S1  

Electronic Supplementary Information (ESI) For

AIE-active tetraphenylethene functionalized metal-organic framework for

selective detection of nitroaromatic explosives and organic photocatalysis

Qiu-Yan Li,‡a Zheng Ma,‡a Wen-Qiang Zhang,a Jia-Long Xu,a Wei Wei,a Han Lu,a Xinsheng Zhaob

and Xiao-Jun Wang*a

aJiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of

Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P. R. China.

E-mail: xjwang@jsnu.edu.cn (X.-J. Wang)

bSchool of Physics and Electronic Engineering, Jiangsu Normal University, Xuzhou 221116, P. R.

China.

‡These authors contributed equally.

Electronic Supplementary Material (ESI) for ChemComm.This journal is © The Royal Society of Chemistry 2016

S2  

General method and materials

Unless specifically mentioned, all chemicals are commercially available and were used as received.

NMR spectra were taken on a Bruker AV400 at room temperature. The powder X-ray diffraction

(PXRD) measurements were taken on a Bruker D8 diffractometer using Cu-Kα radiation (λ = 1.5418

Å) at room temperature. Steady-state fluorescence measurements were carried out using a Hitachi

4500 spectrophotometer. Thermogravimetric analysis (TGA) was carried out on a TGA-Q500

thermoanalyzer with a heating rate of 10 °C/min under nitrogen atmosphere. The solid-state emission

spectra, absolute quantum yield and lifetime data were acquired on Edinburgh FLS920 instrument

consisting integrating sphere. Electron paramagnetic resonance (EPR) spectra were recorded at room

temperature using a Bruker ESP-300E spectrometer at 9.8 GHz, X-band, with 100 Hz field

modulation. ESI-MS experiments were carried out on a ThermoFisher Q-Exactive LC-MS.

Low-pressure gas sorption measurements were performed by using Quantachrome Instruments

Autosorb-iQ (Boynton Beach, Florida USA) with the extra-high pure gases. The as-synthesized

MOF UiO-68-mtpdc/etpdc (50 mg) was immersed in CH3OH (20 mL) for 2 day, during which time

fresh CH3OH was replaced six times. The samples were then moved into a sample cell and dried

under vacuum at 80 °C and 120 °C by using the “outgasser” function of the machine for 3 h and 12 h

before the measurement, respectively.

S3  

Synthesis and Characterizations

Scheme S1. The synthetic route for H2- etpdc. Reagents and conditions: a) methyl 4-boronobenzoate, Cs2CO3, CsF,

Pd(dppf)Cl2, Pd(PPh3)4, THF/H2O, 70 °C for 2 d; b) 4-(1,2,2-triphenylvinyl)benzaldehyde, ZrCl4, CHCl3, 50 °C for

2 d; c) KOH, THF, CH3OH, 90 °C for 2 h; TFA, THF, 1 h, room temperature.

Compound 2: A mixture of Cs2CO3 (7.36 g, 22.5 mmol) and CsF (0.57 g, 3.75 mmol) were

dissolved in water (2 mL) and added into a 250 mL round bottom flask with a magnetic stir bar.

Dried and degassed THF (100 mL) was added to the reaction flask and the reaction mixture was

degassed by sparging with N2 for 2 h. Then, compound 1[S1] (2.0 g, 7.5 mmol), methyl

4-boronobenzoate (4.04 g, 22.5 mmol), Pd(dppf)Cl2 (0.55 g, 0.75 mmol) and Pd(PPh3)4 (0.26 g,

0.023 mmol) were added into the mixture. The round bottom flask was vacuumed and pushed into N2

for 5 times. The reaction was heated at 70 °C for 48 hours under an argon atmosphere. After that, the

reaction mixture was cooled down to room temperature and extracted by DCM (200 mL x 2). The

combined organic layer was washed with water (300 mL x 5), and dried over anhydrous Na2SO4 then

evaporated under reduced pressure. The crude product was further purified using column

chromatograph (DCM/CH3COOC2H5, 100/6) to give orange solid (1.23 g, 3.27 mmol, yield: 43.6%).

1H NMR (400 MHz, d6-DMSO) δ 8.04 (d, J = 8.2 Hz, 4H), 7.60 (d, J = 8.2 Hz, 4H), 6.53 (s, 2H),

4.44 (br, 4H), 3.88 (s, 6H).

Compound 3: The compound 2 (0.30 g, 0.80 mmol) and 4-(1,2,2-triphenylvinyl)benzaldehyde[S2]

(0.30 g, 0.81 mmol) were dissolved in CHCl3 (60 mL) and added into a 100mL round bottom flask

with a magnetic stir bar. Then, ZrCl4 (0.018 g, 0.08 mmol) was added into the mixture. The reaction

mixture was heated at 50°C for 48h. After that, the reaction mixture was cooled down to room

temperature and evaporated under reduced pressure. The crude product was further purified using

NH

N

O O

OO

Br

Br

NH2

NH2

NH2

NH2

O O

OO

NH

N

O OH

OHO

a) b) c)

1 2 3 H2-etpdc

S4  

column chromatograph (DCM/petroleum ether 100/33) to give the orange solid (0.41 g, 0.57 mmol,

yield: 71.5%). 1H NMR (400 MHz, d6-DMSO) δ 12.70 (s, 1H), 8.37 (d, J = 7.9 Hz, 2H), 8.12-8.06

(m, 6H), 7.88 (d, J = 7.6 Hz, 2H), 7.63 (d, J = 7.6 Hz, 1H), 7.40 (d, J = 7.4 Hz, 1H), 7.19-6.99 (m,

17H), 3.90 (d, J = 4.5 Hz, 6H).

Compound H2-etpdc: The compound 3 (0.36 g, 0.50 mmol) was dissolved in THF (50mL) and

KOH (0.28 g, 5 mmol) was dissolved in CH3OH (5mL). Then, the two solution were added into a

100ml round bottom flask with a magnetic stir bar. The reaction mixture was heated at 90°C for 2h.

After cooling down to the room temperature the reaction was separated through the suction filter to

afford the yellow solid which was washed with THF (50mL x 3). Then the solid was dissolved in

THF (50mL) and TFA (6mL). The reaction was stirred at room temperature for 1h. Then the solution

was obtained by centrifugal to get the crude product, which was further washed by THF (50mL x 2),

then washed by water (50mL x 2). At last, the product was dried to give (0.32 g, 0.47 mmol, yield:

93.2%). 1H NMR (400 MHz, d6-DMSO) δ 12.98 (s, 2H), 12.68 (s, 1H), 8.33 (d, J = 8.2 Hz, 2H),

8.14-8.03 (m, 6H), 7.84 (d, J = 8.1 Hz, 2H), 7.62 (d, J = 7.8 Hz, 1H), 7.39 (d, J = 7.8 Hz, 1H),

7.22-6.96 (m, 17H).

Preparation for MOF UiO-68-mtpdc/etpdc: Organic ligands H2-etpdc (66 mg, 0.1 mmol),

H2-mtpdc (33 mg, 0.1 mmol) and ZrCl4 (51 mg, 0.22 mmol) were dissolved in DMF (75 mL), which

was added into a 250 mL round bottom flask with a magnetic stir bar. Then, 3.1 mL HAc was added

to the reaction flask and the reaction mixture was heated at 100 °C for 72 hours under an argon

atmosphere. After cooling to room temperature, the product was separated by centrifugal to afford

the white solid which was washed with DMF (100 mL x 3) and EtOH (100 mL x 3), respectively.

The sample was dried in vacuum. The powder X-ray diffraction (PXRD) pattern of product was

similar to the simulated pattern generated from single crystal data (Fig. S1 and S2), confirming its

UiO-68 topological framework and the phase purity. The molar ratio of etpdc to mtpdc in MOF

UiO-68-mtpdc/etpdc was determined to be 1:1.2. In addition, through the varying the feeding ratio of

H2-etpdc and H2-mtpdc, another two MOF samples with different ratio of linkers were prepared by

the similar procedure (UiO-68-mtpdc/etpdc’ and UiO-68-mtpdc/etpdc” refer to 1:2.2 and 1:0.57 the

ratio of H2-etpdc and H2-mtpdc).

 

Fig. S1 PX

Fig. S2 The z

and UiO-68

Sc

XRD patterns

zoomed-in co

8-mtpdc (bott

tiny shift

cheme S2. Sy

s of MOF as-

omparison of

tom). The pos

may be cause

ynthesis of 1:

synthesized a

contain

f PXRD patte

sition of main

ed by the larg

10 20

2

5

2

1

23

S5 

1 mixed strut

and activated

ns H2-mtpdc

erns (2Theta =

n peaks (1-10

ge ligand H2-e

0 30

activ

as-synthes

2Theta / degre

as-s

10

2Theta /degre

4 5

6 7 8

t MOF UiO-6

UiO-68-mtp

linker.)

= 3-20°) of as

0) matches ve

etpdc in MOF

40

vated UiO-68-mtpd

sized UiO-68-mtpd

ee

simulated

synthesized UiO-68

15

ee

89

68-mtpdc/etpd

dc/etpdc. (M

s-synthesized

ry well. The v

F UiO-68-mtp

50

dc/etpdc

dc/etpdc

d UiO-68

8-mtpdc

20

10

dc.

 

MOF UiO-68-m

d UiO-68-mtp

variation of i

tpdc/etpdc.

mtpdc only

pdc/etpdc (top

intensity and

p)

 

Fig. S3 1H

H2-mtpdc in

ratio of aro

content

Fig. S4 TGA

of activate

0

40

60

80

100

We

igh

t /

%

H NMR of dig

as-prepared

ound 1:1.2, w

of H2-mtpdc

A plot of as-sy

ed sample can

200

Te

gested UiO-68

MOF was ca

which is almo

linker in MO

ynthesized (l

n be attributed

f

400

emperature / o

8-mtpdc/etpd

alculated from

st same to the

OF should be

eft) and deso

d to the re-ad

framework ca

600oC

S6 

dc by HF in D

m the integrati

e initial ratio

ascribed to th

olvated (right)

dsorbed water

an be stable u

800

Wei

gh

t /

%

DMSO-d6. Th

ion of He (H2

of 1:1 in prep

he steric bulk

) MOF UiO-6

r during samp

up to ~500 °C

040

60

80

100

e molar ratio

2-etpdc) and H

paration of M

k of TPE moie

68-mtpdc/etpd

ple weighing

C.

200 4

Tempera

o of linkers H2

H2 (H2-mtpd

MOF. The slig

ety of H2-etpd

dc. The initia

in air. This su

00 600

ature / oC

2-etpdc and

dc), giving the

ghtly higher

dc linker.

al weight loss

uggests the

800

e

s

 

Fig.

Fig

Fig. S7 Em

00

100

200

300

Nit

rog

en a

t S

TP

/ cm

3 g-1

S5 Nitrogen

g. S6 Photogr

mission spect

.0 0.2

Re

adsorptio desorptio

sorption isoth

raphs of MOF

tra of ligand H

0.4 0.6

elative Pressur

onon

4

No

rmal

ized

In

ten

sit

y

herm at 77 K

UiO

F UiO-68-mtp

H2-etpdc and

0.8 1.

re P/P0

400 50

W

S7 

K (left) and BE

O-68-mtpdc/et

pdc/etpdc und

MOF UiO-6

.0

1/[W

((P

0/P

)-1)

]

00 60

Wavelength /

ET specific su

tpdc.

der daylight (

68-mtpdc/etpd

0.020.08

0.12

0.16

0.20

00 70

nm

ligand H2-etpdc MOF UiO-68-mtpd

urface area pl

(left) and 365

 

dc in solid sta

0.03

Relative P

00

dc/etpdc

lot (right) of

5 nm light (rig

ate at room te

0.04

SBET = 960 m2

Pressure P/P0

MOF

ght).

emperature.

0.05

2 g-1

 

Table S1. Ph

H2-etp

UiO-6

UiO-6

UiO-6

Fig. S8 Ph

hotophysical p

pdc

68-mtpdc/etpdc

68-mtpdc/etpdc

68-mtpdc/etpdc

hotographs of

parameters fo

λem, max, n

518

c 490

c’ 488

c” 491

f ligand H2-etp

or ligand H2-e

for

nm Φ, %

32

48

41

53

S8 

tpdc under da

etpdc and MO

r TNP and DN

lifetime, n

τ1 1.83

τ1 1.96

aylight (left) a

OFs as well a

NP.

ns (% contribut

(48), τ2 5.15 (5

(55), τ2 5.11 (4

-

-

and 365 nm li

as their quenc

tion)

2)

5) 2.8

2.9

2.6

ight (right).

ching effect c

ksv, 104 M-1

-

(TNP), 2.3 (DN

(TNP), 2.5 (DN

(TNP), 2.0 (DN

coefficient (ks

NP)

NP)

NP)

sv)

 

Fig. S9 1H N

and H2-

Fig. S10 1H

and H2-

NMR of dige

-mtpdc in as-

NMR of dige

mtpdc in as-p

ested UiO-68-

-prepared MO

ested UiO-68

prepared MO

-mtpdc/etpdc

OF to be 1:2.2

-mtpdc/etpdc

OF to be 1:0.5

S9 

c’ by HF in D

2 from the int

c” by HF in D

7 from the in

MSO-d6, giv

tegration of H

DMSO-d6, giv

ntegration of H

ing the molar

He (H2-etpdc)

ving the mola

He (H2-etpdc

r ratio of link

) and H2 (H2-

ar ratio of link

c) and H2 (H2

kers H2-etpdc

-mtpdc).

kers H2-etpdc

2-mtpdc).

c

S10  

Fig. S11 Emission spectra of MOF UiO-68-mtpdc/etpdc dispersed in CH3OH (0.02 mg/mL) upon incremental

addition of DNP (left); and the corresponding Stern-Volmer plot of the quenching fluorescence intensity as a

function of DNP concentration (right, ksv = 2.3 × 104 M-1).

Fig. S12 Emission spectra of MOF UiO-68-mtpdc/etpdc dispersed in CH3OH (0.02 mg/mL) upon incremental

addition of p-NP (left); and the corresponding Stern-Volmer plot of the quenching fluorescence intensity as a

function of p-NP concentration (right, ksv = 7.2 × 103 M-1).

400 450 500 550 600 6500

200

400

600

800

1000

Inte

ns

ity

/ a

.u.

Wavelength / nm

0

100 M

DNP

10 20 30 40 50

0.3

0.6

0.9

1.2

1.5

(I0/

I) -

1

Concentration / M

400 450 500 550 600 6500

200

400

600

800

1000

Inte

nsi

ty /

a.u

.

Wavelength / nm

0

100 M

p-NP

10 20 30 40 500.0

0.1

0.2

0.3

0.4

(I0/

I) -

1

Concentration / M

 

Fig. S13 Fl

UiO-68-mtpd

2,4,6-trinitro

2,4-dinitrotol

(p-NT), nitro

luorescence q

dc/etpdc (0.0

phenol (TN

luene (DNT)

obenzene (NB

quenching in

02 mg/mL)

NP), 2,4-din

, 1,3-dinitrob

B).

nduced after

in CH3OH

itrophenol (

benzene (DNB

S11 

r addition of

under a U

(DNP), p-n

B), o-nitrotolu

f various nit

UV lamp (36

nitrophenol (

uene (o-NT),

troaromatic c

65 nm). Fro

(p-NP), 2,4

m-nitrotolue

compounds

om left to

4,6-trinitrotolu

ene (m-NT), p

(0.1 mM) to

right: blank

uene (TNT)

p-nitrotoluene

o

k,

),

e

 

Computa

For simplif

software.[S3

functional w

center, Dep

Frequencie

correspond

Fig. S14 T

energy-minim

d(H79-N39) =

ational De

fying the co

3] Density

with the 3-2

partment o

s were also

ed to a min

The optimized

mized structu

= 1.01 Å, d(O

etails

omputation,

functional

21G basis s

of Chemistr

o calculated

imum on th

d complex str

ure are listed b

O16-N38) = 2.5

we only us

theory (DF

set. Four pr

ry, Beijing

d at the sam

he potential

ructure betwe

below (d: dis

59 Å, θ(O16-H

blue, gray

S12 

se TNP and

FT) calcula

rocessing co

Normal U

me level of

energy surf

een TNP and

stance; θ: bon

H19-N38) = 15

and white, re

d etpdc-link

tions were

ores and 8 G

University)

f theory to

face.

etpdc-linker.

nd angle): d(O

6o. Oxygen, n

espectively.

ker for calcu

performed

GB physica

were used

ensure that

Several impo

O16-H19) = 1.5

nitrogen, carb

ulation by G

d by using

al memory

for the o

t each stati

ortant parame

58 Å, d(H19-N

bon and hydro

Gaussian 09

the B3LYP

(Computing

ptimization

ionary poin

eters of the

N38) = 1.07 Å

ogen are red,

9

P

g

n.

nt

Å,

S13  

General procedure for Aerobic CDC reactions of tetrahydroisoquinolines 1 with indoles 2

catalyzed by UiO-68-mtpdc/etpdc: The weighed photocatalyst UiO-68-mtpdc/etpdc (2 mg), 1 (0.1

mmol) and 2 (0.3mmol) were added into 2 mL CH3OH. The reaction mixture with stirring was

irradiated by blue LEDs for 12 hours under air at room temperature. 1H NMR spectroscopy was

employed to determine the yield; and 1H NMR spectra of products 3 are in agreement with reported

literature.[S4] The catalyst for cyclic reaction was recycled by centrifugation at 10 000 rpm and

washed by fresh CH3OH two times.

Table S2 Screening of the model CDC reaction conditionsa

Entry Conditions Solvent Time (h) Yield (%)b

1 UiO-68-mtpdc/etpdc, 1 mg CH3OH 8 41

2 UiO-68-mtpdc/etpdc, 1 mg CH3OH 12 68

3 UiO-68-mtpdc/etpdc, 2 mg CH3OH 8 72

4

5

6

UiO-68-mtpdc/etpdc, 2 mg

UiO-68-mtpdc/etpdc’, 2mg

UiO-68-mtpdc/etpdc”, 2mg

CH3OH

CH3OH

CH3OH

12

12

7

93

79

92

7 UiO-68-mtpdc/etpdc, 2 mg CH3CN 12 87

8 UiO-68-mtpdc/etpdc, 2 mg DMF 12 83

9 No catalyst CH3OH 12 trace

10 In dark CH3OH 12 trace

11

12

In N2 atmosphere

In O2 atmosphere

CH3OH

CH3OH

12

7

trace

90

13c UiO-68-mtpdc, 2 mg CH3OH 12 trace

14d UiO-68-mtpdc/etpdc, 2 mg CH3OH - 61

aReaction conditions: 1a (0.1 mmol) and 2a (0.3 mmol), blue LEDs (λmax = 450 nm), solvent (2

mL). The reaction with stirring was conducted in air at room temperature. bDetermined by 1H NMR. cMOF UiO-68-mtpdc only contains ligand H2-mtpdc.[S1] dAfter 5 h reaction the MOF was filtered

out (yield: 58%) and the filtrate went on for another 8 hours.

S14  

Table S3 The aerobic CDC reactions of tetrahydroisoquinolines 1 with indoles 2 photocatalyzed by

UiO-68-mtpdc/etpdc a

 

aReaction conditions: 1 (0.1 mmol), 2 (0.3 mmol) and UiO-68-mtpdc/etpdc (2 mg) in CH3OH (2

mL) under air at room temperature with 12 h blue LEDs (λmax = 450 nm) irradiation. Yields were

determined by 1H NMR.

 

 

 

 

 

 

 

 

S15  

Table S4 The aerobic CDC reactions of tetrahydroisoquinolines 1 with nitroalkanes 4 photocatalyzed by

UiO-68-mtpdc/etpdc a

 

aReaction conditions: 1 (0.1 mmol) and 4 (1 mL), blue LEDs (λmax = 450 nm). The reaction with

stirring was conducted in air at room temperature. Yields were determined by 1H NMR.

 

 

Fig. S15 Recycling experiments of UiO-68-mtpdc/etpdc for the reaction of N-phenyltetrahydroisoquinoline and

indole.

NAr

NAr

1 4 5

UiO-68-mtpdc/etpdc

blue LEDs, airR4 NO2

NO2R4

1 2 3 4 50

20

40

60

80

100

Yie

ld /

%

Run times

S16  

Fig. S16 PXRD patterns of MOF UiO-68-mtpdc/etpdc after photocatalysis.

 

Fig. S17 EPR measurements of a solution in CH3OH of UiO-68-mtpdc/etpdc without 1a (a) and with 1a (b) in the

presence of TEMP upon the irradiation of blue LEDs for 30 s; a solution in CH3OH of UiO-68-mtpdc/etpdc without

1a (c) and with 1a (d) in the presence of DMPO upon the irradiation of blue LEDs for 30 s. In O2 atmosphere.

 

Scheme S3 Proposed mechanism for the photocatalytic aerobic CDC reaction of N-phenyltetrahydroisoquinoline

and indole by MOF UiO-68-mtpdc/etpdc (photocatalyst, PC). ESI-MS was used to capture the intermediate of

imine cation and peroxide species. Also, the main product and by-product were observed in ESI-MS spectra.

10 20 30 40 50

UiO-68-mtpdc/etpdc (after 5 run photocatalysis)

UiO-68-mtpdc/etpdc (fresh)

simulated UiO-68

2Theta / degree

3450 3480 3510 3540 3570

(d)

(c)

(b)

Field / G

(a)

 

Fig. S18 ES

Fig. S19 ESI

S17 

SI-MS of main

I-MS of by-pr

n product 3a.

roduct amide

e.

 

Fig. S

Fi

S20 ESI-MS o

ig. S21 ESI-M

S18 

of intermedia

MS of interme

ate imine catio

ediate peroxi

on 1a+.

de.

 

Fig.

Fig.

S22 1H NMR

S23 1H NMR

S19 

R of compou

R of compou

und 2 in d6-DM

und 3 in d6-DM

MSO

MSO

 

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[S2] Y. Liu,

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Jaramillo, R.

Martin, K. M

Farkas, J. B.

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