Chinese Journal of Organic Chemistry >
Synthesis and Photovoltaic Properties of Two Dimensional Organic Dyes Containing Benzothiadiazole Unit
Received date: 2013-09-03
Revised date: 2013-10-11
Online published: 2013-10-31
Supported by
Project supported by the National Natural Science Foundation of China (No. 51173154) and the Natural Science Foundation of Hunan Province (No. 13JJ2025).
By introducing the narrow band gap unit (dithiophene-benzothiadiazole) to the organic dye system, two novel organic dyes (DD2, DH2) with two-dimensional structures were designed and synthesized. The influence of dithiophene-ben- zothiadiazole unit acting as side chain or bridge group on the photophysical, electrochemical, and photovoltaic properties of the two dye-sensitizers was studied systematically. Two as-synthsized dyes with dithiophene-benzothiadiazole unit exhibited broad absorption spectra. Under one sun illumination (100 mW·cm-2, AM 1.5 G), DH2- and DD2-based dye-sensitized solar cells showed the power conversion efficiencies (PCE) of 1.67% and 3.26%, respectively. With optimization of co-adsorbent chenodeoxycholic acid (CDCA), DH2 exhibited a relatvely good anti-aggregation ability. Therefore, CDCA had a negligible effect on the PCE of DH2-based DSSCs. However, DD2 achieved an enhanced PCE of 5.53% after adding CDCA as co-adsorbent.
Key words： organic dyes; benzothiadiazole; synthesis; dye-sensitized solar cells
Cao Zhencai , He Zhou , Deng Lijun , Tan Songting . Synthesis and Photovoltaic Properties of Two Dimensional Organic Dyes Containing Benzothiadiazole Unit[J]. Chinese Journal of Organic Chemistry, 2014 , 34(2) : 340 -348 . DOI: 10.6023/cjoc201309006
[1] O'Regan, B.-C.; Grätzel, M. Nature 1991, 335, 7377.
[2] Wang, J.-W.; Li, Y.; Xu, Y.-L.; Li, Y.; Shen, K.-H. Acta Chim. Sinica 2012, 70, 1278 (in Chinese).
(王纪伟, 李莹, 徐艳玲, 李杨, 申凯华, 化学学报, 2012, 70, 1278.)
[3] Mao, L.; Xu, Y.-J.; Wang, X.-D.; Liu, X. –J.; Sun, Z.; Xue, S. Acta Chim. Sinica 2011, 69, 2092 (in Chinese).
(梁茂, 徐英军, 王旭达, 刘秀杰, 孙喆, 薛松, 化学学报, 2011, 69, 2092.)
[4] Feng, X.-M.; Huang, X. –W.; Tan, Z.; Zhao, B.; Tan, S.-T. Acta Chim. Sinica 2011, 69, 653 (in Chinese).
(冯小明, 黄先威, 谭卓, 赵斌, 谭松庭, 化学学报, 2011, 69, 653.)
[5] He, J.-J.; Chen, S.-X.; Wang, T.-T.; Zeng, H.-P. Chin. J. Org. Chem. 2012, 472 (in Chinese).
(何俊杰, 陈舒欣, 王婷婷, 曾和平, 有机化学, 2012, 32, 472.)
[6] Wang, Z.-Y.; Wang, R.-Y.; Fu, N.-Y. Chin. J. Org. Chem. 2011, 31, 415 (in Chinese).
(王振宇, 王如勇, 傅南雁, 有机化学, 2011, 31, 415.)
[7] Yella, A.; Lee, H.; Tsao, H.-N.; Yi, C.; Chandiran, A.-K.; Nazeeruddin, M.-K.; Diau, E.-W.; Yeh, C.; Zakeeruddin, S.-M.; Grätzel, M. Science 2011, 334, 629.
[8] Nazeeruddin, M.-K.; De Angelis, F.; Fantacci, S.; Selloni, A.; Viscardi, G.; Liska, P.; Ito, S.; Takeru, B.; Grätzel, M. J. Am. Chem. Soc. 2005, 127, 16835.
[9] Gao, F.; Wang, Y.; Shi, D.; Zhang, J.; Wang, M.; Jing, X.; Humphry-Baker, R.; Wang, P.; Zakeeruddin, S.-M.; Grätzel, M. J. Am. Chem. Soc. 2008, 130, 10720.
[10] Wang, Q.; Ito, S.; Grätzel, M.; Fabregat-Santiago, F.; Mora-Sero, I.; Bisquert, J.; Bessho, T.; Imai, H. J. Phys. Chem. B 2006, 110, 25210.
[11] Chiba, Y.; Islam, A.; Watanabe, Y.; Komiya, R.; Koide, N.; Han, L. Jpn. J. Appl. Phys. 2006, 45, L638.
[12] Zeng, W.; Cao, Y.; Bai, Y.; Wang, Y.; Shi, Y.; Zhang, M.; Wang, F.; Pan, C.; Wang, P. Chem. Mater. 2010, 22, 1915.
[13] Cai, S.; Hu, X.; Zhang, Z.; Su, J.; Li, X.; Islam, A.; Han, L.; Tian, H. J. Mater. Chem. A 2013, 1, 4763.
[14] Feng, Q.; Jia, X.; Zhou, G.; Wang, Z. Chem. Commun. 2013, 49, 7445.
[15] Liu, B.; Liu, Q.; You, D.; Li, X.; Naruta, Y.; Zhu, W. J. Mater. Chem. 2012, 22, 13348.
[16] Li, L.; Hao, Y.; Yang, X.; Zhao, J.; Tian, H.; Teng, C.; Anders, H.; Licheng, S. ChemSusChem. 2011, 4, 609.
[17] Tang, X.; Wang, Y.-X Acta Chim. Sinica 2013, 71, 193 (in Chinese).
(唐笑, 汪禹汛, 化学学报, 2013, 71, 193.)
[18] Huang, X.-W.; Deng, J.-Y.; Xu, L.; Shen, P.; Zhao, B.; Tan, S.-T. Acta Chim. Sinica 2012, 70, 1604 (in Chinese).
(黄先威, 邓继勇, 许律, 沈平, 赵斌, 谭松庭, 化学学报, 2012, 70, 1604.)
[19] Abbotto, A.; Leandri, V.; Manfredi, N.; De Angelis, F.; Pastore, M.; Yum, J.; Nazeeruddin, M.-K.; Grätzel, M. Eur. J. Org. Chem. 2011, 2011, 6195.
[20] Sirohi, R.; Kim, D.-H.; Yu, S.; Lee, S.-H. Dyes Pigm. 2012, 92, 1132.
[21] Park, S.-S.; Won, Y.-S.; Choi, Y.-C.; Kim, J.-H. Energy Fuels 2009, 23, 3732.
[22] Yen, Y.; Chen, W.; Hsu, C.; Chou, H.; Lin, J.-T.; Yeh, M.-P. Org. Lett. 2011, 13, 4930.
[23] Ji, Z.; Natu, G.; Huang, Z.; Wu, Y Energy Environ. Sci. 2011, 4, 2818.
[24] Heredia, D.; Natera, J.; Gervaldo, M.; Otero, L.; Fungo, F.; Lin, C.; Wong, K. Org. Lett. 2009, 12, 12.
[25] Li, Q.; Shi, J.; Li, H.; Li, S.; Zhong, C.; Guo, F.; Peng, M.; Hua, J.; Qin, J.; Li, Z. J. Mater. Chem. 2012, 22, 6689.
[26] Jiang, S.-H.; Zhou, W.-P.; Tan, Z.; Shen, P.; Zhao, B.; Tan, S.-T. Sci. Sin. Chim. 2011, 41, 982 (in Chinese).
(蒋生辉, 周维平, 谭卓, 沈平, 赵斌, 谭松庭, 中国科学, 2011, 41, 982.)
[27] Wu, W.; Hua, J.; Jin, Y.; Zhan, W.; Tian, H. Photochem. Photobiol. Sci. 2008, 7, 63.
[28] Roquet, S.; Cravino, A.; Leriche, P.; Alévêque, O.; Frère, P.; Roncali, J. J. Am. Chem. Soc. 2006, 128, 3459.
[29] Chen, R.; Yang, X.; Tian, H.; Wang, X.; Hagfeldt, A.; Sun, L. Chem. Mater. 2007, 19, 4007.
[30] Tachibana, Y.; Hara, K.; Sayama, K.; Arakawa, H. Chem. Mater. 2002, 14, 2527.
[31] O'Regan, B.-C.; López-Duarte, I.; Martínez-Díaz, M.-V.; Forneli, A.; Albero, J.; Morandeira, A.; Palomares, E.; Torres, T.; Durrant, J.-R. J. Am. Chem. Soc. 2008, 130, 2906.
[32] O'Regan, B.-C.; Walley, K.; Juozapavicius, M.; Anderson, A.; Matar, F.; Ghaddar, T.; Zakeeruddin, S.-M.; Klein, C.; Durrant, J.-R. J. Am. Chem. Soc. 2009, 131, 3541.
[33] Jena, A.-K.; Bhargava, P. RSC Adv. 2013, 3, 2655.
[34] Gu, Z.; Deng, L.; Luo, H.; Guo, X.; Li, H.; Cao, Z.; Liu, X.; Li, X.; Huang, H.; Tan, Y.; Pei, Y.; Tan, S. J. Polym. Sci., Polym. Chem. 2012, 50, 3848.
[35] Sasaki, K.; Tokuda, O.; Hirota, T.; Luo, J.; Castle, R.-N. J. Heterocycl. Chem. 1996, 33, 847.
[36] Zhang, S.; Guo, Y.; Fan, H.; Liu, Y.; Chen, H.; Yang, G.; Zhan, X.; Liu, Y.; Li, Y.; Yang, Y. J. Polym. Sci., Polym. Chem. 2009, 47(20), 5498.
/
| 〈 |
|
〉 |
