Citation: 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 Chimica Sinica, ;2018, 76(3): 215-223. doi: 10.6023/A17120543 shu

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

Corresponding author: Zhu Yi-Zhou, zhuyizhou@nankai.edu.cn Zheng Jian-Yu, jyzheng@nankai.edu.cn
Received Date: 17 December 2017
Available Online: 22 March 2018
Fund Project: Tianjin Natural Science Foundation 16JCYBJC16700Project supported by the National Natural Science Foundation of China (No. 21572108) and Tianjin Natural Science Foundation (No. 16JCYBJC16700)the National Natural Science Foundation of China 21572108

Figures(7)

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 (V_oc). 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 V_oc, 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 V_oc of 797 mV and J_sc of 14.21 mA·cm^-2.
- phenothiazine,
- benzothiadiazole,
- organic dye,
- dye-sensitized solar cell,
- power conversion efficiency
1. [1]
  Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595. doi: 10.1021/cr900356p
2. [2]
  Liang, M.; Chen, J. Chem. Soc. Rev. 2013, 42, 3453. doi: 10.1039/c3cs35372a
3. [3]
  Li, L. L.; Diau, E. W. G. Chem. Soc. Rev. 2013, 42, 291. doi: 10.1039/C2CS35257E
4. [4]
  Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem. Int. Ed. 2009, 48, 2474. doi: 10.1002/anie.v48:14
5. [5]
  Huang, Z. S.; Meier, H.; Cao, D. R. J. Mater. Chem. C 2016, 4, 2404. doi: 10.1039/C5TC04418A
6. [6]
  Urbani, M.; Grätzel, M.; Nazeeruddin, M. K.; Torres, T. Chem. Rev. 2014, 114, 12330. doi: 10.1021/cr5001964
7. [7]
  Zhao, C.; Wang, Z.; Zhou, K.; Ge, H.; Zhang, Q.; Jin, L.; Wang, W.; Yin, S. Acta Chim. Sinica 2016, 74, 251. doi: 10.3969/j.issn.0253-2409.2016.02.017
8. [8]
  Zhai, W.; Zhou, E. Chin. J. Org. Chem. 2016, 36, 2786.
9. [9]
  Zhou, Q. Q.; Chen, S.; Zhang, M. A.; Wang, L. D.; Li, Y. R.; Shi, G. Q. Chin. J. Chem. 2016, 34, 59. doi: 10.1002/cjoc.201500609
10. [10]
  Ren, J.; Sun, M. Chin. J. Org. Chem. 2016, 36, 2284.
11. [11]
  Li, X.; Zhang, X.; Hua, J.; Tian, H. Mol. Syst. Des. Eng. 2017, 2, 98. doi: 10.1039/C7ME00002B
12. [12]
  O'Regan, B.; Grätzel, M. Nature 1991, 353, 737. doi: 10.1038/353737a0
13. [13]
  Zhang, X. Y.; Ying, W. J.; Wu, W. J.; Li, J.; Hua, J. L. Acta Chim. Sinica 2015, 73, 272. doi: 10.3969/j.issn.0253-2409.2015.03.003
14. [14]
  Li, J.; Kong, F. T.; Zhang, C. N.; Liu, W. Q.; Dai, S. Y. Acta Chim. Sinica 2010, 68, 1357.
15. [15]
  Kou, D. X.; Liu, W. Q.; Hu, L. H.; Chen, S. H.; Huang, Y.; Dai, S. Y. Acta Chim. Sinica 2013, 71, 1149.
16. [16]
  Liang, M.; Xu, Y. J.; Wang, X. D.; Liu, X. J.; Sun, Z.; Xue, S. Acta Chim. Sinica 2011, 69, 2092.
17. [17]
  Feng, X. M.; Huang X. W.; Tan, Z.; Zhao, B.; Tan, S. T. Acta Chim. Sinica 2011, 69, 653.
18. [18]
  Huang, X. W.; Deng, J. Y.; Xu, L.; Shen, P.; Zhao, B.; Tan, S. T. Acta Chim. Sinica 2012, 70, 1604.
19. [19]
  Meier, H.; Huang, Z.-S.; Cao, D. J. Mater. Chem. C 2017, 5, 9828. doi: 10.1039/C7TC03406G
20. [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. doi: 10.1002/aenm.201500300
21. [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. doi: 10.1039/c2cc31384g
22. [22]
  Qian, X.; Zhu, Y. Z.; Song, J.; Gao, X. P.; Zheng, J. Y. Org. Lett. 2013, 15, 6034. doi: 10.1021/ol402931u
23. [23]
  Qian, X.; Gao, H.-H.; Zhu, Y.-Z.; Pan, B.; Zheng, J.-Y. Dyes Pigm. 2015, 121, 152. doi: 10.1016/j.dyepig.2015.05.015
24. [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. doi: 10.1002/anie.201204948
25. [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. doi: 10.1039/C5SC02778K
26. [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. doi: 10.1021/acsami.5b06481
27. [27]
  Wang, Z. H.; Liang, M.; Wang, L. N.; Hao, Y. J.; Wang, C. B.; Sun, Z.; Xue, S. Chem. Commun. 2013, 49, 5748. doi: 10.1039/c3cc42121j
28. [28]
  Ye, T.; Wang, J.; Dong, G.; Jiang, Y.; Feng, C.; Yang, Y. Chin. J. Chem. 2016, 34, 747. doi: 10.1002/cjoc.v34.8
29. [29]
  Han, L.; Wu, L.; Tong, Y.; Zu, X.; Jiang, S. Chin. J. Org. Chem. 2017, 37, 2940.
30. [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. doi: 10.1021/ja00067a063
31. [31]
  Nazeeruddin, Md. K.; Pechy, P.; Grätzel, M. Chem. Commun. 1997, 1705.
32. [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. doi: 10.1021/ic990916a
33. [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. doi: 10.1038/nchem.1861
34. [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. doi: 10.1002/anie.201406190
35. [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. doi: 10.1021/jacs.5b09665
36. [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. doi: 10.1039/C6TA02888H
37. [37]
  Jia, H.-L.; Zhang, M.-D.; Yan, W.; Ju, X.-H.; Zheng, H.-G. J. Mater. Chem. A 2016, 4, 11782. doi: 10.1039/C6TA03740B
38. [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. doi: 10.1021/ja409291g
39. [39]
  Li, W.; Liu, Z.; Wu, H.; Cheng, Y.-B.; Zhao, Z.; He, H. J. Phys. Chem. C 2015, 119, 5265. doi: 10.1021/jp509842p
40. [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. [41]
  Kakiage, K.; Aoyama, Y.; Yano, T.; Oya, K.; Fujisawab, J.; Hanaya, M. Chem. Commun. 2015, 51, 15894. doi: 10.1039/C5CC06759F
42. [42]
  Wu, Y.; Zhu, W. Chem. Soc. Rev. 2013, 42, 2039. doi: 10.1039/C2CS35346F
43. [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. doi: 10.1021/am300925e
44. [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. doi: 10.1039/c2cc31998e
45. [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. doi: 10.1016/j.electacta.2015.05.003
46. [46]
  Pei, K.; Wu, Y. Z.; Li, H.; Geng, Z. Y.; Tian, H.; Zhu, W. H. ACS Appl. Mater. Interfaces 2015, 7, 5296. doi: 10.1021/am508623e
47. [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. doi: 10.1039/C4TA02777A
48. [48]
  Wu, Y.; Zhang, X.; Li, W.; Wang, Z.-S.; Tian, H.; Zhu, W. Adv. Energy Mater. 2012, 2, 149. doi: 10.1002/aenm.201100341
49. [49]
  Li, W.; Wu, Y.; Zhang, Q.; Tian, H.; Zhu, W. ACS Appl. Mater. Interfaces 2012, 4, 1822. doi: 10.1021/am3001049
50. [50]
  Cui, Y.; Wu, Y.; Lu, X.; Zhang, X.; Zhou, G.; Miapeh, F. B.; Zhu, W.; Wang, Z.-S. Chem. Mater. 2011, 23, 4394. doi: 10.1021/cm202226j
51. [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. doi: 10.1039/c2jm35556f
52. [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. doi: 10.1021/cm400800h
53. [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. doi: 10.1016/j.jpowsour.2013.05.157
54. [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. doi: 10.1002/chem.201304897
55. [55]
  Kumar, C. V.; Raptis, D.; Koukaras, E. N.; Sygellou, L.; Lianos, P. Org. Electron. 2015, 25, 66. doi: 10.1016/j.orgel.2015.06.009
56. [56]
  Lin, R. Y. Y.; Wu, F. L.; Li, C. T.; Chen, P. Y.; Ho, K. C.; Lin, J. T. ChemSusChem 2015, 8, 2503. doi: 10.1002/cssc.201500589
57. [57]
  Zhang, X.; Gou, F.; Shi, J.; Gao, H.; Xu, C.; Zhu, Z.; Jing, H. RSC Adv. 2016, 6, 106380. doi: 10.1039/C6RA20769C
58. [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. doi: 10.1016/j.dyepig.2015.09.001
59. [59]
  Du, C. F.; Jiang, L.; Sun, L.; Huang, N. Y.; Deng, W. Q. RSC Adv. 2015, 5, 37574. doi: 10.1039/C5RA05287D
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