Citation: Min-min Sun, Wen Wang, Lu-ying Liang, Shu-hui Yan, Ming-lu Zhou, Qi-dan Ling. 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 shu

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

1.
Fujian Key Laboratory of Polymer Materials, College of Materials Science and Engineering, Fujian Normal University, Fuzhou 350007, China

Received Date: 19 September 2014
Revised Date: 8 October 2014

Fund Project: This work was financially supported by the National Natural Science Foundation of China (Nos. 60976019 and 61250016), Education Department Program (No. JA12069) and Program for Innovative Research Team in Science and Technology in Fujian Province.

Four thiophene derivatives were prepared by replacing the 3,4 positions of thiophene by ―OCH3, ―CH3 ―COOCH3 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 (SEAr) 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.
- Direct arylation polycondensation,
- Alternating copolymers,
- Substituent effects,
- Chemical shift
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沈阳化工大学材料科学与工程学院沈阳 110142