Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization
Over the past decades, π-conjugated polymers (CPs) have drawn more and more attention and been essential materials for applications in various organic electronic devices. Thereinto, conjugated polymers based on the 3,4-ethylenedioxythiophene (EDOT) backbone are among the high-performance materials....
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Frontiers Media S.A.
2021-10-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2021.753840/full |
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| author | Qiang Guo Jincheng Zhang Xiaoyu Li Heqi Gong Shuanghong Wu Jie Li |
| author_facet | Qiang Guo Jincheng Zhang Xiaoyu Li Heqi Gong Shuanghong Wu Jie Li |
| author_sort | Qiang Guo |
| collection | DOAJ |
| description | Over the past decades, π-conjugated polymers (CPs) have drawn more and more attention and been essential materials for applications in various organic electronic devices. Thereinto, conjugated polymers based on the 3,4-ethylenedioxythiophene (EDOT) backbone are among the high-performance materials. In order to investigate the structure–property relationships of EDOT-based polymers and further improve their electrochemical properties, a series of organic solvent–soluble EDOT-based alternative copolymers consisting of electron-rich fragments (fluorene P1, carbazole P2, and 3,4-alkoxythiophene P3) or electron-deficient moieties (benzotriazole P4 and thieno[3,4-c]pyrrole-4,6-dione P5) were synthesized via direct C–H (hetero)arylation polymerization (DHAP) in moderate to excellent yields (60–98%) with medium to high molecular weights (Mn = 3,100–94,000 Da). Owing to their various electronic and structural properties, different absorption spectra (λmax = 476, 380, 558, 563, and 603 nm) as well as different specific capacitances of 70, 68, 75, 51, and 25 F/g with 19, 10, 21, 26, and 69% of capacity retention after 1,000 cycles were observed for P1–P5, respectively. After careful study through multiple experimental measurements and theoretical calculation, appropriate electronic characteristics, small molecular conformation differences between different oxidative states, and well-ordered molecular stacking could improve the electrochemical performance of CPs. |
| first_indexed | 2024-12-22T06:40:18Z |
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| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-22T06:40:18Z |
| publishDate | 2021-10-01 |
| publisher | Frontiers Media S.A. |
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| series | Frontiers in Chemistry |
| spelling | doaj.art-7b7a2e7cf298470b8e09994c33c381d12022-12-21T18:35:26ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-10-01910.3389/fchem.2021.753840753840Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation PolymerizationQiang Guo0Jincheng Zhang1Xiaoyu Li2Heqi Gong3Shuanghong Wu4Jie Li5College of Optoelectronic Engineering, Chengdu University of Information Technology, Chengdu, ChinaCollege of Optoelectronic Engineering, Chengdu University of Information Technology, Chengdu, ChinaSouthwest University of Science and Technology, Mianyang, ChinaCollege of Optoelectronic Engineering, Chengdu University of Information Technology, Chengdu, ChinaSchool of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China, Chengdu, ChinaCollege of Optoelectronic Engineering, Chengdu University of Information Technology, Chengdu, ChinaOver the past decades, π-conjugated polymers (CPs) have drawn more and more attention and been essential materials for applications in various organic electronic devices. Thereinto, conjugated polymers based on the 3,4-ethylenedioxythiophene (EDOT) backbone are among the high-performance materials. In order to investigate the structure–property relationships of EDOT-based polymers and further improve their electrochemical properties, a series of organic solvent–soluble EDOT-based alternative copolymers consisting of electron-rich fragments (fluorene P1, carbazole P2, and 3,4-alkoxythiophene P3) or electron-deficient moieties (benzotriazole P4 and thieno[3,4-c]pyrrole-4,6-dione P5) were synthesized via direct C–H (hetero)arylation polymerization (DHAP) in moderate to excellent yields (60–98%) with medium to high molecular weights (Mn = 3,100–94,000 Da). Owing to their various electronic and structural properties, different absorption spectra (λmax = 476, 380, 558, 563, and 603 nm) as well as different specific capacitances of 70, 68, 75, 51, and 25 F/g with 19, 10, 21, 26, and 69% of capacity retention after 1,000 cycles were observed for P1–P5, respectively. After careful study through multiple experimental measurements and theoretical calculation, appropriate electronic characteristics, small molecular conformation differences between different oxidative states, and well-ordered molecular stacking could improve the electrochemical performance of CPs.https://www.frontiersin.org/articles/10.3389/fchem.2021.753840/fulldirect hetero(arylation) polymerizationconjugated copolymerelectrochemicalstructure–property relationship3,4-ethylenedioxythiophene (EDOT) |
| spellingShingle | Qiang Guo Jincheng Zhang Xiaoyu Li Heqi Gong Shuanghong Wu Jie Li Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization Frontiers in Chemistry direct hetero(arylation) polymerization conjugated copolymer electrochemical structure–property relationship 3,4-ethylenedioxythiophene (EDOT) |
| title | Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization |
| title_full | Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization |
| title_fullStr | Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization |
| title_full_unstemmed | Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization |
| title_short | Physical and Electrochemical Properties of Soluble 3,4-Ethylenedioxythiophene (EDOT)-Based Copolymers Synthesized via Direct (Hetero)Arylation Polymerization |
| title_sort | physical and electrochemical properties of soluble 3 4 ethylenedioxythiophene edot based copolymers synthesized via direct hetero arylation polymerization |
| topic | direct hetero(arylation) polymerization conjugated copolymer electrochemical structure–property relationship 3,4-ethylenedioxythiophene (EDOT) |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2021.753840/full |
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