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.
1. [1]
  Xiaxue Chen , Yuxuan Yang , Ruolin Yang , Yizhu Wang , Hongyun Liu . Adjustable Polychromatic Fluorescence: Investigating the Photoluminescent Properties of Copper Nanoclusters. University Chemistry, 2024, 39(9): 328-337. doi: 10.3866/PKU.DXHX202308019
2. [2]
  Lin Song , Dourong Wang , Biao Zhang . Innovative Experimental Design and Research on Preparing Flexible Perovskite Fluorescent Gels Using 3D Printing. University Chemistry, 2024, 39(7): 337-344. doi: 10.3866/PKU.DXHX202310107
3. [3]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
4. [4]
  Jianjun Liu , Xue Yang , Chi Zhang , Xueyu Zhao , Zhiwei Zhang , Yongmei Chen , Qinghong Xu , Shao Jin . Preparation and Fluorescence Characterization of CdTe Semiconductor Quantum Dots. University Chemistry, 2024, 39(7): 307-315. doi: 10.3866/PKU.DXHX202311031
5. [5]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
6. [6]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
7. [7]
  Xinyuan Shi , Chenyangjiang , Changyu Zhai , Xuemei Lu , Jia Li , Zhu Mao . Preparation and Photoelectric Performance Characterization of Perovskite CsPbBr₃ Thin Films. University Chemistry, 2024, 39(6): 383-389. doi: 10.3866/PKU.DXHX202312019
8. [8]
  Jinfu Ma , Hui Lu , Jiandong Wu , Zhongli Zou . Teaching Design of Electrochemical Principles Course Based on “Cognitive Laws”: Kinetics of Electron Transfer Steps. University Chemistry, 2024, 39(3): 174-177. doi: 10.3866/PKU.DXHX202309052
9. [9]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
10. [10]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
11. [11]
  Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
12. [12]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
13. [13]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
14. [14]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
15. [15]
  Yuping Wei , Yiting Wang , Jialiang Jiang , Jinxuan Deng , Hong Zhang , Xiaofei Ma , Junjie Li . Interdisciplinary Teaching Practice——Flexible Wearable Electronic Skin for Low-Temperature Environments. University Chemistry, 2024, 39(10): 261-270. doi: 10.12461/PKU.DXHX202404007
16. [16]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
17. [17]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . 用于高效制氢的双S型ZnS/ZnO/CdS异质结构光催化剂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-. doi: 10.3866/PKU.WHXB202406020
18. [18]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
19. [19]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
20. [20]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414

Get Citation

PDF

XML

Metrics

PDF Downloads(1484)
Abstract views(2733)
HTML views(5)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142