Synthesis of Polyphenylenes through Bergman Cyclization of Enediynes with Long Chain Alkyl Groups

Shiyuan Sun; Luhua Dong; Depeng Song; Binlei Huang; Aiguo Hu

doi:10.1007/s10118-015-1566-6

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Synthesis of Polyphenylenes through Bergman Cyclization of Enediynes with Long Chain Alkyl Groups

PAPER | Updated：2021-06-21

- Synthesis of Polyphenylenes through Bergman Cyclization of Enediynes with Long Chain Alkyl Groups
- Chinese Journal of Polymer Science Vol. 33, Issue 1, Pages: 184-191(2015)
- Affiliations：
  
  Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China
- Author bio：
  
  **Aiguo Hu (胡爱国), E-mail: hagmhsn@ecust.edu.cn
- Funds：
- DOI：10.1007/s10118-015-1566-6
  CLC：
- Received：18 June 2014，
  
  Revised：2014-07-21，
  
  Accepted：24 July 2014，
  
  Published：2015-01
- Accepted：
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Shiyuan Sun, Luhua Dong, Depeng Song, et al. Synthesis of Polyphenylenes through Bergman Cyclization of Enediynes with Long Chain Alkyl Groups[J]. Chinese Journal of Polymer Science, 2015, 33(1): 184-191.
DOI：

Shiyuan Sun, Luhua Dong, Depeng Song, et al. Synthesis of Polyphenylenes through Bergman Cyclization of Enediynes with Long Chain Alkyl Groups[J]. Chinese Journal of Polymer Science, 2015, 33(1): 184-191. DOI： 10.1007/s10118-015-1566-6.

摘要

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 × 10

g·mol

-1

. The occurrence of Bergman cyclization was confirmed by

H-NMR

C-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.

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