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

doi:10.6023/cjoc201704045

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2940-2947.DOI: 10.6023/cjoc201704045 Previous Articles Next Articles

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以苯并噻二唑为辅助受体的N-苯基咔唑类染料敏化剂的合成及光伏性能

韩亮^a, 吴靓^a, 童永正^a, 祖晓燕^a, 蒋绍亮^a,b

a 浙江工业大学化工学院杭州 310017;
b 浙江工业大学药学院杭州 310017

收稿日期:2017-04-27 修回日期:2017-07-13 发布日期:2017-08-11
通讯作者: 蒋绍亮 E-mail:jslarticle@163.com
基金资助:
国家自然科学基金（No.21406202）资助项目.

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

Han Liang^a, Wu Liang^a, Tong Yongzheng^a, Zu Xiaoyan^a, Jiang Shaoliang^a,b

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

Received:2017-04-27 Revised:2017-07-13 Published:2017-08-11
Contact: 10.6023/cjoc201704045 E-mail:jslarticle@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21406202).

1. Syntheses and Photovoltaic Performance of N-Phenylcarbazole Sensitizers with Benzothiadiazole Auxiliary Acceptor.PDF(435KB)

Abstract

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).

Key words: N-phenylcarbazole, benzothiadiazole, synthesis, spectral property, photoelectric conversion efficiency

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Han Liang, Wu Liang, Tong Yongzheng, Zu Xiaoyan, Jiang Shaoliang. Syntheses and Photovoltaic Performance of N-Phenylcarbazole Sensitizers with Benzothiadiazole Auxiliary Acceptor[J]. Chin. J. Org. Chem., 2017, 37(11): 2940-2947.

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[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.
[2] Gu, C.-Z.; Meng, S.-X.; Feng, Y.-Q. Chin. J. Org. Chem. 2015, 35, 1229(in Chinese). (顾承志, 孟舒献, 冯亚青, 有机化学, 2015, 35, 1229.)
[3] Hafeldt, A.; Boschloo, G.; Sun, L. C.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595.
[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). (马英壮, 郑灵灵, 张立培, 陈志坚, 王树峰, 曲波, 肖立新, 龚旗煌, 化学学报, 2015, 73, 257.)
[5] Chaurasia, S.; Lin, J. T. Chem. Rec. 2016, 16, 1311.
[6] Rong, Y.-G.; Mei, A.-Y.; Liu, L.-F.; Li, X.; Han, H.-W. Acta Chim. Sinica 2015, 73, 237(in Chinese). (荣耀光, 梅安意, 刘林峰, 李雄, 韩宏伟, 化学学报, 2015, 73, 237.)
[7] Ye, T.-L.; Wang, J.-H.; Dong, G.-H.; Jiang, Y.-X.; Feng, C.; Yang, Y.-L. Chin. J. Chem. 2016, 34, 747.
[8] Han, R.-B.; Lu, S.; Wang, Y.-J.; Zhang, X.-H.; Wu, Q.; He, T. Acta Chim. Sinica 2015, 73, 1061(in Chinese). (韩若冰, 芦姗, 王艳杰, 张雪华, 吴强, 贺涛, 化学学报, 2015, 73, 1061.)
[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] Chaurasia, S.; Liang, C. J.; Yen, Y. S.; Lin, J. T. J. Mater. Chem. C 2015, 3, 9765.
[11] Kim, B.; Chung, K.; Kim, J. Chem. Eur. J. 2013, 19, 5220
[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.
[13] Liu, Y.; He, J.; Han, L.; Gao, J. R. J. Photochem. Photobiol. A 2017, 332, 283.
[14] Li, T.; Gao, J. R.; Cui, Y. H.; Zhong, C. J.; Ye, Q; Han, L. J. Photochem. Photobiol. A 2015, 303, 91.
[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.
[16] Han, L.; Zhao, J.; Wang, B.; Jiang, S. L. J. Photochem. Photo-biol. A 2016, 326, 1.
[17] Eom, Y. K.; Hong, J. Y.; Kim, J.; Kim, H. K. Dyes Pigm. 2017, 136, 496.
[18] Huang, H. L.; Chen, H. J.; Long, J.; Wang, G.; Tan, S. T. J. Power Sources 2016, 326, 438.
[19] Wu, F.; Liu, H.-T.; Lee, L. T. L.; Chen, T.; Wang, M.; Zhu, L.-N. Chin. J. Chem. 2015, 33, 925.
[20] Mishra, A.; Fischer, M. K. R.; Bäuerle P. Angew. Chem., Int. Ed. 2009, 48, 2474.
[21] Wu, Y. Z.; Zhu, W. H. Chem. Soc. Rev. 2013, 42, 2039.
[22] Wu, Y.; Zhu, W.; Zakeeruddin, S. M.; Grätzel, M. ACS Appl. Mater. Interfaces 2015, 7, 9307.
[23] Pei, K.; Wu, Y.; Wu, W.; Zhang, Q.; Chen, B.; Tian, H.; Zhu, W. Chem. Eur. J. 2012, 18, 8190.
[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.
[25] Soman, S.; Rahim, M. A.; Lingamoorthy, S.; Suresh, C. H.; Das, S. Phys. Chem. Chem. Phys. 2015, 17, 23095.
[26] Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetra-hedron Lett. 2000, 41, 481.
[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.

以苯并噻二唑为辅助受体的N-苯基咔唑类染料敏化剂的合成及光伏性能

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

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