Synthesis and Fluorescent Properties of Tetra-Biphenyl N-Substituted Phthalimides

Article abstract of DOI:10.1002/jccs.201700137

A series of tetra(biphenyl-4-yl)phthalimide (TBPPI) derivatives with different N-substituents (n-butyl, phenyl, p-methyl phenyl, and p-acetyl phenyl moieties for compounds 7–10, respectively) were prepared to examine their fluorescent behavior under various conditions. The chemical structure of compound 7 has been successfully confirmed by single crystal X-ray diffraction analysis. The photoluminescence (PL) spectra in different ratios of CH₂Cl₂/EtOH mixture solutions revealed that compounds 7 and 8 exhibited both aggregation-induced emission (AIE) and aggregation-caused quenching (ACQ) behaviors, while compounds 9 and 10 displayed AIE and aggregation-induced emission enhancement (AIEE) properties, respectively.

Full text of DOI:10.1002/jccs.201700137

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Article
Synthesis and Fluorescent Properties of Tetra-Biphenyl N-Substituted Phthalimides
*
Sheng-Han Huang, Yu-Wei Shih, Yan-Liang Lin and Te-Fang Yang
Department of Applied Chemistry, National Chi Nan University, Puli 545, Nantou, Taiwan
(Received: April 20, 2017; Accepted: July 4, 2017; DOI: 10.1002/jccs.201700137)
A series of tetra(biphenyl-4-yl)phthalimide (TBPPI) derivatives with different N-substituents
(
n-butyl, phenyl, p-methyl phenyl, and p-acetyl phenyl moieties for compounds 7–10, respectively)
were prepared to examine their fluorescent behavior under various conditions. The chemical struc-
ture of compound 7 has been successfully confirmed by single crystal X-ray diffraction analysis.
The photoluminescence (PL) spectra in different ratios of CH Cl /EtOH mixture solutions
2
2
revealed that compounds 7 and 8 exhibited both aggregation-induced emission (AIE) and
aggregation-caused quenching (ACQ) behaviors, while compounds 9 and 10 displayed AIE and
aggregation-induced emission enhancement (AIEE) properties, respectively.
Keywords: Tetra-biphenyl phthalimide; Photoluminescence spectrum; Aggregation-induced
emission.
INTRODUCTION
Organic semiconductors have drawn much atten-
Since 2001, Tang et al. have been reporting a
series of unusual chromophores including silole and tet-
raphenylethene (TPE) derivatives (Figure 1) that are
nonluminescent in dilute solutions but emit bright lumi-
tion from organic chemists in recent decades owing to
their potential applications to inexpensive, lightweight,
flexible, and large-area electronic devices such as
5,6
nescence in their concentrated solution or cast films.
1
organic light-emitting diodes (OLEDs). Despite this
For example, dilute solutions of hexaphenylsilole (HPS)
in good solvents such as acetonitrile and tetrahydrofu-
ran (THF) are nonemissive because of the free rotation
of the phenyl rings against the silole core, which can
promising potential for commercial optoelectronic
applications, the fundamental intermolecular interac-
tions of a single compound containing the phthalimide
moiety both in dilute solution and in the solid state
have not yet been fully investigated. It is well known
that molecules of organic semiconductors commonly
5c
annihilate its excitons via a nonradiative pathway.
However, when HPS molecules aggregate in the solid
state, the restriction of intramolecular rotations (RIR)
block the nonradiative pathway, thus making the mole-
cules highly luminescent. They termed this abnormal
phenomenon “aggregation-induced emission” (AIE), in
which the π–π interactions cannot be formed because of
the heavy steric hindrance. Since AIE has high potential
for the applications of OLEDs, efforts have been made
to design and synthesize new AIE organic semiconduc-
2
consist of planar aromatic rings. For most organic
semiconductors, the molecules are isolated and lumi-
nescent in dilute solution. However, when the mole-
cules exist in the solid state, or the solution of the
molecules is highly concentrated, the luminescence
might be strongly quenched as a result of the aggrega-
3
tion of the molecules. Such “aggregation-caused
7
quenching” (ACQ) is believed to be due to the forma-
tion of π–π interactions, in which the electrons can be
delocalized over two or more molecules, leading to a
long lifetime of excitons, red-shifting of emission, and
tors. In 2010, Tang et al. utilized the AIE material
3TPETPA and the AIE enhancement (AIEE) material
TTPEPy as emitting layers to fabricate a series of
6a,6b
highly efficient OLEDs.
Because the hole mobility
4
low luminescence quantum efficiency. Therefore, how
in most organic semiconductors is much higher than the
electron mobility, an additional electron-transporting
layer (ETL) is needed to balance the charge mobilities
to reduce the impact of the ACQ effect is a principal
issue for real application of OLEDs.
*Corresponding author. Email: tfyang@ncnu.edu.tw
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Article
Huang et al.
Fig. 1. Chemical structures and abbreviated notations of selected AIE and AIEE materials in the literature.
8
and enhance the performance of OLEDs. To simplify
the fabrication process and lower the construction cost
of OLEDs, Tang et al. combined the electron-
transporting group 2,5-diaryl-1,3,4-oxadiazole (Oxa)
and the AIE chromophore TPE into a single molecule
Scheme 1. The chemical structure of compound 7 was
successfully confirmed by single-crystal X-ray diffrac-
tion analysis. In order to understand the AIE
(or AIEE) properties of TBPPIs, their fluorescent
behavior in different ratios of CH Cl /EtOH mixture
was investigated. Their photoluminescence (PL) spectra
showed that compounds 7 and 8 exhibited both AIE
and ACQ behaviors while compounds 9 and 10 dis-
played AIE and AIEE properties, respectively.
2
2
6c
(
TPE-Oxa). They demonstrated that the performance
of OLEDs based on TPE-Oxa without the ETL was
even better than that with the ETL. To the best of our
knowledge, only a few AIE chromophores with
electron-transporting groups have been reported so
6c–6i
far.
Therefore, the design and synthesis of new AIE
RESULTS AND DISCUSSION
chromophores with electron-transporting groups for
applications in OLEDs are extremely necessary.
In this study, we synthesized four electron-
deficient chromophores, tetra(biphenyl-4-yl)phthalimide
The idea of designing the target materials, namely
compounds 7–10 (Scheme 1), for this work is as follows:
in order to understand how the optical properties of the
tetra-biphenyl isoindole–dione structure could be influ-
enced by the various substituents on the nitrogen atom,
n-butyl moiety was adopted as the alkyl electron-
donating group on 7, phenyl moiety as the aryl electron-
donating group on 8, p-methyl phenyl moiety as the aryl
electron-donating group on 9, and p-acetyl phenyl moi-
ety as the aryl electron-withdrawing group on 10. Thus,
the target molecules 7–10 were synthesized based on the
methodology outlined in Scheme 1. According to the
(
TBPPI) derivatives (compounds 7–10), as shown in
9,10
procedure described in the literature.
periodination
of phthalic anhydride was carried out in concentrated
sulfuric acid to give tetraiodophthalic anhydride (2).
The reaction reported by Golub et al. was then applied
for the conversion of the anhydride 2 to compounds 3–
11
6.
Finally, Suzuki coupling reaction of tetraiodophtha-
limides 3–6 with biphenyl-4-boronic acid furnished the
target compounds 7–10, respectively.
It is noteworthy that a single crystal of compound
7
was obtained, and the structure of which was con-
Scheme 1. Synthetic routes to the tetra(biphenyl-4-yl)
1
phthalimide derivatives.
firmed by X-ray crystallography (Figure 2(a)). The
2
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Tetra-biphenyl Phthalimides
Fig. 2. Crystal structure of compound 7: (a) single
molecule and (b) the dimer packing. Carbon
in gray, hydrogen in white, oxygen in red,
and nitrogen in blue. Space-filling molecular
model presents examples of π-stacking dimers
for clarity.
Fig. 3. Fluorescent character of compound 7. (a) PL
−5
spectra in CH Cl /EtOH mixture (10 M)
2 2
excited at 300 nm. (b) Quantum yield in
CH Cl /EtOH mixture. (c) Photograph taken
2
2
dihedral angles between the phthalimide and substituted
phenyl rings, R1, R2, R3, and R4, were found to be as
under UV illumination.
ꢀ
ꢀ
ꢀ
ꢀ
large as 51.5 , 61.1 , 66.3 , and 64.9 , respectively,
demonstrating that there is steric hindrance between the
phthalimide core and the phenyl rings. The crystal
structure of compound 7 adopts antiparallel π-stacks of
dimers with a short intermolecular distance of 3.73 Å,
which indicates the existence of intermolecular interac-
tions. These antiparalleldimers reveal that the electron-
rich phenyl ring of phthalimide faces the electron-poor
maleinimide of phthalimide, as shown in Figure 2(b).
To investigate the optical properties of TBPPIs,
the fluorescent behaviors of 7–10 in different conditions
were measured using the method reported in the litera-
the phthalimide core. As the ratio of EtOH was
increased, the molecules of compound 7 were closer to
each other such that the intramolecular rotations of
biphenyl rings were restricted and the ΦF values were
enhanced.
At the same time, the molecules formed antiparal-
lel dimers progressively owing to the π–π interactions
Figure 2(b)), which caused the ACQ effect and the red-
shift of the emission.
When the amount of EtOH was less than 45%,
AIE was dominant, and therefore the luminescence was
enhanced and red-shifted. However, ACQ dominated
when the amount of EtOH was over 60%. The green
emission of E90 was similar to that of the cast film
under UV irradiation, which demonstrated that such
emission was from the antiparallel dimers of
compound 7.
(
12
ture. Compounds 7–10 dissolved well in good solvents
such as CH Cl and THF, and the fluorescence quan-
2
2
tum yields of these target molecules were obtained (see
2
Supporting information). In 10 μM of a pure CH Cl2
solution, compound 7 was weakly fluorescent with the
maximum intensity (λmax) at 455 nm and quantum yield
(
Φ ) as low as 17%. The PL intensity and quantum
F
The variations in wavelength of the PL spectra
yields (Φ ) of compound 7 were enhanced (Figure 3)
F
and Φ values of compound 8 (Figure 4) show similar
F
when the volume fraction of the nonsolvent, EtOH, was
increased from 0% (E0) to 45% (E45), while these
values were decreased as the amount of EtOH was lar-
ger than 60% (E60). The λmax values of compound
tendency as those of compounds 9 and 10 (Figures 5
and 6), indicating that the fluorescent behavior of com-
pound 8 at various ratios of CH Cl /EtOH mixture was
also controlled by AIE. In contrast to compound 7,
compounds 8–10 do not show any shift in wavelength
of the PL spectra with the amount of EtOH; at the
2
2
7
were red-shifted gradually from 455 (E0) to 512 nm
(E90) as the ratio of EtOH was increased. These results
indicated that the fluctuating Φ values and red-shifted
luminescence of compound 7 were due to the combined
effects of AIE and ACQ. In a good solvent, compound
F
same time, their Φ values were enhanced with increas-
F
ing fraction of EtOH. We therefore can conclude from
the above discussion that compounds 8–10 were AIE
and AIEE active, respectively. It is speculated that com-
pound 7 shows AIE and ACQ simultaneously such that
7
was weakly fluorescent due to the de-excitation of
excitons by free rotations of the biphenyl rings against
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Huang et al.
its emission spectrum is much broader than those of the
other compounds. The signal at 520 nm in Figure 6
(a) was probably caused by the acetyl group in
compound 10.
CONCLUSIONS
In conclusion, we have synthesized four new N-
substituted phthalimide derivatives (7–10) by the tradi-
tional Suzuki coupling method. The PL spectra demon-
strated that compound 7 presented both AIE and ACQ
behaviors; however, compounds 8–10 displayed AIE
and AIEE properties, respectively. Since compound
Fig. 4. Fluorescent character of compound 8. (a) PL
−5
spectra in CH
excited at 300 nm. (b) Quantum yield in
CH Cl /EtOH mixture. (c) Photograph taken
under UV illumination.
2 2
Cl /EtOH mixture (10 M)
7
could reveal excellent intermolecular π–π stacking
(Figure 2), it exhibited different fluorescent properties
from those of compounds 8–10. Further studies of the
electroluminescence properties of compounds 7–10 are
in progress. The performances of these compounds on
the application to OLEDs are also under investigation.
2
2
EXPERIMENTAL
Materials
Phthalic anhydride and K CO3 were purchased
2
from Showa Co. Ltd. and used as received. Periodic
acid, p-toluidine, iodine, and biphenyl-4-boronic acid
were purchased from Acros and used without further
purification. 4-Aminoacetophenone and n-butylamine
were from Alfa Aesar and used as received.
Palladium(II) acetate was from Lancaster Synthesis.
Dimethyl formamide was obtained from TEDIA as
ACS-grade solvent.
Fig. 5. Fluorescent character of compound 9. (a) PL
−5
spectra in CH Cl /EtOH mixture (10 M)
2
2
excited at 300 nm. (b) Quantum yield in
CH Cl /EtOH mixture. (c) Photograph taken
2
2
under UV illumination.
All reactions were carried out in a round-bottom
flask or a sealed tube. When necessary, moisture-
sensitive solvents were dried in accordance with stand-
ard procedures and transferred via a syringe. Crude
product solutions were dried on Na SO , filtered, and
2
4
ꢀ
then concentrated with a rotary evaporator below 40 C
at ~30 Torr. Flash column chromatography was per-
formed using 230–400 mesh silicagel. TLC was per-
formed on silica gel sheets with an organic binder and
detected by 0.5% phosphor-molybdic acid solution in
9
5% ethanol. The quantum yields of the compounds in
different solvents were calculated using rhodamine as
reference.
Fig. 6. Fluorescent character of compound 10.
(
a) PL spectra in CH
2
Cl
2
/EtOH mixture
−
5
Synthesis of tetraiodophthalic anhydride (2)
(
10 M) excited at 300 nm. (b) Quantum
yield in CH Cl /EtOH mixture. (c) Photograph
taken under UV illumination.
To
a
solution of periodic acid (5.40 g,
2
2
2
3.70 mmol) in concentrated H SO4 (60 mL) was
2
4
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Tetra-biphenyl Phthalimides
added iodine (18 g, 70.89 mmol). After the mixture was
stirred for 30 min, phthalic anhydride (3.0 g,
134.30, 129.45, 129.34, 127.43, 104.66, 20.82. HRMS
calcd. for C H I NO : 740.6656; found: 740.6647.
15
7 4
2
2
0.25 mmol) was slowly added. The reaction mixture
Compound
6
Yellow solid; 78% yield; mp
ꢀ
was stirred at room temperature for 24 h, after which it
was heated up to 110 C and stirred for another 24 h.
3
1
11–313 C; IR (KBr): 3072, 2361, 1755, 1718, 1672,
ꢀ
−1 1
409, 1374, 1229, 1180, 1131, 1100, 883, 636 cm ; H
The mixture was cooled to room temperature and then
poured onto ice–water to form a precipitate, which was
then collected by suction filtration. The collected solid
was thoroughly washed with methanol to remove the
iodine residue. The crude product was finally recrystal-
lized from THF/hexanes to give the pure compound
NMR (300 MHz, Me SO-d ): δ 8.09 (d, J = 7.8 Hz,
2
6
13
2
H), 7.58 (d, J = 7.8 Hz, 2H), 2.63 (s, 3H); C NMR
(
75 MHz, Me SO-d ): δ 197.40, 163.08, 136.23, 136.17,
2
6
1
36.08, 134.23, 128.73, 127.43, 104.84, 26.91. HRMS
calcd. for HRMS calcd. for C H I NO : 768.6605;
16
7 4
3
found: 768.6608.
ꢀ
ꢀ
2
(5.9 g, 45%). mp 324–325 C (lit.[11, 12] 327–331 C);
General procedure for the synthesis of compounds 7–10
IR (KBr): 1859, 1815, 1784, 1776, 1755, 1520, 1329,
−
1
1
A mixture of biphenyl-4-boronic acid (0.32 g,
1
292, 1187, 929, 628 cm ; H NMR (300 MHz,
1
3
1.62 mmol),
palladium(II)
acetate
(2.24 mg,
Me SO-d ): no signal; C NMR (75 MHz, Me SO-d ):
2
6
2
6
0
.013 mmol), K CO (0.3 g, 2.16 mmol), and the corre-
2
3
168.16, 139.76, 126.56, 106.62.
sponding tetraiodophthalimide (0.71 mmol) in DMF
ꢀ
General procedure for the synthesis of compounds 3–6
(
5 mL) in a sealed tube was heated at 115 C for 60 h.
To a mixture of tetraiodophthalic anhydride (2,
.0 g, 1.53 mmol) and the corresponding alkyl or aryl
After the reaction mixture was cooled to room tempera-
ture, saturated aqueous NaCl solution (10 mL) was
1
amine (1.84 mmol) in DMF (10 mL) was added acetic
added. The mixture was extracted with CH Cl2
2
acid (50 mL). The reaction mixture was stirred at reflux
(
(
30 mL × 3). The organic layers were combined, dried
ꢀ
(~150 C) for 24 h, and then cooled to room tempera-
Na SO ), and concentrated under reduced pressure.
2
4
ture. The mixture was poured onto ice–water to form a
precipitate, which was then collected by suction filtra-
tion. The crude product was finally recrystallized to
give the corresponding pure tetraiodophthalimide.
The residue was purified with flash column chromatog-
raphy (n-hexanes:EtOAc = 8:1) to give the correspond-
ing tetra-(biphen-4-yl)phthalimide.
Compound
7
Yellow solid; 36% yield; mp
ꢀ
Compound
3
Yellow solid; 83% yield; mp
2
1
82–283 C; IR (KBr): 3072, 2361, 1755, 1718, 1672,
ꢀ
−1 1
2
1
44–246 C; IR (KBr): 3064, 2960, 2859, 1768, 1749,
409, 1374, 1229, 1180, 1162, 1100, 883, 636 cm ; H
−1
1
704, 1438, 1393, 626 cm ; H NMR (300 MHz,
NMR (300 MHz, Me SO-d ): δ 7.59–6.86 (m, 36 H),
2
6
Me SO-d ): δ 3.53 (t, J = 7.2 Hz, 2H), 1.54–1.43 (m,
2
6
3.60 (t, J = 7.5 Hz, 2H), 1.64–1.60 (m, 2H), 1.36–1.29
13
13
2H), 1.26–1.12(m, 2H), 0.87 (t, J = 7.5 Hz, 3H);
C
(m, 2H), 0.90 (t, J = 7.5 Hz, 3H); C NMR (75 MHz,
NMR (75 MHz, Me SO-d ): δ 164.25, 135.54, 134.34,
2
6
Me SO-d ): δ 167.61, 147.66, 140.75, 140.36, 140.05,
2
6
104.00, 38.23, 29.64, 19.50, 13.50. HRMS calcd. for
1
39.28, 138.9, 137.30, 134.76, 131.46, 130.65, 128.76,
C H I NO : 706.6812; found: 706.6815.
1
2
9 4
2
127.35, 127.17, 126.92, 126.13, 125.82, 30.69, 20.39,
13.80. ESI-MS calcd. for C H NO : 812.3523; found:
812.3520.
Compound
4
Yellow solid; 81% yield; mp
60
46
2
ꢀ
3
09–310 C; IR (KBr): 3065, 1715, 1598, 1494, 1401,
−1
1
384, 1291, 1161, 1109, 1099, 889, 748, 733, 632 cm ;
Compound
8
Yellow solid; 34% yield; mp
1
ꢀ
H NMR (300 MHz, Me SO-d ): δ 7.55–7.38 (m, 5H);
2
6
337–338 C; IR (KBr): 3070, 3026, 2922, 1769, 1722,
1
3
C NMR (75 MHz, Me SO-d ): δ 163.49, 135.97,
2
6
1693, 1680, 1598, 1513, 1485, 1366, 1310, 1156, 1114,
−
1
1
134.34, 132.09, 128.89, 128.53, 127.69, 104.64. HRMS
1
070, 748, 729, 695 cm ; H NMR (300 MHz,
calcd. for C H I NO : 726.6499; found: 726.6495.
14
5 4
2
Me SO-d ): δ 7.56–7.18 (m, 39 H), 6.90 (d, J = 8.4 Hz,
2H); C NMR (75 MHz, Me SO-d ): δ 166.49, 148.27,
2 6
2
6
13
Compound
5
Yellow solid; 83% yield; mp
ꢀ
3
05–306 C; IR (KBr): 3066, 2976, 2854, 1829, 1789,
140.71, 140.31, 140.14, 139.89, 139.02, 138.42, 137.20,
134.59, 131.79, 131.44, 130.66, 128.89, 128.75, 128.08,
127.37, 127.15, 126.92, 126.18, 125.87. ESI-MS calcd.
for C H NO : 832.3210; found: 832.3247.
−1
1
1758, 1718, 1389, 629 cm ; H NMR (300 MHz,
13
Me SO-d ): δ 7.33–7.24 (m, 4H), 2.36 (s, 3H);
C
2
6
NMR (75 MHz, Me SO-d ): δ 163.56, 138.04, 136.06,
2
6
62 42
2
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5

Article
Huang et al.
Compound
9
Yellow solid; 35% yield; mp
(c) R. Jakubiak, Z. Bao, L. Rothberg, Synth. Met. 2000,
114, 61. (d) B. S. Gaylord, S. Wang, A. J. Heeger,
G. C. Bazan, J. Am. Chem. Soc. 2001, 123, 6417.
ꢀ
3
1
33–334 C;IR (KBr): 3065, 2921, 2360, 1771, 1720,
−1
1
600, 1513, 1487, 1371, 1124, 1007, 697 cm ;
H
(
e) L. Chen, S. Xu, D. McBranch, D. Whitten, J. Am.
NMR (300 MHz, Me SO-d ): δ 7.56–6.89 (m, 40 H),
2
6
Chem. Soc. 2000, 122, 9302.
1
3
2
1
1
1
1
8
.33 (s, 3H); C NMR (75 MHz, Me SO-d ): δ 166.61,
2 6
4
. (a) E. M. Conwell, Synth. Met. 1997, 85, 995.
48.11, 140.68, 140.25, 140.04, 139.76, 138.90, 137.92,
37.19, 134.55, 131.42, 130.65, 130.20, 129.49, 128.73,
28.08, 127.66, 127.34, 127.13, 126.88, 126.68, 126.40,
26.13, 125.84, 21.27. ESI-MS calcd. for C H NO :
(
1
b) M. W. Wu, E. M. Conwell, Phys. Rev. B 1998, 57,
4200. (c) M. W. Wu, E. M. Conwell, Phys. Rev. B 1997,
56, R10060. (d) T. -Q. Nguyen, I. B. Martini, J. Liu,
B. J. Schwartz, J. Phys. Chem. B 2000, 104, 237.
6
3
44
2
46.3367; found: 846.3406.
5. (a) B. Z. Tang, X. Zhan, G. Yu, P. P. S. Lee, Y. Liu,
D. Zhu, J. Mater. Chem. 2001, 11, 2974. (b) J. Luo,
Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu,
H. S. Kwok, X. Zhan, Y. Liu, D. Zhu, B. Z. Tang, Chem.
Commun. 2001, 37, 1740. (c) J. Chen, C. C. W. Law,
J. W. Y. Lam, Y. Dong, S. M. F. Lo, I. D. Williams,
D. Zhu, B. Z. Tang, Chem. Mater. 2003, 15, 1535.
(d) Z. Li, Y. Dong, B. Mi, Y. Tang, M. Häussler,
H. Tong, Y. Dong, J. W. Y. Lam, Y. Ren, H. H. Y. Sung,
K. S. Wong, P. Gao, I. D. Williams, H. S. Kwok,
B. Z. Tang, J. Phys. Chem. B 2005, 109, 10061.
Compound 10
Yellow solid; 36% yield; mp
ꢀ
2
52–254 C; IR (KBr): 3066, 3028, 2358, 1723, 1681,
−
1
1
599, 1516, 1487, 1359, 1268, 1178, 838, 764, 696 cm ;
1
H NMR (300 MHz, Me SO-d ): δ 7.87–6.98 (m,
2
6
1
3
4
1
1
1
1
1
0 H), 2.47 (s, 3H); C NMR (75 MHz, Me SO-d ): δ
2 6
96.94, 167.94, 143.73, 141.99, 141.21, 140.30, 140.10,
39.70, 139.59, 139.47, 138.73, 138.22, 137.78, 137.48,
35.24, 132.36, 132.08, 131.00, 130.68, 129.75, 129.39,
29.31, 128.40, 127.85, 127.16, 126.93, 126.72, 126.64,
26.49, 126.11, 125.66, 125.31, 119.09, 26.86. ESI-MS
6
. Selected examples for aggregation-induced emission: (a)
W. Z. Yuan, P. Lu, S. Chen, J. W. Y. Lam, Z. Wang,
Y. Liu, H. S. Kwok, Y. Ma, B. Z. Tang, Adv. Mater.
calcd. for C H NO : 874.3316; found: 874.3347.
64
44
3
2
010, 22, 2159. (b) Z. Zhao, S. Chen, J. W. Y. Lam, P. Lu,
ACKNOWLEDGMENTS
Y. Zhong, K. S. Wong, H. S. Kwok, B. Z. Tang, Chem.
Commun. 2010, 46, 2221. (c) Y. Liu, S. Chen,
J. W. Y. Lam, F. Mahtab, H. S. Kwok, B. Z. Tang,
J. Mater. Chem. 2012, 22, 5184. (d) W. Z. Yuan, S. Chen,
J. W. Y. Lam, C. Deng, P. Lu, H. H. Y. Sung,
I. D. Williams, H. S. Kwok, Y. Zhang, B. Z. Tang, Chem.
Commun. 2011, 47, 11216. (e) X. Feng, B. Tong, J. Shen,
J. Shi, T. Han, L. Chen, J. Zhi, P. Lu, Y. Ma, Y. Dong,
J. Phys. Chem. B 2010, 114, 1673. (f ) J. Huang, X. Yang,
X. Li, P. Chen, R. Tang, F. Li, P. Lu, Y. Ma, L. Wang,
J. Qin, Q. Li, Z. Li, Chem. Commun. 2012, 48, 9586.
The authors thank Ms. Chia-Chen Chang and the
Regional Instruments Centre, National Chung-Hsing
University, for the data of the single-crystal structure of
compound 7. This work was supported by the National
Science Council of Taiwan (NSC-98-2113-M-260-001).
Supporting information
Additional supporting information is available in
the online version of this article.
(
g) S. K. Lanke, Dyes Pigm. 2016, 124, 82. (h) R. S. Singh,
REFERENCES
A. Kumar, S. Mukhopadhyay, G. Sharma, B. Koch,
D. S. Pandey, J. Phys. Chem. C 2016, 120, 22605.
1
. (a) C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett. 1987,
5
1, 913. (b) R. H. Friend, R. W. Gymer, A. B. Holmes,
(i) C. Xia, Y. Qian, New J. Chem. 2016, 40, 144.
J. H. Burroughes, R. N. Marks, C. Taliani,
D. D. C. Bradley, D. A. dos Santos, J. L. Brédas,
M. Lögdlund, W. R. Salaneck, Nature 1999, 397, 121.
7
. (a) X. Zhou, H. Li, Z. Chi, X. Zhang, J. Zhang, B. Xu,
Y. Zhang, S. Liu, J. Xu, New J. Chem. 2012, 36, 685.
(
b) Z. Ning, Z. Chen, Q. Zhang, Y. Yan, S. Qian,
Y. Cao, H. Tian, Adv. Funct. Mater. 2007, 17, 3799.
c) Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Commun.
009, 45, 4332. (d) Y. Hong, J. W. Y. Lam, B. Z. Tang,
(
2
c) M. A. Baldo, M. E. Thompson, S. R. Forrest, Nature
000, 403, 750. (d) A. C. Grimsdale, K. L. Chan,
R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev.
009, 109, 897.
(
2
2
Chem. Soc. Rev. 2011, 40, 5361. (e) Y. T. Wu,
M. Y. Kuo, Y. T. Chang, C. C. Shin, T. C. Wu,
C. C. Tai, T. C. Cheng, W. Z. Liu, Angew. Chem. Int.
Ed. 2008, 47, 9891.
2
. J. B. Birks, Photophysics of aromatic molecules, Wiley,
London, UK, 1970.
. (a) S. Setayesh, A. C. Grimsdale, T. Weil, V. Enkelmann,
K. Mullen, F. Meghdadi, E. J. W. List, G. Leising,
J. Am. Chem. Soc. 2001, 123, 946. (b) S. Hecht,
J. M. J. Frechet, Angew. Chem. Int. Ed. 2001, 40, 74.
3
8. (a) H. Antoniadis, M. A. Abkowitz, B. R. Hsieh, Appl.
Phys. Lett. 1994, 65, 2030. (b) A. P. Kulkarni,
6
www.jccs.wiley-vch.de
© 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2017

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Tetra-biphenyl Phthalimides
C. J. Tonzola, A. S. Babel, A. Jenekhe, Chem. Mater.
11. A. G. Golub, O. Y. Yakovenko, A. O. Prykhodko,
S. S. Lukashov, V. G. Bdzhola, S. M. Yarmoluk, Bio-
chim. Biophys. Acta 2008, 1784, 143.
12. R. Schmidt, K. Seikel, H. -D. Brauer, J. Phys. Chem.
1989, 93, 4507.
2
004, 16, 4556.
9
. C. F. H. Allen, H. W. J. Cressman, H. B. Johnson, Organic
syntheses, Wiley, New York, 1955. Collect. III, 769.
0. D. L. Mattern, J. Org. Chem. 1984, 49, 3051.
1
J. Chin. Chem. Soc. 2017
© 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.jccs.wiley-vch.de
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