Citation: Han Liang, Wu Liang, Tong Yongzheng, Zu Xiaoyan, Jiang Shaoli-ang. Syntheses and Photovoltaic Performance of N-Phenylcarbazole Sensitizers with Benzothiadiazole Auxiliary Acceptor[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2940-2947. doi: 10.6023/cjoc201704045 shu

Syntheses and Photovoltaic Performance of N-Phenylcarbazole Sensitizers with Benzothiadiazole Auxiliary Acceptor

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310017
b.
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310017

Corresponding author: Jiang Shaoli-ang, jslarticle@163.com
Received Date: 27 April 2017
Revised Date: 13 July 2017
Available Online: 11 November 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21406202)the National Natural Science Foundation of China 21406202

Figures(6)

Four N-phenylcarbazole sensitizers were designed and synthesized with N-phenylcarbazole as the electron donor, benzothiadiazole as the auxiliary acceptor, thiophene or benzene as π bridge, cyanoacetic acid or rhodanine acetic acid as the an-choring acceptor. The spectral properties and photovoltaic performance of the sensitizers were investigated. Though with short maximum absorption wavelength and low molar extinction coefficient, dyes with cyanoacetic acid acceptor show higher electron injection efficiency than dyes with rhodanine acetic acid acceptor, and hence obtain superior photocurrent and photovoltage. Dyes with benzene bridge exhibit higher photocurrent and photovoltage than dyes with thiophene bridge. Therefore, among four sensitizers, dye with benzene bridge and cyanoacetic acid acceptor obtains better photoelectric conversion efficiency of 5.28% (J_SC=9.14 mA/cm², V_OC=0.74 V, FF=0.78).
- N-phenylcarbazole,
- benzothiadiazole,
- synthesis,
- spectral property,
- photoelectric conversion efficiency
1. [1]
  Al-Alwani, M. A. M.; Mohamad, A. B.; Ludin, N. A.; Kadhum, A. A. H.; Sopian, K. Renewable Sustainable Energy Rev. 2016, 65, 183. doi: 10.1016/j.rser.2016.06.045
2. [2]
  Gu, C.-Z.; Meng, S.-X.; Feng, Y.-Q. Chin. J. Org. Chem. 2015, 35, 1229(in Chinese).
3. [3]
  Hafeldt, A.; Boschloo, G.; Sun, L. C.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595. doi: 10.1021/cr900356p
4. [4]
  Ma, Y.-Z.; Zheng, L.-L.; Zhang, L.-P.; Chen, Z.-J.; Wang, S.-F.; Qu, B.; Xiao, L.-X.; Gong, Q.-H. Acta Chim. Sinica 2015, 73, 257(in Chinese). doi: 10.3969/j.issn.0253-2409.2015.03.001
5. [5]
  Chaurasia, S.; Lin, J. T. Chem. Rec. 2016, 16, 1311. doi: 10.1002/tcr.201500288
6. [6]
  Rong, Y.-G.; Mei, A.-Y.; Liu, L.-F.; Li, X.; Han, H.-W. Acta Chim. Sinica 2015, 73, 237(in Chinese). doi: 10.3866/PKU.WHXB201411242
7. [7]
  Ye, T.-L.; Wang, J.-H.; Dong, G.-H.; Jiang, Y.-X.; Feng, C.; Yang, Y.-L. Chin. J. Chem. 2016, 34, 747. doi: 10.1002/cjoc.v34.8
8. [8]
  Han, R.-B.; Lu, S.; Wang, Y.-J.; Zhang, X.-H.; Wu, Q.; He, T. Acta Chim. Sinica 2015, 73, 1061(in Chinese). doi: 10.3969/j.issn.0253-2409.2015.09.006
9. [9]
  (a) Xie, Y.; Tang, Y.; Wu, W.; Wang, Y.; Liu, J.; Li, X.; Tian, H.; Zhu, W. J. Am. Chem. Soc. 2015, 137, 14055.
  (b) Tang, Y.; Wang, Y.; Li, X.; Ågren, H.; Zhu, W.; Xie, Y. ACS Appl. Mater. Interfaces 2015, 7, 27976.
  (c) Wei, T.; Sun, X.; Li, X.; Ågren, H.; Xie, Y. ACS Appl. Mater. Interfaces 2015, 7, 21956.
  (d) Wang, Y.; Chen, B.; Wu, W.; Li, X.; Zhu, W.; Tian, H.; Xie, Y. Angew. Chem., Int. Ed. 2014, 53, 10779.
  (e) Wang, Y.; Li, X.; Liu, B.; Wu, W.; Zhu, W.; Xie, Y. RSC Adv. 2013, 3, 14780.
10. [10]
  Chaurasia, S.; Liang, C. J.; Yen, Y. S.; Lin, J. T. J. Mater. Chem. C 2015, 3, 9765. doi: 10.1039/C5TC02356D
11. [11]
  Kim, B.; Chung, K.; Kim, J. Chem. Eur. J. 2013, 19, 5220 doi: 10.1002/chem.201204343
12. [12]
  Lee, C. P.; Lin, R. Y. Y.; Lin, L. Y.; Li, C. T.; Chu, T. C.; Sun, S. S.; Lin, J. T.; Ho, K. C. RSC Adv. 2015, 5, 23810. doi: 10.1039/C4RA16493H
13. [13]
  Liu, Y.; He, J.; Han, L.; Gao, J. R. J. Photochem. Photobiol. A 2017, 332, 283. doi: 10.1016/j.jphotochem.2016.08.033
14. [14]
  Li, T.; Gao, J. R.; Cui, Y. H.; Zhong, C. J.; Ye, Q; Han, L. J. Photochem. Photobiol. A 2015, 303, 91.
15. [15]
  Wang, Y.; Zheng, Z.; Li, T.; Robertson, N.; Xiang, H.; Wu, W.; Hua, J.; Zhu, W. H.; Tian, H. ACS Appl. Mater. Interfaces 2016, 8, 31016. doi: 10.1021/acsami.6b11152
16. [16]
  Han, L.; Zhao, J.; Wang, B.; Jiang, S. L. J. Photochem. Photo-biol. A 2016, 326, 1. doi: 10.1016/j.jphotochem.2016.04.011
17. [17]
  Eom, Y. K.; Hong, J. Y.; Kim, J.; Kim, H. K. Dyes Pigm. 2017, 136, 496. doi: 10.1016/j.dyepig.2016.09.007
18. [18]
  Huang, H. L.; Chen, H. J.; Long, J.; Wang, G.; Tan, S. T. J. Power Sources 2016, 326, 438. doi: 10.1016/j.jpowsour.2016.06.099
19. [19]
  Wu, F.; Liu, H.-T.; Lee, L. T. L.; Chen, T.; Wang, M.; Zhu, L.-N. Chin. J. Chem. 2015, 33, 925. doi: 10.1002/cjoc.v33.8
20. [20]
  Mishra, A.; Fischer, M. K. R.; Bäuerle P. Angew. Chem., Int. Ed. 2009, 48, 2474. doi: 10.1002/anie.v48:14
21. [21]
  Wu, Y. Z.; Zhu, W. H. Chem. Soc. Rev. 2013, 42, 2039. doi: 10.1039/C2CS35346F
22. [22]
  Wu, Y.; Zhu, W.; Zakeeruddin, S. M.; Grätzel, M. ACS Appl. Mater. Interfaces 2015, 7, 9307. doi: 10.1021/acsami.5b02475
23. [23]
  Pei, K.; Wu, Y.; Wu, W.; Zhang, Q.; Chen, B.; Tian, H.; Zhu, W. Chem. Eur. J. 2012, 18, 8190. doi: 10.1002/chem.v18.26
24. [24]
  Chai, Z.; Wan, S.; Zhong, C.; Xu, T.; Fang, M.; Wang, J.; Xie, Y.; Zhang, Y.; Mei, A.; Han, H.; Peng, Q.; Li, Q.; Li, Z. ACS Appl. Mater. Interfaces 2016, 8, 28652. doi: 10.1021/acsami.6b10030
25. [25]
  Soman, S.; Rahim, M. A.; Lingamoorthy, S.; Suresh, C. H.; Das, S. Phys. Chem. Chem. Phys. 2015, 17, 23095. doi: 10.1039/C5CP03371C
26. [26]
  Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetra-hedron Lett. 2000, 41, 481. doi: 10.1016/S0040-4039(99)02096-1
27. [27]
  Liu, Y.; Wang, H.-Y.; Chen, G.; Xu, X.-P.; Ji, S.-J. Aust. J. Chem. 2009, 62, 934
  Keerthi, A.; Sriramulu, D.; Liu, Y.; Timothy C. T. Y.; Wang, Q.; Valiyaveettil S. Dyes Pigm. 2013, 99, 787.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142