Chemistry Lettershttp://www.csj.jp/journals/chem-lett/
Vol.39 No.8 CMLTAGAugust, 2010 ISSN 0366-7022
Copyright © 2010 The Chemical Society of Japan
Highlight Review
796 Chemistry in Calixarenes and Radicals:Inclusion, Spin Label, Reaction, and ESRStudies
Br
Br
O
O
ON
OO
ON
Br
Br
O
O
ON
OO
ON
Br
Br
O O
ON
OO
O
N
partial cone partial cone
1,2-alternate
353K
room temperature
353K
short long
a
c
b
Yong Li* and Haijun Yangdoi:10.1246/cl.2010.796
Radicals used as spin probes can provide important information on structures and conformational changes of calixarenesthrough inclusion complexes of radicals or spin labels. Multispin-labeled calixarenes and polyradicals based calixarene skeletonsshould provide chances to study magnetic interaction and develop potential applications. In the present review, recent progresses inchemistry of calixarene and free radicals are described.
Letter
803 Triazolyl-linked 8-Hydroxyquinoline Dimeras a Selective Turn-on Fluorosensor for Cd2+
350 400 450 500 550
0
500
1000
1500
2000
OO
O
NNN
NN
O
NN
N
Flou
resc
ence
Int
ensi
ty (
arb
unit)
Wavelength/nm
none, Na+, K+, Ca2+, Mg2+, Mn2+, Pb2+, Ni2+
Zn2+
Cd2+
Hg2+, Cu2+
A novel 1,2,3-triazolyl-linked8-hydroxyquinoline dimer as a highly selectiveturn-on fluorosensor for Cd2+
over a range of other metalions, including Zn2+, wasefficiently synthesized fromthe “click” reaction andshowed weak fluorescencein protic solvents.
(8-HQ)
Lijuan Jiao,* Ting Meng, Yongmin Chen, MinZhang, Xiaolong Wang, and Erhong Hao*doi:10.1246/cl.2010.803Electronic Supporting Information
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
806 Novel Synthesis of LiFePO4 and Li4Ti5O12
from Natural IlmeniteXRD patterns of FePO4·xH2O precursor, LiFePO4, Ti-containing precursor, and Li4Ti5O12.
Ling Wu, Xinhai Li,* Zhixing Wang, FeixiangWu, Xiaojuan Wang, Jie Fang, Huajun Guo,and Lingjun Lidoi:10.1246/cl.2010.806Electronic Supporting Information
808 Oxidative Coupling of N,N-DialkylanilinesUsing Iodic Acid and Sodium Nitrite
H2O, rt
HIO3, NaNO2 NN +
NR1R2
N
NO2
R1R2
R1
R2 R2
R1
R1, R2, = alkyl, allyl, cyclic (62-74%) (15-30 %)Sameerana N. Huddar, Ulhas S. Mahajan, andKrishnacharya G. Akamanchi*doi:10.1246/cl.2010.808Electronic Supporting Information
810 Surface Reorganization of Thin Poly(methylmethacrylate) Films Induced by Water
hPMMA
dPMMA monolayer water neutron
Ayanobu Horinouchi, Yoshihisa Fujii, NorifumiL. Yamada, and Keiji Tanaka*doi:10.1246/cl.2010.810
812 Supramolecular Stacks of Asymmetric ZincPhthalocyanines Functionalized with OneTetrathiafulvalene Unit
Mutsumi Kimura,* Satoshi Otsuji, JunkoTakizawa, Yoko Tatewaki, Tadashi Fukawa,and Hirofusa Shiraidoi:10.1246/cl.2010.812
814 Preparation of a Water-based Al/Fe/MoCatalyst Using a Microfluidic System
Hyoseung Moon, Seok Jae Jeong, Yun TackLee, and Daewon Sohn*doi:10.1246/cl.2010.814
Chemistry Letters Vol.39, No.8 (2010)C-90
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
816 Stability of Superhydrophobicity of LotusLeaf under Extreme Humidity
The influece of environmental conditions on stability of superhydrophobicity of the lotusleaf was studied in the range of -10~80°C under extremely low or high relative humidity.The correlation of superhydrophobic behavior with structural destruction is revealed(see picture).
Long Yin, Qingjun Wang, Jian Xue, JianfuDing, and Qingmin Chen*doi:10.1246/cl.2010.816Electronic Supporting Information
818 Introduction of a Highly Photodurable andCommon-laser Excitable Fluorescent AminoAcid into a Peptide as a FRET Acceptor forProtease Cleavage Detection
A peptide-containing laser-excitablefluorescent nonnatural amino acidswas used to measure caspase-3activity via fluorescence resonanceenergy transfer (FRET).
Masumi Taki,* Yoshito Yamazaki, Yuto Suzuki,and Masahiko Sisidodoi:10.1246/cl.2010.818Electronic Supporting Information
820 Near-infrared Reflecting Yellow InorganicPigments Based on Molybdenum-dopedYttrium Cerate: Synthesis, Characterization,and Optical Properties
A new series of yellow inorganic pigments possessing high near-infrared reflectance withgeneral formula Y2Ce2−xMoxO7+ (x ranges from 0 to 0.5) was synthesized and investigatedfor optical properties.
δ
Viswanadhan Sarasamma Vishnu andMundlapudi Lakshmipathi Reddy*doi:10.1246/cl.2010.820Electronic Supporting Information
822 Semisolid Phase Synthesis of Metal-com-plexed Organic Nanotubes
Mixing an aqueous soluion of metal salt with an alcoholic dispersion of peptide lipid gavehighly concentrated nanotube dispersions.
Masaki Kogiso,* Masaru Aoyagi, MasumiAsakawa, and Toshimi Shimizudoi:10.1246/cl.2010.822Electronic Supporting Information
824 Ion-exchange-induced Phase Separation andPreparation of Porous Glass
Monolithic borosilicate glasses, the surface regions of which are porous and the other parts aretransparent and homogeneous, were prepared through ion-exchange-induced phase separationand acid treatment.
Before ion exchange After ion exchange andcut along the dotted lines
3 µm
Post heat treatmentand acid treatment
After acid treatment
Kohei Kadono,* Yuki Hattori, TakashiWakasugi, Haruhisa Shiomi, and Junji Nishiidoi:10.1246/cl.2010.824
Chemistry Letters Vol.39, No.8 (2010) C-91
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
826 Lithium-ion Transfer at the Interface be-tween Solid and Liquid Electrolytes underApplying DC Voltage
Fumihiro Sagane, Kohei Miyazaki, TomokazuFukutsuka, Yasutoshi Iriyama, Takeshi Abe,*and Zempachi Ogumidoi:10.1246/cl.2010.826
828 Diastereoselective [2 + 2] Photocycloadditionof Chiral Cyclic Enone and CyclopenteneUsing a Microflow Reactor System
CO2R*
O
+
R*:O
R*O2C
H
H
O
R*O2C
H
H
H
O
R*O2C
H
H
O
R*O2C
H
H
H
cis -syn -cis cis -anti -cis
hν ( > 280 nm)
H
HKen Tsutsumi, Kimitada Terao, HirokiYamaguchi, Syogo Yoshimura, TsumoruMorimoto, Kiyomi Kakiuchi,* TakahideFukuyama, and Ilhyong Ryu*doi:10.1246/cl.2010.828Electronic Supporting Information
830 Hg(OTf)2-catalyzed Cycloisomerization ofAryl- and Hetero-substituted 1,3-Dienes
OMe OMe
OMe OMe
C-C Cyclization
NHTs NTsHg(OTf)2 (2 mol%)
C-N Cyclization
Hg(OTf)2 (1 mol%)
Hirofumi Yamamoto,* Shinya Shiomi, DaikiOdate, Ikuo Sasaki, Kosuke Namba, HiroshiImagawa, and Mugio Nishizawa*doi:10.1246/cl.2010.830Electronic Supporting Information
832 Fine Tuning of Pd0 Nanoparticle Formationon Hydroxyapatite and Its Application forRegioselective Quinoline Hydrogenation
Norifumi Hashimoto, Yusuke Takahashi,Takayoshi Hara, Shogo Shimazu, TakatoMitsudome, Tomoo Mizugaki, KoichiroJitsukawa, and Kiyotomi Kaneda*doi:10.1246/cl.2010.832Electronic Supporting Information
835 Asymmetric Total Synthesis of Glycinoecle-pin A: Generation of a Novel BridgeheadAnion Species
Glycinoeclepin A
O
NNMe2
Li
HOCO2H
O CO2HO
AcO
OTf
TsO+
Yasuhiro Shiina, Yoshihide Tomata, MasaakiMiyashita, and Keiji Tanino*doi:10.1246/cl.2010.835
Chemistry Letters Vol.39, No.8 (2010)C-92
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
838 One-pot Formation of Furfural from Xylosevia Isomerization and Successive Dehydra-tion Reactions over Heterogeneous Acid andBase Catalysts
An efficient furfural formation from xylose was demonstrated using a solid acid and a base inone-pot via aldose−ketose isomerization and successive dehydration of xylulose to furfural.
OH-OH- OH-HCO3-
SO3H
Hydrotalcite Amberlyst-15
O
OH
OHOH
OHO
OH
OHOH
OH
O
O
Xylose Xylulose Furfural
Isomerization Dehydration
Atsushi Takagaki, Mika Ohara, ShunNishimura, and Kohki Ebitani*doi:10.1246/cl.2010.838Electronic Supporting Information
841 Poly-L-lysine-induced Self-association andLuminescence of Dicyanoaurate(I)
P(Lys)-Au
−Au
−Au
−Au
−Au
−Au
NH3+
NH3+
NH3+
NH3+NH3+
NH3
NH3NH3NH3
NH3
+
+
++
+
Poly-L-lysine (P(Lys))
[Au(CN)2] −
NH3+
+
NH3+
+
NH3+
+
NH3+
+
NH3+
+
NH3
+
NH3
+
NH3
+
NH3
+
NH3
+
+ + + +
NH3
+−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
−Au
Toshiyuki Moriuchi,* Kazuki Yoshii, ChiakiKatano, and Toshikazu Hirao*doi:10.1246/cl.2010.841Electronic Supporting Information
844 Enhancement of Discrimination Ability forcis- and trans-Decalins through Side-chainOrdering in Comb-shaped Polymer
Atsuomi Shundo, Abul K. Mallik, HisakiNakashima, Makoto Takafuji, Shoji Nagaoka,M. A. Jamil Chowdhury, and Hirotaka Ihara*doi:10.1246/cl.2010.844
846 Significant Effects of Anion in AqueousReactant Solution on Photocatalytic O2
Evolution and Fe(III) Reduction
Photocatalytic Osolution.
2 evolution in the presence of Fe3+ ion only changing the condition of reactant
0
50
100
150
200
250
300
350
400
0 1 2Time / h
Am
ount
of
O2
evol
ved
/ µm
ol Reactant solution: (a) FeCl3 aq., (b)Fe2(SO4)3 aq.Light source: 300W Xe-lampIncident light: λ > 300 nm
(a)
(b)
10 times
AQY : 51% at 365 nm
Stoichiometricamount of O2
0.5 1.5
Yugo Miseki,* Hitoshi Kusama, HidekiSugihara, and Kazuhiro Sayama*doi:10.1246/cl.2010.846Electronic Supporting Information
848 Adsorption of Cl¹ Ion with Pyrolysis Prod-ucts of Yttrium Oxynitrate Hydrate,Y2(OH)6¹x(NO3)x¢nH2O
Upt
ake
amou
nt o
f C
l-io
n/m
equi
v g−1
0
1.0
2.0
3.0
4.0
Temperature /°C200 400 600300100 500
0.1M HCl
0.1M NaClNobuhiro Kumada,* Go Kato, YoshinoriYonesaki, Takahiro Takei, NobukazuKinomura, and Yasuharu Oonodoi:10.1246/cl.2010.848
Chemistry Letters Vol.39, No.8 (2010) C-93
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
850 Reactive Template Fabrication of UniformCoreShell Polyaniline/Multiwalled CarbonNanotube Nanocomposite and Its Electro-chemical Capacitance
Uniform core−shell polyaniline/multiwalledcarbon nanotube nanocomposite was syn-thesized by a facile and efficient reactivetemplate method. The mesoporous core−shellnanocomposite provides much richer channelsfor electrolyte ions and electrons to contacteven more electroactive sites for fast energystorage.Changzhou Yuan,* Laifa Shen, Fang Zhang,
Xiangjun Lu, and Xiaogang Zhang*doi:10.1246/cl.2010.850
852 XAFS Analysis of the Bronchoalveolar Lav-age Fluid of a Tungsten Carbide Pneumo-coniosis Patient
Motohiro Uo,* Kiyotaka Asakura, KanaWatanabe, and Fumio Wataridoi:10.1246/cl.2010.852
854 Formation of Hydroxyapatite MicrotubesAssisted with Anatase under HydrothermalConditions
Masanobu Kamitakahara,* Setsuaki Murakami,Hiroko Takahashi, Noriaki Watanabe, and KojiIokudoi:10.1246/cl.2010.854
856 An Efficient and Practical Method for thePreparation of a Branched Oligoglycerolwith Acetonide Protection Groups
O
O
O
O
O
O
HOHO
O
O
O Cl
KOHBu4NBrH2O
OAc
O
O
O
O
O
O
HO
CommerciallyAvailable A New
IntermediateBGL003(Atn)2
Atn = acetonide [−C(CH3)2−]
Hisao Nemoto,* Masaki Kamiya, AkiNakamoto, Ayato Katagiri, Kohsuke Yoshitomi,Tomoyuki Kawamura, and Hatsuhiko Hattoridoi:10.1246/cl.2010.856Electronic Supporting Information
858 Plate Anodic Alumina-supported NickelCatalysts in Steam Reforming of Methane:Effects of Hydrogen Addition, ElectricalHeating, and Pt Doping
Lu Zhou, Yu Guo, Jian Chen, Wen Zhao,Makoto Sakurai, and Hideo Kameyama*doi:10.1246/cl.2010.858
Chemistry Letters Vol.39, No.8 (2010)C-94
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
861 Observation of Electrochemiluminescencefrom Indolo[2,3-b]tropone Zinc(II) ComplexUsing Benzoyl Peroxide as Coreactant
Jiye Jin,* Kunihiro Ito, Fumiki Takahashi, andMitsunori Oda*doi:10.1246/cl.2010.861
864 Structure and Photovoltaic Properties of (E)-2-Cyano-3-[4-(diphenylamino)phenyl]acrylicAcid Substituted by tert-Butyl Groups
Katsuhiko Ono,* Tomoya Yamaguchi, andMasaaki Tomuradoi:10.1246/cl.2010.864Electronic Supporting Information
867 Niobium-catalyzed Activation of CF3 Groupon Alkene: Synthesis of Substituted Indenes
Ar1
HAr2
CF3
R Ar1
Ar2
H HNbCl5 30 mol%NaAlH4 4 equiv
1,4-dioxane, refluxR52-83% yield
A CF3 group attached to an alkene moiety was catalytically activated with a low-valent niobiumspecies. A niobium carbenoid center, generated in situ, underwent insertion to an internalaromatic C–H σ bond and indene derivatives were obtained in good yields.
Kohei Fuchibe, Kohei Atobe, Yukari Fujita,Keiji Mori, and Takahiko Akiyama*doi:10.1246/cl.2010.867Electronic Supporting Information
870 Speciation of Tungsten in Natural Ferro-manganese Oxides Using Wavelength Dis-persive XAFS
Tungsten in natural ferromanganese oxides is in distorted octahedral symmetry.
Teruhiko Kashiwabara,* Yoshio Takahashi,Tomoya Uruga, Hajime Tanida, Yasuko Terada,Yasuhiro Niwa, and Masaharu Nomuradoi:10.1246/cl.2010.870
872 Study on the Rapid Spin Equilibrium inPh4P[ZnIIFeIII(mto)3] (mto =Monothiooxa-lato)
t2g
eg
t2g
eg
10−10 <ττ < 10−7
HS (S = 5/2)
LS (S = 1/2)
FeIII site
FeIII ZnII
OS
OO O
S
S
O
O
OS
O
OO
OO
OO
SOKoichi Kagesawa, Atsushi Okazawa, Masaya
Enomoto, and Norimichi Kojima*doi:10.1246/cl.2010.872Electronic Supporting Information
Chemistry Letters Vol.39, No.8 (2010) C-95
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
874 Di(hydroxo)porphyrin GeIV Complex/SilicaGel Composite as Visible Light-assistedRadical Generator
R
R•
Ge(tpp)+•
OH
SiO2/HON
N
N
NPh
Ph
Ph
Ph
Ge
HO
OH
Ge(tpp)
OH
OH/SiO2
Ge(tpp)
O•
OH/SiO2
SiO2
O2
HOO•
hνO2
−•
H
Tsutomu Shiragami,* Ryuichi Shiraki, RyuichiMakise, Jin Matsumoto, and Masahide Yasudadoi:10.1246/cl.2010.874
876 Highly Stable Solubilization of MembraneProtein Bacteriorhodopsin with a Short-chain Phospholipid Diheptanoylphosphati-dylcholine
Masashi Sonoyama,* Mina Fukumoto, andYumiko Kuwabaradoi:10.1246/cl.2010.876
878 Hydrogen Production from Water UsingNovel Three-dimensional InterpenetratedZnPd Coordination Polymer
Yuhei Miyazaki, Yusuke Kataoka, YasutakaKitagawa, Mitutaka Okumura, and WasukeMori*doi:10.1246/cl.2010.878
881 Microporous Acidic Cesium Salt of 12-Tungstosilicic Acid Cs3HSiW12O40 as a Size-selective Solid Acid Catalyst
Cs+ Cs+
Cs+
Cs+
Cs + Cs +
Cs + Cs+ Cs +
Cs + Cs+Cs + Cs +
H+
H+
H+
H+
H+
MicroporeMicropore
O
O
O
O O
O
OH
OHYuichi Kamiya,* Shogo Sano, Yu-ki Miura,Yohei Uchida, Yuki Ogawa, Yukari Iwase, andToshio Okuharadoi:10.1246/cl.2010.881Electronic Supporting Information
884 Photocatalytic and Antibacterial Activitiesover WO3 on Glass Filters
WO3 with cocatalyst on glass filter
Organic compounds CO2
Photocatalytic effectunder light
Antibacterial effectIn dark
Kazuhiro Sayama,* Hiroki Hayashi, YoshiyaKonishi, Takahiro Gunji, and Hideki Sugiharadoi:10.1246/cl.2010.884Electronic Supporting Information
Chemistry Letters Vol.39, No.8 (2010)C-96
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
886 Eu(TTA)3phen Nanobelts with EnhancedLuminescent Properties Prepared by Self-assembly
Meili Guan, Dekun Ma,* Sensen Liu,Dongpeng Yang, Jinglu Jiang, and ShaomingHuang*doi:10.1246/cl.2010.886Electronic Supporting Information
888 Synthesis ofMgSiN2 Cuboids by a Solid-stateReaction MgSiN2 cuboids were prepared
350−500 °C for 12 h. SEM, TEM,
the product is composed of
amount of Mg and NaN3 favors
using Si, Mg, and NaN3 powdersas reactants in autoclaves at
and HRTEM images reveal that
crystalline MgSiN2 cuboids. It isfound that an appropriate excess
the formation of MgSiN2.
Yajun Li, Liqiang Xu,* Liancheng Wang,Zhicheng Ju, Lishan Yang, Zheng Xing, andYitai Qian*doi:10.1246/cl.2010.888
890 Spectroscopic Changes of Silicon NanowiresInduced by Femtosecond Laser Pulses When HF-treated silicon nanowires
levels, especially oxygen and silicon
(SiNWs) were irradiated by femtosecondlaser pulses, three new energy transitionsappeared in the UV region, which mightbe attributed to defect-related deep
vacancies rather than their morphologyand structure changes.
200 220 240 260 280 300
0.00
0.04
0.08
0.12
∆ A
Wavelength/nm
0 s 9 s 13 s 17 s 21 s
235 nm244 nm
253 nm
Xiaodan Zhang, Hua Tian, Junhui He,* andXiangyun Fangdoi:10.1246/cl.2010.890Electronic Supporting Information
892 Preparation of Loose-fit Polyrotaxane Com-posed of ¢-Cyclodextrin and Poly(ethyleneglycol) Derivatives through the SlippingExpanding Protocol
Ryo Katoono,* Yuichiro Kobayashi, andNobuhiko Yuidoi:10.1246/cl.2010.892Electronic Supporting Information
894 Rhenium-catalyzed Regioselective Synthesisof Phenol Derivatives from 1,3-Diesters andTerminal Alkynes
cat. Re2(CO)10R+
MeO
O O
OMe
OHR
R
O
OMe
cat. Re2(CO)10R+
EtO
O O
OEt
OHR
R
cat. In(OTf)3Yoichiro Kuninobu,* Takashi Iwanaga,Mitsumi Nishi, and Kazuhiko Takai*doi:10.1246/cl.2010.894Electronic Supporting Information
Chemistry Letters Vol.39, No.8 (2010) C-97
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
896 Nickel-catalyzed [4 + 2] Cycloaddition ofAlkynes to Carbonylsalicylamides via Elim-ination of Isocyanates
An intermolecular nickel-catalyzed [4 + 2] cycloaddition has been developed wherecarbonylsalicylamides react with alkynes to afford substituted chromones. The reactioninvolves an elimination of isocyanates and an addition of alkynes, that is, a formalsubstitution reaction of an isocyanate by an alkyne.
O
N
O
O
PhR1 R2+
O
OR1
R2
Ni cat.
Ph−NCO
Yasufumi Yoshino, Takuya Kurahashi,* andSeijiro Matsubara*doi:10.1246/cl.2010.896
898 Mutual Separation of Actinides from MiddleLanthanides by the Combination of TwoNeutral Donors, N,N,N¤,N¤-Tetraoctyl-3,6-di-oxaoctanediamide and N,N,N¤,N¤-Tetraethyl-diglycolamide
The combination of the extractant (DOODA) and masking agent (TEDGA) shows the betterseparation between lanthanides and actinides.
OH2C
H2C CH2
CONR
R
O CH2
CO N
R
R
DOODA (R: C8H17 or C12H25)
O
H2C
C
OO
C
CH2
N
N
C2H5
C2H5C2H5
C2H5
TEDGA
Yuji Sasaki,* Yasuji Morita, YoshihiroKitatsuji, and Takaumi Kimuradoi:10.1246/cl.2010.898
900 Bimolecular Rate Constants between Levo-glucosan and Hydroxyl Radical: Effects ofpH and Temperature
(1/T )/K−1
0.0031 0.0032 0.0033 0.0034 0.0035 0.0036
ln(k
)Le
v+O
H
19.0
20.0
21.0
22.0
23.0
24.0 pH 3.0 pH 5.5 pH 8.0
kLev+OH
Levoglucosan + •OH Product
Takashi Teraji and Takemitsu Arakaki*doi:10.1246/cl.2010.900Electronic Supporting Information
902 A Simple and Convenient Method to Fab-ricate Hexagonally Ordered Gold Nano-particle Arrays Using Diblock CopolymerMicelle Template spin-coat
++ ++ ++ ++ ++
16.7
/nm
0
27.1
/nm
0
(a) (b)
AuNPs
(a)
(b)
+ + + + + +
- - - - - -
Shigeru Watanabe,* Shin Nakano, Chie Imai,Inamur R. Laskar, Tomonori Komura, ShingoHadano, and Tomokazu Iyodadoi:10.1246/cl.2010.902
905
Additions and Corrections
Structure Determination of H-LDS: AnAcidified Form of the Layered Silicate K-LDS
Takuji Ikeda,* Manami Uenaka, KenichiKomura, and Yoshihiro Sugidoi:10.1246/cl.2010.905
Chemistry Letters Vol.39, No.8 (2010)C-98
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan