Chinese Journal of Polymer Science

, Volume 33, Issue 1, pp 184–191 | Cite as

Synthesis of polyphenylenes through bergman cyclization of enediynes with long chain alkyl groups

  • Shiyuan Sun
  • Luhua Dong
  • Depeng Song
  • Binlei Huang
  • Aiguo Hu (胡爱国)Email author


Several new enediynes with long chain alkyl groups were synthesized through Sonogashira coupling reactions between long chain alkynes and (Z)-1,2-dichloroethene. These enediynes (1) were then subjected to thermal Bergman cyclization in a refluxing diphenyl ether bath under vacuum to obtain conjugated polyphenylenes with the weight-average molecular weights up to 4.9 × 103 g·mol−1. The occurrence of Bergman cyclization was confirmed by 1H-NMR, 13C-NMR, and IR spectroscopic analysis. These polyphenylenes are fully soluble in common organic solvents and exhibit good thermal stability. The optical properties of the polyphenylenes were investigated by UV-Vis absorption and photoluminescence (PL) spectroscopies. A blue emission was observed for all these polyphenylenes.


Enediyne Bergman cyclization Polyphenylene 


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  1. 1.
    Cheng, Y.J., Yang, S.H. and Hsu, C.S., Chem. Rev., 2009, 109(11): 5868CrossRefGoogle Scholar
  2. 2.
    Grimsdale, A.C., Chan, K.L., Martin, R.E., Jokisz, P.G. and Holmes, A.B., Chem. Rev., 2009, 109(3): 897CrossRefGoogle Scholar
  3. 3.
    Liu, J.Z., Lam, J.W.Y. and Tang, B.Z., Chem. Rev., 2009, 109(11): 5799CrossRefGoogle Scholar
  4. 4.
    Chochos, C.L. and Choulis, S.A., Prog. Polym. Sci., 2011, 36(10): 1326CrossRefGoogle Scholar
  5. 5.
    Cloutier, R. and Leclerc, M., J. Chem. Soc., Chem. Commun., 1991, (17): 1194Google Scholar
  6. 6.
    Wang, H.B., Jost, R. and Wudl, F., J. Polym. Sci., Part A: Polym. Chem., 2007, 45(5): 800CrossRefGoogle Scholar
  7. 7.
    Yurteri, S., Cianga, A., Demirel, A.L. and Yagci, Y., J. Polym. Sci., Part A: Polym. Chem., 2005, 43(4): 879CrossRefGoogle Scholar
  8. 8.
    Cheuk, K.K.L., Li, B.S., Lam, J.W.Y., Xie, Y. and Tang, B.Z., Macromolecules, 2008, 41(16): 5997CrossRefGoogle Scholar
  9. 9.
    Hargadon, M.T., Davey, E.A., McIntyre, T.B., Gnanamgari, D., Wynne, C.M., Swift, R.C., Zimbalist, J.R., Fredericks, B.L., Nicastro, A.J. and Goodson, F.E., Macromolecules, 2008, 41(3): 741CrossRefGoogle Scholar
  10. 10.
    Li, Z., Dong, Y., Häussler, M., Lam, J.W., Dong, Y., Wu, L., Wong, K.S. and Tang, B.Z., J. Phys. Chem. B, 2006, 110(5): 2302CrossRefGoogle Scholar
  11. 11.
    Nehls, B.S., Galbrecht, F., Brauer, D.J., Lehmann, C.W., Scherf, U. and Farrell, T., J. Polym. Sci., Part A: Polym. Chem., 2006, 44(19): 5533CrossRefGoogle Scholar
  12. 12.
    Zhang, X.A., Qin, A.J., Tong, L., Zhao, H., Zhao, Q.L., Sun, J.Z. and Tang, B.Z., ACS Macro Lett., 2012, 1(1): 75CrossRefGoogle Scholar
  13. 13.
    Bryan, Z.J. and McNeil, A.J., Macromolecules, 2013, 46(21): 8395CrossRefGoogle Scholar
  14. 14.
    Witteler, H., Lieser, G., Wegner, G. and Schulze, M., Makromol. Chem., Rapid Commun., 1993, 14(8): 471CrossRefGoogle Scholar
  15. 15.
    Economopoulos, S.P., Govaris, G.K., Chochos, C.L., Tzanetos, N.P., Andreopoulou, A.K., Kallitsis, J.K., Yianoulis, P. and Gregoriou, V.G., Macromolecular Symposia, 2004, 205: 19CrossRefGoogle Scholar
  16. 16.
    Lupshak, N. and Aksimentyeva, O., Synth. Met., 2001, 119(1–3): 95CrossRefGoogle Scholar
  17. 17.
    List, E.J.W., Holzer, L., Tasch, S., Leising, G., Catellani, M. and Luzzati, S., Optical Materials, 1999, 12(2–3): 311CrossRefGoogle Scholar
  18. 18.
    List, E.J.W., Holzer, L., Tasch, S., Leising, G., Scherf, U., Müllen, K., Catellani, M. and Luzzati, S., Solid State Commun., 1999, 109(7): 455CrossRefGoogle Scholar
  19. 19.
    Kim, D.Y., Cho, H.N. and Kim, C.Y., Prog. Polym. Sci., 2000, 25(8): 1089CrossRefGoogle Scholar
  20. 20.
    Yamamoto, T. and Koizumi, T.-a., Polymer, 2007, 48(19): 5449CrossRefGoogle Scholar
  21. 21.
    Fiesel, R. and Scherf, U., Acta Polym., 1998, 49(8): 445CrossRefGoogle Scholar
  22. 22.
    Miyakoshi, R., Yokoyama, A. and Yokozawa, T., J. Polym. Sci., Part A: Polym. Chem., 2008, 46(3): 753CrossRefGoogle Scholar
  23. 23.
    Kobayashi, K., Yang, T.X., Maruyama, K., Shimomura, M. and Miyauchi, S., Synth. Met., 1995, 69(1–3): 475CrossRefGoogle Scholar
  24. 24.
    Jones, R.R. and Bergman, R.G., J. Am. Chem. Soc., 1972, 94(2): 660CrossRefGoogle Scholar
  25. 25.
    Spence, J.D., Lackie, M.L., Clayton, N.A., Toscano, S.A., Farmer, M.A., Popova, E. and Olmstead, M.M., Tetrahedron Lett., 2014, 55(9): 1569CrossRefGoogle Scholar
  26. 26.
    Sun, Q., Zhang, C., Li, Z., Kong, H., Tan, Q., Hu, A. and Xu, W., J. Am. Chem. Soc., 2013, 135(23): 8448CrossRefGoogle Scholar
  27. 27.
    Lindahl, S.E., Park, H., Pink, M. and Zaleski, J.M., J. Am. Chem. Soc., 2013, 135(10): 3826CrossRefGoogle Scholar
  28. 28.
    Greer, E.M., Cosgriff, C.V. and Doubleday, C., J. Am. Chem. Soc., 2013, 135(28): 10194CrossRefGoogle Scholar
  29. 29.
    Joshi, M.C. and Rawat, D.S., Chemistry & Biodiversity, 2012, 9(3): 459CrossRefGoogle Scholar
  30. 30.
    Laroche, C., Li, J. and Kerwin, S.M., J. Med. Chem., 2011, 54(14): 5059CrossRefGoogle Scholar
  31. 31.
    Yang, X., Li, Z., Zhi, J., Ma, J. and Hu, A., Langmuir, 2010, 26(13): 11244CrossRefGoogle Scholar
  32. 32.
    Kar, M. and Basak, A., Chem. Rev., 2007. 107(7): 2861CrossRefGoogle Scholar
  33. 33.
    Xiao, Y. and Hu, A., Macromol. Rapid Commun., 2011. 32(21): 1688CrossRefGoogle Scholar
  34. 34.
    John, J.A. and Tour, J.M., J. Am. Chem. Soc., 1994, 116(11): 5011CrossRefGoogle Scholar
  35. 35.
    Nakamura, T., Yonesu, K., Mizuno, Y., Suzuki, C., Sakata, Y., Takuwa, Y., Nara, F. and Satoh, S., Bioorg. Med. Chem., 2007, 15(10): 3548CrossRefGoogle Scholar
  36. 36.
    Carballeira, N.M., Sanabria, D. and Oyola, D., Arkivoc, 2007: 49Google Scholar
  37. 37.
    Sun, S., Zhu, C., Song, D., Li, F. and Hu, A., Polym. Chem., 2014, 5(4): 1241CrossRefGoogle Scholar
  38. 38.
    Taguchi, M., Suzuki, N. and Fujiki, M., Polym. J., 2013, 45(10): 1047CrossRefGoogle Scholar

Copyright information

© Chinese Chemical Society, Institute of Chemistry, Chinese Academy of Sciences and Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Shiyuan Sun
    • 1
  • Luhua Dong
    • 1
  • Depeng Song
    • 1
  • Binlei Huang
    • 1
  • Aiguo Hu (胡爱国)
    • 1
    Email author
  1. 1.Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and EngineeringEast China University of Science and TechnologyShanghaiChina

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