Citation: 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 Physico-Chimica Sinica, ;2011, 27(06): 1516-1524. doi: 10.3866/PKU.WHXB20110609 shu

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

1.
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 Date: 13 January 2011
Available Online: 22 April 2011
Fund Project: 国家重点基础研究发展计划(973)前期专项(2010CB635108, 2011CB201608) (973)前期专项(2010CB635108, 2011CB201608) 浙江省自然科学基金(Y4090260) (Y4090260)中国博士后基金(20100471755)资助项目 (20100471755)

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 od morphological stability. The thermogravimetric (TG) curves of the compounds show a thermal-decomposition temperature of higher than 400 °C.
- Photoluminence,
- Electron donor-acceptor structure,
- Intramolecular charge-transfer,
- Dual fluorescence,
- Twisted intramolecular charge transfer
1. [1]
  
  1. Tang, C.W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
2. [2]
  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. [3]
  3 Tsutsui, T.; Fujita, K. Adv. Mater. 2002, 14, 949.
4. [4]
  4 Chen, J. S.; Ma, D. J. Luminescence 2007, 122-123, 636.
5. [5]
  5 Okumoto, K.; Kanno, H.; Hamaa, Y.; Takahashi, H.; Shibata, K. Appl. Phys. Lett. 2006, 89, 063504.
6. [6]
  6 Jou, J. H.; Chiang, P. H.; Lin, Y. P.; Chang, C. Y.; Lai, C. L. Appl. Phys. Lett. 2007, 91, 043504.
7. [7]
  7 Wolfgang, R.; Barbara, B.; Klaus, D. Chemical Physics Letters 1999, 305, 8.
8. [8]
  8 Yang, J. S.; Liau, K. L.;Wang, C. M.; Hwang, C. Y. J. Am. Chem. Soc. 2004, 126, 12325.
9. [9]
  9 Chen, C. H.; Shi, J.; Tang, C.W.; Klubek, K. P. Thin Solid Films 2000, 363, 327.
10. [10]
  10 Kong, S.; Xiao, L. X.; Liu, Y. L.; Chen, Z. J.; Qu, B.; ng, Q. H. New J. Chem. 2010, 34, 1994.
11. [11]
  11 Tang, C.W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610.
12. [12]
  12 Bhaskar, A.; Ramakrishna, G.; Lu, Z. K.; Twieg, R.; Hales, J. M.; Hagan, J. D.; van Stryland, E.; odson T. J. Am. Chem. Soc. 2006, 128, 11840.
13. [13]
  13 Wang, Y.; He, G. S.; Prasad, P. N.; Doodson, T. J. Am. Chem. Soc. 2005, 127, 10128.
14. [14]
  14 Koene, B. E.; Loy, D. F.; Thompson, M. E. Chem. Mater. 1998, 10, 2235.
15. [15]
  15 VanSlyke, S. A.; Chen, C. H.; Tang, C.W. Appl. Phys. Lett. 1996, 69, 2160.
16. [16]
  16 Vestwever, H.; Rieβ,W. Synth. Met. 1997, 91, 181.
17. [17]
  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. [18]
  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. [19]
  19 Zhang, C.; Zhang, Y. J.; Xiang,W. Q.; Hu, B.; Ouyang, M.; Ma, C. A. Chem. Lett. 2010, 39, 520.
20. [20]
  20 Sukumaran, M.;Wolfgang, R. J. Phys. Chem. A 2006, 110, 28.
21. [21]
  21 Adhikari, R. M.; Shah, B. K.; Palayan da, S. S.; Neckers, D. C. Langmuir 2009, 25, 2402.
22. [22]
  22 Nikolaev, A. E.; Myszkiewicz, G.; Berden, G.; Meerts,W. L.; Pfanstiel, J. F.; Pratt, D.W. J. Chem. Phys. 2005, 122, 84309.
23. [23]
  23 Adhikari, R. M.; Neckers, D. C.; Shah, B. K. J. Org. Chem. 2009, 74, 3341.
24. [24]
  24 Zhang, C.; Yan, Y.; Chen, L. T.; Ma, C. A. Acta. Phys. -Chim. Sin. 2010, 26, 1075.
25. [25]
  [张诚, 严妍, 陈丽涛, 马淳安. 物理化学学报, 2010, 26, 1075.]
26. [26]
  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.
27. [27]
  26 Wang, P. F.;Wu, S. K. Acta Phys. -Chim. Sin. 1992, 8, 405.
28. [28]
  [汪鹏飞, 吴世康. 物理化学学报, 1992, 8, 405.]
29. [29]
  27 Wang, P. F.; Yue, Z. J.;Wu, S. K. Acta Phys. -Chim. Sin. 1994, 11, 1020.
30. [30]
  [汪鹏飞, 岳志军, 吴世康. 物理化学学报, 1994, 11, 1020.]
31. [31]
  28 Retting,W. Angew. Chem. Int. Edit. Engl. 1986, 25, 971.
32. [32]
  29 Kong, Q.; Zhu, D.; Quan, Y.; Chen, Q.; Ding, J.; Lu, J.; Tao, Y. Chem. Mater. 2007, 19, 3309.
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