D-A结构的9,9-二芳基芴类发光材料的合成、表征及性能

doi:10.3866/PKU.WHXB20110609

Acta Phys. -Chim. Sin. ›› 2011, Vol. 27 ›› Issue (06): 1516-1524.doi: 10.3866/PKU.WHXB20110609

• PHOTOCHEMISTRY AND RADIATION CHEMISTRY • Previous Articles Next Articles

Synthesis, Characterization and Properties of Electron Donor-Acceptor Complexes Based on 9,9-Diarylfluorene

OUYANG Mi¹, XIANG Wen-Qin¹, ZHANG Yu-Jian¹, JIN Yan-Xian², ZHANG Cheng¹

1. State Key Laboratory Breeding Base for Green Chemistry Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, P. R. China;
2. School of Chemical Engineering, Taizhou College, Linhai 317000, Zhejiang Province, P. R. China

Received:2011-01-13 Revised:2011-03-04 Published:2011-05-31
Contact: ZHANG Cheng E-mail:czhang@zjut.edu.cn
Supported by:
The project was supported by the National Key Basic Research Program of China (2010CB635108, 2011CB201608), Natural Science Foundation of Zhejiang Province, China (Y4090260) and National Science Foundation for Post-doctoral Scientists of China (20100471755).

Abstract

Abstract:

A series of fluorene-triphenylamine derivatives containing an electron donor-acceptor (D-A) structure based on 9,9-diarylfluorene was designed and synthesized. Their optical properties were investigated by UV-Vis spectroscopy and photoluminescence (PL) techniques in solution as well as in the solid state. The maximum PL emission wavelengths of the compounds ranged from 430 to 530 nm. A dual fluorescence phenomenon was observed in particular polar solvents and the relationship between emission properties and molecular structures was studied. The results reveal the existence of a charge transfer (CT) excited state in the molecules and the PL properties of these compounds depend on the structure of the compound and also on the polarity of the solvent. The molecular constitution of the compounds improves the hole-injection issues for fluorene-based materials because of the introduction of a triphenylamine group. Cyclic voltammetry (CV) shows that the highest occupied molecular orbital (HOMO) energy level of the compounds is located between -5.24 and -5.50 eV and it can be tailored by changing the electronegativity of the substituent group. Simultaneously, the spiro-skeleton molecular structure leads to an excellent glass transition temperature (192-206 °C) and it retains good morphological stability. The thermogravimetric (TG) curves of the compounds show a thermal-decomposition temperature of higher than 400 °C.

Key words: Photoluminence, Electron donor-acceptor structure, Intramolecular charge-transfer, Dual fluorescence, Twisted intramolecular charge transfer

OUYANG Mi, XIANG Wen-Qin, ZHANG Yu-Jian, JIN Yan-Xian, ZHANG Cheng. Synthesis, Characterization and Properties of Electron Donor-Acceptor Complexes Based on 9,9-Diarylfluorene[J]. Acta Phys. -Chim. Sin. 2011, 27(06), 1516-1524. doi: 10.3866/PKU.WHXB20110609

References

1. Tang, C.W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
2 Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
3 Tsutsui, T.; Fujita, K. Adv. Mater. 2002, 14, 949.
4 Chen, J. S.; Ma, D. J. Luminescence 2007, 122-123, 636.
5 Okumoto, K.; Kanno, H.; Hamaa, Y.; Takahashi, H.; Shibata, K. Appl. Phys. Lett. 2006, 89, 063504.
6 Jou, J. H.; Chiang, P. H.; Lin, Y. P.; Chang, C. Y.; Lai, C. L. Appl. Phys. Lett. 2007, 91, 043504.
7 Wolfgang, R.; Barbara, B.; Klaus, D. Chemical Physics Letters 1999, 305, 8.
8 Yang, J. S.; Liau, K. L.;Wang, C. M.; Hwang, C. Y. J. Am. Chem. Soc. 2004, 126, 12325.
9 Chen, C. H.; Shi, J.; Tang, C.W.; Klubek, K. P. Thin Solid Films 2000, 363, 327.
10 Kong, S.; Xiao, L. X.; Liu, Y. L.; Chen, Z. J.; Qu, B.; Gong, Q. H. New J. Chem. 2010, 34, 1994.
11 Tang, C.W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610.
12 Bhaskar, A.; Ramakrishna, G.; Lu, Z. K.; Twieg, R.; Hales, J. M.; Hagan, J. D.; van Stryland, E.; Goodson T. J. Am. Chem. Soc. 2006, 128, 11840.
13 Wang, Y.; He, G. S.; Prasad, P. N.; Doodson, T. J. Am. Chem. Soc. 2005, 127, 10128.
14 Koene, B. E.; Loy, D. F.; Thompson, M. E. Chem. Mater. 1998, 10, 2235.
15 VanSlyke, S. A.; Chen, C. H.; Tang, C.W. Appl. Phys. Lett. 1996, 69, 2160.
16 Vestwever, H.; Rieβ,W. Synth. Met. 1997, 91, 181.
17 Wong, K. T.; Chien, Y. Y.; Chen, R. T.;Wang, C. F.; Lin, Y. T.; Chiang, H. H.; Hsieh, P. Y.;Wu, C. C.; Chou, C. H.; Su, Y. O.; Lee, G. H.; Peng, S. M. J. Am. Chem. Soc. 2002, 24, 11576.
18 Wu, C. C.; Liu, T. L.; Huang,W. Y.; Lin, Y. T.;Wong, K. T.; Chen, R. T.; Chen, Y. M.; Chien, Y. Y. J. Am. Chem. Soc. 2003, 125, 3710.
19 Zhang, C.; Zhang, Y. J.; Xiang,W. Q.; Hu, B.; Ouyang, M.; Ma, C. A. Chem. Lett. 2010, 39, 520.
20 Sukumaran, M.;Wolfgang, R. J. Phys. Chem. A 2006, 110, 28.
21 Adhikari, R. M.; Shah, B. K.; Palayangoda, S. S.; Neckers, D. C. Langmuir 2009, 25, 2402.
22 Nikolaev, A. E.; Myszkiewicz, G.; Berden, G.; Meerts,W. L.; Pfanstiel, J. F.; Pratt, D.W. J. Chem. Phys. 2005, 122, 84309.
23 Adhikari, R. M.; Neckers, D. C.; Shah, B. K. J. Org. Chem. 2009, 74, 3341.
24 Zhang, C.; Yan, Y.; Chen, L. T.; Ma, C. A. Acta. Phys. -Chim. Sin. 2010, 26, 1075.
[张诚, 严妍, 陈丽涛, 马淳安. 物理化学学报, 2010, 26, 1075.]
25 Hu, R. R.; Erik, L.; Angélica, A. A.; Liu, J. Z.; Jacky,W. Y. L.; Herman, H. Y. S.; Ian, D.W.; Zhong, Y. C.; Kan, S.W. J. Phys. Chem. C 2009, 113, 15845.
26 Wang, P. F.;Wu, S. K. Acta Phys. -Chim. Sin. 1992, 8, 405.
[汪鹏飞, 吴世康. 物理化学学报, 1992, 8, 405.]
27 Wang, P. F.; Yue, Z. J.;Wu, S. K. Acta Phys. -Chim. Sin. 1994, 11, 1020.
[汪鹏飞, 岳志军, 吴世康. 物理化学学报, 1994, 11, 1020.]
28 Retting,W. Angew. Chem. Int. Edit. Engl. 1986, 25, 971.
29 Kong, Q.; Zhu, D.; Quan, Y.; Chen, Q.; Ding, J.; Lu, J.; Tao, Y. Chem. Mater. 2007, 19, 3309.

[1]	LIN Cui-Ying; SONG Li; ZHAO Jian-Xi. Determination of the Critical Micelle Concentration of Surfactant in Aqueous Solution by Twisted Intramolecular Charge Transfer Probe DMABN [J]. Acta Phys. -Chim. Sin., 2007, 23(12): 1846-1850.
[2]	DU Xin-Zhen;ZHOU Rong;TAO Xiao-Juan;WANG Fang-Ping;CHEN Hui. A Study of Cage-type Inclusion Complexes of Modified β-cyclodextrins with 2′-ethylhexyl-4-(N,N-dimethylamino)-benzoate [J]. Acta Phys. -Chim. Sin., 2006, 22(09): 1065-1070.
[3]	Lin Li-Rong,Jiang Yun-Bao,Huang Xian-Zhi,Chen Guo-Zhen. A Study of the Interaction of Methyl β-CD with Cetyltrimethylammonium Bromide in Aqueous Solution [J]. Acta Phys. -Chim. Sin., 1997, 13(08): 747-751.
[4]	Wang Peng-Fei, Yue Zhi-Jun, Wu Shi-Kang. A Study on the Photophysical Behavior of Cross-conjugate Enone Compounds [J]. Acta Phys. -Chim. Sin., 1994, 10(11): 1020-1025.
[5]	Jiang Yun-Bao, Wang Xiu-Juan. Effect of Aliphatic Alcohol on the Twisted Intramolecular Charge Transfer in Charged Micelle Studied by Dual Fluorescence [J]. Acta Phys. -Chim. Sin., 1994, 10(09): 856-859.
[6]	Jiang Yun-Bao, Wang Xiu-Juan. Cyclodextrin Induced Micelle Formation as Studied by TICT Fluorescent Probe [J]. Acta Phys. -Chim. Sin., 1994, 10(08): 716-719.

Synthesis, Characterization and Properties of Electron Donor-Acceptor Complexes Based on 9,9-Diarylfluorene

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Metrics

Recommended 0