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Substituent effects on direct arylation polycondensation and optical properties of alternating fluorene-thiophene copolymers

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Abstract

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.

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Authors and Affiliations

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

    Min-min Sun, Wen Wang  (王文), Lu-ying Liang, Shu-hui Yan, Ming-lu Zhou & Qi-dan Ling  (凌启淡)

Authors
  1. Min-min Sun
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  2. Wen Wang  (王文)
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  3. Lu-ying Liang
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  4. Shu-hui Yan
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  5. Ming-lu Zhou
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  6. Qi-dan Ling  (凌启淡)
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Corresponding authors

Correspondence to Wen Wang  (王文) or Qi-dan Ling  (凌启淡).

Additional information

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.

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Sun, Mm., Wang, W., Liang, Ly. et al. Substituent effects on direct arylation polycondensation and optical properties of alternating fluorene-thiophene copolymers. Chin J Polym Sci 33, 783–791 (2015). https://doi.org/10.1007/s10118-015-1555-9

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  • DOI: https://doi.org/10.1007/s10118-015-1555-9

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