Z.-Q. Liang et al. / Tetrahedron Letters 52 (2011) 1329–1333
1333
Figure 5. Normalized PL spectra of PVPP and TPVPP in crystalline state.
Acknowledgments
This work was supported by the State National Natural Science
Foundation of China (Grant Nos. 50721002, 50802054, and
50873001) and the 973 Program of the People’s Republic of China
(Grant No. 2010CB630702).
Supplementary data
Supplementary data (synthetic procedures, characterization,
and crystal packing diagram, crystallographic data) associated with
this Letter can be found, in the online version, at doi:10.1016/
References and notes
1. (a) Kim, D. Y.; Cho, H. N.; Kim, C. Y. Prog. Polym. Sci. 2000, 25, 1089; (b) Chen, C.
T. Chem. Mater. 2004, 16, 4389–4400.
2. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Plenum Press: New York,
1999.
3. (a) Zachariasse, K. A. Trends Photochem. Photobiol. 1994, 3, 211; (b) Birks, J. B.;
Dyson, D. J.; Munro, I. H. Proc. R. Soc. London, Ser. A 1963, 275, 575.
4. Mikroyannidis, J. A.; Fenenko, L.; Adachi, C. J. Phys. Chem. B 2006, 110, 20317–
20326.
5. (a) Moorthy, J. N.; Natarajan, P.; Venkatakrishnan, P.; Huang, D. F.; Chow, T. J.
Org. Lett. 2007, 9, 5215–5218; (b) Tao, S. L.; Peng, Z. K.; Zhang, X. H.; Wang, P. F.;
Lee, C. S.; Lee, S. T. Adv. Funct. Mater. 2005, 15, 1716–1721; (c) Wu, K. C.; Ku, P. J.;
Lin, C. S.; Shih, H. T.; Wu, F. I.; Huang, M. J.; Lin, J. J.; Chen, I.-C.; Cheng, C. H. Adv.
Funct. Mater. 2008, 18, 67–75; (d) Zhao, Z. J.; Li, J. H.; Chen, X. P.; Wang, X. M.; Lu,
P.; Yang, Y. J. Org. Chem. 2009, 74, 383–395; (e) Figueira-Duarte, T. M.; Del Rosso,
P. G.; Trattnig, R.; Sax, S.; List, E. J. W.; Müllen, K. Adv. Mater. 2009, 21, 1–4.
6. (a) Oyamada, T.; Uchiuzou, H.; Akiyama, S.; Oku, Y.; Shimoji, N.; Matsushige, K.;
Sasabe, H.; Adachi, C. J. Appl. Phys. 2005, 98, 074506; (b) Sonar, P.; Soh, M. S.;
Cheng, Y. H.; Henssler, J. T.; Sellinger, A. Org. Lett. 2010, 12, 3292–3295.
7. Luo, J. D.; Xie, Z. L.; Lam, J. W. Y.; Cheng, L.; Chen, H. Y.; Qiu, C. F.; Kwok, H. S.;
Zhan, X. W.; Liu, Y. Q.; Zhu, D. B.; Tang, B. Z. Chem. Commun. 2001, 1740–1741.
8. (a) Jiang, Y. H.; Wang, Y. C.; Hua, J. L.; Tang, J.; Li, B.; Qian, S. X.; Tian, H. Chem.
Commun. 2010, 46, 4689–4691; (b) An, B. K.; Kwon, S. K.; Jung, S. D.; Park, S. Y. J.
Am. Chem. Soc. 2002, 124, 14410–14415; (c) Liu, Y.; Tao, X. T.; Wang, F. Z.; Shi, J.
H.; Sun, J. L.; Yu, W. T.; Ren, Y.; Zou, D. C.; Jiang, M. H. J. Phys. Chem. C 2007, 111,
6544–6549; (d) Xie, Z. Q.; Yang, B.; Cheng, G.; Liu, L. L.; He, F.; Shen, F. Z.; Ma, Y.
G.; Liu, S. Y. Chem. Mater. 2005, 17, 1287–1289.
9. Zhao, Z. J.; Chen, S. M.; Lam, J. W. Y.; Lu, P.; Zhong, Y. C.; Wong, K. S.; Kwoka, H.
S.; Tang, B. Z. Chem. Commun. 2010, 46, 2221–2223.
10. (a) Turro, N. J. Modern Molecular Photochemistry; University Science Books:
Sausalito, 1991. pp 170–172; (b) Itami, K.; Yoshida, J. Bull. Chem. Soc. Jpn. 2006,
79, 811–824.
11. Qiu, Y.; Wei, P.; Zhang, D. Q.; Qiao, J.; Duan, L.; Li, Y. K.; Gao, Y. D.; Wang, L. D.
Adv. Mater. 2006, 18, 1607–1611.
12. (a) Winnik, F. M. Chem. Rev. 1993, 93, 587; (b) Pope, M.; Swenberg, C. E.
Electronic Processes in Organic Crystals and Polymers; Oxford University Press:
Oxford, 1999. pp 48–53.
13. (a) Wang, Z. X.; Shao, H. X.; Ye, J. C.; Zhang, L.; Lu, P. Adv. Funct. Mater. 2007, 17,
253–263; (b) Matsui, M.; Ikeda, R.; Kubota, Y.; Funabiki, K. Tetrahedron Lett.
2009, 50, 5047–5049.
Figure 4. (a) Molecular structure of TPVPP. (b) Weak C–Hꢀ ꢀ ꢀ
p
interactions between
for
adjacent molecules of TPVPP. The interaction distance and the angle of C–Hꢀ ꢀ ꢀ
p
interaction IV are 2.87 Å and 128°, those for interaction V are 2.90 Å and 116°, those
for interaction VI are 2.83 Å and 126°, and those for interaction VII are 2.86 Å and
132°, respectively.
14. (a) Ye, S. H.; Liu, Y. Q.; Di, C.; Xi, H. X.; Wu, W. P.; Wen, Y. G.; Lu, K.; Du, C. Y.; Liu,
Y.; Yu, G. Chem. Mater. 2009, 21, 1333–1342; (b) Zhao, H. P.; Wang, F. Z.; Yuan, C.
X.; Tao, X. T.; Sun, J. L.; Zou, D. C.; Jiang, M. H. Org. Electron. 2009, 10, 925–931.
cules provide a possible design strategy to prevent the aggrega-
tion-induced fluorescence quenching of pyrene units.