Z. Zhao, H. Qiu, B. Z. Tang et al.
Experimental Section
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Dong, B. Mi, Y. Tang, M. Hꢂussler, H. Tong, Y. Dong, J. W. Y. Lam,
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23726; b) Z. Zhao, S. Chen, X. Shen, F. Mahtab, Y. Yu, P. Lu,
686; c) Z. Zhao, S. Chen, J. W. Y. Lam, P. Lu, Y. Zhong, K. S. Wong,
Chang, Y. Jiang, B. He, J. Chen, Z. Yang, P. Lu, H. S. Kwok, Z.
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Lam, W. Qin, P. Lu, Z. Wang, H. S. Kwok, Y. Ma, H. Qiu, B. Z.
Compound TPEPBN: BBr3 (1.0m in dichloromethane, 3.0 mL, 3.0 mmol)
was added to a stirred solution of 2 (0.4 g, 1.0 mmol) and iPr2NEt (0.13 g,
1.0 mmol) in dry dichloromethane (20 mL) at 08C. After being stirred at
room temperature for 24 h, saturated K2CO3 aqueous solution was added
to the reaction mixture. The reaction was poured into water and extract-
ed with dichloromethane twice. The combined organic layers were
washed with water, and then dried over magnesium sulfate. After filtra-
tion and solvent evaporation, the resulting crude product was added with
toluene (20 mL) and Me3Al (1.1m in hexane, 2.0 mL, 2.2 mmol), and
then stirred at room temperature for 0.5 h. The reaction was poured into
water and extracted with dichloromethane twice. The combined organic
layers were washed with water, and then dried over magnesium sulfate.
After filtration and solvent evaporation, the residue was purified by
silica-gel column chromatography by using hexane/dichloromethane mix-
ture as eluent. A pale yellow solid was obtained in 42% yield (0.19 g).
1H NMR (400 MHz, CDCl3, TMS): d=8.52 (d, 1H, J=5.6 Hz), 8.07–8.03
(m, 1H), 7.98 (d, 1H, J=8.0 Hz), 7.75 (d, 1H, J=8.0 Hz), 7.45–7.39 (m,
3H), 7.28–7.21 (m, 14H), 7.10 (d, 1H, J=6.8 Hz), 0.02 ppm (s, 6H);
13C NMR (100 MHz, CDCl3, TMS): d=156.8, 145.6, 143.9, 143.8, 142.7,
141.8, 139.0, 132.6, 131.5, 131.4, 131.3, 128.4, 127.6, 126.3, 120.9, 120.6,
117.8, 8.8 ppm; HRMS: m/z 434.19 (M+ÀCH3, calcd 434.2080); elemen-
tal analysis calcd (%) for C33H28BN: C 88.20, H 6.28, N 3.12; found: C
88.09, H 6.18, N 3.04.
1
Compound TPEQBN: Pale yellow solid, yield 55%. H NMR (400 MHz,
CDCl3, TMS): d=8.54 (d, 1H, J=8.8 Hz), 8.30 (d, 1H, J=8.8 Hz), 7.92
(d, 1H, J=8.8 Hz), 7.88 (d, 1H, J=8.0 Hz), 7.81–7.77 (m, 1H), 7.69 (d,
1H, J=8.8 Hz), 7.57–7.53 (m, 1H), 7.33–7.30 (m, 1H), 7.25–7.23 (m,
1H), 7.12–7.07 (m, 13H), 6.98–6.94 (m, 2H), 0.05 ppm (s, 6H); 13C NMR
(100 MHz, CDCl3, TMS): d=157.4, 146.2, 143.9, 143.8, 142.0, 141.7,
141.5, 140.0, 133.6, 132.2, 131.5, 131.4, 131.3, 131.2, 130.8, 128.7, 128.5,
127.7, 127.6, 127.4, 126.4, 126.1, 123.3, 121.5, 115.8, 9.0 ppm; HRMS: m/z
484.23 (M+ÀCH3, calcd 484.2237); elemental analysis calcd (%) for
C37H30BN: C 88.98, H 6.05, N 2.80; found: C 88.85, H 5.92, N 2.63.
Crystal data for TPEPBN: C33H28BN, Mr =449.37, monoclinic, P21/c, a=
12.734(2),
2584.2(7) ꢁ3, Z=4, 1cald =1.155 gcmÀ3
0.71073), F
b=11.0252(18),
c=18.552(3) ꢁ,
b=97.165(3)8,
V=
l=
,
m=0.066 mmÀ1 (MoKa
,
(000)=952, T=296(2) K, 14089 measured reflections, 4649 in-
dependent reflections (Rint =0.0284), GOF on F2 =1.059, R1 =0.0675,
wR2 =0.1700 (all data), De 0.218 and À0.244 eꢁÀ3
.
Crystal data for TPEQBN: C37H30BN, Mr =499.43, orthorhombic,
P2(1)2(1)2(1), a=9.8722(14), b=12.5757(17), c=23.444(3) ꢁ, V=
2910.6(7) ꢁ3, Z=4, 1cald =1.140 gcmÀ3
,
m=0.065 mmÀ1 (MoKa
,
l=
0.71073), FACHTUNGTRENNUNG(000)=1056, T=296(2) K, 9596 measured reflections, 5135 in-
dependent reflections (Rint =0.0420), GOF on F2 =1.069, R1 =0.1130,
wR2 =0.1881 (all data), De 0.275 and À0.191 eꢁÀ3
.
CCDC-854152 (TPEPBN) and -854153 (TPEQBN) contain the supple-
mentary crystallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data Centre via
[12] Z. Zhao, P. Lu, J. W. Y. Lam, Z. Wang, C. Y. K. Chan, H. H. Y.
[13] Z. Chi, X. Zhang, B. Xu, X. Zhou, C. Ma, Y. Zhang, S. Liu, J. Xu,
[14] a) Z. Zhao, J. W. Y. Lam, C. Y. K. Chan, S. Chen, J. Liu, P. Lu, M.
Rodriguez, J.-L. Maldonado, G. Ramos-Ortiz, H. H. Y. Sung, I. D.
Williams, H. Su, K. S. Wong, Y. Ma, H. S. Kwok, H. Qiu, B. Z. Tang,
Wang, P. Lu, F. Mahtab, H. H. Y. Sung, I. D. Williams, Y. Ma, H. S.
Acknowledgements
We acknowledge the financial support from the National Natural Science
Foundation of China (51273053, 21104012, 21284034 and 21074028), the
Natural Science Foundation of Zhejiang Province (Y4110331), the Pro-
gram for Changjiang Scholars and Innovative Research Teams in Chinese
Universities (IRT 1231) and the Project of Zhejiang Key Scientific and
Technological Innovation Team (2010R50017).
Keywords: aggregation-induced emission · crystallography ·
energy levels · fluorescence · organoborons
[15] a) G. Yu, S. Yin, Y. Liu, J. Chen, X. Xu, X. Sun, D. Ma, X. Zhan, Q.
Peng, Z. Shuai, B. Z. Tang, D. Zhu, W. Fang, Y. Luo, J. Am. Chem.
&
6
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ꢀ 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 0000, 00, 0 – 0
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