Citation: Shiyuan Sun, Luhua Dong, Depeng Song, Binlei Huang, Aiguo Hu. 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 shu

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

1.
Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Aiguo Hu,
Received Date: 18 June 2014
Revised Date: 24 July 2014

Fund Project: 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.

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 gmol-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
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
33. [33]
34. [34]
35. [35]
36. [36]
37. [37]
38. [38]
1. [1]
  Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870
2. [2]
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3. [3]
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4. [4]
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5. [5]
  Yi-Kao Xu , Guo-Ping Luo , Liang-Bin Hu , Wei-Min He . Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes. Chinese Chemical Letters, 2025, 36(8): 111226-. doi: 10.1016/j.cclet.2025.111226
6. [6]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
7. [7]
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