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Enhanced thermo-stability and luminecent property of D-A copolymer based on fluorene and thieno[3,4-c]pyrrole-4,6-dione by incorporation of pentafluorobenzene group

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Abstract

A new monomer 1,3-dibromo-5-perfluorophenyl-thieno[3,4-c]pyrrole-4,6-dione was synthesized and the corresponded D-A copolymer poly{9,9-dioctylfluorene-2,7-diyl-alt-5-perfluorophenylthieno[3,4-c]pyrrole-4,6-dione} (PFFTPD) based on fluorene unit was synthesized. In order to investigate the effect of pentafluorobenzene substitution on the photo-physics and stability properties, the compared D-A copolymer poly{9,9-dioctylfluorene-2,7-diylalt-5-octylthieno[3,4-c]pyrrole-4,6-dione} (PFCTPD) based on fluorene and octyl-thieno[3,4-c]pyrrole-4,6-dione was synthesized also. The obtained copolymer PFFTPD had a weight average molecular weight of 12178 with a narrow polydispersity index of 1.51, good solubility and higher thermal stability with T g of 131 ℃ and T d of 410 ℃. Compared to that of PFCTPD, the PL spectra of PFFTPD in solution and in thin film showed narrower half peak width and weaker shoulder peak in the long wavelength region. The luminescent efficiency and color purity were enhanced while lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) levels were decreased by incorporation of pentafluorobenzene group. Thus, the copolymer PFFTPD may be good candidate as emitting material applied in polymer light emitting diode (PLED).

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References

  1. R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. C. Marks, C. Taliani, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Brédas, M. Lögdlund, and W. R. Salaneck, Nature, 397, 6715 (1999).

    Article  Google Scholar 

  2. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burns, and A. B. Holmes, Nature, 347, 6293 (1990).

    Article  Google Scholar 

  3. H. J. Song, J. Y. Lee, I. S. Song, D. K. Moon, and J. R. Haw, J. Ind. Eng. Chem., 17, 352 (2011).

    Article  CAS  Google Scholar 

  4. C. Cabanetos, A. E. Labban, J. Bartelt, J. D. Douglas, W. R. Mateker, J. M. J. Fréchet, M. D. McGehee, and P. M. Beaujuge, J. Am. Chem. Soc., 135, 4656 (2013).

    Article  CAS  Google Scholar 

  5. A. Najari, S. Beaupré, P. Berrouard, Y. P. Zou, J. Pouliot, C. Lepage-Pérusse, and M. Leclerc, Adv. Funct. Mater., 21, 718 (2011).

    Article  CAS  Google Scholar 

  6. R. S. Kularatne, F. J. Taenzler, H. D. Magurudeniya, J. Du, J. W. Murphy, E. E. Sheina, B. E. Gnade, M. C. Biewer, and M. C. Stefan, J. Mater. Chem. A, 48, 15535 (2013).

    Article  Google Scholar 

  7. M. J. Baek, S. H. Lee, D. H. Kim, and Y. S. Lee, Macromol. Res., 20, 147 (2012).

    Article  CAS  Google Scholar 

  8. I. Mcculloch, M. Heeney, C. Bailey, K. Genevicius, I. Macdonald, M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. M. Zhang, M. L. Chabinyc, R. Joseph Kline, M. D. McGehee, and M. F. Toney, Nat. Mater., 5, 328 (2006).

    Article  CAS  Google Scholar 

  9. T. Yasuda, T. Imase, and T. Yamamoto, Macromolecules, 38, 7378 (2005).

    Article  CAS  Google Scholar 

  10. G. B. Lee, R. Kim, H. J. Cha, C. E. Park, J. H. Kim, and Y. H. Kim, Macromol. Res., 22, 569 (2014).

    Article  CAS  Google Scholar 

  11. I. Kang, J. A. Hong, R. Kim, J. W. Jang, J. Y. Hwang, J. H. Kim, S. K. Kwon, and Y. H. Kim, Macromol. Res., 21, 450 (2013).

    Article  CAS  Google Scholar 

  12. G. Gustafsson, Y. Cgo, G. M. Treacy, F. Klavetter, N. Colaneri, and A. J. Heeger, Nature, 357, 477 (1992).

    Article  CAS  Google Scholar 

  13. M. M. Alam and S. A. Jenekhe, Chem. Mater., 14, 4775 (2002).

    Article  CAS  Google Scholar 

  14. N. S. Cho, J. H. Park, S. K. Lee, J. Lee, H. K. Shim, M. J. Park, D. H. Hwang, and B. J. Jung, Macromolecules, 39, 177 (2006).

    Article  CAS  Google Scholar 

  15. P. Kulkarni, X. Kong, and S. A. Jenekhe, Macromolecules, 39, 8699 (2006).

    Article  CAS  Google Scholar 

  16. M. Kreyenschmidt, G. Klaerner, T. Fuhrer, J. Ashenhurst, S. Karg, W. D. Chen, V. Y. Lee, J. C. Scott, and R. D. Miller, Macromolecules, 31, 1099 (1998).

    Article  CAS  Google Scholar 

  17. J. W. Park, S. J. Park, Y. H. Kim, D. C. Shin, H. You, and S. K. Kwon, Polymer, 50, 102 (2009).

    Article  CAS  Google Scholar 

  18. M. Nakamura, K. Yamabuki, T. Oishi, and K. Onimura, Polym. Chem., 51, 4945 (2013).

    Article  CAS  Google Scholar 

  19. W. C. Wua, C. L. Liu, and W. C. Chen, Polymer, 47, 527 (2006).

    Article  Google Scholar 

  20. L. P. Lu, C. E. Finlayson, D. Kabra, S. Albert-Seifried, M. H. Song, R. W. A. Havenith, G. T. Wilhelm, T. S. Huck, and R. H. Friend, Macromol. Chem. Phys., 214, 967 (2013).

    Article  CAS  Google Scholar 

  21. H. J. Song, D. H. Kim, T. H. Lee, and D. K. Moon, Eur. Polym. J., 48, 1485 (2012).

    Article  CAS  Google Scholar 

  22. X. G. Guo, H. Xin, F. S. Kim, A. D. T. Liyanage, S. A. Jenekhe, and M. D. Watson, Macromolecules, 44, 269 (2011).

    Article  CAS  Google Scholar 

  23. J. H. Huang, X. H. Ye, C. L. Zhan, G. Yu, Y. Q. Liu, and J. N. Yao, Adv. Mater. Res., 295, 274 (2011).

    Article  Google Scholar 

  24. T. Zhang, R. J. Wang, H. C. Ren, Z. G. Chen, and J. Y. Li, Polymer, 53, 1529 (2012).

    Article  CAS  Google Scholar 

  25. J. Min, Z. G.. Zhang, S. Zhang, and Y. Li, Chem. Mater., 24, 3247 (2012).

    Article  CAS  Google Scholar 

  26. N. Wang, Z. Chen, W. Wei, and Z. H. Jiang, J. Am. Chem. Soc., 135, 17060 (2013).

    Article  CAS  Google Scholar 

  27. D. Bondarev, J. Zednik, J. Vohlidal, K. Podhajecka, and J. Sedlacek, Polym. Chem., 47, 4532 (2009).

    Article  CAS  Google Scholar 

  28. T. X. Liu, G. Z. Yang, and C. Wei, Acta Chim. Sin., 69, 1415 (2011).

    CAS  Google Scholar 

  29. S. Setayesh, A. C. Grimsdale, T. Weil, V. Enkelmann, K. Müllen, F. Meghdadi, E. J. W. List, and G. Leising, J. Am. Chem. Soc., 123, 946 (2001).

    Article  CAS  Google Scholar 

  30. L. O. Palsson, C. S. Wang, D. L. Russell, A. P. Monkman, M. R. Bryce, G. Rumbles, and I. D. W. Samuel, Chem. Phys., 279, 229 (2002).

    Article  CAS  Google Scholar 

  31. M. Ranger, D. Rondeau, and M. Leclerc, Macromolecules, 30, 7686 (1997).

    Article  CAS  Google Scholar 

  32. S. C. Price, A. C. Stuart, L. Yang, H. Zhou, and W. You, J. Am. Chem. Soc., 133, 4625 (2011).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Fujian Key Laboratory of Polymer Materials, College of Materials Science and Engineering, Fujian Normal University, Fuzhou, 350007, P. R. China

    Wen Wang, Luying Liang, Minglu Zhou, Minmin Sun, Shuhui Yan & Qidan Ling

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  1. Wen Wang
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  2. Luying Liang
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  3. Minglu Zhou
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  4. Minmin Sun
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  5. Shuhui Yan
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  6. Qidan Ling
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Correspondence to Qidan Ling.

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Wang, W., Liang, L., Zhou, M. et al. Enhanced thermo-stability and luminecent property of D-A copolymer based on fluorene and thieno[3,4-c]pyrrole-4,6-dione by incorporation of pentafluorobenzene group. Macromol. Res. 23, 30–37 (2015). https://doi.org/10.1007/s13233-015-3003-7

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