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

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.

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Correspondence to Aiguo Hu.

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This work was financially supported by the National Natural Science Foundation of China (Nos. 20874026 and 91023008), Ph. D. Programs Foundation of Ministry of Education of China (20100074110002), the Fundamental Research Funds for the Central Universities, Shanghai Leading Academic Discipline Project (B502). AH thanks the “Eastern Scholar Professorship” support from Shanghai local government.

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Sun, S., Dong, L., Song, D. et al. Synthesis of polyphenylenes through bergman cyclization of enediynes with long chain alkyl groups. Chin J Polym Sci 33, 184–191 (2015). https://doi.org/10.1007/s10118-015-1566-6

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  • DOI: https://doi.org/10.1007/s10118-015-1566-6

Keywords

  • Enediyne
  • Bergman cyclization
  • Polyphenylene