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)
Papers

Abstract

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.

Keywords

Enediyne Bergman cyclization Polyphenylene 

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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
  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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