo
rm46
6m
bZ
22!
10K
46
(1.3
4)1
4
15018—Chapter7—26/8/2006—22:14—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-46 Handbook of Photonics
Article in Press
2296
2297
2298
2299
2300
2301
2302
2303
2304
2305
2306
2307
2308
2309
2310
2311
2312
2313
2314
2315
2316
2317
2318
2319
2320
2321
2322
2323
2324
2325
2326
2327
2328
2329
2330
2331
2332
2333
2334
2335
2336
2337
2338
2339
2340
2341
2342
2343
2344
2345
2346
S
CO
HS
Ch
loro
form
500
mb
Z73
!10
K4
6(1
.34)
14
CO
HD
MSO
380
mb
Z23
!10
K4
7(1
.06)
10
1
CN
CN
DM
SO47
0R
e(m
b)Z
13!
10K
46
(1.0
6)1
01
Im(m
b)Z
15!
10K
46
(1.0
6)1
01
CN
NO
2
DM
SO48
0R
e(m
b)Z
14!
10K
46
(1.0
6)1
01
Im(m
b)Z
35!
10K
46
(1.0
6)1
01
N
N
DM
SO44
0R
e(m
b)Z
15!
10K
46
(1.0
6)1
01
Im(m
b)Z
17!
10K
46
(1.0
6)1
01
CO
HC
l 2C
HC
HC
l 247
0R
e(m
b)Z
10!
10K
47
(1.0
6)1
01
Im(m
b)Z
44!
10K
46
(1.0
6)1
01
Ch
loro
form
476
mb
Z96
!10
K4
7(1
.9)5
3
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:14—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-47
Article in Press
2347
2348
2349
2350
2351
2352
2353
2354
2355
2356
2357
2358
2359
2360
2361
2362
2363
2364
2365
2366
2367
2368
2369
2370
2371
2372
2373
2374
2375
2376
2377
2378
2379
2380
2381
2382
2383
2384
2385
2386
2387
2388
2389
2390
2391
2392
2393
2394
2395
2396
2397
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
NO
2C
l 2C
HC
HC
l 250
0R
e(m
b)Z
K20
!10
K4
6(1
.06)
10
1
Im(m
b)Z
25!
10K
46
(1.0
6)1
01
CN
CN
Cl 2
CH
CH
Cl 2
570
Re(
mb
)Z35
!10
K4
6(1
.06)
10
1
Im(m
b)Z
47!
10K
46
(1.0
6)1
01
Ch
loro
form
566
mb
Z44
!10
K4
6(1
.9)5
3
CN
CO
2C2H
5R
e(m
b)Z
K12
!10
K4
5(1
.06)
10
1
Cl 2
CH
CH
Cl 2
510
Im(m
b)Z
73!
10K
46
(1.0
6)1
01
Ch
loro
form
502
mb
Z15
!10
K4
6(1
.9)5
3
a-P
hen
ylpo
lyen
eD
eriv
ativ
es
nY
X
nZ
2X
ZC
OH
YZ
OC
H3
Ch
loro
form
350
4.3
28(1
.9)4
5
nZ
3X
ZC
OH
YZ
OC
H3
Ch
loro
form
376
4.6
42(1
.9)4
5
nZ
2X
ZC
OH
YZ
N(C
H3) 2
Ch
loro
form
412
6.0
52(1
.9)4
5
nZ
3X
ZC
OH
YZ
N(C
H3) 2
Ch
loro
form
434
6.3
88(1
.9)4
5
Ch
loro
form
6.6
105
(1.9
)43
15018—Chapter7—26/8/2006—22:14—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-48 Handbook of Photonics
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2433
2434
2435
2436
2437
2438
2439
2440
2441
2442
2443
2444
2445
2446
2447
2448
nZ
4X
ZC
OH
YZ
N(C
H3) 2
Ch
loro
form
8.0
138
(1.9
)43
nZ
2X
ZC
OC
F3
YZ
N(C
H3) 2
Ch
loro
form
6.6
126
(1.9
)43
nZ
2X
ZN
O2
YZ
OC
H3
DM
SO37
0m
bZ
81!
10K
48
(1.0
6)1
02
Ch
loro
form
4.6
42(1
.9)4
5
nZ
3X
ZN
O2
YZ
OC
H3
DM
SO40
0m
bZ
30!
10K
47
(1.0
6)1
02
nZ
2X
ZN
O2
YZ
N(C
H3) 2
Ace
ton
e8.
863
0(1
.06)
18
9
DM
SO46
0m
bZ
17!
10K
46
(1.0
6)1
02
Ch
loro
form
466
6.5
140
(1.9
)25
4
nZ
3X
ZN
O2
YZ
N(C
H3) 2
DM
SO49
0m
bZ
55!
10K
46
(1.0
6)1
02
Ch
loro
form
487
6.6
240
(1.9
)25
4
nZ
4X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
502
7.6
280
(1.9
)25
4
nZ
2X
ZC
HC
(CN
) 2Y
ZN
(CH
3) 2
DM
SO50
0m
bZ
36!
10K
46
(1.0
6)1
02
Ch
loro
form
520
9.0
163
(1.9
)45
nZ
3X
ZC
HC
(CN
) 2Y
ZN
(CH
3) 2
Ch
loro
form
8.8
432
(1.9
)43
nX
N
nZ
3X
ZC
OH
Ch
loro
form
7.1
162
(1.9
)43
nZ
3X
ZN
O2
Ch
loro
form
7.8
287
(1.9
)43
nZ
4X
ZN
O2
Ch
loro
form
mb
Z26
!10
K4
6(1
.9)4
3
nZ
3X
ZC
HC
(CN
) 2C
hlo
rofo
rm8.
748
5(1
.9)4
3
NC
OH
Ch
loro
form
450
mb
Z20
!10
K4
6(1
.34)
14
N
CO
H
Ch
loro
form
461
mb
Z42
!10
K4
6(1
.34)
14
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:15—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-49
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2491
2492
2493
2494
2495
2496
2497
2498
2499
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
NC
OH
Ch
loro
form
498
mb
Z89
!10
K4
6(1
.34)
14
Dip
hen
ylpo
lyen
ed
eriv
ativ
es
nY
X
nZ
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3C
hlo
rofo
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327
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)45
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CH
3C
hlo
rofo
rm38
04.
640
(1.9
)45
nZ
2X
ZN
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YZ
Br
Ch
loro
form
378
3.5
21(1
.9)4
5
nZ
3X
ZN
O2
YZ
Br
Ch
loro
form
400
3.8
35(1
.9)4
5
nZ
2X
ZN
O2
YZ
OC
H3
p-D
ioxa
ne
6.0
135
(1.0
6)9
8
Ch
loro
form
397
4.8
47(1
.9)4
5
nZ
3X
ZN
O2
YZ
OC
H3
p-D
ioxa
ne
6.6
274
(1.0
6)9
8
Ch
loro
form
414
5.1
76(1
.9)4
5
nZ
4X
ZN
O2
YZ
OC
H3
p-D
ioxa
ne
6.7
367
(1.0
6)9
8
Ch
loro
form
430
5.8
55(1
.9)4
5
nZ
5X
ZN
O2
YZ
OC
H3
p-D
ioxa
ne
7.0
623
(1.0
6)9
8
nZ
2X
ZN
O2
YZ
SCH
3C
hlo
rofo
rm39
84.
510
1(1
.9)4
5
nZ
2X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
442
7.6
107
(1.9
)45
p-D
ioxa
ne
mb
Z75
!10
K4
7(1
.9)1
07
nZ
3X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
458
8.2
131
(1.9
)45
NZ
4X
ZN
O2
YZ
N(C
H3) 2
Ch
loro
form
464
919
0(1
.9)4
5
NZ
2X
ZC
2H
CN
2Y
ZN
(CH
3) 2
DM
SO48
1m
bZ
13!
10K
46
(1.3
6)2
31
n
Y
X
nZ
2X
ZC
NY
ZO
CH
3C
hlo
rofo
rm35
43.
84.
5(1
.9)4
5
nZ
3X
ZC
NY
ZO
CH
3C
hlo
rofo
rm37
63.
87.
1(1
.9)4
5
15018—Chapter7—26/8/2006—22:15—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-50 Handbook of Photonics
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2543
2544
2545
2546
2547
2548
2549
2550
nZ
2X
ZN
O2
YZ
OC
H3
Ch
loro
form
376
3.7
6.4
(1.9
)45
nZ
3X
ZN
O2
YZ
OC
H3
Ch
loro
form
392
4.1
11(1
.9)4
5
n
Y
X
nZ
2X
ZO
CH
3Y
ZC
NC
hlo
rofo
rm35
63.
92.
6(1
.9)4
5
nZ
3X
ZO
CH
3Y
ZC
NC
hlo
rofo
rm37
83.
94.
3(1
.9)4
5
nZ
2X
ZC
NY
ZO
CH
3C
hlo
rofo
rm35
84.
94.
3(1
.9)4
5
nZ
2X
ZO
CH
3Y
ZN
O2
Ch
loro
form
376
3.8
4.9
(1.9
)45
nZ
3X
ZO
CH
3Y
ZN
O2
Ch
loro
form
392
3.8
11(1
.9)4
5
nZ
2X
ZN
O2
YZ
OC
H3
Ch
loro
form
380
4.3
17(1
.9)4
5
nZ
3X
ZN
O2
YZ
OC
H3
Ch
loro
form
412
4.8
56(1
.9)4
5
NO
2
NO
2
Np-
Dio
xan
e48
07.
198
(1.9
)25
5
p-D
ioxa
ne
mb
Z13
!10
K4
6(1
.9)1
07
NN
O2
NO
2
Ch
loro
form
6.2
71(1
.9)2
55
a,u
-Dip
hen
ylpo
lyen
ed
eriv
ativ
es
XY
n
nZ
2X
ZC
NY
ZSC
H3
Ch
loro
form
330
3.7
17(1
.9)4
5
nZ
2X
ZC
NY
ZN
H2
NM
P38
8m
bZ
11!
10K
47
(1.9
)45
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:15—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-51
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2600
2601
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
nZ
2X
ZN
O2
YZ
SCH
3C
hlo
rofo
rm33
83.
917
(1.9
)45
nZ
2X
ZN
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YZ
NH
2C
hlo
rofo
rm33
46.
328
(1.9
)45
nZ
2X
ZN
O2
YZ
NH
2N
MP
416
mb
Z24
!10
K4
7(1
.9)4
5
nZ
3X
ZN
O2
YZ
NH
2N
MP
440
mb
Z41
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.9)4
5
Cu
mu
len
ed
eriv
ativ
es
XY
CC
CC
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ZH
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ne
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.9)6
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ZH
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ne
442
mb
Z66
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.06)
61
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ZC
H3
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ne
448
mb
Z60
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K4
7(1
.06)
61
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47
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6)6
1
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2) 1
1
CH
3
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ioxa
ne
461
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.9)6
1
a,u
-Pol
yph
enyl
der
ivat
ives
XY
n
nZ
3X
ZN
O2
YZ
OC
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p-D
ioxa
ne
340
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11(1
.9)4
5
nZ
3X
ZN
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NH
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MP
360
7.8
24(1
.9)4
5
nZ
4X
ZN
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YZ
NH
2N
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344
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16(1
.9)4
5
Pyr
rol
der
ivat
ives
CN
CF
3
N
p-d
ioxa
ne
376
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11(1
.06)
24
4
CN
CF
3
Np-
dio
xan
e38
17.
212
(1.0
6)2
44
15018—Chapter7—26/8/2006—22:15—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-52 Handbook of Photonics
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2641
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2645
2646
2647
2648
2649
2650
2651
2652
NO
2
Np-
dio
xan
e41
05.
526
(1.9
)43
N
N
X
O XZ
OC
H3
DM
SO48
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S)6
4
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243
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64
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Y
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539
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.9S)
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S)6
4
N
NS S
OD
MSO
553
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S)6
4
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ran
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ivat
ives
CF
3
CN
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p-D
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ne
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44
CF
3
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xan
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.06)
24
4
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:16—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-53
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2701
2702
2703
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
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30
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Th
ioph
ene
der
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NO
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220
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6)1
17
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2
S
Ch
loro
form
382
5.4
67(1
.06)
11
7
15018—Chapter7—26/8/2006—22:16—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
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2743
2744
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2747
2748
2749
2750
2751
2752
2753
2754
CN
CF
3
S
p-D
ioxa
ne
346
6.8
6.6
(1.0
6)2
44
CN
CF
3
Sp-
Dio
xan
e32
16.
75.
4(1
.06)
24
4
CH
ON
SC
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rofo
rm5.
87.
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.9)4
3
NS
CN
CN
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loro
form
9.0
21(1
.9)4
3
NS
CN
CN
Ch
loro
form
8.8
21(1
.9)4
3
SO
N
CN
CN
Ch
loro
form
5.9
23(1
.9)4
3
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:16—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
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2797
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2800
2801
2802
2803
2804
2805
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
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(10K
18
esu
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(10K
30
esu
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MM
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47
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m
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CN
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(1.9
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NN
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loro
form
492
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98(1
.9)4
5
S
NN
O2
p-D
ioxa
ne
478
mb
Z60
!10
K4
7(1
.9)2
03
N
SN
O2
Ch
loro
form
7.0
197
(1.9
)43
15018—Chapter7—26/8/2006—22:17—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
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2847
2848
2849
2850
2851
2852
2853
2854
2855
2856
S
NC
N
CN
p-D
ioxa
ne
584
mb
Z26
!10
K4
6(1
.9)1
06
S
NC
N
CN
CN
p-D
ioxa
ne
640
mb
Z62
!10
K4
6(1
.9)2
03
S
NC
N
CN
Ch
loro
form
7.5
161
(1.9
)43
S
SN
CN
CN
Ch
loro
form
7.6
250
(1.9
)72
S
S
N
CN
CN
CN
p-D
ioxa
ne
718
mb
Z69
!10
K4
6(1
.9)2
03
S
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CN
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ioxa
ne
662
mb
Z91
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.9)2
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nN
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6
nZ
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xan
e54
7m
bZ
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10K
46
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)10
6
nZ
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xan
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bZ
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10K
46
(1.9
)10
6
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:17—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-57
Article in Press
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2858
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2873
2874
2875
2876
2877
2878
2879
2880
2881
2882
2883
2884
2885
2886
2887
2888
2889
2890
2891
2892
2893
2894
2895
2896
2897
2898
2899
2900
2901
2902
2903
2904
2905
2906
2907
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
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18
esu
)b
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)ref.
(10K
30
esu
)
S
2N
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CN
CN
p-d
ioxa
ne
653
mb
Z74
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ne
354
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ne
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16(1
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6
XZ
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ne
354
4.1
42(1
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16
6
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CH
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Dio
xan
e37
07.
048
(1.0
6)1
66
15018—Chapter7—26/8/2006—22:17—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-58 Handbook of Photonics
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2908
2909
2910
2911
2912
2913
2914
2915
2916
2917
2918
2919
2920
2921
2922
2923
2924
2925
2926
2927
2928
2929
2930
2931
2932
2933
2934
2935
2936
2937
2938
2939
2940
2941
2942
2943
2944
2945
2946
2947
2948
2949
2950
2951
2952
2953
2954
2955
2956
2957
2958
Z
XN
N
Y
XZ
NO
2Y
Zp-
CH
3O
C6H
4C
bC
–Z
ZH
p-d
ioxa
ne
340
5.6
20(1
.06)
16
6
XZ
NO
2Y
Zp-
CH
3O
C6H
4C
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CH
–Z
ZH
p-D
ioxa
ne
358
5.1
63(1
.06)
16
6
Z
XN
N
Y
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2Y
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ne
306
6.3
13(1
.06)
16
6
XZ
NO
2Y
ZC
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HZ
CH
–Z
ZH
p-D
ioxa
ne
298
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.06)
16
6
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6
XZ
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.06)
16
6
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2) 6
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79(1
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76
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ne
344
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53(1
.06)
17
6
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2) 5
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46(1
.9)1
76
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ne
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8.1
69(1
.06)
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6
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25(1
.9)1
76
XZ
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2Y
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CH
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loro
form
412
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20(1
.9)1
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2H
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loro
form
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6.5
14(1
.9)1
76
XZ
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CH
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ioxa
ne
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.06)
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6
XZ
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17
6
XZ
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loro
form
370
8.0
32(1
.06)
17
6
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:17—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-59
Article in Press
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2960
2961
2962
2963
2964
2965
2966
2967
2968
2969
2970
2971
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2974
2975
2976
2977
2978
2979
2980
2981
2982
2983
2984
2985
2986
2987
2988
2989
2990
2991
2992
2993
2994
2995
2996
2997
2998
2999
3000
3001
3002
3003
3004
3005
3006
3007
3008
3009
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
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esu
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(10K
30
esu
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6
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13(1
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6
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17
6
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2Y
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21(b
0)1
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.9)4
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Cl
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loro
form
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83(1
.9)4
3
CO
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3
NN
N
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H
Cl
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S
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loro
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.9)4
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N
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CH
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l 257
98.
526
0(1
.58)
54
15018—Chapter7—26/8/2006—22:18—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-60 Handbook of Photonics
Article in Press
3010
3011
3012
3013
3014
3015
3016
3017
3018
3019
3020
3021
3022
3023
3024
3025
3026
3027
3028
3029
3030
3031
3032
3033
3034
3035
3036
3037
3038
3039
3040
3041
3042
3043
3044
3045
3046
3047
3048
3049
3050
3051
3052
3053
3054
3055
3056
3057
3058
3059
3060
NO
N
NO
2N
N
SC
hlo
rofo
rm58
29.
052
(b0)1
77
NN
NO
2
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6
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form
582
6.9
68(b
0)1
77
NN
Cl
NN
SC
N CN
CH
2C
l 264
510
530
(1.5
8)5
4
NN
Cl
N-C
O2C
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NN
SC
N CN
Ch
loro
form
634
6.9
100
(1.9
)43
NN
Cl
N-C
O2C
H3
OC
H3
NN
SC
N CN
Ch
loro
form
670
6.9
130
(1.9
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Azu
len
ed
eriv
ativ
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loro
form
1.2
!1
(1.9
)43
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H
Ch
loro
form
2.5
!1
(1.9
)43
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:18—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-61
Article in Press
3061
3062
3063
3064
3065
3066
3067
3068
3069
3070
3071
3072
3073
3074
3075
3076
3077
3078
3079
3080
3081
3082
3083
3084
3085
3086
3087
3088
3089
3090
3091
3092
3093
3094
3095
3096
3097
3098
3099
3100
3101
3102
3103
3104
3105
3106
3107
3108
3109
3110
3111
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
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18
esu
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m(l
)ref.
(10K
30
esu
)
NO
2
Ch
loro
form
4!
1(1
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3
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tafu
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loro
form
17
(1.9
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Ch
loro
form
15
(1.9
)43
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3O
Ch
loro
form
210
(1.9
)43
N
Ch
loro
form
330
(1.9
)43
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44!
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47
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02
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bZ
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48
(1.0
6)1
02
15018—Chapter7—26/8/2006—22:18—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-62 Handbook of Photonics
Article in Press
3112
3113
3114
3115
3116
3117
3118
3119
3120
3121
3122
3123
3124
3125
3126
3127
3128
3129
3130
3131
3132
3133
3134
3135
3136
3137
3138
3139
3140
3141
3142
3143
3144
3145
3146
3147
3148
3149
3150
3151
3152
3153
3154
3155
3156
3157
3158
3159
3160
3161
3162
N
Ch
loro
form
3.6
74(1
.9)4
3
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bZ
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46
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n
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loro
form
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idin
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190
(1.9
)15
3
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:18—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-63
Article in Press
3163
3164
3165
3166
3167
3168
3169
3170
3171
3172
3173
3174
3175
3176
3177
3178
3179
3180
3181
3182
3183
3184
3185
3186
3187
3188
3189
3190
3191
3192
3193
3194
3195
3196
3197
3198
3199
3200
3201
3202
3203
3204
3205
3206
3207
3208
3209
3210
3211
3212
3213
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
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lven
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esu
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(10K
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NN
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loro
form
580
4.0
79(1
.9)1
53
O
NN
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loro
form
610
4.3
91(1
.9)1
53
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NX X
ZH
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loro
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428
1.5
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(1.9
)15
4
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form
432
1.3
13(1
.9)1
54
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loro
form
469
2.4
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.9)1
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4
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3.3
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loro
form
558
3.9
78(1
.9)1
54
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CH
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H3
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loro
form
497
2.6
48(1
.9)1
54
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form
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3.7
116
(1.9
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4
NN
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10K
47
(1.0
6)1
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04
15018—Chapter7—26/8/2006—22:19—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-64 Handbook of Photonics
Article in Press
3214
3215
3216
3217
3218
3219
3220
3221
3222
3223
3224
3225
3226
3227
3228
3229
3230
3231
3232
3233
3234
3235
3236
3237
3238
3239
3240
3241
3242
3243
3244
3245
3246
3247
3248
3249
3250
3251
3252
3253
3254
3255
3256
3257
3258
3259
3260
3261
3262
3263
3264
Im(m
b)Z
61!
10K
45
(1.0
6)1
04
N
O
N
X
Y
DM
SO55
0R
e(m
b)Z
48!
10K
45
(1.0
6)1
04
Im(m
b)Z
61!
10K
45
(1.0
6)1
04
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NY
ZO
DM
SO39
0m
bZ
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10K
47
(1.0
6)1
03
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b)Z
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46
(1.0
6)1
03
Im(m
b)Z
31!
10K
47
(1.0
6)1
03
N
2
OO
ON
N
S
DM
SO53
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b)Z
21!
10K
45
(1.0
6)1
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tin
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)
15018—Chapter7—26/8/2006—22:19—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-65
Article in Press
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3287
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3295
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3298
3299
3300
3301
3302
3303
3304
3305
3306
3307
3308
3309
3310
3311
3312
3313
3314
3315
TA
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15018—Chapter7—26/8/2006—22:19—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-66 Handbook of Photonics
Article in Press
3316
3317
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3321
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3333
3334
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3352
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3355
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3357
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3360
3361
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3363
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3365
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tin
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15018—Chapter7—26/8/2006—22:19—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-67
Article in Press
3367
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3387
3388
3389
3390
3391
3392
3393
3394
3395
3396
3397
3398
3399
3400
3401
3402
3403
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3410
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3412
3413
3414
3415
3416
3417
TA
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15018—Chapter7—26/8/2006—22:20—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-68 Handbook of Photonics
Article in Press
3418
3419
3420
3421
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3423
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3426
3427
3428
3429
3430
3431
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3434
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3436
3437
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3440
3441
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3443
3444
3445
3446
3447
3448
3449
3450
3451
3452
3453
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tin
ued
)
15018—Chapter7—26/8/2006—22:20—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-69
Article in Press
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3497
3498
3499
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3501
3502
3503
3504
3505
3506
3507
3508
3509
3510
3511
3512
3513
3514
3515
3516
3517
3518
3519
TA
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15018—Chapter7—26/8/2006—22:20—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-70 Handbook of Photonics
Article in Press
3520
3521
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3539
3540
3541
3542
3543
3544
3545
3546
3547
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3552
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3555
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tin
ued
)
15018—Chapter7—26/8/2006—22:20—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-71
Article in Press
3571
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3587
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3590
3591
3592
3593
3594
3595
3596
3597
3598
3599
3600
3601
3602
3603
3604
3605
3606
3607
3608
3609
3610
3611
3612
3613
3614
3615
3616
3617
3618
3619
3620
3621
TA
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15018—Chapter7—26/8/2006—22:21—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-72 Handbook of Photonics
Article in Press
3622
3623
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3625
3626
3627
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3629
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3632
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3636
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3638
3639
3640
3641
3642
3643
3644
3645
3646
3647
3648
3649
3650
3651
3652
3653
3654
3655
3656
3657
3658
3659
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3661
3662
3663
3664
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3666
3667
3668
3669
3670
3671
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(con
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15018—Chapter7—26/8/2006—22:21—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-73
Article in Press
3673
3674
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3676
3677
3678
3679
3680
3681
3682
3683
3684
3685
3686
3687
3688
3689
3690
3691
3692
3693
3694
3695
3696
3697
3698
3699
3700
3701
3702
3703
3704
3705
3706
3707
3708
3709
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3711
3712
3713
3714
3715
3716
3717
3718
3719
3720
3721
3722
3723
TA
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3
nZ
2C
hlo
rofo
rm6.
853
4(1
.9)4
3
NN
CN
CN
O
Ch
loro
form
5.0
98(1
.9)4
3
NN
N CO
2CH
3
O CN
CN
Ch
loro
form
5.6
64(1
.9)4
3
15018—Chapter7—26/8/2006—22:21—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-74 Handbook of Photonics
Article in Press
3724
3725
3726
3727
3728
3729
3730
3731
3732
3733
3734
3735
3736
3737
3738
3739
3740
3741
3742
3743
3744
3745
3746
3747
3748
3749
3750
3751
3752
3753
3754
3755
3756
3757
3758
3759
3760
3761
3762
3763
3764
3765
3766
3767
3768
3769
3770
3771
3772
3773
3774
N
CN
CN
NC
CN
Ch
loro
form
6.7
97(1
.9)4
3
CN
CN
NC
N
CN
Ch
loro
form
8.0
89(1
.9)4
3
SX
CN
CN
NC
CN
XZ
OC
H3
Ch
loro
form
6.0
165
(1.9
)43
XZ
N(C
H3) 2
Ch
loro
form
6.0
1024
(1.9
)43
NN
N
OC
N
O
Ch
loro
form
7.8
169
(1.9
)43
NN
N CO
2CH
3
N
CN
O
O
Ch
loro
form
7.7
83(1
.9)4
3
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:21—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-75
Article in Press
3775
3776
3777
3778
3779
3780
3781
3782
3783
3784
3785
3786
3787
3788
3789
3790
3791
3792
3793
3794
3795
3796
3797
3798
3799
3800
3801
3802
3803
3804
3805
3806
3807
3808
3809
3810
3811
3812
3813
3814
3815
3816
3817
3818
3819
3820
3821
3822
3823
3824
3825
TA
BL
E7.
1(C
on
tin
ued
)
Stru
ctu
reSo
lven
tl
max
(nm
)m
(10K
18
esu
)b
m(l
)ref.
(10K
30
esu
)
CN
NN
N
N
SN
N
O
O
CI
NC
O2C
H3
Ch
loro
form
696
8.1
432
(1.9
)43
NO
2N
NN
NX X
O
XZ
C2H
5;
XZ
HO
(CH
2) 6
Ch
loro
form
548
9.5
60(b
0)1
77
XZ
4-C
H3C
5H
4C
hlo
rofo
rm55
07.
272
(b0)1
77
NN
N
N
SN O
CI
CI
NC
O2C
H3
Ch
loro
form
5.5
164
(1.9
)43
N
CN
CN
Ch
loro
form
8.7
129
(1.9
)43
CN
CN
N
Ch
loro
form
7.0
87(1
.9)4
3
15018—Chapter7—26/8/2006—22:22—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-76 Handbook of Photonics
Article in Press
3826
3827
3828
3829
3830
3831
3832
3833
3834
3835
3836
3837
3838
3839
3840
3841
3842
3843
3844
3845
3846
3847
3848
3849
3850
3851
3852
3853
3854
3855
3856
3857
3858
3859
3860
3861
3862
3863
3864
3865
3866
3867
3868
3869
3870
3871
3872
3873
3874
3875
3876
N
CN
CN
Ch
loro
form
7.5
93(1
.9)4
3
CN
CN
NO
Ch
loro
form
8.6
82(1
.9)4
3
N
O
N
NC
CN
Ch
loro
form
7.9
102
(1.9
)43
NC
CN
O
NN
Ch
loro
form
8.5
95(1
.9)4
3
15018—Chapter7—26/8/2006—22:22—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-77
Article in Press
3877
3878
3879
3880
3881
3882
3883
3884
3885
3886
3887
3888
3889
3890
3891
3892
3893
3894
3895
3896
3897
3898
3899
3900
3901
3902
3903
3904
3905
3906
3907
3908
3909
3910
3911
3912
3913
3914
3915
3916
3917
3918
3919
3920
3921
3922
3923
3924
3925
3926
3927
TA
BL
E7.
2Si
ngl
eC
ryst
alR
esu
lts
on
Org
anic
No
nli
nea
rM
ater
ials
:ni,
refr
acti
vein
dex
at63
3n
m;l
NC
(q),
q-n
on
crit
ical
ph
ase-
mat
chin
gw
avel
engt
h;l
NC
(l),
l-n
on
crit
ical
ph
ase-
mat
chin
gw
avel
engt
h;
and
at1.
064
mm
:D
T(t
),o
pti
cal
dam
age
thre
sho
ld(p
uls
ed
ura
tio
n);
def
f,ef
fect
ive
no
nli
nea
rity
(ph
ase-
mat
chin
gty
pe)
;D
ql,
angu
lar
acce
pta
nce
;D
Tl,
tem
per
atu
reac
cep
tan
ce;
dq
pm
/dT
,te
mp
erat
ure
tun
ing
of
ph
ase-
mat
chin
gan
gle;
and
r,w
alk-
off
angl
e(p
has
e-m
atch
ing
typ
e)
Ab
stra
ct
Stru
ctu
rean
dN
om
encl
atu
re(a
cro
nym
)P
oin
t
Gro
up
SHG
dij(l
)&
EO
r ij(
l)
(pm
/v)
(mm
)
Cu
t-O
ffl
(nm
)R
ef.
Pro
per
ties
H2N
H2N
O
Ure
a
md
36(1
.06)
z1.
3
r 41(0
.63)
z1.
9
r 63(0
.63)
z0.
83
200
&18
0021
2
80 18,2
1,
172
DT
(10
ns)
Z5
GW
/cm
2.
noZ
1.48
5,n
eZ1.
567.
O
HO
OH
O
S
p,p0 -D
ihyd
roxy
dip
hen
ylsu
lfo
ne
(DH
DP
S)
mm
2d
33(1
.06)
z7
d3
2(1
.06)
z0.
4
D1
1(1
.06)
z3
300
&15
0027
5R
elat
ivel
yh
igh
har
dn
ess,
no
nh
ygro
sco
pic
,an
d
ph
oto
chem
ical
lyst
able
.
Cry
stal
scl
eave
atin
pu
tp
ow
erO
400
MW
/cm
2,
nxZ
2.00
9,n
yZ2.
000,
nzZ
1.92
1.l
NC
(q)Z
865
nm
.
OC
H3
CH
OH
O
3-M
eth
oxy
-4-h
ydro
xy-b
enza
ldeh
yde
(MH
BA
)
2d
13(1
.06)
z13
d1
1(1
.06)
z9.
8
d1
2(1
.06)
z3.
9
d1
4(1
.06)
z3.
2
370
248
286
DT
(10
ns)
Z2
GW
/cm
2.
nxZ
1.54
5,n
yZ1.
685,
nzZ
1.78
0.
Dq
lZ0.
9m
rad
-cm
.
rZ
68
O
O ON
8-(4
0 -Ace
tylp
hen
yl)-
1,4-
dio
xa-8
-
azas
pir
o[4
,5]d
ecan
e(A
PD
A)
mm
2d
33(1
.06)
z50
d3
2(1
.06)
z7
384
217
nxZ
1.56
,n
yZ1.
66,
nzZ
1.68
.
def
f(1.
06)z
14.9
pm
/V.
NO
2
HH
O
ONN
5-N
itro
ura
cil
(5N
U)
222
d1
4(1
.06)
z8.
741
0&
1550
201
Rel
ativ
ely
tran
spar
ent
atn
ear
IR,
DT
(10
ns)
Z3
GW
/cm
2.
nxZ
1.56
9,n
yZ1.
901,
nzZ
1.70
7.
Dq
lZ8
mra
d-c
m,
rZ
78,
lN
C(l
)Z14
40n
m.
15018—Chapter7—26/8/2006—22:22—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-78 Handbook of Photonics
Article in Press
3928
3929
3930
3931
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3933
3934
3935
3936
3937
3938
3939
3940
3941
3942
3943
3944
3945
3946
3947
3948
3949
3950
3951
3952
3953
3954
3955
3956
3957
3958
3959
3960
3961
3962
3963
3964
3965
3966
3967
3968
3969
3970
3971
3972
3973
3974
3975
3976
3977
3978
H2N
OH
m-A
min
op
hen
ol
(mA
P)
mm
2d
33(1
.06)
z3.
3
d3
2(1
.06)
z2.
4
d3
1(1
.06)
z0.
7
320
&17
0036
Po
or
mec
han
ical
stre
ngt
h,
nxZ
1.65
9,n
yZ1.
765,
nzZ
1.57
8.
CI
NO
2
m-C
hlo
ron
itro
ben
zen
e(m
CN
B)
mm
2d
33(1
.06)
z7.
8
d3
2(1
.06)
z4
d3
1(1
.06)
z4.
5
400
&20
0036
Cle
aves
easi
ly,
no
tp
has
e-m
atch
able
for
SHG
at1.
064
mm
,n
xZ
1.67
6,n
yZ1.
684,
nzZ
1.64
9.
Br
NO
2
m-B
rom
on
itro
ben
zen
e(m
BN
B)
mm
2d
33(1
.06)
z8
d3
2(1
.06)
z4.
5
d3
1(1
.06)
z4
420
&21
0036
lN
C(q
)at
1.06
4m
mfo
rso
lid
solu
tio
no
f
mC
0.9
5B
r 0.0
5N
B,
nxZ
1.64
9,n
yZ1.
729,
nzZ
1.67
8.
–O Na+
NO
2
4-N
itro
ph
eno
lso
diu
md
ihyd
rate
(NP
Na)
mm
2T
ype
I
def
f(1.
06)z
8
515
167
Vic
kers
har
dn
ess:
34,
goo
dth
erm
alco
nd
uct
ivit
y.
H2N
NO
2
m-N
itro
anil
ine
(mN
A)
mm
2d
33(1
.06)
z20
d3
2(1
.06)
z1.
5
d3
1(1
.06)
z20
r 33(0
.63)
z17
r 23(0
.63)
z0.
1
r 13(0
.63)
z7.
5
500
&19
0025
6
36 240
Cle
aves
easi
ly,
mel
tgr
ow
nin
toch
ann
elw
aveg
uid
e
(un
favo
ura
ble
ori
enta
tio
nfo
rSH
G),
nxZ
1.75
2,n
yZ1.
715,
nzZ
1.66
5.
H2N
NO
2
2-M
eth
yl-4
-nit
roan
ilin
e(M
NA
)
md
11(1
.06)
z16
7
d1
2(1
.06)
z25
r 11(0
.63)
z67
500
&19
0014
3
170
181
150
Mel
tgr
ow
nin
toch
ann
elw
aveg
uid
e(o
rien
tati
on
con
tro
lled
by
elec
tric
or
tem
per
atu
regr
adie
nts
).
DT
(20
ns)
Z0.
2G
W/c
m2.
nxZ
2.00
1,n
yZ1.
658,
nzZ
1.43
5,
nea
ro
pti
mu
mm
ole
cula
ral
ign
men
tfo
rE
O.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:23—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-79
Article in Press
3979
3980
3981
3982
3983
3984
3985
3986
3987
3988
3989
3990
3991
3992
3993
3994
3995
3996
3997
3998
3999
4000
4001
4002
4003
4004
4005
4006
4007
4008
4009
4010
4011
4012
4013
4014
4015
4016
4017
4018
4019
4020
4021
4022
4023
4024
4025
4026
4027
4028
4029
TA
BL
E7.
2(C
on
tin
ued
)
Ab
stra
ct
Stru
ctu
rean
dN
om
encl
atu
re(a
cro
nym
)P
oin
t
Gro
up
SHG
dij(l
)&
EO
r ij(
l)
(pm
/v)
(mm
)
Cu
t-O
ffl
(nm
)R
ef.
Pro
per
ties
N
HN
O
NO
2
4-(N
,N-d
imet
hyl
amin
o)-
3-ac
etam
ido
nit
rob
enze
ne
(DA
N)
2d
21(1
.06)
z1.
5
d2
2(1
.06)
z5.
2
d2
3(1
.06)
z50
d2
5(1
.06)
z1.
5
r 11(0
.63)
z13
485
&22
7012
1
122
123
Fib
erw
aveg
uid
eal
low
sfu
llu
seo
fn
on
zero
dij,
DT
(15
ns)
Z80
MW
/cm
2
def
fz35
.5(I
)&
9(I
I)p
m/v
.
nxZ
1.53
9,n
yZ1.
682,
nzZ
1.94
9.
Dq
lz1.
5m
rad
-cm
.
OH
NO
2N
N-(
4-n
itro
ph
enyl
)-(s
)-p
roli
no
l(N
PP
)
2d
22(1
.06)
z28
d2
1(1
.06)
z85
500
&20
0028
9
138
Nea
ro
pti
mu
mm
ole
cula
ral
ign
men
tfo
rla
rges
td
21
.
nxZ
2.06
6,n
yZ1.
876,
nzZ
1.47
8.
lN
C(q
)Z1.
15m
mu
sin
gd
21
lN
C(l
)Z1.
5m
m.
NO
2H
N
2-M
eth
yl-4
-nit
ro-N
-met
hyl
anil
ine
(MN
MA
)
mm
2d
33(1
.06)
z2.
6
d3
1(1
.06)
z13
d1
5(1
.06)
z12
r 13(0
.63)
z8
r 33(0
.63)
z7.
5
510
245
nxZ
2.14
8,n
xZ
1.52
0.
NC
NO
2N
N-(
4-n
itro
ph
enyl
)-N
-am
ino
acet
on
itri
le(N
PAN
)
mm
2d
33(1
.06)
z27
d3
2(1
.06)
z57
d3
3(1
.34)
z24
d3
2(1
.34)
z48
500
171
15
Nea
ro
pti
mu
mm
ole
cula
ral
ign
men
tfo
rla
rges
td
32.
Dq
lz2
mra
d-c
m.
DT
1z58
C-c
m
OH
NO
2N
L-N
-(5-
nit
ro-2
-pyr
idyl
)leu
cin
ol(
NP
LO
)
2T
ype
I:d
eff(
1.06
)z37
Typ
eII
:d
eff(
1.06
)z3
480
263
Vic
kers
har
dn
ess:
34,
no
nh
ygro
sco
pic
,D
T(8
ns)
Z6
GW
/cm
2.
nxZ
1.45
7,n
yZ1.
631,
nzZ
1.93
3.
rZ
0.22
(I)
&0.
24(I
)m
rad
.
15018—Chapter7—26/8/2006—22:23—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-80 Handbook of Photonics
Article in Press
4030
4031
4032
4033
4034
4035
4036
4037
4038
4039
4040
4041
4042
4043
4044
4045
4046
4047
4048
4049
4050
4051
4052
4053
4054
4055
4056
4057
4058
4059
4060
4061
4062
4063
4064
4065
4066
4067
4068
4069
4070
4071
4072
4073
4074
4075
4076
4077
4078
4079
4080
NN
O2
3,5-
Dim
eth
yl-1
-(4-
nit
rop
hen
yl)
pyr
azo
le(D
MN
P)
mm
2d
33(0
.84)
z29
d3
2(0
.84)
z90
450
83 100
(100
)o
rien
ted
core
fib
ers
allo
wfu
llu
seo
fd
32,
lN
C(q
)Z94
4n
mu
sin
gd
32
.
NO
2
NO
2
m-D
init
rob
enze
ne
(mD
B)
mm
2d
33(1
.06)
z0.
7
d3
2(1
.06)
z2.
7
d3
1(1
.06)
z1.
8
400
&22
0020
nxZ
1.73
8,n
yZ1.
680,
nzZ
1.48
3.
NO
2
NO
2
HN
O
CH
3O
Met
hyl
-(2,
4-d
init
rop
hen
yl)-
amin
op
rop
ano
ate
(MA
P)
2d
22(1
.06)
z18
d2
1(1
.06)
z17
d2
3(1
.06)
z3.
7
500
&20
0019
2D
T(1
0n
s)Z
3G
W/c
m2.
def
fz3.
8(I
)&
8.8
(II)
pm
/v.
nxZ
1.53
1,n
yZ1.
653,
nzZ
1.93
5.
Dq
lz1.
5m
rad
-cm
.
rZ
11.58
(I)
&2.
48(I
)
NO
2N
O 3-M
eth
yl-4
-nit
rop
yrid
ine-
N-o
xid
e(P
OM
)
222
d1
4(1
.06)
z10
r 52(0
.63)
z5.
2
450
&21
0028
8
230
DT
(20
ps)
Z2
GW
/cm
2.
def
fz7.
9(I
)&
4.0
(II)
pm
/v.
nxZ
1.66
3,n
yZ1.
829,
nzZ
1.62
5.
rZ
6.38
(I)
1.48
(I).
NO
2H
2N
HP
O4H
2–
N+
2-A
min
o-5
-nit
rop
yrid
iniu
m-d
ihyd
roge
n
ph
osp
hat
e(2
A5N
PD
P)
mm
2d
33(1
.06)
z12
d1
5(1
.06)
z7
d2
4(1
.06)
z1
420
&20
0013
5n
xZ
1.75
2,n
yZ1.
715,
nzZ
1.66
5.
lN
C(q
)Z10
84&
1129
nm
.
lN
C(l
)Z13
40n
m.
No
tp
has
e-m
atch
able
for
typ
e-II
SHG
at1.
064
mm
.
Typ
e-I
def
fz2
pm
/V..
dq
pm
/dT
Z2.
40 /8
Cat
1.3
mm
.
HN
N
NO
2
(K)2
-(a
-Met
hyl
ben
zyla
min
o)-
5-n
itro
pyr
idin
e
(MB
AN
P)
2d
22(1
.06)
z60
58
d2
2(1
.06)
z35
57
430
&15
0012 11 13
4
DT
(425
ns)
Z1
GW
/cm
2.
nyZ
1.81
3,n
cZ1.
676.
def
fz1.
2!L
iIO
3z
6p
m/V
.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:23—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-81
Article in Press
4081
4082
4083
4084
4085
4086
4087
4088
4089
4090
4091
4092
4093
4094
4095
4096
4097
4098
4099
4100
4101
4102
4103
4104
4105
4106
4107
4108
4109
4110
4111
4112
4113
4114
4115
4116
4117
4118
4119
4120
4121
4122
4123
4124
4125
4126
4127
4128
4129
4130
4131
TA
BL
E7.
2(C
on
tin
ued
)
Ab
stra
ct
Stru
ctu
rean
dN
om
encl
atu
re(a
cro
nym
)P
oin
t
Gro
up
SHG
dij(l
)&
EO
r ij(
l)
(pm
/v)
(mm
)
Cu
t-O
ffl
(nm
)R
ef.
Pro
per
ties
N
HN
NO
2
2-N
-cyc
loo
ctyl
amin
o-5
-nit
rop
yrid
ine
(CO
AN
P)
mm
2d
33(1
.06)
z14
d3
2(1
.06)
z32
d3
1(1
.06)
z15
r 33(0
.63)
z15
r 13(0
.63)
z3.
4
r 23(0
.63)
z13
470
77 26 27
lN
C(q
)Z10
23n
mu
sin
gd
32.
lN
C(q
)Z14
13n
mu
sin
gd
31.
nxZ
1.68
,n
yZ1.
78,
nzZ
1.64
.
def
fz24
pm
/V
r 33(0
.52)
z28
,r 3
3(1
.06)
z7.
7.
r 13(0
.52)
z6.
8,r 1
3(1
.06)
z0.
9.
r 23(0
.52)
z26
,r 2
3(1
.06)
z6.
3.
N
HN
NO
2
2-A
dam
anty
lam
ino
-5-n
itro
pyr
idin
e(A
AN
P)
mm
2d
33(1
.06)
z60
d3
1(1
.06)
z80
460
257
At
533
nm
:
nxZ
1.77
,n
yZ1.
61,
nzZ
1.86
.
At
1.06
mm
:
nxZ
1.67
,n
yZ1.
59,
nzZ
1.71
.
N
NH
OH
NO
2
N-(
4-n
itro
-2-p
yrid
inyl
)-(s
)-p
hen
ylal
anin
ol
(NP
PA)
2d
22(1
.06)
z2.
6
d2
1(1
.06)
z0.
4
d2
3(1
.06)
z31
d1
6(1
.06)
z0.
5
d3
4(1
.06)
z25
480
261
247
lN
C(q
)fo
rSH
Gan
dSF
Gw
ith
inab
sorp
tio
ned
ge,
calc
ula
ted
def
fz31
pm
/V.
nxZ
1.52
4,n
yZ1.
694,
nzZ
1.90
7.
N
NO
H
NO
2
2-(N
-pro
lin
ol)
-5-n
itro
pyr
idin
e(P
NP
)
2d
22(1
.06)
z17
d2
1(1
.06)
z48
r 22(0
.63)
z13
490
&20
8024
6
27
lN
C(q
)Z10
20n
mu
sin
gd
21.
def
fz47
pm
/V.
nxZ
1.99
0,n
yZ1.
788,
nzZ
1.46
7.
rZ
78
r 22(0
.52)
z28
,r 1
2(0
.52)
z20
.
r 22(1
.06)
z8,
r 12(1
.06)
z9.
15018—Chapter7—26/8/2006—22:23—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-82 Handbook of Photonics
Article in Press
4132
4133
4134
4135
4136
4137
4138
4139
4140
4141
4142
4143
4144
4145
4146
4147
4148
4149
4150
4151
4152
4153
4154
4155
4156
4157
4158
4159
4160
4161
4162
4163
4164
4165
4166
4167
4168
4169
4170
4171
4172
4173
4174
4175
4176
4177
4178
4179
4180
4181
4182
O
CN
CN
2-D
icya
no
vin
ylan
iso
le(D
IVA
)
2d
22(1
.06)
z10
78d
eff(
1.06
)z20
pm
/V.
nZ
1.65
.
NN
CN
CN
3-(1
,1-D
icya
no
eth
enyl
)-1-
ph
enyl
-4,5
-dih
ydro
-1H
-
pyr
azo
le(D
CN
P)
mr 3
3(0
.63)
z87
700
&16
003
Hig
hm
elti
ng
po
int:
1908
C,
nea
ro
pti
mu
m
mo
lecu
lar
alig
nm
ent
for
EO
,n
xZ
1.9,
nzZ
2.7.
OC
H3
u-(
p-M
eth
oxy
ph
enyl
)b
enzo
fulv
ene
(MP
BF
)
mm
2d
eff(
1.06
)z7
O45
013
3d
effz
7p
m/V
.
Dq
lZ0.
32m
rad
-cm
.
DT
1z4.
68C
-cm
.
CN
OC
H3C
OO
CH
3
2-C
yan
o-3
-(2-
met
ho
xyp
hen
yl)-
2-p
rop
eno
icac
id
met
hyl
este
r(C
MP
-met
hyl
)
2d
22(1
.06)
z29
410
183
nyZ
1.85
N
NO O
O
p-M
eth
ylb
enza
l-1,
3-d
imet
hyl
bar
bit
uri
cac
id
2d
eff(
1.06
)z8
460
132
Vic
kers
har
dn
ess:
25.5
.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:24—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-83
Article in Press
4183
4184
4185
4186
4187
4188
4189
4190
4191
4192
4193
4194
4195
4196
4197
4198
4199
4200
4201
4202
4203
4204
4205
4206
4207
4208
4209
4210
4211
4212
4213
4214
4215
4216
4217
4218
4219
4220
4221
4222
4223
4224
4225
4226
4227
4228
4229
4230
4231
4232
4233
TA
BL
E7.
2(C
on
tin
ued
)
Ab
stra
ct
Stru
ctu
rean
dN
om
encl
atu
re(a
cro
nym
)P
oin
t
Gro
up
SHG
dij(l
)&
EO
r ij(
l)
(pm
/v)
(mm
)
Cu
t-O
ffl
(nm
)R
ef.
Pro
per
ties
Br
O
OC
H3
4-B
r-40 -m
eth
oxy
chal
con
e
md
33(1
.06)
z6
d1
3(1
.06)
z27
420
285
nxZ
1.55
,n
yZ1.
47,
nzZ
1.90
.
EtO
O
OC
H3
4-E
thox
y-40 -m
eth
oxy
chal
con
e
mm
2d
eff(
1.06
)z5.
743
012
9L
ow
har
dn
ess,
DT
(1n
s)O
30G
W/c
m2.
At
532
nm
:
nxZ
1.49
3,n
yZ1.
710,
nzZ
1.98
3.
At
1.06
mm
:
nxZ
1.47
7,n
yZ1.
663,
nzZ
1.85
0.
def
fz3.
5(I)
&5.
7(I
I)p
m/v
.
O
S
4-M
eth
yl-2
-th
ien
ylch
alco
ne
2d
eff(
1.06
)z7
430
128
Lo
wh
ard
nes
s,n
xZ
1.64
8,n
yZ1.
696,
nzZ
1.77
5.
def
fz7
pm
/V.
Dq
lZ0.
9m
rad
-cm
.
rZ
3.68
DT
1Z2.
28C
-cm
CH
3ON
O2
3-M
eth
yl-4
-met
hox
y-40 -n
itro
stil
ben
e(M
MO
NS)
mm
2d
33(1
.06)
z18
4
d3
2(1
.06)
z41
d2
4(1
.06)
z71
r 33(0
.63)
z40
515
&20
0022 22
0
lN
C(q
)Z10
28n
mu
sin
gd
24.
def
fz43
pm
/V.7
1
nxZ
1.56
9,n
yZ1.
693,
nzZ
2.12
9.
rZ
9.68
DT
1Z0.
178C
-cm
15018—Chapter7—26/8/2006—22:24—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-84 Handbook of Photonics
Article in Press
4234
4235
4236
4237
4238
4239
4240
4241
4242
4243
4244
4245
4246
4247
4248
4249
4250
4251
4252
4253
4254
4255
4256
4257
4258
4259
4260
4261
4262
4263
4264
4265
4266
4267
4268
4269
4270
4271
4272
4273
4274
4275
4276
4277
4278
4279
4280
4281
4282
4283
4284
NO
2
N
4-N
itro
-40 -m
eth
ylb
enzy
lid
ien
ean
ilin
e(N
MB
A)
md
11(1
.06)
z13
9
d3
3(1
.06)
z0.
6
d3
1(1
.06)
z41
r 11(0
.63)
z25
480
&16
008,
9N
ear
op
tim
um
mo
lecu
lar
alig
nm
ent
for
EO
,lN
C(q
)
for
SHG
wit
hin
abso
rpti
on
edge
,l
NC
(l)Z
1500
nm
.
nxZ
1.95
1,n
yZ1.
657,
nzZ
1.51
0.
dD
n/d
TZ
15.8
!10
K5
KK
1.
def
fz2
pm
/V.
O
NH
CO
CH
3
NO
2
N
40 -N
itro
ben
zyli
den
e-3-
acet
amin
o-4
-
met
hox
ylan
ilin
e(M
NB
A)
md
11(1
.06)
z17
5
d3
1(1
.06)
z2
d3
3(1
.06)
z2
r 11(0
.63)
z29
r 13(0
.63)
z0.
5
r 33(0
.63)
z2.
4
505
131
Nea
ro
pti
mu
mm
ole
cula
ral
ign
men
tfo
rE
O,
nxZ
2.02
4,n
yZ1.
648,
nzZ
1.58
3.
CH
N+
– SO
3
Cya
no
stil
baz
oli
um
p-to
luen
esu
lfo
nat
eco
mp
lex
mm
2d
33(1
.06)
z21
415
258
Mel
tin
gp
oin
t:27
98C
,n
zZ1.
775.
N+ CH
3SO
4–N 40 -D
imet
hya
min
o-N
-met
hyl
-4-s
tilb
azo
liu
mm
eth
yl
sulf
ate
(SP
CD
)
mm
2r 3
3(0
.63)
z43
060
028
2O
nly
thin
-film
cyst
alre
po
rted
,n
yZ1.
31,
nzZ
1.55
.
N+
N– S
O3
40 -D
imet
hya
min
o-N
-met
hyl
-4-s
tilb
azo
liu
m
tosu
late
(DA
ST)
md
11(1
.91)
z60
0
d2
2(1
.91)
z10
0
d1
2(1
.91)
z30
r 33(0
.82)
z40
0
700
&20
0015
7
198
Nea
ro
pti
mu
mm
ole
cula
ral
ign
men
tfo
rE
O.
At
820
nm
:
nxZ
2.21
6,n
yZ1.
66,
nzZ
1.65
.
Die
lect
ric
con
stan
t:3 a
bZ
5.1,
3 cZ
3.1.
15018—Chapter7—26/8/2006—22:24—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-85
Article in Press
4285
4286
4287
4288
4289
4290
4291
4292
4293
4294
4295
4296
4297
4298
4299
4300
4301
4302
4303
4304
4305
4306
4307
4308
4309
4310
4311
4312
4313
4314
4315
4316
4317
4318
4319
4320
4321
4322
4323
4324
4325
4326
4327
4328
4329
4330
4331
4332
4333
4334
4335
TA
BL
E6.
3E
xper
imen
tal
Res
ult
so
fP
ole
dP
oly
mer
Stu
die
s:M
w,
mo
lecu
lar
wei
ght;
r#,
chro
mo
ph
ore
nu
mb
erd
ensi
ty;
a(w
avel
engt
h),
op
tica
lp
rop
agat
ion
loss
;t
1an
dt
2,
rela
xati
on
tim
ein
def
f(t)
/def
f(0)
ZA
eKt/
t1C
BeK
t/t
2
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
Gu
est-
hos
tpo
lym
erco
mpo
site
s
NN
NN
O2
CH
3O
CH
3
On
HO
(4[N
-eh
tyl-
N-(
2-h
ydro
xyet
hyl
)]am
ino
-40 -n
itro
azo
ben
zen
e)(D
R1)
do
ped
inp
oly
-(m
eth
ylm
eth
acry
late
)(P
MM
A)
(Sin
ger
etal
.19
86)
Tgz
1008
C.
lm
axz
470
nm
.
r#Z
2.4!
102
0cm
K3
low
die
lect
ric
con
stan
t:3Z
3.6.
con
tact
po
led
wit
h62
V/m
mat
1008
C.
d3
3(1
.58
mm
)Z2.
5p
m/V
.
No
velt
y:fi
rst
stu
dy
of
amo
rph
ou
sgu
est–
ho
stsy
stem
.
NOO
CN
FF
7n3n
F
FF
OO
NN
4-(4
0 -Cya
no
ph
enyl
azo
)-N
,N-b
is-(
met
ho
xyca
rbo
nyl
met
hyl
)-an
ilin
ed
op
edin
cop
oly
mer
of
vin
ylid
ene
flu
ori
de
and
trifl
uo
roet
hyl
ene
(Fo
rafl
onw
,70
:30
mo
l%)
(Pan
teli
set
al.
1988
;H
ill
etal
.19
87)
Tgz
1008
C.
lm
axZ
400
nm
.
UP
to10
wt%
do
pin
g.
a(1
mm
)zK
1.5
dB
/cm
.
Co
ron
ap
ole
dat
258C
.
d3
3(1
.06
mm
)u
pto
2.6
pm
/V.
Stab
len
on
lin
eari
tyaf
ter
300
day
sat
amb
ien
tco
nd
itio
n.
No
velt
y:fe
rro
elec
tric
ho
stp
oly
mer
pro
vid
esa
stab
lein
tern
alfi
eld
of
150
V/m
m.
NN
O2
OH
OH
RR
'N
N
4-N
,N-d
imet
hyl
amin
o-4
0 -nit
rost
ilb
ene
do
ped
inth
erm
ose
ttin
gep
oxy
(EP
O-T
EKw
301-
2)(H
ub
bar
det
al.
1989
)
Pre
cure
at808C
pri
or
top
oli
ng.
lm
axz
430
nm
.
r#Z
0.2!
102
0cm
K3
Co
nta
ctp
ole
dat
60V
/mm
.
Tem
po
ral
stab
ilit
y:t
1(2
58C
)Z7
day
san
dt
2(2
58C
)Z72
day
s.
No
velt
y:u
seo
fcr
oss
lin
ked
po
lym
eras
ho
st.
HO
N
n
O
NO
2
p-N
itro
ph
eno
ld
op
edin
typ
eA
gela
tin
(Ho
etal
.19
92)
Tgz
60–7
08C
.
lm
ax!
350
nm
.
UP
to35
wt%
do
pin
g.
Spin
coat
ing
fro
maq
ueo
us
solu
tio
n.
Co
nta
ctp
ole
dat
40V
/mm
.
r 33
(633
nm
)Z10
–40
pm
/V.
40%
acti
vity
rem
ain
saf
ter
5d
ays.
No
velt
y:u
seo
fcr
oss
-lin
ked
bio
po
lym
eras
ho
st.
15018—Chapter7—26/8/2006—22:25—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-86 Handbook of Photonics
Article in Press
4336
4337
4338
4339
4340
4341
4342
4343
4344
4345
4346
4347
4348
4349
4350
4351
4352
4353
4354
4355
4356
4357
4358
4359
4360
4361
4362
4363
4364
4365
4366
4367
4368
4369
4370
4371
4372
4373
4374
4375
4376
4377
4378
4379
4380
4381
4382
4383
4384
4385
4386
N
NOF
3CC
F3
O
O O
O
NC O
2n
CN
N
(Dic
yan
om
eth
ylen
e)-2
-met
hyl
-6-(
p-d
imet
hyl
amin
ost
yryl
-4H
-pyr
an(D
CM
)d
op
edin
po
lym
ide
(Am
oco
Ult
rad
elw
)(E
rmer
etal
.19
92)
TgZ
2208
C.
lm
axZ
474
nm
.
Do
pin
gle
vel:
20w
t%
n(8
30n
m)Z
1.65
1
a(8
30n
m)z
K1.
5d
B/c
m.
Mu
ltil
ayer
sco
nta
ctp
ole
dw
ith
312
V=~m
1908
C.
r 33
(830
nm
)Z3.
4p
m/V
.
Lo
wp
oli
ng
fiel
dat
NLO
laye
rd
ue
toh
igh
con
du
ctiv
ity.
No
velt
y:u
seo
fh
igh
Tg
ho
stp
oly
mer
.
N NN
O2
H3C
O
H3C
OH
3CC
H3
NO
nO
NO O
O
O
2,4,
5-T
riar
ylim
idaz
ole
der
ivat
ive
(lo
ph
ine)
do
ped
inp
oly
imid
e(U
ltem
w)
(Sta
hel
inet
al.
1992
a)
TgZ
210–
1508
Cfo
r0–
35w
t%.
lm
axZ
410
nm
.
Ch
rom
op
ho
re:m
gZ7!
10K
18,
b0Z
18!
10K
30
(esu
).
Hig
hlo
adin
g,u
pto
35w
t%.
Fo
r0–
35w
t%d
op
ing,
coro
na
po
lin
ggi
ves
d3
3(1
.047
mm
)Z6–
17p
m/V
.
Fo
r20
wt%
do
pin
g,co
ron
ap
oli
ng
give
sT
gZ
1808
C,
d3
3Z
10.5
pm
/V.,
t(8
08C
)Z1.
5ye
ar.
No
velt
y:u
seo
fth
erm
ally
stab
lech
rom
op
ho
re.
NN
O2
HO
NN
DR
1d
op
edin
ph
enyl
silo
xan
ep
oly
mer
(All
ied
Sign
alA
ccu
glas
s20
4w)
(Jen
get
al.
1992
a)
lm
axZ
493
nm
.
n(5
33n
m)Z
1.62
8.
Do
pin
gle
vel:
35m
gd
yein
2g
of
A20
4.
Co
ron
ap
ole
dat
2008
Cfo
r10
min
.
d3
3(1
.06
mm
)Z11
.43
pm
/V.
d3
3(4
0h
,10
08C
)Z3.
8p
m/V
.
No
velt
y:U
seo
fso
l-ge
las
ho
stp
oly
mer
.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:25—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-87
Article in Press
4387
4388
4389
4390
4391
4392
4393
4394
4395
4396
4397
4398
4399
4400
4401
4402
4403
4404
4405
4406
4407
4408
4409
4410
4411
4412
4413
4414
4415
4416
4417
4418
4419
4420
4421
4422
4423
4424
4425
4426
4427
4428
4429
4430
4431
4432
4433
4434
4435
4436
4437
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
Sid
e-C
hain
acry
late
poly
mer
s
N
O
O O
O1-
x
x
NN
NO
2
Met
hyl
met
hac
ryla
te(M
MA
)/D
R1
fun
ctio
nal
ized
met
hac
ryla
teco
po
lym
er(E
ssel
inet
al.
1988
)
TgZ
128–
1348
Cfo
r1–
19m
ol%
.
lm
axZ
470
nm
.
r#:
up
to7.
5!
102
0cm
K3.
Co
nta
ctp
ole
dw
ith
90V
/mm
at13
08C
.
d3
3(1
.064
mm
)Z3–
58p
m/V
.fo
r1–
19m
ol%
No
velt
y:h
igh
r#.
N
O
O O
O1-
x
x
CN
CN
NN
MM
A/4
-dic
yan
ovi
nyl
-40 -(
N,N
-dia
lkyl
amin
o)a
zob
enze
ne
fun
ctio
nal
ized
met
hac
ryla
teco
po
lym
er(S
inge
ret
al.
1988
)
TgZ
1278
C.
r#Z
8!10
20
cmK
3
n(8
00n
m)Z
1.58
.
Co
ron
ap
ole
dab
ove
Tg.
d3
3(1
.58
mm
)Z21
pm
/V.
r 33
(799
nm
)Z15
pm
/V.
90%
of
acti
vity
rem
ain
sst
able
afte
r35
day
sat
amb
ien
tco
nd
itio
ns.
NN
O2
O
On
NN
Po
ly-4
-(40 -n
itro
ph
enyl
azo
)-N
-met
hyl
-N-(
2-ac
royl
oxy
eth
yl)a
nil
ine
(Hil
let
al.
1989
,19
88)
TgZ
1058
C.
lm
axz
470
nm
.
Mw
Z4.
9!10
3.
Co
nta
ctp
oli
ng
at19
0V
/mm
give
sd
33
(1.0
6m
m)Z
55p
m/V
.
Co
nta
ctp
oli
ng
at20
V/m
mgi
ves
r 33
(633
nm
)Z30
pm
/V.
Act
ivit
yre
mai
ns
stab
lefo
ro
ver
2ye
ars
atam
bie
nt
con
dit
ion
s.
15018—Chapter7—26/8/2006—22:25—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-88 Handbook of Photonics
Article in Press
4438
4439
4440
4441
4442
4443
4444
4445
4446
4447
4448
4449
4450
4451
4452
4453
4454
4455
4456
4457
4458
4459
4460
4461
4462
4463
4464
4465
4466
4467
4468
4469
4470
4471
4472
4473
4474
4475
4476
4477
4478
4479
4480
4481
4482
4483
4484
4485
4486
4487
4488
NO
2
O
O O
O1-
x
x
NN
N
MM
A/4
-(N
-eth
yl-N
-2-m
eth
acro
ylo
xyet
ho
xy)-
2-m
eth
yl-4
0 -nit
roaz
ob
enze
ne
cop
oly
mer
(Ore
etal
.19
89)
lm
axZ
486
nm
.
Mw
Z10
!10
3.
r#Z
9.2!
102
0cm
K3
Co
ron
ap
ole
dd
33
(1.0
6m
m)Z
41p
m/V
.
Stab
len
on
lin
eari
tyaf
ter
75d
ays
atam
bie
nt
con
dit
ion
s.
NO
2N
O
On
Po
ly-N
-(2-
met
hac
royl
oxy
eth
yl)-
N-m
eth
yl-4
0 -nit
roan
ilin
e(H
ayas
hi
etal
.19
92)
TgZ
1008
C.
lm
axZ
390
nm
.
Mw
Z11
–17!
103.
n(6
33n
m)Z
1.66
.
Co
ron
ap
ole
dd
33
(1.5
8m
m)Z
30p
m/V
.
Act
ivit
yd
ecay
sto
65%
in40
day
sat
amb
ien
tco
nd
itio
ns.
O
O O O1-
x
x
NO
2
NN
NN
N
MM
A/4
-N-(
2-m
eth
acro
ylo
xyet
hyl
)-N
-eth
yl-4
0 -am
ino
ph
enyl
azo
-400-n
itro
azo
ben
zen
eco
po
lym
er(A
man
oet
al.
1990
)
Tg
z10
08C
.
lm
axZ
500
nm
.
r#Z
4.3!
102
0cm
K3
Co
ron
ap
ole
dat
1008
C.
d3
3(1
.06
mm
)Z14
2p
m/V
.
d3
3(1
.7m
m)Z
70p
m/V
.
O
O O
O1-
x
x
CN
CN
NN
NN
N
MM
A/2
,5-d
imet
hyl
-4-N
-(2-
met
hac
royl
oxy
eth
yl)-
N-e
thyl
-40 -a
min
op
hen
ylaz
o-4
00-d
icya
no
azo
ben
zen
eco
po
lym
er
(Sh
uto
etal
.19
91)
Tgz
1408
C.
lm
axZ
510
nm
.
r#Z
4!10
20
cmK
3
a(6
33n
m)Z
K50
dB
/cm
du
eto
abso
rpti
on
.
Co
ron
ap
oli
ng
wit
h20
0V
/mm
at14
08C
give
sd
33
(1.0
6m
m)Z
417
pm
/V.
Co
nta
ctp
oli
ng
at15
0V
/mm
at14
08C
give
sr 3
3(6
33n
m)Z
40p
m/V
.
Exc
elle
nt
tem
po
ral
stab
ilit
yat
808C
.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:26—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-89
Article in Press
4489
4490
4491
4492
4493
4494
4495
4496
4497
4498
4499
4500
4501
4502
4503
4504
4505
4506
4507
4508
4509
4510
4511
4512
4513
4514
4515
4516
4517
4518
4519
4520
4521
4522
4523
4524
4525
4526
4527
4528
4529
4530
4531
4532
4533
4534
4535
4536
4537
4538
4539
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
O
O O O1-
x
x
CN
NN
N
MM
A/4
-(N
-met
hyl
-N-2
-met
hac
royl
oxy
eth
oxy
)-40 -c
yan
oab
enze
ne
ho
mo
-an
dco
po
lym
ers
(S’h
eere
net
al.
1993
a)
Co
ron
ap
ole
dn
ear
Tg.
d3
3va
lues
are
mea
sure
d10
day
saf
ter
po
lin
gat
1.06
4m
m.
O
O O O1-
x
x
NO
2
X
1 2X
= H C
N
N
MM
A/4
-(N
-met
hyl
-N-2
-met
hac
royl
oxy
eth
oxy
)-40 -n
itro
stil
ben
eco
-po
lym
ers
(S’h
eere
net
al.
1993
c)
Co
ron
ap
ole
dn
ear
Tg.
d3
3va
lues
are
mea
sure
dse
vera
ld
ays
afte
rp
oli
ng
at1.
064
mm
.
O
O
O1-
x
x
N
NO
O
O
O
MM
A/N
-(3-
met
hac
rylo
xyal
ky)-
7-d
ieth
ylam
ino
cou
mar
in-3
-car
bo
xam
ide
(76:
23m
ol%
)co
po
lym
er(M
ort
azav
i
etal
.19
91)
TgZ
1358
C.
lm
axZ
410
nm
.
r#Z
9.8!
102
0cm
K3
Mw
Z89
!10
3.
Co
ron
ap
ole
dfo
rSH
Gan
dco
nta
ctp
ole
dw
ith
100
V/m
mfo
rE
Oat
608C
.
d3
3(1
.06
mm
)Z13
pm
/V.
r 33
(477
–11
00n
m)Z
2–12
pm
/V.
d3
3d
ecay
sb
y25
%at
1008
Cin
50h
.
15018—Chapter7—26/8/2006—22:26—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-90 Handbook of Photonics
Article in Press
4540
4541
4542
4543
4544
4545
4546
4547
4548
4549
4550
4551
4552
4553
4554
4555
4556
4557
4558
4559
4560
4561
4562
4563
4564
4565
4566
4567
4568
4569
4570
4571
4572
4573
4574
4575
4576
4577
4578
4579
4580
4581
4582
4583
4584
4585
4586
4587
4588
4589
4590
O
O
O1-
x
x
N
NO
O
O
O
Iso
bo
rnyl
met
hac
ryla
te/N
-(3-
met
hac
rylo
xyal
kyl)
-7-d
ieth
lam
ino
cou
mar
in-3
-car
bo
xam
ide
(76:
23m
ol%
)
cop
oly
mer
(Mo
rtaz
avi
etal
.19
91)
TgZ
1708
C.
lm
axZ
410
nm
.
Mw
Z50
!10
3.
Co
ron
ap
ole
dat
2008
C.
d3
3(1
.06
mm
)Z11
pm
/V.
d3
3d
ecay
sb
y10
%at
1008
Can
db
y40
%at
1408
Cin
50h
.
O
R NS
NR
R =
A BO
NO
n
O
Po
ly(p
-N-(
2-m
eth
acro
ylo
xeth
yl)-
N-e
thyl
amin
ob
enza
ll-1
-3-d
ieth
yl(o
rd
iph
enyl
thio
bar
bit
uri
cac
id)
(Ch
eng
and
Tan
1993
)
Co
ron
ap
ole
dn
ear
Tg.
d3
3an
dr 3
3va
lues
are
mea
sure
dat
1.06
4m
m.
At
1008
Cd
33
of
A(B
)d
ecay
sb
y80
%(1
0%)
in15
0m
in(1
5d
ays)
O
ON
O2
On
Po
ly-4
-(6-
acro
ylo
xyh
exyl
oxy
)-40 -n
itro
stil
ben
e(H
uij
tset
al.
1989
b)
TgZ
658C
.
lm
axZ
380
nm
.
r#:1
8!10
20
cmK
3
n(6
33n
m)Z
1.62
.
a(1
.3m
m)z
K1.
5d
B/c
m.
Co
nta
ctp
ole
dw
ith
23V
/mm
at658C
.
r 33
(633
nm
)Z0.
9p
m/V
.
O
NC
H3
SNN
O
On
O
Po
ly-4
0 -N-(
6-m
eth
acro
ylo
xyh
exyl
)-N
-met
hyl
-am
ino
-4-m
eth
ylsu
lfo
nyl
azo
ben
zen
e(R
ob
ello
etal
.19
91a,
1992
)
TgZ
998C
.
lm
axZ
446
nm
.
r#Z
17!
102
0cm
K3
Mw
Z89
!10
3.
n(6
33n
m)Z
1.76
.
a(8
30n
m)Z
K1
dB
/cm
.
Co
nta
ctp
ole
dw
ith
90V
/mm
at10
08C
.
r 33
(633
nm
)Z39
pm
/V.;
r 33
(860
nm
)Z13
pm
/V.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:26—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-91
Article in Press
4591
4592
4593
4594
4595
4596
4597
4598
4599
4600
4601
4602
4603
4604
4605
4606
4607
4608
4609
4610
4611
4612
4613
4614
4615
4616
4617
4618
4619
4620
4621
4622
4623
4624
4625
4626
4627
4628
4629
4630
4631
4632
4633
4634
4635
4636
4637
4638
4639
4640
4641
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
OC
H3
SO O
O
O O O1-
x
x MM
A/4
0 -(6-
met
hac
royl
oxy
hex
loxy
)-4-
met
hyl
sulf
on
ylst
ilb
ene
(55:
45w
t%)
cop
oly
mer
(Rik
ken
etal
.19
91;
Sep
pen
etal
.19
91)
TgZ
1178
C.
lm
axZ
355
nm
.
Lo
wab
sorp
tio
nat
420
nm
.
Co
ron
ap
ole
dw
ith
120
V/m
mat
1008
C.
d3
3(8
20n
m)Z
9p
m/V
.
Act
ivit
yd
ecre
ases
toa
qu
asi-
stab
le70
%va
lue
afte
r12
0d
ays
at
amb
ien
t.
Wav
egu
ide
form
atio
nb
yU
Vp
ho
tob
leac
hin
g.
N
O
OSO O
O O1-
x
x MM
A/4
0 -(6-
met
hac
royl
oxy
hex
ylsu
lfo
ny)
-4-N
,Nd
imet
hyl
amin
o-b
iph
enyl
(50:
50w
t%)
cop
oly
mer
(Rik
ken
etal
.
1992
)
Tgz
1008
C.
lm
axZ
340
nm
.
Co
ron
ap
ole
dw
ith
120
V/m
at10
08C
.
d3
3(8
20n
m)Z
45p
m/V
.
po
or
tem
po
ral
stab
ilit
yat
608C
.
N
O
O O O1-
x
x
NO
2N
N
MM
A/4
-(40 -n
itro
ph
enyl
azo
)-N
-met
hyl
-N-(
6-m
eth
acro
ylo
xyh
exyl
)an
ilin
e(8
1:19
mo
l%)
cop
oly
mer
(Mu
ller
etal
.
1992
a)
TgZ
1048
C.
lm
axz
470
nm
.
Mw
Z10
0!10
3.
Th
erm
ally
dec
om
po
ses
at26
78C
.
Po
led
wit
h11
0V
/mm
.
r 33–
r 13
(1.3
mm
)Z9
pm
/V.
15018—Chapter7—26/8/2006—22:26—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-92 Handbook of Photonics
Article in Press
4642
4643
4644
4645
4646
4647
4648
4649
4650
4651
4652
4653
4654
4655
4656
4657
4658
4659
4660
4661
4662
4663
4664
4665
4666
4667
4668
4669
4670
4671
4672
4673
4674
4675
4676
4677
4678
4679
4680
4681
4682
4683
4684
4685
4686
4687
4688
4689
4690
4691
4692
N
O
O O O O1-
xx
NO
2N
N
Met
hac
ryli
can
hyd
rid
e/4-
(40 -n
itro
ph
enyl
azo
)-N
-met
hyl
-N-(
6-m
eth
acro
ylo
xyl)
anil
ine
(33:
67m
ol%
)co
po
lym
er
(Str
oh
rieg
l19
93;
Mu
ller
etal
.19
92a)
TgZ
908C
.
lm
axz
470
nm
.
Th
erm
ally
dec
om
po
ses
at22
78C
.
Po
led
wit
h11
0V
/mm
.
r 33–
r 13
(1.5
mm
)Z19
pm
/V.
N+
O–
O
O O O1-
x
x MM
A/[
2,6-
di-
tert
-bu
tyl-
4-(1
-u-m
eth
acro
ylo
xyal
yl)-
4-p
yrid
ino
]ph
eno
late
s(8
5:15
mo
l%)
cop
oly
mer
(Co
mb
ella
s
etal
.19
92)
TgZ
1308
C.
lm
axz
525
nm
.
Co
nta
ins
zwit
teri
on
icch
rom
op
ho
rew
ith
b0Z
K30
!10
K3
0es
u.
Solu
ble
inT
HF.
N
O
OSO O
O O3nn
NN
MM
A/4
0 -(6-
met
hac
royl
oxy
hex
lsu
lfo
nyl
)-4-
N,N
-dim
eth
ylam
ino
-azo
ben
zen
e(2
5m
ol%
)co
po
lym
er(X
uet
al.
1993
)
TgZ
1248
C.
lm
axZ
437
nm
.
Mw
Z17
!10
3.
Co
ron
ap
ole
dat
1258
Cfo
r45
min
.
d3
3(1
.06
mm
)Z10
0p
m/V
.
Act
ivit
yst
abil
izes
at95
%va
lue
afte
r10
day
sat
amb
ien
tco
nd
itio
ns.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:27—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-93
Article in Press
4693
4694
4695
4696
4697
4698
4699
4700
4701
4702
4703
4704
4705
4706
4707
4708
4709
4710
4711
4712
4713
4714
4715
4716
4717
4718
4719
4720
4721
4722
4723
4724
4725
4726
4727
4728
4729
4730
4731
4732
4733
4734
4735
4736
4737
4738
4739
4740
4741
4742
4743
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
OO N
Ozy
x
O
OO R
N
OO
NS
O2C
3F7
R =
A
B C
N NN
NN
O2
NO
2
Fu
nct
ion
aliz
edh
om
o-a
nd
cop
oly
mer
so
fis
ocy
anat
oet
hyl
met
hac
ryla
te,
MM
A,
and
dim
eth
ylam
ino
eth
yl
met
hac
ryla
te.
(Ch
eng
etal
.19
92)
Co
ron
ap
ole
dn
ear
Tg.
d3
3va
lues
are
mea
sure
dat
1.06
4m
m.
d3
3o
fA
&C
are
stab
leat
roo
mte
mp
erat
ure
.P
oly
mer
Bis
stab
leat
808C
.
a(1
.06
mm
)zK
(1.5
–3)
dB
/cm
.
Sid
e-ch
ain
Non
-acr
ylat
epo
lym
ers
N
n
NO
2
Po
ly-4
-[N
-(40 -n
itro
ph
enyl
)am
ino
-met
hyl
]eth
ylen
e(E
ich
etal
.19
89b
)
TgZ
1258
C.
lm
axz
390
nm
.
Th
erm
ally
dec
om
po
ses
at26
08C
.
Co
ron
ap
ole
dat
1408
C.
d3
3(1
.06
mm
)Z31
pm
/V.
d3
3re
laxe
sto
19p
m/V
in5
day
s.
n
NN
O2
Po
ly-4
-[N
-met
hyl
-N-(
40 -n
itro
ph
enyl
)am
ino
-met
hyl
]sty
ren
e(H
ayas
hi
1991
)
TgZ
1038
C.
lm
axZ
393
nm
.
Mw
Z12
!10
3.
n(6
33n
m)Z
1.73
.
a(6
33n
m)Z
K10
dB
/cm
.
Co
ron
ap
ole
dat
1108
C.
d3
3(1
.06
mm
)Z28
pm
/Vw
hic
hst
abil
izes
to18
pm
/Vin
5m
on
ths
at
amb
ien
tco
nd
itio
ns.
n
NN
O2
Po
ly-4
-[N
-(40 -n
itro
ph
enyl
)am
ino
-met
hyl
]sty
ren
e(H
ayas
hi
etal
.19
92)
TgZ
1238
C.
lm
axZ
383
nm
.
Mw
Z15
!10
3.
n(6
33n
m)Z
1.70
.
Co
ron
ap
ole
dat
Tg.
d3
3(1
.06
mm
)Z10
pm
/V.
Lo
wd
33
du
eto
po
lin
g-in
du
ced
dec
om
po
siti
on
.
15018—Chapter7—26/8/2006—22:27—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-94 Handbook of Photonics
Article in Press
4744
4745
4746
4747
4748
4749
4750
4751
4752
4753
4754
4755
4756
4757
4758
4759
4760
4761
4762
4763
4764
4765
4766
4767
4768
4769
4770
4771
4772
4773
4774
4775
4776
4777
4778
4779
4780
4781
4782
4783
4784
4785
4786
4787
4788
4789
4790
4791
4792
4793
4794
n
NC
N
Po
ly-4
-[N
-(40 -c
yan
op
hen
yl)a
min
o-m
eth
yl]s
tyre
ne
(Hay
ash
i,et
al.
1992
)
TgZ
1328
C.
lm
axZ
288
nm
.
Mw
Z15
!10
3.
n(6
33n
m)Z
1.65
.
Co
ron
ap
ole
dat
Tg.
d3
3(1
.06
mm
)Z1
pm
/V.
NO
2
1-x
x
O
NN
N
Styr
ene/
p-[4
-nit
ro-4
0 -(N
-eth
yl-N
-2-o
xyet
hyl
)azo
ben
zen
e]m
eth
ylst
yren
eco
po
lym
er(8
8:12
mo
l%)
(Ye
etal
.19
87)
TgZ
1108
C.
lm
axz
470
nm
.
Co
nta
ctp
ole
dw
ith
30V
/mm
atz
1108
C.
d3
3(1
.06
mm
)Z1.
1p
m/V
.
Stab
leac
tivi
tyat
roo
mte
mp
erat
ure
.
NO
2
1-x
x
O
N
Styr
ene/
N-(
4-n
itro
ph
enyl
)-S-
pro
lin
oxy
met
hyl
styr
ene
cop
oly
mer
(64:
36m
ol%
)(Y
eet
al.
1989
)
TgZ
1108
C.
lm
axz
380
nm
.
Co
nta
ctp
ole
dw
ith
70V
/mm
atz
1108
C.
d3
3(1
.06
mm
)Z1.
6p
m/V
.
Lo
wd
33
du
eto
mat
eria
lim
pu
rity
.
NO
2
1-x
x
O
NO
H
p-h
ydro
xyst
yren
e/N
-(4-
nit
rop
hen
yl)-
S-p
roli
no
xyst
yren
eco
po
lym
er(1
0:90
mo
l%)
(Ye
etal
.19
89)
TgZ
968C
.
lm
axz
380
nm
.
r#Z
2.3!
102
1cm
K3
Co
ron
ap
ole
dat
Tg.
d3
3(1
.06
mm
)Z33
pm
/V.
Tg
incr
ease
to14
68C
at16
mo
l%fu
nct
ion
aliz
atio
n.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:27—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-95
Article in Press
4795
4796
4797
4798
4799
4800
4801
4802
4803
4804
4805
4806
4807
4808
4809
4810
4811
4812
4813
4814
4815
4816
4817
4818
4819
4820
4821
4822
4823
4824
4825
4826
4827
4828
4829
4830
4831
4832
4833
4834
4835
4836
4837
4838
4839
4840
4841
4842
4843
4844
4845
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
n
nO H
N
O
CN
CN
NN
p-h
ydro
xyst
yren
e/p-
[4-(
2,2-
dic
ryan
ovi
nyl
)-40 -(
N-e
thyl
-N-2
-oxy
eth
yl)a
zob
enze
ne]
styr
ene
cop
oly
mer
(Ye
etal
.
1992
)
Co
ron
ap
ole
dat
1178
Cfo
r15
h.
Th
erm
alan
del
ectr
och
emic
ald
eco
mp
osi
tio
no
bse
rved
at14
78C
.
NO
2
O
NO
Br 1
-y
n
Ry
Br 1
-xR
x
R =
Po
ly-(
2,6-
dim
eth
ylb
rom
o-1
,4-p
hen
ylen
eo
xid
e)p
arti
ally
fun
ctio
nal
ized
wit
hN
-(4-
nit
rop
hen
yl)-
S-p
roli
no
l(D
ai
etal
.19
90)
TgZ
1708
C.
r#Z
2.6!
102
1cm
K3
n(6
33n
m)Z
1.58
4.
Co
ron
ap
ole
dat
1908
Cfo
r30
min
.
aZ
K1
dB
/cm
.
Tem
po
ral
stab
ilit
y:t
1(2
58C
)Z0.
3d
ays
and
t2(2
58C
)Z39
day
s.
O On
NO
CO
NN
N NO
2
OO N
p-n
itro
anil
ine
fun
ctio
nal
ized
po
lyim
ide
(Lin
etal
.19
92)
TgZ
2368
C.
lm
axZ
390
nm
.
r#Z
7!10
20
cmK
3
Fil
ms
are
cure
dan
dco
ron
ap
ole
dat
2408
C.
d3
3(1
.06
mm
)Z5.
4p
m/V
.
d3
3(2
4h
,858C
)z5
pm
/Van
dst
able
.
15018—Chapter7—26/8/2006—22:27—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-96 Handbook of Photonics
Article in Press
4846
4847
4848
4849
4850
4851
4852
4853
4854
4855
4856
4857
4858
4859
4860
4861
4862
4863
4864
4865
4866
4867
4868
4869
4870
4871
4872
4873
4874
4875
4876
4877
4878
4879
4880
4881
4882
4883
4884
4885
4886
4887
4888
4889
4890
4891
4892
4893
4894
4895
4896
NO
2n
OO
NN
Po
ly-(
4-n
itro
-40 -(
vin
ylo
oxy
eth
ylo
xy)a
zob
enze
ne,
1,an
do
ther
po
ly-(
vin
ylet
her
s)(S
0 hee
ren
etal
.19
92)
CN
n
OO
NN
Po
ly-(
4-cy
ano
-40 -(
vin
ylo
oxy
eth
ylo
xy)
azo
ben
zen
e2
n
O
CN
CN
O
Po
ly-(
4-d
icya
no
vin
yl-4
0 -(vi
nyl
oo
xyet
hyl
oxy
)b
enze
ne
3
n
OO
NC
OC
H3
O
Po
ly-(
4-cy
ano
-4-c
arb
om
eth
oxy
vin
yl-4
0 -(vi
nyl
oo
xyet
hyl
oxy
)b
enze
ne
4
OH O
NN
O2
O x1-x
Po
lyvi
nyl
alco
ho
l/N
-eth
yl-N
-met
hyl
amin
on
itro
anil
ine
cop
oly
mer
(Sas
aki
1993
)
TgZ
1208
C.
lm
axz
380
nm
.
Co
ron
ap
ole
dat
Tg.
d3
3(1
.06
mm
)Z10
pm
/V.
d3
3re
laxe
sto
7p
m/V
in40
day
s.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:28—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-97
Article in Press
4897
4898
4899
4900
4901
4902
4903
4904
4905
4906
4907
4908
4909
4910
4911
4912
4913
4914
4915
4916
4917
4918
4919
4920
4921
4922
4923
4924
4925
4926
4927
4928
4929
4930
4931
4932
4933
4934
4935
4936
4937
4938
4939
4940
4941
4942
4943
4944
4945
4946
4947
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
NO
2N
O
O OH O
n
NN
DR
1/P
oly
(mal
eic
anh
ydri
de-
co-p
rop
ylen
eco
po
lym
er(1
6:84
mo
l%)
(Bau
eret
al.
1993
)
TgZ
1808
C.
lm
axz
470
nm
.
Co
ron
ap
ole
dat
1858
C.
r 33
(780
nm
)Z6
pm
/V.
wit
h38
C/m
inh
eati
ng
rate
,r 3
3is
stab
leu
pto
1008
C.
NO
2R =
A BO
n
R
O
NN
N
N
Azo
dye
/Po
ly(m
alei
can
hyd
rid
e-co
-sty
ren
eo
rco
-no
rbo
rnad
ien
eco
po
lym
er(A
hlh
eim
and
Leh
r19
94)
Mai
n-C
hai
nP
olym
ers
CN
CN
O
O n
Vin
ylid
ene
cyan
ide/
vin
ylac
etat
eco
po
lym
er(5
0:50
mo
l%)
(Azu
mai
etal
.19
90;
Eic
het
al.
1988
;Sa
toet
al.
1987
)
TgZ
1808
C.
Mw
Z47
0!10
3.
n(2
.94
mm
)Z1.
434.
a(2
.94
mm
)Z1.
4m
mK
1.
Co
ron
ap
ole
dat
1808
Cfo
r2
h.
d3
3(1
.064
mm
)Z0.
3p
m/V
.[E
ich
].
No
te:
larg
ed
iscr
epan
cyin
SHG
dco
effi
cien
ts.
15018—Chapter7—26/8/2006—22:28—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-98 Handbook of Photonics
Article in Press
4948
4949
4950
4951
4952
4953
4954
4955
4956
4957
4958
4959
4960
4961
4962
4963
4964
4965
4966
4967
4968
4969
4970
4971
4972
4973
4974
4975
4976
4977
4978
4979
4980
4981
4982
4983
4984
4985
4986
4987
4988
4989
4990
4991
4992
4993
4994
4995
4996
4997
4998
O
NN
Nn
O
N
Aro
mat
icp
oly
ure
a(N
agam
ori
etal
.19
92;
kaji
kaw
aet
al.
1991
)
Th
infi
lmp
rep
ared
by
vap
or
dep
osi
tio
np
oly
mer
izat
ion
.
TgZ
O15
08C
.
lcu
t-o
ffZ
400
nm
.
Co
ron
ap
ole
dat
1808
Cfo
r3
min
.
d3
3(1
.06
mm
)Z1.
7p
m/V
.
Neg
ligi
ble
rela
xati
on
of
acti
vity
ove
r2
mo
nth
sat
amb
ien
tco
nd
itio
ns.
Act
ivit
yre
mai
ns
stab
leaf
ter
sho
rt-t
erm
hea
tin
gto
2008
C.
O
NN
N
nO
N
N-p
hen
ylat
edp
oly
ure
a(N
alw
aet
al.
1993
a;N
alw
aet
al.
1993
b;
Azu
mai
etal
.19
90;
Stat
oet
al.
1987
)
TgZ
1238
C.
lm
axZ
253
nm
.
n(6
33n
m)Z
1.57
7.
a(6
33n
m)Z
K1.
2d
B/c
m.
Co
ron
ap
ole
dat
1308
Cfo
r1
h.
d3
3(1
.064
mm
)Z5.
5p
m/V
.
90%
of
acti
vity
rem
ain
sst
able
afte
r40
day
sat
amb
ien
t.
N NO
2
OO
n
1
OH
OH
n
2
O
N NO
2
N
OH
OO
H
Ep
oxy
po
lym
ers
con
tain
ing
4-am
ino
-40 -n
itro
azo
ben
zen
e(T
erao
kaet
al.
1991
)
Po
lym
ers
pre
par
edb
ym
elt
con
den
sati
on
at15
08C
un
der
N2
.
d3
3va
lues
are
mea
sure
dat
1.06
4m
md
uri
ng
coro
na
po
lin
g. (con
tin
ued
)
15018—Chapter7—26/8/2006—22:28—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-99
Article in Press
4999
5000
5001
5002
5003
5004
5005
5006
5007
5008
5009
5010
5011
5012
5013
5014
5015
5016
5017
5018
5019
5020
5021
5022
5023
5024
5025
5026
5027
5028
5029
5030
5031
5032
5033
5034
5035
5036
5037
5038
5039
5040
5041
5042
5043
5044
5045
5046
5047
5048
5049
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
OO
n
NO
2
N N
N
OH
OH
Ep
oxy
po
lym
ers
con
tain
ing
p-am
ino
nit
rob
enze
ne
(Gad
ret
etal
.19
91)
TgZ
778C
.
lm
axZ
480
nm
.
Co
ron
ap
ole
daf
ter
pro
curi
ng.
d3
3(1
.06
mm
)Z25
pm
/V.
Stab
leac
tivi
tyat
amb
ien
tco
nd
itio
ns
for
O20
day
s.A
ctiv
ity
dec
reas
es
rap
idly
toze
row
hen
hea
ted
abo
ve808C
.
OO
n
NO
2
N
OH
OH
Ep
oxy
po
lym
erco
nta
inin
g4-
amin
o-4
0 nit
roto
lan
e(J
un
gbau
eret
al.
1991
)
TgZ
1258
C.
lm
axZ
418
nm
.
n(6
33n
m)Z
1.71
.
Co
ron
ap
ole
dat
1358
Cfo
r1
h.
d3
3(1
.064
mm
)Z89
pm
/V.
r 13
(633
nm
)Z8
pm
/V.
Stab
leb
iref
rin
gen
ceat
amb
ien
tco
nd
itio
ns.
Bir
frin
gen
ced
ecay
sw
ith
tZ
448
han
db
Z0.
45at
1008
C.
15018—Chapter7—26/8/2006—22:28—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-100 Handbook of Photonics
Article in Press
5050
5051
5052
5053
5054
5055
5056
5057
5058
5059
5060
5061
5062
5063
5064
5065
5066
5067
5068
5069
5070
5071
5072
5073
5074
5075
5076
5077
5078
5079
5080
5081
5082
5083
5084
5085
5086
5087
5088
5089
5090
5091
5092
5093
5094
5095
5096
5097
5098
5099
5100
OO
n
SO
2CH
3
N
OH
12
OH
SO
2CH
3
N
nO
H
Ep
oxy
po
lym
ers
con
tain
ing
4-am
ino
-40 m
eth
ylsu
lfo
nyl
tola
ne
(Tw
ieg
etal
.19
92)
Po
lym
ers
pre
par
edb
ym
elt
con
den
sati
on
at15
08C
.
d3
3va
lues
are
mea
sure
dat
1.06
4m
md
uri
ng
coro
na
po
lin
g.
O
O
OO
O
On
NO
2N N
N
Ep
oxy
po
lym
ers
con
tain
ing
4-am
ino
-40 n
itro
azo
ben
zen
e(J
eng
etal
.19
92c)
TgZ
1158
C.
lm
axZ
461
nm
.
n(5
33n
m)Z
1.71
8.
Co
ron
ap
ole
dat
1158
Cfo
r1
h.
d3
3(1
.06
mm
)Z34
pm
/V.
70%
of
SHG
acti
vity
rem
ain
sst
able
afte
r20
day
sat
amb
ien
t
con
dit
ion
s.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:28—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-101
Article in Press
5101
5102
5103
5104
5105
5106
5107
5108
5109
5110
5111
5112
5113
5114
5115
5116
5117
5118
5119
5120
5121
5122
5123
5124
5125
5126
5127
5128
5129
5130
5131
5132
5133
5134
5135
5136
5137
5138
5139
5140
5141
5142
5143
5144
5145
5146
5147
5148
5149
5150
5151
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
OO
NX
OO
nX
=
1 2 3
NN N
N NO
2
Po
lyu
reth
anes
con
tain
ing
4-am
ino
-40 n
itro
azo
ben
zen
e[M
eyru
eix
etal
.19
91a,
1991
b]
Po
lym
ers
pre
par
edb
ym
elt
con
den
sati
on
at15
08C
.
c3
33
(Ku
,u
,0)
valu
esar
em
easu
red
at83
0n
maf
ter
con
tact
po
lin
g
wit
h25
V/m
mat
1008
C.
OO
O
O
X =
O1
X
nO O
N N
N NO
2
OO
NN
O
O
O
O
O
O3
4
2
O
Po
lyu
reth
anes
con
tain
ing
4-am
ino
-40 n
itro
azo
ben
zen
e[C
hen
etal
.19
91]
Po
lym
ers
pre
par
edb
yco
nd
ensa
tio
nin
dio
xan
eso
luti
on
.
d3
3is
stab
iliz
edva
lue
mea
sure
dat
1.06
4m
maf
ter
coro
na
po
lin
gat
abo
ut
1308
C.
Act
ivit
yis
stab
leat
amb
ien
tco
nd
itio
ns.
15018—Chapter7—26/8/2006—22:29—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-102 Handbook of Photonics
Article in Press
5152
5153
5154
5155
5156
5157
5158
5159
5160
5161
5162
5163
5164
5165
5166
5167
5168
5169
5170
5171
5172
5173
5174
5175
5176
5177
5178
5179
5180
5181
5182
5183
5184
5185
5186
5187
5188
5189
5190
5191
5192
5193
5194
5195
5196
5197
5198
5199
5200
5201
5202
NO
2
NO
2
O
OO
NN
n
R =
N R
1
2 3
4
5
O
NN
CN
CN
CN
O
O
NN
NO
2
Po
lyu
reth
anes
der
ived
fro
m2,
4-to
luen
edii
socy
anat
e/2-
met
hyl
-4-n
itro
-[N
,N-b
is(2
-hyd
roxy
eth
yl)]
-an
ilin
ean
d
oth
erd
iols
[Kit
ipic
hai
etal
.199
3]
Insi
tuco
ron
ap
oli
ng
du
rin
gm
elt
po
lym
eriz
atio
nat
1208
C.
d3
3va
lues
are
mea
sure
dat
1.06
4m
m;
stab
iliz
edva
lues
afte
r18
0d
ays
at258C
are
give
nin
ital
ics.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:29—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-103
Article in Press
5203
5204
5205
5206
5207
5208
5209
5210
5211
5212
5213
5214
5215
5216
5217
5218
5219
5220
5221
5222
5223
5224
5225
5226
5227
5228
5229
5230
5231
5232
5233
5234
5235
5236
5237
5238
5239
5240
5241
5242
5243
5244
5245
5246
5247
5248
5249
5250
5251
5252
5253
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
O(C
H2)
3O
OC
H3
N N
x x
CN
OO
O(C
H2)
11
1-x
CN
O
1 2O
O(C
H2)
11
1-x
O
O(C
H2)
θS
xC
N
3O
O(C
H2)
11
1-x
O
Mai
n-c
hai
np
oly
mer
sd
eriv
edfr
om
(1)
a-c
yan
o-e
ster
qu
ino
dim
eth
anes
,(2)
p-o
xy-a
-cya
no
cin
nam
ates
,(3)
p-th
io-
a-c
yan
oci
nn
amat
es[F
uso
1991
;Hal
let
al.
1988
;G
reen
1987
a,19
87b
]
Po
lym
ers
pre
par
edb
yh
igh
tem
per
atu
retr
anse
ster
ifica
tio
n.
Ho
mo
po
lym
ers
are
typ
ical
lyin
solu
ble
and
hig
hm
elti
ng.
Un
itm
ole
cula
rn
on
lin
eari
tym
b/n
valu
esar
em
easu
red
at1.
064
mm
.
nC
N
O
ON
Mai
n-c
hai
nh
om
op
oly
mer
sd
eriv
edfr
om
(4-N
-eth
yl-N
-(2-
hyd
roxy
eth
yl)a
min
o-a
-cya
no
cin
nam
ates
(1)
and
the
corr
esp
on
din
gac
id(2
)[S
ten
ger-
Smit
het
al.
1991
,19
90]
Po
lym
eriz
atio
n:
(1)
mel
ttr
anse
ster
ifica
tio
nat
1608
C;
(2)
solu
tio
n
po
lyco
nd
ensa
tio
nat
258C
.
15018—Chapter7—26/8/2006—22:29—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-104 Handbook of Photonics
Article in Press
5254
5255
5256
5257
5258
5259
5260
5261
5262
5263
5264
5265
5266
5267
5268
5269
5270
5271
5272
5273
5274
5275
5276
5277
5278
5279
5280
5281
5282
5283
5284
5285
5286
5287
5288
5289
5290
5291
5292
5293
5294
5295
5296
5297
5298
5299
5300
5301
5302
5303
5304
SN
On
O
SO
N
Mai
n-c
hai
np
oly
mer
der
ived
fro
m3-
[(m
eth
yoxy
carb
on
yl)m
eth
yl]-
5-[4
0 -[N
-eth
yl-N
-(200-h
ydro
xyet
hyl
)am
ino
]
ben
zyli
den
e]rh
od
anin
e[F
ran
cis
etal
.19
93b
]
Po
lym
ers
are
pre
par
edb
ytr
anse
ster
icat
ion
inm
elt
at14
08C
for
8h
.
TgZ
638C
.
Mw
Z13
!10
3.
lm
axZ
473
nm
.
n(7
90n
m)Z
1.76
0.
Co
nta
ctp
ole
dw
ith
43V
/mm
at658C
.
d3
3(1
.58
mm
)Z7.
3p
m/V
.
O S O
OH
n
N
C4H
9
4-am
ino
-40 -a
lkyl
sulf
on
ylto
lan
em
ain
-ch
ain
po
lym
er[Z
ente
let
al.
1993
]
Po
lym
ers
are
coro
na
po
led
du
rin
gm
elt
po
lym
eriz
atio
nat
1508
Cfo
ra
few
ho
urs
.
TgZ
608C
.
lm
axZ
366
nm
.
d3
3(1
.064
mm
)Z12
.5p
m/V
.
Act
ivit
yd
ecay
sb
y40
%in
25d
ays
atam
bie
nt
con
dit
ion
s.
1 4
2 &
3
O(C
H2)
6O
O(C
H2)
6O
O(C
H2)
6O
O(C
H2)
15
O(C
H2)
15
O(C
H2)
15
OO
CN
xO
O
OO
N
N
1-x
x1-
x
x1-
x
Mai
n-c
hai
np
oly
este
rsd
eriv
edfr
om
6-h
ydro
xyh
exyl
oxy
ph
enyl
pro
pen
oic
,az
ob
enzo
ic,
or
eth
enyl
ben
zoic
acid
s
[S’h
eere
net
al.
1993
b]
Po
lym
ers
are
pre
par
edb
ym
elt
po
lyco
nd
ensa
tio
nat
2208
C,
1.3
mb
ar
for
4h
.
Fil
ms
are
of
pal
eye
llo
win
colo
r.
d3
3va
lues
are
mea
sure
dat
1.06
4m
maf
ter
coro
na
po
lin
gat
108C
abo
veT
g.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:29—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-105
Article in Press
5305
5306
5307
5308
5309
5310
5311
5312
5313
5314
5315
5316
5317
5318
5319
5320
5321
5322
5323
5324
5325
5326
5327
5328
5329
5330
5331
5332
5333
5334
5335
5336
5337
5338
5339
5340
5341
5342
5343
5344
5345
5346
5347
5348
5349
5350
5351
5352
5353
5354
5355
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
1
2
NN
CN
NC
OO
O
OO
n
N
CN
NC
N
n
N
NO
Mai
n-c
hai
nac
cord
ion
po
lym
ers
of
a-c
yan
oci
nn
amam
ides
[Lin
dsa
yet
al.
1992
;W
ang
and
Gu
an19
92]
Po
lym
er2
was
coro
na
po
led
.A
ctiv
ity
isfo
un
dto
be
stab
leat
roo
m
tem
per
atu
re.
X =
1 2 3
NN
NO
SO
OO O
NN
O
O
O
(CH
2)6O
X
n
O
Ran
do
mm
ain
-ch
ain
po
lym
ers
con
tain
ing
4-N
,N-d
ialk
ylam
ino
-40 -h
exyl
sulf
on
ylaz
ob
enze
ne
[Xu
etal
.199
3,19
92a]
Po
lym
ers
are
pre
par
edb
yC
on
den
sati
on
ind
ioxa
ne
solu
tio
n.
d3
3va
lues
are
mea
sure
dat
1.06
4m
maf
ter
coro
na
po
lin
gat
abo
ut
1208
C.
15018—Chapter7—26/8/2006—22:30—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-106 Handbook of Photonics
Article in Press
5356
5357
5358
5359
5360
5361
5362
5363
5364
5365
5366
5367
5368
5369
5370
5371
5372
5373
5374
5375
5376
5377
5378
5379
5380
5381
5382
5383
5384
5385
5386
5387
5388
5389
5390
5391
5392
5393
5394
5395
5396
5397
5398
5399
5400
5401
5402
5403
5404
5405
5406
Cro
ss-l
inke
dpo
lym
ers
N NO
2
OO
nN
OH
OH
Cro
ss-L
inke
dep
oxy
po
lym
erfr
om
4-n
itro
-1,
2-p
hen
ylen
edia
min
ean
db
isp
hen
ol-
Ad
igly
cid
ylet
her
[Eic
het
al.
1989
a]
Th
erm
alcr
oss
-lin
kin
gis
ach
ieve
db
yp
rocu
rin
gat
1008
Cfo
r3
hat
1408
Cfo
r16
hu
nd
era
coro
na
po
lin
gfi
eld
.
lm
axZ
410
nm
.
n(6
33n
m)
Z1.
629.
d3
3(1
.06
mm
)Z13
.5p
m/V
.
No
dec
ayo
fSH
Gac
tivi
tyis
ob
serv
edfo
r36
min
sat
808C
.
OH
N NO
2N
O2
N
OH
Nn
Cro
ss-l
inke
dep
oxy
po
lym
erfr
om
N,N
-(d
igly
cid
yl)-
4-n
itro
anil
ine
and
N-(
2-am
ino
ph
enyl
)-4-
nit
roan
ilin
e
[Ju
ngb
auer
etal
.19
90]
Th
erm
alcr
oss
-lin
kin
gis
ach
ieve
db
yp
rocu
rin
gat
1308
Cfo
r4
min
and
at12
08C
for
24h
un
der
aco
ron
ap
oli
ng
fiel
d.
lm
axZ
397
nm
.
Hig
hd
yeco
nte
nt:
63w
t%.
n(6
33n
m)Z
1.74
.
d3
3(1
.064
mm
)Z50
pm
/V.
Stab
leac
tivi
tyis
ob
serv
edat
80%
of
init
ial
valu
eat
808C
. (con
tin
ued
)
15018—Chapter7—26/8/2006—22:30—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-107
Article in Press
5407
5408
5409
5410
5411
5412
5413
5414
5415
5416
5417
5418
5419
5420
5421
5422
5423
5424
5425
5426
5427
5428
5429
5430
5431
5432
5433
5434
5435
5436
5437
5438
5439
5440
5441
5442
5443
5444
5445
5446
5447
5448
5449
5450
5451
5452
5453
5454
5455
5456
5457
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
O
O
O
O
ON
N
N
NO
SN
O
O
O
OO
OON
NN
O
O
S
O
A
B
Cro
ss-l
inke
dm
eth
acry
late
po
lym
erco
nta
inin
g4-
N,N
-dia
lkyl
amin
o-4
0 -N,N
-dia
lkyl
amin
osu
lfo
nyl
azo
ben
zen
e
[Wan
get
al.
1993
;A
llen
etal
.19
91]
Cro
ss-l
inki
ng
isin
itia
ted
wit
hfr
eera
dic
als
un
der
aco
ron
ap
oli
ng
fiel
d.
lm
axZ
480
nm
.
r 33
(633
mm
)Z36
pm
/V;
r 33
(1.3
mm
)Z6.
6p
m/V
.
No
dec
ayo
fac
tivi
tyis
ob
serv
edo
ver
8m
on
ths
atam
bie
nt
con
dit
ion
s
for
A.
Hig
her
tem
po
ral
stab
ilit
yfo
un
dfo
rB
.
OO
OH
OH
OO
OH
OH
OO
OH
OH
N NO
2
OO
OH
OH
OO
OH
OH
N
N N
N
A B
Cro
ss-l
inke
dp
oly
mer
fro
ma
reac
tive
dia
min
ed
eriv
ativ
eo
f4-
N,
N-d
imet
hyl
amin
o-4
0 -nit
roaz
ob
enze
ne
and
oli
gom
eric
der
ivat
ive
of
dig
lyci
dyl
eth
ero
fb
isp
hen
ol
A[H
ub
bar
d19
92]
Th
erm
alcr
oss
-lin
kin
gis
ach
ieve
dp
rocu
rin
gat
1008
Cfo
r3
han
dat
1308
Cfo
r2
ho
ur
aco
ron
ap
oli
ng
fiel
d.
r#Z
6!10
20
cm-3
for
B.
d3
3(1
.064
mm
)Z3(
A)-
6(B
)p
m/V
.
Tem
po
ral
stab
ilit
y:t
1(2
58C
)Z6(
A)–
4.1(
B)
day
san
dt
2(2
58C
)Z12
0(A
)K30
0(B
)d
aya;
t1(8
58C
)Z1.
6(B
)d
ays
and
t2(8
58C
)Z12
0(B
)
day
s.
15018—Chapter7—26/8/2006—22:30—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-108 Handbook of Photonics
Article in Press
5458
5459
5460
5461
5462
5463
5464
5465
5466
5467
5468
5469
5470
5471
5472
5473
5474
5475
5476
5477
5478
5479
5480
5481
5482
5483
5484
5485
5486
5487
5488
5489
5490
5491
5492
5493
5494
5495
5496
5497
5498
5499
5500
5501
5502
5503
5504
5505
5506
5507
5508
N
O
N
N
NN
NR
O O
N
OO
R
N
ON
R
N
NR
=
NC
CN
CN
Tri
azin
ecr
oss
-lin
ked
po
lym
ero
bta
ined
fro
mp(
N,N
-bis
(40 -c
yan
ato
ben
zyl)
amin
o-p
0 -(2,
2dic
yan
ovi
nyl
)azo
ben
zen
e
(Ho
llan
dan
dF
ang
1992
;Si
nge
ret
al.
1991
)
Po
lym
ers
are
pre
par
edb
yp
oly
-acy
clo
trim
eriz
atio
nat
1508
Cu
nd
era
po
lin
gfi
eld
for
seve
ral
ho
urs
.
r 33(8
30n
m)Z
11p
m/V
.
Hig
hst
abil
ity
iso
bse
rved
at858C
.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:30—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-109
Article in Press
5509
5510
5511
5512
5513
5514
5515
5516
5517
5518
5519
5520
5521
5522
5523
5524
5525
5526
5527
5528
5529
5530
5531
5532
5533
5534
5535
5536
5537
5538
5539
5540
5541
5542
5543
5544
5545
5546
5547
5548
5549
5550
5551
5552
5553
5554
5555
5556
5557
5558
5559
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
O
N
NC
O
NC
O
OO
OC
NON
NN
S
SN N
H2
HO
Iso
cyan
ate
cro
ss-l
inke
dp
oly
mer
der
ived
fro
mtr
is-1
-hex
amet
hyl
enei
socy
anat
eis
ocy
anu
rate
and
3-am
ino
-5-[
40 (N
-
eth
yl-N
-(200-h
ydro
xyet
hyl
)am
ino
)ben
zyli
den
e]-r
ho
dan
ine
(Fra
nci
set
al.
1993
a)
Th
erm
ally
cro
ss-l
inke
dat
1358
Cfo
r16
h.
lm
axZ
470
nm
.
n(1
.3m
m)Z
1.61
1.
Do
pin
gle
vel:
60m
ol%
.
Co
nta
ctp
ole
dw
ith
100
V/m
mat
1358
C.
d3
3(1
.58
mm
)Z6.
9p
m/V
.
r 33(1
.3m
m)Z
3.6
pm
/V.
Act
ivit
yd
ecay
sb
y30
%in
150
day
sat
1008
Cd
ue
toth
erm
al
dec
om
po
siti
on
.
O
Nx
1-x
O
O*
NO
2
OO
Cro
ss-l
inke
dep
oxy
po
lym
erfr
om
1,2,
7,8-
die
po
xyo
ctan
ean
dN
-(3-
hyd
roxy
-4-n
itro
ph
enly
)-(S
)-p
roli
no
xy
fun
ctio
nal
ized
po
ly(p
-hyd
roxy
styr
ene)
cop
oly
mer
(Par
ket
al.
1990
)
Th
erm
alcr
oss
-lin
kin
gis
ach
ieve
db
yp
rocu
rin
gat
1008
Cfo
r24
han
d
at18
08C
for
1h
ou
ru
nd
era
coro
na
po
lin
gfi
eld
.
Hig
hd
yeco
nte
nt:
16w
t%.
die
po
xid
e/p
hen
ol
rati
o:
0.5.
d3
3(1
.06
mm
)Z3
pm
/V.
Tem
po
ral
stab
ilit
y:t
1(2
58C
)Z79
day
san
dt
2(2
58C
)Z10
0d
ays.
15018—Chapter7—26/8/2006—22:31—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-110 Handbook of Photonics
Article in Press
5560
5561
5562
5563
5564
5565
5566
5567
5568
5569
5570
5571
5572
5573
5574
5575
5576
5577
5578
5579
5580
5581
5582
5583
5584
5585
5586
5587
5588
5589
5590
5591
5592
5593
5594
5595
5596
5597
5598
5599
5600
5601
5602
5603
5604
5605
5606
5607
5608
5609
5610
N N
N
SO
2C3F
7
NO
2
NO
2
R =
ZY
X
OO
OO
OO N
A B C
N
OO
Cro
ss-l
inke
dh
om
o-a
nd
cop
oly
mer
so
fis
ocy
anat
oet
hyl
met
hac
ryla
te,
MM
A,
and
dim
eth
ylam
ino
eth
yl
met
hac
ryla
te.
(Ch
eng
etal
.19
92)
Co
ron
ap
ole
dn
ear
Tg.
d3
3va
lues
are
mea
sure
dat
1.06
4m
m.
d3
3o
fA
are
stab
leat
roo
mte
mp
erat
ure
.
Act
ivit
yd
ecay
sb
y10
%in
100
day
sat
808C
for
po
lym
erB
and
C.
a(1
.06
mm
)z-(
1.5-
3)d
B/c
m.
O O
O
O O
O
O
m
n
n
NN
NSO
O
OO
SN
NN
O O
O OO
O
N
n
O
ON
1 2
Cro
ss-l
inke
dsi
de-
chai
np
oly
mer
sco
nta
inin
g4-
N,N
-dia
lkyl
amin
o-4
0 -alk
ylsu
lfo
nyl
azo
ben
zen
e[X
uet
al.1
992b
;Sh
i
etal
.19
93]
Th
erm
alcr
oss
-lin
kin
gu
nd
erco
ron
ap
oli
ng
fiel
d:
(1)
wit
hin
itia
tors
;
(2)
wit
ho
ut
init
iato
r.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:31—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-111
Article in Press
5611
5612
5613
5614
5615
5616
5617
5618
5619
5620
5621
5622
5623
5624
5625
5626
5627
5628
5629
5630
5631
5632
5633
5634
5635
5636
5637
5638
5639
5640
5641
5642
5643
5644
5645
5646
5647
5648
5649
5650
5651
5652
5653
5654
5655
5656
5657
5658
5659
5660
5661
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
O O O
O
O
O
OH
N
NO
2
NO
2
O2N
O
NO
OH
O
O
OH
NN
NN
NO
O
OH
O
OO
H
with
1,2
, or
30.
4
0.6
1 2 3
NN N
N
NN
Cro
ss-l
inke
dep
oxy
po
lym
ers
con
tain
ing
dia
lkya
min
on
itro
azo
ben
zen
ed
eriv
ativ
es[M
ull
eret
al.
1993
]
Cro
ss-l
inke
dp
oly
mer
sar
ep
rep
ared
wit
h10
–20
wt%
PM
MA
asa
bin
der
.
Fil
ms
are
char
acte
rize
das
hav
ing
goo
dto
exce
llen
to
pti
cal
qu
alit
y.
r 33
valu
esar
em
easu
red
at1.
32m
maf
ter
coro
na
po
lin
gat
abo
ut
1408
Cfo
r8
h.
NN
N
OO
NN N
O2
n
Cro
ss-L
inke
dp
oly
mer
con
tain
ing
4-am
ino
-40 -n
itro
azo
ben
zen
e(Y
uet
al.
1992
)
Pre
po
lym
erco
nta
inin
get
hyn
ylgr
ou
pis
ther
mal
lycr
oss
-lin
ked
at
1908
Cfo
r2
hu
nd
era
coro
na
po
lin
gfi
eld
.
lm
axz
470
nm
.
d3
3(1
.064
mm
)Z20
pm
/V.
Act
ivit
yd
ecay
sto
75%
of
init
ial
valu
eaf
ter
30d
ays
at908C
.
15018—Chapter7—26/8/2006—22:31—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-112 Handbook of Photonics
Article in Press
5662
5663
5664
5665
5666
5667
5668
5669
5670
5671
5672
5673
5674
5675
5676
5677
5678
5679
5680
5681
5682
5683
5684
5685
5686
5687
5688
5689
5690
5691
5692
5693
5694
5695
5696
5697
5698
5699
5700
5701
5702
5703
5704
5705
5706
5707
5708
5709
5710
5711
5712
NN
NN N
O2
N
OO
O
O
O
O
OO
N
O
On
N
O
O
N
O
Cro
ss-L
inke
dp
oly
ure
than
eco
nta
inin
g4-
N,N
-dia
lkyl
amin
o-4
0 -nit
roaz
ob
enze
ne(
Ch
enet
al.
1992
;Sh
iet
al.
1992
)
Oli
gom
eric
pre
po
lym
eris
ther
mal
lycr
oss
-lin
ked
wit
h
trie
than
ola
min
eat
1608
Cfo
ran
ho
ur
un
der
aco
ron
ap
oli
ng
fiel
d.
lm
axZ
475
nm
.
n(6
33n
m)Z
1.75
3;n
(800
nm
)Z1.
692.
d3
3(1
.06
mm
)Z12
0p
m/V
.
r 13(6
33m
m)Z
13p
m/V
.;r 1
3(8
00n
m)Z
5p
m/V
.
No
dec
ayo
fac
tivi
tyis
ob
serv
edat
amb
ien
tfo
r4
mo
nth
s;ac
tivi
ty
stab
lize
sto
70%
of
init
ial
valu
eaf
ter
4m
on
ths
at908C
.
ON
OO
NN
On
(CH
2)6
O
O
O
ONNO
S(C
H2)
6ON
N
Cro
ss-L
inke
dra
nd
om
mai
n-c
hai
np
oly
mer
con
tain
ing
4-N
,N-d
ialk
amin
o-4
0 -hex
ylsu
lfo
nyl
azo
ben
zen
ean
d3,
30 -
dia
nis
idin
ed
iiso
cyan
ate
(Xu
1992
;R
ano
net
al.
1993
;X
uet
al.
1993
)
Th
erm
ally
cro
ss-l
inke
du
nd
era
coro
na
po
lin
gfi
eld
at12
58C
for
2h
.
Pre
po
lym
erM
wZ
8!10
3.
lm
axZ
440
nm
.
d3
3(1
.064
mm
)Z40
pm
/V.
90%
acti
vity
rem
ain
sst
able
atam
bie
nt
con
dit
ion
sfo
rO
3m
on
ths.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:31—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-113
Article in Press
5713
5714
5715
5716
5717
5718
5719
5720
5721
5722
5723
5724
5725
5726
5727
5728
5729
5730
5731
5732
5733
5734
5735
5736
5737
5738
5739
5740
5741
5742
5743
5744
5745
5746
5747
5748
5749
5750
5751
5752
5753
5754
5755
5756
5757
5758
5759
5760
5761
5762
5763
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
NN
O2
O
OO
OS
i
OH
NN
Alk
oxy
sila
ne
der
ivat
ive
of
4(-4
0 nit
rop
hen
ylaz
o)-
ph
enyl
amin
ecr
oss
-lin
ked
wit
h1,
1,1-
tris
(4-h
ydro
yph
enyl
)eth
ane
(Jen
get
al.
1993
)
Th
erm
ally
cro
ss-l
inki
ng
occ
urs
at20
08C
.
TgZ
1108
C.
lm
axZ
493
nm
.
n(5
33n
m)Z
1.74
4.
Do
pin
gle
vel:
50m
ol%
.
Co
ron
ap
ole
dat
2008
Cfo
r30
min
.
d3
3(1
.06
mm
)Z77
pm
/V.
d3
3(2
4h
rs,
1058
C)Z
62p
m/V
.
No
dec
ayo
fac
tivi
tyis
ob
serv
edfo
r7
day
sat
amb
ien
tco
nd
itio
ns.
OH
(H3C
O) 3
Si
NO
2
[(S
iO)
>1
(C6H
5) <
0.5
(OC
2H5)
<0.
5 (O
H)
<0.
5 ] n
NN
ON
Alk
oxy
sila
ne
der
ivat
ive
of
4-(4
0 nit
rop
hen
ylaz
o)-
ph
enyl
amin
ecr
oss
-lin
ked
wit
hp
hen
ylsi
loxa
ne
po
lym
er(A
llie
d
Sign
alA
ccu
glas
s20
4w)
(Jen
get
al.
1992
a)
Th
erm
alcr
oss
-lin
kin
go
ccu
rsat
2008
C.
lm
axZ
493
nm
.
n(5
33n
m)Z
1.53
7.
Do
pin
gle
vel:
0.1
gd
yein
4g
of
A20
4.
Co
ron
ap
ole
dat
2008
Cfo
r10
min
.
d3
3(1
.06
mm
)Z5.
28p
m/V
.
d3
3(4
0h
,10
08C
)Z2.
9p
m/V
.
NN
OH
(H3C
O) 3
Si
O O
N
HO
NO
2
OO
OH
N
nO
ON
Alk
oxy
sila
ne
der
ivat
ive
of
4-(4
0 -nit
rop
hen
ylaz
o)p
hen
ylam
ine/
po
lyim
ide(
Skyb
on
dw
)co
mp
osi
te(J
eng
etal
.199
2b)
Tg
O27
58C
.
lm
axZ
466
nm
.
Do
pin
gle
vel:1
6w
t%.
Exc
elle
nt
op
tica
lq
ual
ity.
Co
ron
ap
ole
dat
2208
C.
d3
3(1
.06
mm
)Z13
.7p
m/V
.
Stab
led
33
(168
h,
1208
C)Z
10p
m/V
.
No
velt
y:co
mp
osi
teo
fp
oly
imid
ean
dSi
-O-S
in
etw
ork
.
15018—Chapter7—26/8/2006—22:32—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-114 Handbook of Photonics
Article in Press
5764
5765
5766
5767
5768
5769
5770
5771
5772
5773
5774
5775
5776
5777
5778
5779
5780
5781
5782
5783
5784
5785
5786
5787
5788
5789
5790
5791
5792
5793
5794
5795
5796
5797
5798
5799
5800
5801
5802
5803
5804
5805
5806
5807
5808
5809
5810
5811
5812
5813
5814
O N
O
OO
O
O
O
O
NO
2
O
n
N
NO
2
N
Si
OH
NN
ON
Inte
rpen
etra
tin
gn
etw
ork
of
epo
xyan
dsi
lico
n-b
ased
cro
ss-l
inke
dp
oly
mer
s(M
artu
run
kaku
let
al.
1993
)
Eq
ual
wei
ght
rati
oo
fth
etw
op
oly
mer
sis
hea
ted
at20
08C
for
1h
un
der
aco
ron
ap
oli
ng
fiel
d.
Fil
ms
are
hig
ho
pti
cal
qu
alit
y.
TgZ
1768
C.
lm
axZ
458
nm
.
N(5
33n
m)Z
1.70
8.
d3
3(1
.064
mm
)Z33
pm
/V.
No
dec
ayo
fac
tivi
tyis
ob
serv
edat
1008
Cfo
r7
day
s,50
%d
ecay
is
ob
serv
edaf
ter
15h
at16
08C
.
O
ON
SO
2CH
3
O
O
Cro
ss-l
inke
dac
ryla
tep
oly
mer
of
40 -N
,N-b
is(6
-met
hac
royl
oxy
hex
yl)-
amin
o-4
-met
hyl
sulf
on
ylst
ilb
ene
(Ro
bel
lo
etal
.19
91b
)
Liq
uid
mo
no
mer
sar
ecr
oss
-lin
ked
by
UV
irra
dia
tio
nw
ith
init
iato
rat
roo
mte
mp
erat
ure
.
Tg
!708C
.
Go
od
op
tica
lq
ual
ity.
Co
nta
ctp
ole
dw
ith
6.7
V/m
m.
d3
3(1
.06
mm
)Z0.
7p
m/V
.
Act
ivit
yd
ecay
sto
zero
inse
vera
lm
on
ths
atam
bie
nt
con
dit
ion
s.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:32—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-115
Article in Press
5815
5816
5817
5818
5819
5820
5821
5822
5823
5824
5825
5826
5827
5828
5829
5830
5831
5832
5833
5834
5835
5836
5837
5838
5839
5840
5841
5842
5843
5844
5845
5846
5847
5848
5849
5850
5851
5852
5853
5854
5855
5856
5857
5858
5859
5860
5861
5862
5863
5864
5865
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
O
On
O
N
ON
NO
O
NO
2
Cro
ss-l
inke
dp
oly
mer
of
po
lyvi
nyl
cin
nam
ate
do
ped
wit
h3-
cin
nam
oyl
oxy
-4-[
4-(N
,N-d
ieth
ylam
ino
)-2-
cin
nam
oyl
oxy
ph
enyl
azo
]n
itro
ben
zen
e(M
and
alet
al.
1991
a,19
91b
)
Cro
ss-l
inki
ng
isin
du
ced
by
UV
irra
dia
tio
n(2
mw
/cm
2at
254
nm
for
3to
10m
in)
at708C
.
TgZ
848C
(bef
ore
cro
ss-l
inki
ng)
.
lm
axZ
520
nm
.
Do
pin
gle
vel:
10w
t%.
n(6
33n
m)Z
1.67
7.
Co
ron
ap
ole
dat
708C
du
rin
gU
Vir
rad
iati
on
.
d3
3(1
.064
mm
)Z11
.5p
m/V
.
d3
3(1
.54
mm
)Z3.
7p
m/V
.
r 33(6
33n
m)Z
9pm
/V.
No
dec
ayo
fac
tivi
tyis
ob
serv
edin
22h
atam
bie
nt
con
dit
ion
s
N
O
NO
2
O
N
NO
O
O
RO O
O
OO
O
R
Br
R =
A
= B
R
0.72
Cro
ss-l
inke
dsi
de-
chai
nci
nn
amat
eo
rfu
ryla
cryl
ate
po
lym
ers
do
ped
wit
hci
nn
amo
ylo
xyo
rfu
ryla
cryl
oyl
oxy
fun
ctio
nal
ized
4-N
,N-d
ieth
ylam
ino
40 -a
zon
itro
ben
zen
e(M
ull
eret
al.
1992
b)
Ph
oto
-cro
ss-l
inki
ng
wit
h1.
8m
w/c
m2
at31
2n
mat
758C
for
4(A
)
and
2(B
)h
toac
hie
ve60
%re
acti
on
.
Bca
nn
ot
be
po
led
un
der
irra
dia
tio
nan
dis
po
led
wit
ha
cycl
eo
f
po
lin
g(1
0m
inat
258C
)an
dcr
oss
-lin
kin
g(2
0m
inat
K158C
)fo
ra
tota
lex
po
sure
tim
eo
f2
h.
r 33(1
.32
mm
)Z0.
6p
m/V
.
Act
ivit
yre
mai
ns
stab
leaf
ter
3h
at808C
.
15018—Chapter7—26/8/2006—22:32—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-116 Handbook of Photonics
Article in Press
5866
5867
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5869
5870
5871
5872
5873
5874
5875
5876
5877
5878
5879
5880
5881
5882
5883
5884
5885
5886
5887
5888
5889
5890
5891
5892
5893
5894
5895
5896
5897
5898
5899
5900
5901
5902
5903
5904
5905
5906
5907
5908
5909
5910
5911
5912
5913
5914
5915
5916
O
O
O
O
O R
NO
2
N
NN
NO
2
mn
R =
AB
Cro
ss-l
inke
dsi
de-
chai
nci
nn
amat
eco
po
lym
ers
fun
ctio
nal
ized
wit
h4-
alko
xy-4
0 -bip
hen
ylo
f4-
N,N
-die
thyl
amin
o
40 -a
zon
itro
ben
zen
e[K
ato
etal
.19
93]
Ph
oto
-cro
ss-l
inki
ng
wit
hU
Vli
ght
un
der
coro
na
po
lin
gfi
eld
:(A
)
1.5
min
at508C
;(B
)10
min
atro
om
tem
per
atu
re.
Bo
thp
oly
mer
s
wer
esu
bse
qu
entl
yp
ole
dat
1508
Cfo
r20
min
.
Act
ivit
ies
are
stab
leat
roo
mte
mp
erat
ure
.
N N
N NO
2
O
O
OO
nO
O
Cro
ss-l
inke
dep
oxy
po
lym
erco
nta
inin
g4-
amin
o-4
0 -nit
roaz
ob
enze
ne
(Jen
get
al.
1992
c)
Pre
po
lym
erco
nta
inin
gci
nn
amo
ylgr
ou
pis
cro
ss-l
inke
db
yU
V
irra
dia
tio
nat
3M
W/c
m2
for
10m
in.
lm
axZ
461
nm
.
n(5
33n
m)Z
1.71
8.
Co
ron
ap
ole
dat
1158
Cfo
r1
ho
ur.
d3
3(1
.064
mm
)Z22
pm
/V.
95%
of
SHG
acti
vity
rem
ain
sst
able
afte
r20
day
sat
amb
ien
t
con
dit
ion
s.
(con
tin
ued
)
15018—Chapter7—26/8/2006—22:32—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
Second- and Third-Order Nonlinear Optical Materials 7-117
Article in Press
5917
5918
5919
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5921
5922
5923
5924
5925
5926
5927
5928
5929
5930
5931
5932
5933
5934
5935
5936
5937
5938
5939
5940
5941
5942
5943
5944
5945
5946
5947
5948
5949
5950
5951
5952
5953
5954
5955
5956
5957
5958
5959
5960
5961
5962
5963
5964
5965
5966
5967
TA
BL
E6.
3(C
on
tin
ued
)
Stru
ctu
rean
dN
om
encl
atu
re(R
ef)
Pro
per
ties
NS
(CH
2)6O
OOO
O
On
NN
Cro
ss-l
inke
d,
ran
do
m,
mai
n-c
hai
np
oly
mer
con
tain
ing
4-N
,N-d
ialk
yam
ino
-40 -h
exyl
sulf
on
ylaz
ob
enze
ne
and
cin
nam
oyl
gro
up
s(X
uet
al.
1993
;C
hen
etal
.19
91)
Ph
oto
-cro
ss-l
inke
du
nd
era
coro
na
po
lin
gfi
eld
.
Pre
po
lym
erM
wZ
8.5!
103.
Dye
con
ten
tZ53
wt%
.
lm
axZ
443
nm
.
d3
3(1
.064
mm
)Z15
0p
m/V
.
90%
acti
vity
rem
ain
sst
able
atam
bie
nt
con
dit
ion
sfo
r25
day
s.
15018—Chapter7—26/8/2006—22:33—SJAPPIYAR—15018—XML MODEL CRC12a – pp. 1–126.
7-118 Handbook of Photonics
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5984
5985
5986
5987
5988
5989
5990
5991
5992
5993
5994
5995
5996
5997
5998
5999
6000
6001
6002
6003
6004
6005
6006
6007
6008
6009
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Q2
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Article in Press
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6047
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6146
6147
6148
6149
6150
6151
6152
6153
6154
6155
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Author Queries
JOB NUMBER: BK14885 / 15018
TITLE: Second- and Third-Order Nonlinear Optical Materials
Q1 We have made a change to the word ’plasticization’. Please approve.
Q2 References ’118 and 119’ are provided in the list but not cited in the text. Please supply citation
details or delete the reference from the reference list.
Q3 Please provide forename for the author ’Torreuellas’ in reference 28.