Citation: HAO Xue-Liang, ZHAO Jin-Ge, GAO Jian-Rong, HAN Liang. Synthesis and Photoelectric Properties of Carbazole Sensitizing Dyes Based on a Benzoic Acid Acceptor[J]. Acta Physico-Chimica Sinica, ;2015, 31(10): 1977-1984. doi: 10.3866/PKU.WHXB201509075 shu

Synthesis and Photoelectric Properties of Carbazole Sensitizing Dyes Based on a Benzoic Acid Acceptor

1.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. China

Received Date: 13 July 2015
Available Online: 7 September 2015
Fund Project: 国家自然科学基金(21406202, 21176223) (21406202, 21176223)浙江省自然科学基金(LY13B020012)资助项目 (LY13B020012)

4-(6-(N-butylcarbazole-3-yl)-9-oxo-9H-fluoren-3-yl)benzoic acid (HXL-3W) and 4-(7-(Nbutylcarbazole-3-yl)-9-oxo-9H-fluoren-2-yl)benzoic acid (HXL-4Z), were designed and synthesized through the linking position variation of the fluorenone π-bridge with the N-butylcarbazole donor and a benzoic acid acceptor. The spectra, electrochemistry and photoelectric conversion properties of these carbazole dyes were investigated and their geometric structure and UV-Vis spectra were optimized and calculated using the density functional theory (DFT) method. The results show two distinct absorption peaks, ascribed to the π→π^* transition, along with a small peak corresponding to intramolecular charge transfer in the absorption spectrum of HXL-4Z. However, only one π→π^* transition absorption peak is found in the spectrum of HXL-3W and its molar extinction coefficient is far smaller than that of HXL-4Z. The reason for this may be a closer distance between the donor and acceptor of HXL-3W leading to a large tension, causing inferior molecular planarity and intramolecular charge transfer. Therefore, HXL-4Z which possesses superior light absorptivity and electron injection efficiency, shows an enhanced photoelectric conversion efficiency of 2.03% (short-circuit photocurrent density (J_sc) = 3.88 mA·cm^-2, open-circuit photovoltage (V_oc) = 700 mV, fill factor (FF) = 0.75).
- Carbazole,
- Sensitizing dye,
- Benzoic acid acceptor,
- Synthesis,
- Photoelectric property
1. [1]
  
  (1) Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem. Int. Edit. 2009, 48, 2474. doi: 10.1002/anie.v48:14
2. [2]
  (2) Hou, L. M.; Wen, Z.; Li, Y. X.; Hu, H. Y.; Kan, Y. H.; Su, Z. M. Acta Phys. -Chim. Sin. 2015, 31, 1504. [候丽梅, 温智, 李银祥, 胡华友, 阚玉和, 苏忠民. 物理化学学报,2015, 31, 1504.] doi: 10.3866/PKU.WHXB201505211
3. [3]
  (3) Li, H. X.; Zuo, G. F.; Li, Z. F.; Wang, X. F.; Zheng, R. H. Acta Phys. -Chim. Sin. 2015, 31, 866. [李会学, 左国防, 李志峰, 王晓峰, 郑仁慧. 物理化学学报, 2015, 31, 866.] doi: 10.3866/PKU.WHXB201503254
4. [4]
  (4) Zhan, W. S.; Li, R.; Pan, S.; Guo, Y. N.; Zhang, Y. Acta Phys. -Chim. Sin. 2013, 29, 255. [詹卫伸, 李睿, 潘石, 郭英楠, 张毅. 物理化学学报, 2013, 29, 255.] doi: 10.3866/PKU.WHXB201211221
5. [5]
  (5) Polo, A. S.; Itokazu, M. K.; Iha, N. Y. M. Coordin. Chem. Rev. 2004, 248, 1343. doi: 10.1016/j.ccr.2004.04.013
6. [6]
  (6) Zhang, S. F.; Yang, X. D.; Numata, Y. H.; Han, L. Y. Energy Environ. Sci. 2013, 6, 1443. doi: 10.1039/c3ee24453a
7. [7]
  (7) Gupta, K. S. V.; Suresh, T.; Singh, S. P.; Islam, A.; Han, L. Y.; Chandrasekharam, M. Org. Electron. 2014, 15, 266. doi: 10.1016/j.orgel.2013.11.020
8. [8]
  (8) Li, T.; Cui, Y. H.; Zhong, C. J.; Ye, Q.; Han, L. J. Photochem. Photobiol. A: Chem. 2015, 303, 91.
9. [9]
  (9) Seo, K. D.; Choi, I. T.; Park, Y. G.; Kang, S.; Lee, J. Y.; Kim, H. K. Dyes Pigm. 2012, 94, 469. doi: 10.1016/j.dyepig.2012.02.015
10. [10]
  (10) Han, L.; Wu, H. B.; Cui, Y. H.; Zu, X. Y.; Ye, Q.; Gao, J. R. J. Photochem. Photobiol. A: Chem. 2014, 290, 54.
11. [11]
  (11) Wang, L.; Liang, M.; Zhang, Y.; Cheng, F.; Wang, X.; Sun, Z.; Xue, S. Dyes Pigm. 2014, 101, 270. doi: 10.1016/j.dyepig.2013.10.016
12. [12]
  (12) Liang, G. J.; Zhong, Z. C.; Chen, M. H.; Xu, J.; Xu, W. L.; He, P.; Hou, Q. F.; Li, Z. F. Acta Phys. -Chim. Sin. 2012, 28, 1885. [梁桂杰, 钟志成, 陈美华, 许杰, 徐卫林, 和平, 候秋飞, 李在房. 物理化学学报, 2012, 28, 1885.] doi: 10.3866/PKU.WHXB201205301
13. [13]
  (13) Liang, M.; Chen, J. Chem. Soc. Rev. 2013, 42, 3453. doi: 10.1039/c3cs35372a
14. [14]
  (14) Zhong, C. J.; Gao, J. R.; Cui, Y. H.; Li, T.; Han, L. J. Power Sources 2015, 273, 831.
15. [15]
  (15) Tang, J.; Hua, J. L.; Wu, W. J.; Li, J.; Jin, Z. G.; Long, Y. T.; Tian, H. Energy Environ. Sci. 2010, 3, 1736. doi: 10.1039/c0ee00008f
16. [16]
  (16) Li, P. P.; Chen, Y.; Zhu, J.; Feng, M.; Zhuang, X.; Lin, Y.; Zhan, H. Chem. -Eur. J. 2010, 17, 780.
17. [17]
  (17) Duan, T. N.; Fan, K.; Zhong, C.; Peng, T. Y.; Qin, J. G.; Chen, X. G. RSC Adv. 2012, 2, 7081. doi: 10.1039/c2ra20777j
18. [18]
  (18) Han, L.; Zu, X. Y.; Cui, Y. H.; Wu, H. B.; Ye, Q.; Gao, J. R. Org. Electron. 2014, 15, 1536. doi: 10.1016/j.orgel.2014.04.016
19. [19]
  (19) Liu, J.; Yang, X. D.; IsIam, A.; Numata, Y. H.; Zhang, S. F.; Salim, N. T.; Chen, H.; Han, L. Y. J. Mater. Chem. A 2013, 1, 10889. doi: 10.1039/c3ta12368e
20. [20]
  (20) Liu, B.; Wang, R.; Mi, W. J.; Li, X. Y.; Yu, H. T. J. Mater. Chem. 2012, 22, 15379. doi: 10.1039/c2jm32333h
21. [21]
  (21) Venkateswararao, A.; Justin Thomas, K. R.; Lee, C. P.; Ho, K. C. Tetrahedron Lett. 2013, 54, 3985. doi: 10.1016/j.tetlet.2013.05.069
22. [22]
  (22) Wang, X. Z.; Yang, J.; Yu, H.; Li, F.; Fan, L.; Sun, W.; Liu, Y.; Koh, Z. Y.; Pan, J.; Yim, W. L.; Yan, L.; Wang, Q. Chem. Commun. 2014, 50, 3965. doi: 10.1039/c4cc00577e
23. [23]
  (23) Liu, B.; Wang, B.; Wang, R.; Gao, L.; Huo, S.; Liu, Q.; Li, X.; Zhu, W. J. Mater. Chem. A 2014, 2, 804. doi: 10.1039/C3TA13993J
24. [24]
  (24) Yu, H. H. Synthesis and Properties of Novel Organic Sensitizers Based on Indoline for Dye-Sensitized Solar Cells. Master Dissertation, East China University of Science and Technology, Shanghai, 2012. [于晖晖. 新型含吲哚啉纯有机太阳能电池敏化染料的合成与性能研究[D]. 上海: 华东理工大学, 2012.]
25. [25]
  (25) Katono, M.; Bessho, T.; Wielopolski, M.; Marszalek, M.; Moser, J. E.; Baker-Humphry, R.; Zakkeruddin, S. M.; Grätzel, M. J. Phys. Chem. C 2012, 116, 16876. doi: 10.1021/jp304490a
26. [26]
  (26) Zhang, M.; Wang, Y.; Xu, M.; Ma, W.; Li, R.; Wang, P. Energy Environ. Sci. 2013, 6, 2944. doi: 10.1039/c3ee42331j
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