Skip to main content
Log in

Novel benzo(1,2-b:4,5-b’)dithiophene-based donor–acceptor conjugated polymes for polymer solar cells

  • Published:
Journal of Materials Science: Materials in Electronics Aims and scope Submit manuscript

Abstract

Two new donor–acceptor (D-A) alternative copolymers, poly{4-(5-(4,8-bis(dodecyloxy)-6-methylbenzo[1,2-b:4,5-b’]-dithiophen-2-yl) -4–dodecylthiophen-2-yl)-2-dodecyl-7-(4-dodecyl-5-methylthiophen-2-yl)-2H-benzo[d] [13] triazole} (P1) and poly{4-(5-(4,8-bis(dodecyloxy)-6-methylbenzo -[1,2-b:4,5-b’]dithiophen-2-yl)-4-dodecylthiophen-2-yl)-2-dodecyl-9-(4-dodecyl-5methylthiophen-2-yl)-6,7-dimethyl-2H- [13] triazolo[4,5-g]quinoxaline} (P2), were designed and synthesized. Also, the effects of the structural variation on their properties, especially their UV and electrochemical behaviors, were studied. The polymers were verified by NMR and characterized by TGA, UV–vis absorption and electrochemical cyclic voltammetry. It was found that P1 exhibits stronger π-π stacking and aggregation in solid film related to in solution state than those of P2. All the polymers show narrow band gaps, with the electro-chemical band gaps (E ECg ) 1.45 eV for P1 and 1.61 eV for P2. Interestingly, the polymer P2 exhibits power conversion efficiency (PCE) of 2.2 %, while the copolymer P1 shows an improvement PCE of 2.9 %. It indicates that mildly tailoring the acceptor segments of the D-A copolymer is a facile and promising approach for active layer engineering to developing high performance polymer solar cells.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, A.J. Heeger, Science 270, 1789 (1995)

    Article  Google Scholar 

  2. N. Shin, H.J. Yun, Y. Yoon, H.J. Son, S.Y. Ju, S.K. Kwon, Y.H. Kim, Macromolecules 48, 3890 (2015)

    Article  Google Scholar 

  3. J. Chen, Y. Cao, Acc. Chem. Res. 42, 1709 (2009)

    Article  Google Scholar 

  4. Y. Lin, Q. He, F. Zhao, L. Huo, J. Mai, X. Lu, Y. Sun, J. Am. Chem. Soc. 138, 2973 (2016)

    Article  Google Scholar 

  5. P.P. Khlyabich, B. Burkhart, B.C. Thompson, J. Am. Chem. Soc. 134, 9074 (2012)

    Article  Google Scholar 

  6. F. Livi, N.K. Zawacka, D. Angmo, M. Jørgensen, F.C. Krebs, E. Bundgaard, Macromolecules 48, 3481 (2015)

    Article  Google Scholar 

  7. Q. Hou, T. Jia, J. Liu, S. Luo, G. Shi, J. Mater. Sci. Mater. Electron. 24, 4284 (2013)

    Article  Google Scholar 

  8. D. Gao, G.L. Gibson, J. Hollinger, P. Li, D.S. Seferos, Polym. Chem. 6, 3353 (2015)

    Article  Google Scholar 

  9. P. Huang, J. Du, S.S. Gunathilake, E.A. Rainbolt, J.W. Murphy, K.T. Black, M.C. Biewer, J. Mater. Chem. A 3, 6980 (2015)

    Article  Google Scholar 

  10. Z. Wu, C. Sun, S. Dong, X.F. Jiang, S. Wu, H. Wu, Y. Cao, J. Am. Chem. Soc. 138, 2004 (2016)

    Article  Google Scholar 

  11. Y.F. Li, Acc. Chem. Res. 45, 723 (2012)

    Article  Google Scholar 

  12. C.-Y. Chang, Y.-J. Cheng, S.-H. Hung, J.-S. Wu, W.-S. Kao, C.-H. Lee, C.-S. Hsu, Adv. Mater. 24, 549 (2012)

    Article  Google Scholar 

  13. Y. Liang, L. Yu, Acc. Chem. Res. 43, 1227 (2010)

    Article  Google Scholar 

  14. R.M. Duan, L. Ye, X. Guo, Y. Huang, P. Wang, S.Q. Zhang, J.P. Zhang, L.J. Huo, J.H. Hou, Macromolecules 45, 3032 (2012)

    Article  Google Scholar 

  15. B. Burkhart, P.P. Khlyabich, B.C. Thompson, Macromolecules 45, 3740 (2012)

    Article  Google Scholar 

  16. D. Lee, E. Hubijar, G.J.D. Kalaw, J.P. Ferraris, Chem. Mater. 24, 2534 (2012)

    Article  Google Scholar 

  17. L. Huo, X. Guo, S. Zhang, Y. Li, J. Hou, Macromolecules 44, 4035 (2011)

    Article  Google Scholar 

  18. Z.G. Zhang, K.L. Zhang, G. Liu, C.X. Zhu, K.G. Neoh, E.T. Kang, Macromolecules 42, 3104 (2009)

    Article  Google Scholar 

  19. S. Subramaniyan, H. Xin, F.S. Kim, S.A. Jenekhe, Macromolecules 44, 6245 (2011)

    Article  Google Scholar 

  20. H. Wettach, F. Pasker, S. Hoger, Macromolecules 41, 3104 (2008)

    Article  Google Scholar 

  21. Y. Liang, D. Feng, Y. Wu, S.T. Tsai, G. Li, C. Ray, L. Yu, J. Am. Chem. Soc. 131, 7792 (2009)

    Article  Google Scholar 

  22. L. Dou, J. Gao, E. Richard, J. You, C.-C. Chen, K.C. Cha, Y. He, G. Li, Y. Yang, J. Am. Chem. Soc. 134, 10071 (2012)

    Article  Google Scholar 

  23. A. Balan, D. Baran, L. Toppare, Polym. Chem. 2, 1029 (2011)

    Article  Google Scholar 

  24. J. Hou, M.H. Park, S.Q. Zhang, Y. Yao, L.-M. Chen, J.-H. Li, Y. Yang, Macromolecules 41, 6012 (2008)

    Article  Google Scholar 

  25. M. Icli, M. Pamuk, F. Algi, A.M. Onal, A. Cihaner, Chem. Mater. 22, 4034 (2010)

    Article  Google Scholar 

  26. H. Zhou, L. Yang, A.C. Stuart, S.C. Price, S. Liu, W. You, Angew. Chem. Int. Ed. 50, 2995 (2011)

    Article  Google Scholar 

  27. S. Das, P.B. Pati, S.S. Zad, Macromolecules 45, 5410 (2012)

    Article  Google Scholar 

  28. M. Zhang, H. Fan, X. Guo, Y. He, Z. Zhang, J. Min, J. Zhang, G. Zhao, X. Zhan, Y. Li, Macromolecules 43, 5706 (2010)

    Article  Google Scholar 

  29. Q. Sun, H. Wang, C. Yang, Y. Li, J. Mater. Chem. 13, 800 (2003)

    Article  Google Scholar 

  30. R. Mondal, S. Ko, J.E. Norton, N. Miyaki, H.A. Becerril, E. Verploegen, M.F. Toney, J.-L. Bredas, M.D. McGehee, Z. Bao, J. Mater. Chem. 19, 7195 (2009)

    Article  Google Scholar 

  31. A. Hayakawa, O. Yoshikawa, T. Fujieda, K. Uehara, S. Yoshikawa, Appl. Phys. Lett. 90, 163517 (2007)

    Article  Google Scholar 

  32. Q. Wei, T. Nishizawa, K. Tajima, K. Hashimoto, Adv. Mater. 20, 2211 (2008)

    Article  Google Scholar 

Download references

Acknowledgments

The work was financially supported by Natural Science Foundation of Jiangxi Province (Grant no. 20142BAB213015) and Jiangxi Province Education Department of Science and Technology Project (No: GJJ150743).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Dan Zhou or Yuancheng Qin.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhou, D., Chen, K., Zhong, X. et al. Novel benzo(1,2-b:4,5-b’)dithiophene-based donor–acceptor conjugated polymes for polymer solar cells. J Mater Sci: Mater Electron 27, 9920–9928 (2016). https://doi.org/10.1007/s10854-016-5061-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10854-016-5061-9

Keywords

Navigation