Citation: Zhou Xinyun, Xie Lingchao, Wu Kaile, Tan Songting. Synthesis and Photovoltaic Properties of Organic Dyes Containing Dendritic and 3D Triphenylamine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2589-2598. doi: 10.6023/cjoc201902023 shu

Synthesis and Photovoltaic Properties of Organic Dyes Containing Dendritic and 3D Triphenylamine Derivatives

Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105

Corresponding author: Tan Songting, tanst2008@163.com

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Received Date: 21 February 2019
Revised Date: 14 April 2019
Available Online: 19 September 2019
Fund Project: the National Natural Science Foundation of China 21875204Project supported by the National Natural Science Foundation of China (Nos. 21875204, 51173154)the National Natural Science Foundation of China 51173154

Figures(10)

Three organic dyes with dendritic and 3D triphenylamine derivatives as the donor unit, benzoic acid as the acceptor unit and benzothiadiazole (BT) or difluorobenzothiadiazole (DFBT) as the second acceptor were designed and synthesized. The influences of different donors and second acceptors on the photophysical, electrochemical and photovoltaic properties of dye-sensitizers were systematically investigated. The organic dye with dendritic triphenylamine derivative as a donor unit possesses a higher molar absorption coefficient, and the organic dye with 3D triphenylamine derivative (IDTTPA) as a donor unit has a broader absorption spectrum. The dye-sensitized solar cells based on three organic dyes achieved power conversion efficiencies of 5.27%, 4.22% and 5.50%, respectively. After optimizing the battery with 1 mmol·L^-1 co-adsorbent chenodeoxycholic acid (CDCA), the power conversion efficiencies of the organic dyes were increased to 5.46%, 4.98% and 6.26%, respectively.
- triphenylamine,
- benzothiadiazole,
- organic dye,
- photovoltaic property
1. [1]
  O'regan, B.; Grätzel, M. Nature 1991, 353, 737. doi: 10.1038/353737a0
2. [2]
  Hagfeldt, A.; Boschloo, G.; Sun, L. C.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595. doi: 10.1021/cr900356p
3. [3]
  Clifford, J. N.; Martínez-Ferrero, E.; Viterisi, A.; Palomares, E. Chem. Soc. Rev. 2011, 40, 1635. doi: 10.1039/B920664G
4. [4]
  Wu, Y.-Z.; Zhu, W. H. Chem. Soc. Rev. 2013, 42, 2039. doi: 10.1039/C2CS35346F
5. [5]
  Kou, D.-X.; Liu, W.-Q.; Hu, L.-H.; Chen, S.-H.; Huang, Y.; Dai, S.-Y. Acta Chim. Sinica 2013, 71, 1149 (in Chinese).
6. [6]
  Feng, X.-M.; Huang, X.-W.; Tan, Z.; Zhao, B.; Tan, S.-T. Acta Chim. Sinica 2011, 69, 653 (in Chinese).
7. [7]
  Huang, X.-W.; Deng, J.-Y.; Xu, L.; Shen, P.; Zhao, B.; Tan, S.-T. Acta Chim. Sinica 2012, 70, 1604 (in Chinese).
8. [8]
  Li, J.; Kong, F.-T.; Zhang, C.-N.; Liu, W.-Q.; Dai, S.-Y. Acta Chim. Sinica 2010, 68, 1357 (in Chinese).
9. [9]
  Tang, X.; Wang, Y.-X. Acta Chim. Sinica 2013, 71, 193 (in Chinese).
10. [10]
  Wang, J.-W.; Li, Y.; Xu, Y.-L.; Li, Y.; Shen, K.-H. Acta Chim. Sinica 2012, 70, 1278 (in Chinese). doi: 10.3969/j.issn.0251-0790.2012.06.026
11. [11]
  He, J.-J.; Chen, S.-X.; Wang, T.-T.; Zeng, H.-P. Chin. J. Org. Chem. 2012, 32, 472 (in Chinese).
12. [12]
  Cao, Y.-M.; Bai, Y.; Yu, Q.-J.; Cheng, Y.-M.; Liu, S.; Shi, D.; Gao, F.-F.; Wang, P. J. Phys. Chem. C 2009, 113, 6290.
13. [13]
  Yella, A.; Mai, C. L.; Zakeeruddin, S. M.; Chang, S. N.; Hsieh, C. H.; Yeh, C. Y.; Grätzel, M. Angew. Chem., Int. Ed. 2014, 53, 2973. doi: 10.1002/anie.201309343
14. [14]
  Gupta, K.; Singh, S. P.; Islam, A.; Han, L.; Chandrasekharam, M. Electrochim. Acta 2015, 174, 581. doi: 10.1016/j.electacta.2015.05.158
15. [15]
  Mishra, A.; Fischer, M. K.; Bäuerle, P. Angew. Chem., Int. Ed. 2009, 48, 2474. doi: 10.1002/anie.200804709
16. [16]
  Han, L.; Zhou, X.; Ye, Q.; Li, Y.-J.; Gao, J.-R. Chin. J. Org. Chem. 2013, 33, 1000 (in Chinese).
17. [17]
  Wang, Z.-S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara, K. J. Phys. Chem. C 2008, 112, 17011. doi: 10.1021/jp806927b
18. [18]
  Su, J.-Y.; Chen, Y.; Wu, Y.-G.; Ghimire, R. P.; Xu, Y.-J.; Liu, X.-J.; Wang, Z.-H.; Liang, M. Electrochim. Acta 2017, 254, 191. doi: 10.1016/j.electacta.2017.09.133
19. [19]
  Han, L.; Wu, L.; Tong, Y.-Z.; Zu, X.-Y.; Jiang, S.-L. Chin. J. Org. Chem. 2017, 37, 2940 (in Chinese).
20. [20]
  Chen, S.-G.; Jia, H.-L.; Ju, X.-H.; Zheng, H.-G. Dyes Pigm. 2017, 146, 127. doi: 10.1016/j.dyepig.2017.06.068
21. [21]
  Zhu, B.-Y.; Wu, L.; Ye, Q.; Gao, J.-R.; Han, L. Tetrahedron 2017, 73, 6307. doi: 10.1016/j.tet.2017.09.018
22. [22]
  Liang, M.; Xu, Y.-J.; Wang, X.-D.; Liu, X.-J.; Sun, Z.; Xue, S. Acta Chim. Sinica 2011, 69, 2092 (in Chinese).
23. [23]
  Cao, Z.-C.; He, Z.; Deng, L.-J.; Tan, S.-T. Chin. J. Org. Chem. 2014, 34, 340 (in Chinese).
24. [24]
  Li, Q.-Q.; Shi, J.; Li, H.-Y.; Li, S.; Zhong, C.; Guo, F.-L.; Peng, M.; Hua, J.-L.; Qin, J.-G.; Li, Z. J. Mater. Chem. 2012, 22, 6689. doi: 10.1039/c2jm30200d
25. [25]
  Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska, P.; Comte, P.; Péchy, P.; Grätzel, M. Chem. Commun. 2008, 5194.
26. [26]
  Wu, Y.-Z.; Zhang, X.; Li, W.-Q.; Wang, Z.-S.; Tian, H.; Zhu, W.-H. Adv. Energy Mater. 2012, 2, 149. doi: 10.1002/aenm.201100341
27. [27]
  Li, Q.-Q.; Lu, L.-L.; Zhong, C.; Shi, J.; Huang, Q.; Jin, X.-B.; Peng, T.-Y.; Qin, J.-G.; Li, Z. J. Phys. Chem. B 2009, 113, 14588. doi: 10.1021/jp906334w
28. [28]
  Kakiage, K.; Aoyama, Y.; Yano, T.; Oya, K.; Fujisawa, J.; Hanaya, M. Chem. Commun. 2015, 51, 15894. doi: 10.1039/C5CC06759F
29. [29]
  Liu, Z.-X.; Duan, K.-K.; Guo, H.; Deng, Y.-H.; Huang, H.-L.; Yi, X.-Y.; Chen, H.-J.; Tan, S.-T. Dyes Pigm. 2017, 140, 312. doi: 10.1016/j.dyepig.2017.01.026
30. [30]
  Zhu, H.-B.; Li, W.-Q.; Wu, Y.-Z.; Liu, B.; Zhu, S.-Q.; Li, X.; Agren, H.; Zhu, W.-H. ACS Sustainable Chem. Eng. 2014, 2, 1026. doi: 10.1021/sc500035j
31. [31]
  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
32. [32]
  Pan, B.; Zhu, Y.-Z.; Qiu, C.-J.; Wang, B.; Zheng, J.-O. Acta Chim. Sinica 2018, 76, 215 (in Chinese).
33. [33]
  Chen, H.-J.; Huang, H.; Huang, X.-W.; Clifford, J. N.; Forneli, A.; Palomares, E.; Zheng, X.-Y.; Zheng, L.-P.; Wang, X.-Y.; Shen, P.; Zhao, B.; Tan, S.-T. J. Phys. Chem. C 2010, 114, 3280.
34. [34]
  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
35. [35]
  Forster, F.; Rendón López, V.-M.; Oestreich, M. J. Am. Chem. Soc. 2018, 140, 1259. doi: 10.1021/jacs.7b13088
36. [36]
  Song, X.-R.; Zhang, W.-W.; Li, X.; Jiang, H.-Y.; Shen, C.; Zhu, W.-H. J. Mater. Chem. C 2016, 4, 9203. doi: 10.1039/C6TC03418G
37. [37]
  Liu, Y.-H.; Cao, Y.-M.; Zhang, W.-W.; Stojanovic, M.; Dar, M I.; Péchy, P.; Saygili, Y.; Hagfeldt, A.; Zakeeruddin, S. M.; Grätzel, M. Angew. Chem., Int. Ed. 2018, 130, 14321. doi: 10.1002/ange.201808609
38. [38]
  Chen, R.-K.; Yang, X.-C.; Tian, H.-N.; Sun, L.-C. J. Photochem. Photobiol. A 2007, 189, 295. doi: 10.1016/j.jphotochem.2007.02.018
39. [39]
  Shen, P.; Liu, Y.-J.; Huang, X.-W.; Zhao, B.; Xiang, N.; Fei, J.-J.; Liu, L.-M.; Wang, X.-Y.; Huang, H.; Tan, S.-T. Dyes Pigm. 2009, 83, 187. doi: 10.1016/j.dyepig.2009.04.005
40. [40]
  Liu, X.-S.; Cao, Z.-C.; Huang, H.-L.; Liu, X.-X.; Tan, Y.-Z.; Chen, H.-J.; Pei, Y.; Tan, S.-T. J. Power Sources 2014, 248, 400. doi: 10.1016/j.jpowsour.2013.09.106
41. [41]
  Hara, K.; Sato, T.; Katoh, R.; Furube, A.; Ohga, Y.; Shinpo, A.; Suga, S.; Sayama, K.; Sugihara, H.; Arakawa, H. J. Phys. Chem. B 2003, 107, 597. doi: 10.1021/jp026963x
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