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

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

通讯作者: Aiguo Hu,

基金项目:
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.

摘要: 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.

关键词:

English

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
Available Online: 05 January 2015
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.

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 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.

Key words:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

通讯作者: Aiguo Hu,

English

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

Corresponding author: Aiguo Hu,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

通讯作者: Aiguo Hu,

English

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

Corresponding author: Aiguo Hu,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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