Issue

Vol. 26 No. 18 (2014): Vol 26 Issue 18

Copyright (c) 2014 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Photovoltaic Properties of Conjugated Copolymers Bearing bis(9,9-di(2-ethylhexyl)-9H-fluoren-2-yl)quinoxaline Subunit with Deep HOMO Level

https://doi.org/10.14233/ajchem.2014.16346
Jing Chen
College of Chemistry, Sichuan University, Chengdu 610064, P.R. China
Xianping Deng
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Hunan 411105, P.R. China
Daobin Yang
College of Chemistry, Sichuan University, Chengdu 610064, P.R. China
Erfu Huo
College of Chemistry, Sichuan University, Chengdu 610064, P.R. China
Yunqing Chen
College of Chemistry, Sichuan University, Chengdu 610064, P.R. China
Yan Huang
College of Chemistry, Sichuan University, Chengdu 610064, P.R. China
Zhiyun Lu
College of Chemistry, Sichuan University, Chengdu 610064, P.R. China

Corresponding Author(s) : Yan Huang

huangyan@scu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 18 (2014): Vol 26 Issue 18

Abstract

A series of alternating copolymers (PT-BDFQx, PC-BDFQx and PBDT-BDFQx) have been synthesized bearing novel planar bis(9,9-di(2-ethylhexyl)-9H-fluoren-2-yl)quinoxaline (BDFQx) as acceptor unit, using benzo[1,2-b:4,5-b']dithiophene (BDT), thiophene (T) and carbazole (C) as donor units via Stille or Suzuki coupling reactions. XRD characterization indicated that the presence of planar BDFQx unit (monomer 8) is favorable for the promotion of crystallization in the solid state and GPC results illustrated that the import of multiple chains in planar BDFQx unit raises the polymers molecular weight. Electrochemical measurement results suggested that three copolymers possess deep HOMO energy level of -5.50-5.77 eV. The polymer solar cell with structure of ITO/PEDOT:PSS (30 nm)/polymer: PCBM (60 nm)/Bphen (10 nm)/Ag (100 nm) exhibited the highest Voc of 0.80 V with PBDT-BDFQx as p-type polymer, while the best power conversion efficiency (PCE) of 0.9 % was obtained using a blend of PBDT-BDFQx and PCBM(1:4) as active layer.

Keywords

Conjugated polymers Polymer solar cells Donor-acceptor Bulk heterojunction Deep HOMO energy level
Chen, J., Deng, X., Yang, D., Huo, E., Chen, Y., Huang, Y., & Lu, Z. (2014). Synthesis and Photovoltaic Properties of Conjugated Copolymers Bearing bis(9,9-di(2-ethylhexyl)-9H-fluoren-2-yl)quinoxaline Subunit with Deep HOMO Level. Asian Journal of Chemistry, 26(18), 5959–5966. https://doi.org/10.14233/ajchem.2014.16346
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. (a) M. Gratzel, Inorg. Chem., 44, 6841 (2005); doi:10.1021/ic0508371.; (b) J.R. Durrant, S.A. Haque and E. Palomares, Chem. Commun., 3279 (2006); doi:10.1039/b601785c.; (c) S. Gunes, H. Neugebauer and N.S. Sariciftci, Chem. Rev., 107, 1324 (2007); doi:10.1021/cr050149z; (d) E. Bundgaard and F.C. Krebs, Sol. Energy Mater. Sol. Cells, 91, 954 (2007); doi:10.1016/j.solmat.2007.01.015; (e) B.C. Thompson and J.M. Frechet, J. Angew. Chem. Int. Ed., 47, 58 (2008); doi:10.1002/anie.200702506; (f) A. Mishra, M.K.R. Fischer and P. Bäuerle, Angew. Chem. Int. Ed., 48, 2474 (2009); doi:10.1002/anie.200804709.
  2. C.W. Tang, Appl. Phys. Lett., 48, 183 (1986); doi:10.1063/1.96937.
  3. Z. He, C. Zhong, S. Su, M. Xu, H. Wu and Y. Cao, Nat. Photonics, 6, 591 (2012); doi:10.1038/nphoton.2012.190.
  4. L. Dou, J. You, J. Yang, C.C. Chen, Y. He, S. Murase, T. Moriarty, K. Emery, G. Li and Y. Yang, Nat. Photonics, 6, 180 (2012); doi:10.1038/nphoton.2011.356.
  5. L. Dou, W.H. Chang, J. Gao, C.C. Chen and J. You, Y. Yang, Adv. Mater., 25, 825 (2012); doi:10.1002/adma.201203827.
  6. E. Wang, L. Hou, Z. Wang, Z. Ma, S. Hellström, W. Zhuang, F. Zhang, O. Inganäs and M.R. Andersson, Macromolecules, 44, 2067 (2011); doi:10.1021/ma102783d.
  7. J.E. Carlé, M. Jørgensen, M. Manceau, M. Helgesen, O. Hagemann, R. Søndergaard and F.C. Krebs, Sol. Energy Mater. Sol. Cells, 95, 3222 (2011); doi:10.1016/j.solmat.2011.07.016.
  8. Y. Zou, Z. Guan, Z. Zhang, Y. Huang, N. Wang, Z.Y. Lu, Q. Jiang, J. Yu, Y. Liu and X. Pu, J. Mater. Sci., 47, 5535 (2012); doi:10.1007/s10853-012-6446-7.
  9. M.C. Scharber, D. Mu¨hlbacher, M. Koppe, P. Denk, C. Waldauf, A.J. Heeger and C.J. Brabec, Adv. Mater., 18, 789 (2006); doi:10.1002/adma.200501717.
  10. E. Wang, L. Hou, Z. Wang, S. Hellström, F. Zhang, O. Inganäs and M.R. Andersson, Adv. Mater., 22, 5240 (2010); doi:10.1002/adma.201002225.
  11. W.-H. Lee, S.K. Son, K. Kim, S.K. Lee, W.S. Shin, S.-J. Moon and I.-N. Kang, Macromolecules, 45, 1303 (2012); doi:10.1021/ma2020112.
  12. M.H. Lai, J.H. Tsai, C.C. Chueh, C.F. Wang and W.C. Chen, Macromol. Chem. Phys., 211, 2017 (2010); doi:10.1002/macp.201000234.
  13. M. Ranger, D. Rondeau and M. Leclerc, Macromolecules, 30, 7686 (1997); doi:10.1021/ma970920a.
  14. D.J. Hong, E. Lee, H. Jeong, J.K. Lee, W.C. Zin, T.D. Nguyen, S.C. Glotzer and M. Lee, Angew. Chem. Int. Ed., 48, 1664 (2009); doi:10.1002/anie.200804307.
  15. T. Ishiyama, M. Murata and N. Miyaura, J. Org. Chem., 60, 7508 (1995); doi:10.1021/jo00128a024.
  16. J. Hou, Z.A. Tan, Y. Yan, Y. He, C. Yang and Y. Li, J. Am. Chem. Soc., 128, 4911 (2006); doi:10.1021/ja060141m.
  17. Y. Nie, B. Zhao, P. Tang, P. Jiang, Z. Tian, P. Shen and S. Tan, J. Polym. Sci. A: Polym. Chem., 49, 3604 (2011); doi:10.1002/pola.24799.
  18. Y.P. Yu, L.M. Sun and Q. Zhang, J. Shanghai Jiaotong Univ. (Sci.), 10, 1662 (2007).
  19. M. Helgesen, T.J. Sorensen, M. Manceau and F.C. Krebs, Polym. Chem., 2, 1355 (2011); doi:10.1039/c1py00017a.
  20. Z. Qi, B. Wei, Y. Sun, X. Wang, F. Kang, M. Hong and L. Tang, Polym. Bull., 66, 905 (2011); doi:10.1007/s00289-010-0324-8.
  21. Y. Lee, Y.M. Nam and W.H. Jo, J. Mater. Chem., 21, 8583 (2011); doi:10.1039/c1jm10877h.
  22. R. Mondal, N. Miyaki, H.A. Becerril, J.E. Norton, J. Parmer, A.C. Mayer, M.L. Tang, J.-L. Brédas, M.D. McGehee and Z. Bao, Chem. Mater., 21, 3618 (2009); doi:10.1021/cm900788e.
  23. Y.F. Li, Y. Cao, J. Gao, D.L. Wang, G. Yu and A.J. Heeger, Synth. Met., 99, 243 (1999); doi:10.1016/S0379-6779(99)00007-7.
  24. J. Pommerehne, H. Vestweber, W. Guss, R.F. Mahrt, H. Bässler, M. Porsch and J. Daub, Adv. Mater., 7, 551 (1995); doi:10.1002/adma.19950070608.
  25. C. Hu, Y. Fu, S. Li, Z. Xie and Q. Zhang, Polym. Chem., 3, 2949 (2012); doi:10.1039/c2py20504a.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0