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Impact of π-spacers of dithieno[3,2-f:2′,3′-h]quinoxaline-based organic dyes with three π-spacers on the solar cell performance

  • Tai Xiao
  • Zu-Sheng HuangEmail author
  • Lingyun Wang
  • Derong CaoEmail author
Article
  • 84 Downloads

Abstract

Three novel dithieno[3,2-f:2′,3′-h]quinoxaline-based organic dyes (IQ-C, IQ-D and IQ-F) with three π-spacers were synthesized and developed for dye sensitized solar cells, where dithieno[3,2-f:2′,3′-h]quinoxaline was used as electron-withdrawing π-spacers, and 2,3-diphenylquinoxaline or dibenzo[a,c]phenazine as auxiliary electron-withdrawing π-spacers. The dye IQ-D with 2,3-diphenylquinoxaline as auxiliary electron-withdrawing π-spacer exhibited higher photocurrent (Jsc) and photovoltage (Voc) than that of the dye IQ-C with 2,3-bis(4-(octyloxy)phenyl)quinoxaline as the additional electron-withdrawing π-spacer, due to the larger adsorption amount of IQ-D. The dye IQ-F with a rigid conjugated dibenzo[a,c]phenazine as additional electron-withdrawing π-spacer showed the highest efficiency of 6.54% under AM 1.5 G irradiation. It was demonstrated that the π-spacers influence the photovoltaic performance of the dithieno[3,2-f:2′,3′-h]quinoxaline-based organic dyes significantly. The results indicated that the dyes with three π-spacers are promising candidates for efficient dye-sensitized solar cells.

Notes

Acknowledgements

We are grateful to the National Natural Science Foundation of China (21772045, 21572069, 21702147), the National Key Research Development Program of China (2016YFA0602900) and the Fund from the Guangzhou Science and Technology Project, China (201607010265).

References

  1. 1.
    B. O’Regan, M. Grätzel, Nature 353, 737–740 (1991)CrossRefGoogle Scholar
  2. 2.
    K. Kakiage, Y. Aoyama, T. Yano, K. Oya, J. Fujisawa, M. Hanaya, Chem. Commun. 51, 15894–15897 (2015)CrossRefGoogle Scholar
  3. 3.
    M. Freitag, J. Teuscher, Y. Saygili, X. Zhang, F. Giordano, P. Liska, J. Hua, S.M. Zakeeruddin, J.-E. Moser, M. Grätzel, A. Hagfeldt, Nat. Photonics 11, 372–378 (2017)CrossRefGoogle Scholar
  4. 4.
    Y.C. Liu, H.H. Chou, F.Y. Ho, H.J. Wei, T.C. Wei, C.Y. Yeh, J. Mater. Chem. A 4, 11878–11887 (2016)CrossRefGoogle Scholar
  5. 5.
    Y.S. Tingare, N.S.n. Vinh, H.-H. Chou, Y.-C. Liu, Y.-S. Long, T.-C. Wu, T.-C. Wei, C.-Y. Yeh, Adv. Energy Mater. 7, 1700032 (2017)CrossRefGoogle Scholar
  6. 6.
    K.S.K. Reddy, Y.C. Chen, C.C. Wu, C.W. Hsu, Y.C. Chang, C.M. Chen, C.Y. Yeh, ACS Appl. Mater. Interfaces 10, 2391–2399 (2018)CrossRefGoogle Scholar
  7. 7.
    A. Yella, C.L. Mai, S.M. Zakeeruddin, S.N. Chang, C.H. Hsieh, C.Y. Yeh, M. Grätzel, Angew. Chem. Int. Ed. Engl. 53, 2973–2977 (2014)CrossRefGoogle Scholar
  8. 8.
    S. Mathew, A. Yella, P. Gao, R. Humphry-Baker, B.F. Curchod, N. Ashari-Astani, I. Tavernelli, U. Rothlisberger, M.K. Nazeeruddin, M. Grätzel, Nat. Chem. 6, 242–247 (2014)CrossRefGoogle Scholar
  9. 9.
    J. Luo, M. Xu, R. Li, K.W. Huang, C. Jiang, Q. Qi, W. Zeng, J. Zhang, C. Chi, P. Wang, J. Wu, J. Am. Chem. Soc. 136, 265–272 (2014)CrossRefGoogle Scholar
  10. 10.
    Y. Ren, D. Sun, Y. Cao, H.N. Tsao, Y. Yuan, S.M. Zakeeruddin, P. Wang, M. Grätzel, J. Am. Chem. Soc. 140, 2405–2408 (2018)CrossRefGoogle Scholar
  11. 11.
    H. Meier, Z.-S. Huang, D. Cao, J. Mater. Chem. C 5, 9828–9837 (2017)CrossRefGoogle Scholar
  12. 12.
    P. Ferdowsi, Y. Saygili, W. Zhang, T. Edvinson, L. Kavan, J. Mokhtari, S.M. Zakeeruddin, M. Grätzel, A. Hagfeldt, ChemSusChem 11, 494–502 (2018)CrossRefGoogle Scholar
  13. 13.
    X. Li, B. Xu, P. Liu, Y. Hu, L. Kloo, J. Hua, L. Sun, H. Tian, J. Mater. Chem. A 5, 3157–3166 (2017)CrossRefGoogle Scholar
  14. 14.
    K. Pei, Y. Wu, H. Li, Z. Geng, H. Tian, W.H. Zhu, ACS Appl. Mater. Interfaces 7, 5296–5304 (2015)CrossRefGoogle Scholar
  15. 15.
    Z.S. Huang, C. Cai, X.F. Zang, Z. Iqbal, H.P. Zeng, D.B. Kuang, L.Y. Wang, H. Meier, D.R. Cao, J. Mater. Chem. A 3, 1333–1344 (2015)CrossRefGoogle Scholar
  16. 16.
    X. Yang, J. Zhao, L. Wang, J. Tian, L. Sun, RSC Adv. 4, 24377 (2014)CrossRefGoogle Scholar
  17. 17.
    X. Zhang, Y. Xu, F. Giordano, M. Schreier, N. Pellet, Y. Hu, C. Yi, N. Robertson, J. Hua, S.M. Zakeeruddin, H. Tian, M. Grätzel, J. Am. Chem. Soc. 138, 10742–10745 (2016)CrossRefGoogle Scholar
  18. 18.
    Y. Hao, Y. Saygili, J. Cong, A. Eriksson, W. Yang, J. Zhang, E. Polanski, K. Nonomura, S.M. Zakeeruddin, M. Grätzel, A. Hagfeldt, G. Boschloo, ACS Appl. Mater. Interfaces 8, 32797–32804 (2016)CrossRefGoogle Scholar
  19. 19.
    Y.J. Chen, Y. Ling, L. Ding, C.L. Xiang, G. Zhou, J. Mater. Chem. C 4, 8496–8505 (2016)CrossRefGoogle Scholar
  20. 20.
    L. Wang, X. Yang, X. Wang, L. Sun, Dyes Pigm. 113, 581–587 (2015)CrossRefGoogle Scholar
  21. 21.
    H. Zhu, B. Liu, J. Liu, W. Zhang, W.-H. Zhu, J. Mater. Chem. C 3, 6882–6890 (2015)CrossRefGoogle Scholar
  22. 22.
    X. Li, F. Yu, S. Stappert, C. Li, Y. Zhou, Y. Yu, X. Li, H. Agren, J. Hua, H. Tian, ACS Appl. Mater. Interfaces 8, 19393–19401 (2016)CrossRefGoogle Scholar
  23. 23.
    M.-L. Han, Y.-Z. Zhu, S. Liu, Q.-L. Liu, D. Ye, B. Wang, J.-Y. Zheng, J. Power Sources 387, 117–125 (2018)CrossRefGoogle Scholar
  24. 24.
    X. Lu, T. Lan, Z. Qin, Z.S. Wang, G. Zhou, ACS Appl. Mater. Interfaces 6, 19308–19317 (2014)CrossRefGoogle Scholar
  25. 25.
    H. Ji, Z.-S. Huang, L. Wang, D. Cao, Dyes Pigm. 159, 8–17 (2018)CrossRefGoogle Scholar
  26. 26.
    Z.S. Huang, X.F. Zang, T. Hua, L. Wang, H. Meier, D. Cao, ACS Appl. Mater. Interfaces 7, 20418–20429 (2015)CrossRefGoogle Scholar
  27. 27.
    J.S. Ni, T.Y. Chiu, W.S. Kao, H.J. Chou, C.C. Su, J.T. Lin, ACS Appl. Mater. Interfaces 8, 23066–23073 (2016)CrossRefGoogle Scholar
  28. 28.
    H. Zhang, J. Fan, Z. Iqbal, D.-B. Kuang, L. Wang, H. Meier, D. Cao, Org. Electron. 14, 2071–2081 (2013)CrossRefGoogle Scholar
  29. 29.
    K. Pei, Y. Wu, W. Wu, Q. Zhang, B. Chen, H. Tian, W. Zhu, Chem. Eur. J. 18, 8190–8200 (2012)CrossRefGoogle Scholar
  30. 30.
    K. Pei, Y. Wu, A. Islam, Q. Zhang, L. Han, H. Tian, W. Zhu, ACS Appl. Mater. Interfaces 5, 4986–4995 (2013)CrossRefGoogle Scholar
  31. 31.
    Y. Wen, H. Yang, D. Zheng, K. Sun, L. Wang, J. Zhang, J. Phys. Chem. C 121, 14019–14026 (2017)CrossRefGoogle Scholar
  32. 32.
    G. Yang, Y. Tang, X. Li, H. Agren, Y. Xie, ACS Appl. Mater. Interfaces 9, 36875–36885 (2017)CrossRefGoogle Scholar
  33. 33.
    Z. Iqbal, W.-Q. Wu, Z.-S. Huang, L. Wang, D.-B. Kuang, H. Meier, D. Cao, Dyes Pigm. 124, 63–71 (2016)CrossRefGoogle Scholar
  34. 34.
    H.H. Chou, Y.C. Liu, G. Fang, Q.K. Cao, T.C. Wei, C.Y. Yeh, ACS Appl. Mater. Interfaces 9, 37786–37796 (2017)CrossRefGoogle Scholar
  35. 35.
    X. Qian, Y.Z. Zhu, W.Y. Chang, J. Song, B. Pan, L. Lu, H.H. Gao, J.Y. Zheng, ACS Appl. Mater. Interfaces 7, 9015–9022 (2015)CrossRefGoogle Scholar
  36. 36.
    X.F. Zang, T.L. Zhang, Z.S. Huang, Z. Iqbal, D.B. Kuang, L.Y. Wang, H. Meier, D.R. Cao, Dyes Pigm. 104, 89–96 (2014)CrossRefGoogle Scholar
  37. 37.
    Y. Wang, Z. Zheng, T. Li, N. Robertson, H. Xiang, W. Wu, J. Hua, W.H. Zhu, H. Tian, ACS Appl. Mater. Interfaces 8, 31016–31024 (2016)CrossRefGoogle Scholar
  38. 38.
    A. Pradhan, T. Morimoto, M. Saikiran, G. Kapil, S. Hayase, S.S. Pandey, J. Mater. Chem. A 5, 22672–22682 (2017)CrossRefGoogle Scholar
  39. 39.
    Z.-S. Huang, H. Meier, D. Cao, J. Mater. Chem. C 4, 2404–2426 (2016)CrossRefGoogle Scholar
  40. 40.
    Z. Chai, S. Wan, C. Zhong, T. Xu, M. Fang, J. Wang, Y. Xie, Y. Zhang, A. Mei, H. Han, Q. Peng, Q. Li, Z. Li, ACS Appl. Mater. Interfaces 8, 28652–28662 (2016)CrossRefGoogle Scholar
  41. 41.
    M.C. Sil, V. Sudhakar, M.F. Mele Kavungathodi, V. Punitharasu, J. Nithyanandhan, ACS Appl. Mater. Interfaces 9, 34875–34890 (2017)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and DevicesSouth China University of TechnologyGuangzhouPeople’s Republic of China
  2. 2.School of Pharmaceutical SciencesWenzhou Medical UniversityWenzhouPeople’s Republic of China

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