Synthesis of Phenothiazine Dyes Featuring Benzothiadiazole Unit for Efficient Dye-sensitized Solar Cells

doi:10.6023/A17120543

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (3): 215-223.DOI: 10.6023/A17120543 Previous Articles

Special Issue: 纪念南开大学化学学科创建100周年

Article

含苯并噻二唑的吩噻嗪染料分子的设计合成及其在染料敏化太阳能电池中的应用

潘彬^a,b, 朱义州^a, 邱昌娟^a, 王冰^a, 郑健禺^a,b

a 南开大学化学学院元素有机化学国家重点实验室天津 300071;
b 天津化学化工协同创新中心天津 300071

投稿日期:2017-12-17 发布日期:2018-01-22
通讯作者: 朱义州, 郑健禺 E-mail:zhuyizhou@nankai.edu.cn;jyzheng@nankai.edu.cn
基金资助:
项目受国家自然科学基金（No.21572108）和天津市自然科学基金（No.16JCYBJC16700）资助.

Synthesis of Phenothiazine Dyes Featuring Benzothiadiazole Unit for Efficient Dye-sensitized Solar Cells

Pan Bina^a,b, Zhu Yi-Zhou^a, Qiu Changjuana^a, Wang Binga^a, Zheng Jian-Yu^a,b

a State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071;
b Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300071

Received:2017-12-17 Published:2018-01-22
Contact: 10.6023/A17120543 E-mail:zhuyizhou@nankai.edu.cn;jyzheng@nankai.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572108) and Tianjin Natural Science Foundation (No. 16JCYBJC16700).

1. Synthesis of Phenothiazine Dyes Featuring Benzothiadiazole Unit for Efficient Dye-sensitized Solar Cells.PDF(939KB)

Abstract

Dye-sensitized solar cells (DSSCs), as an emerging solar energy conversion technology, have attracted increasing attention for their ease of fabrication, low production cost, wide variety of dye structure, and high power conversion efficiency (PCE). As the critical component of DSSCs, photosensitizers play an important role in photon capturing, charge generation and separation, as well as electron injection at the semiconductor interface. Efforts on the design and synthesis of photosensitizers are thus an effective and straightforward way to tune the photovoltaic performance. In this article, three novel phenothiazine-based D-A-π-A type organic dyes (JY50~JY52) featuring benzothiadiazole units as auxiliary acceptors have been synthesized and applied in DSSCs. The introduction of auxiliary acceptor would take the advantages of the optimization of the dyes' energy levels and light absorption. To get more impressive device efficiency, 4-hexylbenzene group was decorated onto phenothiazine donor and has proved to be effective for improving the molar absorption coefficient and suppressing the charge recombination, finally resulting in the enhancement of photocurrent (J_sc) and photovoltage (Voc). In order to investigate the effect of different electron acceptor/anchoring group, benzoic acid and cyanoacrylic acid, which are widely applied in porphyrin-based dyes and metal-free organic dyes, respectively, are employed here to construct the target dyes. As we can see from the obtained photovoltaic performance data, dyes (JY50 and JY51) with benzoic acid anchor seem more beneficial to gain a higher Voc, this may be ascribed to its nearly vertical adsorption geometry on the TiO₂ interface and the resulting decrease of the charge recombination. As for dye (JY52) with cyanoacrylic acid anchor, a better J_sc value is achieved because cyanoacrylic acid endows dye an extended conjugated system and an enhanced intramolecular charge transfer. Under AM 1.5 solar light conditions, the dye JY51 with 4-hexylbenzene unit and benzoic acid acceptor exhibited the highest PCE of 7.61%, with Voc of 797 mV and J_sc of 14.21 mA·cm^-2.

Key words: phenothiazine, benzothiadiazole, organic dye, dye-sensitized solar cell, power conversion efficiency

Cite this article

Pan Bina, Zhu Yi-Zhou, Qiu Changjuana, Wang Binga, Zheng Jian-Yu. Synthesis of Phenothiazine Dyes Featuring Benzothiadiazole Unit for Efficient Dye-sensitized Solar Cells[J]. Acta Chim. Sinica, 2018, 76(3): 215-223.

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[1] Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595.
[2] Liang, M.; Chen, J. Chem. Soc. Rev. 2013, 42, 3453.
[3] Li, L. L.; Diau, E. W. G. Chem. Soc. Rev. 2013, 42, 291.
[4] Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem. Int. Ed. 2009, 48, 2474.
[5] Huang, Z. S.; Meier, H.; Cao, D. R. J. Mater. Chem. C 2016, 4, 2404.
[6] Urbani, M.; Grätzel, M.; Nazeeruddin, M. K.; Torres, T. Chem. Rev. 2014, 114, 12330.
[7] Zhao, C.; Wang, Z.; Zhou, K.; Ge, H.; Zhang, Q.; Jin, L.; Wang, W.; Yin, S. Acta Chim. Sinica 2016, 74, 251. (赵蔡斌, 王占领, 周科, 葛红光, 张强, 靳玲侠, 王文亮, 尹世伟, 化学学报, 2016, 74, 251.)
[8] Zhai, W.; Zhou, E. Chin. J. Org. Chem. 2016, 36, 2786. (翟文超, 周二军, 有机化学, 2016, 36, 2786.)
[9] Zhou, Q. Q.; Chen, S.; Zhang, M. A.; Wang, L. D.; Li, Y. R.; Shi, G. Q. Chin. J. Chem. 2016, 34, 59.
[10] Ren, J.; Sun, M. Chin. J. Org. Chem. 2016, 36, 2284. (任静, 孙明亮, 有机化学, 2016, 36, 2284.)
[11] Li, X.; Zhang, X.; Hua, J.; Tian, H. Mol. Syst. Des. Eng. 2017, 2, 98.
[12] O'Regan, B.; Grätzel, M. Nature 1991, 353, 737.
[13] Zhang, X. Y.; Ying, W. J.; Wu, W. J.; Li, J.; Hua, J. L. Acta Chim. Sinica 2015, 73, 272. (张晓瑜, 应伟江, 武文俊, 李晶, 花建丽, 化学学报, 2015, 73, 272.).
[14] Li, J.; Kong, F. T.; Zhang, C. N.; Liu, W. Q.; Dai, S. Y. Acta Chim. Sinica 2010, 68, 1357. (李洁, 孔凡太, 张昌能, 刘伟庆, 戴松元, 化学学报, 2010, 68, 1357.)
[15] Kou, D. X.; Liu, W. Q.; Hu, L. H.; Chen, S. H.; Huang, Y.; Dai, S. Y. Acta Chim. Sinica 2013, 71, 1149. (寇东星, 刘伟庆, 胡林华, 陈双宏, 黄阳, 戴松元, 化学学报, 2013, 71, 1149.)
[16] Liang, M.; Xu, Y. J.; Wang, X. D.; Liu, X. J.; Sun, Z.; Xue, S. Acta Chim. Sinica 2011, 69, 2092. (梁茂, 徐英军, 王旭达, 刘秀杰, 孙喆, 薛松, 化学学报, 2011, 69, 2092.)
[17] Feng, X. M.; Huang X. W.; Tan, Z.; Zhao, B.; Tan, S. T. Acta Chim. Sinica 2011, 69, 653. (冯小明, 黄先威, 谭卓, 赵斌, 谭松庭, 化学学报, 2011, 69, 653.)
[18] Huang, X. W.; Deng, J. Y.; Xu, L.; Shen, P.; Zhao, B.; Tan, S. T. Acta Chim. Sinica 2012, 70, 1604. (黄先威, 邓继勇, 许律, 沈平, 赵斌, 谭松庭, 化学学报, 2012, 70, 1604.)
[19] Meier, H.; Huang, Z.-S.; Cao, D. J. Mater. Chem. C 2017, 5, 9828.
[20] Eom, Y. K.; Choi, I. T.; Kang, S. H.; Lee, J.; Kim, J.; Ju, M. J.; Kim, H. K. Adv. Energy Mater. 2015, 5, 1500300.
[21] Kang, M. S.; Kang, S. H.; Kim, S. G.; Choi, I. T.; Ryu, J. H.; Ju, M. J.; Cho, D.; Lee, J. Y.; Kim, H. K. Chem. Commun. 2012, 48, 9349.
[22] Qian, X.; Zhu, Y. Z.; Song, J.; Gao, X. P.; Zheng, J. Y. Org. Lett. 2013, 15, 6034.
[23] Qian, X.; Gao, H.-H.; Zhu, Y.-Z.; Pan, B.; Zheng, J.-Y. Dyes Pigm. 2015, 121, 152.
[24] Mao, J. Y.; He, N. N.; Ning, Z. J.; Zhang, Q.; Guo, F. L.; Chen, L.; Wu, W. J.; Hua, J. L.; Tian, H. Angew. Chem. Int. Ed. 2012, 51, 9873.
[25] Xie, Y. S.; Wu, W. J.; Zhu, H. B.; Liu, J. C.; Zhang, W. W.; Tian, H.; Zhu, W. H. Chem. Sci. 2016, 7, 544.
[26] Dai, P. P.; Yang, L.; Liang, M.; Dong, H. H.; Wang, P.; Zhang, C. Y.; Sun, Z.; Xue, S. ACS Appl. Mater. Interfaces 2015, 7, 22436.
[27] Wang, Z. H.; Liang, M.; Wang, L. N.; Hao, Y. J.; Wang, C. B.; Sun, Z.; Xue, S. Chem. Commun. 2013, 49, 5748.
[28] Ye, T.; Wang, J.; Dong, G.; Jiang, Y.; Feng, C.; Yang, Y. Chin. J. Chem. 2016, 34, 747.
[29] Han, L.; Wu, L.; Tong, Y.; Zu, X.; Jiang, S. Chin. J. Org. Chem. 2017, 37, 2940. (韩亮, 吴靓, 童永正, 祖晓燕, 蒋绍亮, 有机化学, 2017, 37, 2940.)
[30] Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Mueller, E.; Liska, P.; Vlachopoulos, N.; Grätzel, M. J. Am. Chem. Soc. 1993, 115, 6382.
[31] Nazeeruddin, Md. K.; Pechy, P.; Grätzel, M. Chem. Commun. 1997, 1705.
[32] Nazeeruddin, M. K.; Zakeeruddin, S. M.; Humphry-Baker, R.; Jirousek, M.; Liska, P.; Vlachopoulos, N.; Shklover, V.; Fischer, C.-H.; Grätzel, M. Inorg. Chem. 1999, 38, 6298.
[33] Mathew, S.; Yella, A.; Gao, P.; Humphry-Baker, R.; CurchodBasile, F. E.; Ashari-Astani, N.; Tavernelli, I.; Rothlisberger, U.; Nazeeruddin, Md. K.; Grätzel, M. Nat. Chem. 2014, 6, 242.
[34] Wang, Y. Q.; Chen, B.; Wu, W. J.; Li, X.; Zhu, W. H.; Tian, H.; Xie, Y. S. Angew. Chem. Int. Ed. 2014, 53, 10779.
[35] Xie, Y. S.; Tang, Y. Y.; Wu, W. J.; Wang, Y. Q.; Liu, J. C.; Li, X.; Tian, H.; Zhu, W. H. J. Am. Chem. Soc. 2015, 137, 14055.
[36] Li, C. M.; Luo, L.; Wu, D.; Jiang, R. Y.; Lan, J. B.; Wang, R. L.; Huang, L. Y.; Yang, S. Y.; You, J. S. J. Mater. Chem. A 2016, 4, 11829.
[37] Jia, H.-L.; Zhang, M.-D.; Yan, W.; Ju, X.-H.; Zheng, H.-G. J. Mater. Chem. A 2016, 4, 11782.
[38] Luo, J.; Xu, M. F.; Li, R. Z.; Huang, K. W.; Jiang, C. Y.; Qi, Q. B.; Zeng, W. D.; Zhang, J.; Chi, C. Y.; Wang, P.; Wu, J. S. J. Am. Chem. Soc. 2014, 136, 265.
[39] Li, W.; Liu, Z.; Wu, H.; Cheng, Y.-B.; Zhao, Z.; He, H. J. Phys. Chem. C 2015, 119, 5265.
[40] Kang, S. H.; Jeong, M. J.; Eom, Y. K.; Choi, I. T.; Kwon, S. M.; Yoo, Y.; Kim, J.; Kwon, J.; Park, J. H.; Kim, H. K. Adv. Energy Mater. 2016, 1602117.
[41] Kakiage, K.; Aoyama, Y.; Yano, T.; Oya, K.; Fujisawab, J.; Hanaya, M. Chem. Commun. 2015, 51, 15894.
[42] Wu, Y.; Zhu, W. Chem. Soc. Rev. 2013, 42, 2039.
[43] Ying, W. J.; Guo, F. L.; Li, J.; Zhang, Q.; Wu, W. J.; Tian, H.; Hua, J. L. ACS Appl. Mater. Interfaces 2012, 4, 4215.
[44] Qu, S. Y.; Qin, C. J.; Islam, A.; Wu, Y. Z.; Zhu, W. H.; Hua, J. L.; Tian, H.; Han, L. Y. Chem. Commun. 2012, 48, 6972.
[45] Mao, J. Y.; Zhang, X. Y.; Liu, S. H.; Shen, Z. J.; Li, X.; Wu, W. J.; Chou, P. T.; Hua, J. L. Electrochim. Acta 2015, 179, 179.
[46] Pei, K.; Wu, Y. Z.; Li, H.; Geng, Z. Y.; Tian, H.; Zhu, W. H. ACS Appl. Mater. Interfaces 2015, 7, 5296.
[47] Li, H.; Wu, Y. Z.; Geng, Z. Y.; Liu, J. C.; Xu, D. D.; Zhu, W. H. J. Mater. Chem. A 2014, 2, 14649.
[48] Wu, Y.; Zhang, X.; Li, W.; Wang, Z.-S.; Tian, H.; Zhu, W. Adv. Energy Mater. 2012, 2, 149.
[49] Li, W.; Wu, Y.; Zhang, Q.; Tian, H.; Zhu, W. ACS Appl. Mater. Interfaces 2012, 4, 1822.
[50] Cui, Y.; Wu, Y.; Lu, X.; Zhang, X.; Zhou, G.; Miapeh, F. B.; Zhu, W.; Wang, Z.-S. Chem. Mater. 2011, 23, 4394.
[51] Chang, Y. J.; Chou, P.-T.; Lin, Y.-Z.; Watanabe, M.; Yang, C.-J.; Chin, T.-M.; Chow, T. J. J. Mater. Chem. 2012, 22, 21704.
[52] Hua, Y.; Chang, S.; Huang, D. D.; Zhou, X.; Zhu, X. J.; Zhao, J. Z.; Chen, T.; Wong, W. Y.; Wong, W. K. Chem. Mater. 2013, 25, 2146.
[53] Hua, Y.; Chang, S.; Wang, H.; Huang, D.; Zhao, J.; Chen, T.; Wong, W.-Y.; Wong, W.-K.; Zhu, X. J. Power Sources 2013, 243, 253.
[54] Hua, Y.; Chang, S.; He, J.; Zhang, C. S.; Zhao, J. Z.; Chen, T.; Wong, W. Y.; Wong, W. K.; Zhu, X. J. Chem.-Eur. J. 2014, 20, 6300.
[55] Kumar, C. V.; Raptis, D.; Koukaras, E. N.; Sygellou, L.; Lianos, P. Org. Electron. 2015, 25, 66.
[56] Lin, R. Y. Y.; Wu, F. L.; Li, C. T.; Chen, P. Y.; Ho, K. C.; Lin, J. T. ChemSusChem 2015, 8, 2503.
[57] Zhang, X.; Gou, F.; Shi, J.; Gao, H.; Xu, C.; Zhu, Z.; Jing, H. RSC Adv. 2016, 6, 106380.
[58] Iqbal, Z.; Wu, W. Q.; Huang, Z. S.; Wang, L. Y.; Kuang, D. B.; Meier, H.; Cao, D. R. Dyes Pigm. 2016, 124, 63.
[59] Du, C. F.; Jiang, L.; Sun, L.; Huang, N. Y.; Deng, W. Q. RSC Adv. 2015, 5, 37574.

含苯并噻二唑的吩噻嗪染料分子的设计合成及其在染料敏化太阳能电池中的应用

Synthesis of Phenothiazine Dyes Featuring Benzothiadiazole Unit for Efficient Dye-sensitized Solar Cells

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