Substituent Effects on Direct Arylation Polycondensation and Optical Properties of Alternating Fluorene-Thiophene Copolymers

Min-min Sun; Wen Wang; Lu-ying Liang; Shu-hui Yan; Ming-lu Zhou; Qi-dan Ling

doi:10.1007/s10118-015-1555-9

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Substituent Effects on Direct Arylation Polycondensation and Optical Properties of Alternating Fluorene-Thiophene Copolymers

PAPER | Updated：2021-06-21

- Substituent Effects on Direct Arylation Polycondensation and Optical Properties of Alternating Fluorene-Thiophene Copolymers
- Chinese Journal of Polymer Science Vol. 33, Issue 5, Pages: 783-791(2015)
- Affiliations：
  
  Fujian Key Laboratory of Polymer Materials, College of Materials Science and Engineering, Fujian Normal University, Fuzhou 350007, China
- Author bio：
  
  **Wen Wang (王文), E-mail: wangwen@fjnu.edu.cn
  Qi-dan Ling (凌启淡), E-mail: qdling@fjnu.edu.cn
- Funds：
- DOI：10.1007/s10118-015-1555-9
  CLC：
- Received：19 September 2014，
  
  Revised：2014-10-03，
  
  Accepted：08 October 2014，
  
  Published：2015-05
- Accepted：
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Min-min Sun, Wen Wang, Lu-ying Liang, et al. Substituent Effects on Direct Arylation Polycondensation and Optical Properties of Alternating Fluorene-Thiophene Copolymers[J]. Chinese Journal of Polymer Science, 2015, 33(5): 783-791.
DOI：

Min-min Sun, Wen Wang, Lu-ying Liang, et al. Substituent Effects on Direct Arylation Polycondensation and Optical Properties of Alternating Fluorene-Thiophene Copolymers[J]. Chinese Journal of Polymer Science, 2015, 33(5): 783-791. DOI： 10.1007/s10118-015-1555-9.

摘要

Abstract

Four thiophene derivatives were prepared by replacing the 3

4 positions of thiophene by ―OCH

―CH

―COOCH

and ―CN

respectively. The polycondensations

via

direct arylation took place between the four thiophene derivatives and 2

7-dibromo-9

9-dioctylfluorene under six various catalytic conditions to investigate the substituent effects. The substituent can affect the electron cloud density of the active C―H bond

which can be monitored by the NMR chemical shift. The experimental results show that the reactivity decreases with increasing the chemical shift of active C―H bonds in the four thiophene derivatives

and thus can promote the direct arylation polycondensation. This phenomenon is explained by the electrophilic aromatic substitution (S

Ar) mechanism. UV-Visible absorption and photoluminescence were studied to investigate the substituent effect on optical properties of the four copolymers. The results show that these alternating fluorene-thiophene copolymers with different substituents are good fluorescent materials and promising in PLED applications.

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