The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers
Abstract Although the effects of electron‐deficient group substitution on isoindigo on the corresponding conjugated polymers are extensively studied, the modification of isoindigo core with electron‐rich groups has not been investigated. It is envisioned that the introduction of the methoxy group on...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2023-07-01
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| Series: | Macromolecular Materials and Engineering |
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| Online Access: | https://doi.org/10.1002/mame.202200688 |
| _version_ | 1797743205893013504 |
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| author | Zihan Xiong Wei Wen Yifei Zhu Youbing Mu Zhiyuan Zhao Zhenggang Lan Xiaobo Wan Yunqi Liu |
| author_facet | Zihan Xiong Wei Wen Yifei Zhu Youbing Mu Zhiyuan Zhao Zhenggang Lan Xiaobo Wan Yunqi Liu |
| author_sort | Zihan Xiong |
| collection | DOAJ |
| description | Abstract Although the effects of electron‐deficient group substitution on isoindigo on the corresponding conjugated polymers are extensively studied, the modification of isoindigo core with electron‐rich groups has not been investigated. It is envisioned that the introduction of the methoxy group on isoindigo will not only tune the highest occupied molecular orbital (HOMO) energy level of the corresponding polymers but also introduce O···S “conformation lock” to increase the coplanarity of the polymers, which should facilitate hole transport. Herein, the syntheses of two methoxylated isoindigos and the investigations on the charge transport behaviors of their copolymers with bisthiophene (2T) and bisthiazole (2Tz) are reported. It is found that the substitution positions have a drastic influence on the UV–vis absorption and electrochemical properties for both monomers and polymers. Theoretical calculations and single crystal structure analysis confirm the existence of O···S “conformation lock”, however, both methoxy substitutions also change the aggregation behaviors of the corresponding polymers to a mixed face‐on/edge‐on orientation which has an adverse effect for charge transport. Among the four polymers, the polymer of 5,5'‐methoxylated isoindigo and 2T exhibit the best hole mobility of 1.9 × 10−1 cm2 V−1 s−1. |
| first_indexed | 2024-03-12T14:52:11Z |
| format | Article |
| id | doaj.art-e9db031a28224d60b4ee850d2b4e8198 |
| institution | Directory Open Access Journal |
| issn | 1438-7492 1439-2054 |
| language | English |
| last_indexed | 2024-03-12T14:52:11Z |
| publishDate | 2023-07-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | Macromolecular Materials and Engineering |
| spelling | doaj.art-e9db031a28224d60b4ee850d2b4e81982023-08-15T09:10:29ZengWiley-VCHMacromolecular Materials and Engineering1438-74921439-20542023-07-013087n/an/a10.1002/mame.202200688The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding PolymersZihan Xiong0Wei Wen1Yifei Zhu2Youbing Mu3Zhiyuan Zhao4Zhenggang Lan5Xiaobo Wan6Yunqi Liu7Key Laboratory of Optoelectronic Chemical Materials and Devices School of Optoelectronic Materials & Technology Ministry of Education Jianghan University Wuhan 430056 P. R. ChinaInstitute of Chemistry Chinese Academy of Sciences Beijing 100080 P. R. ChinaSCNU Environmental Research Institute Guangdong Provincial Key Laboratory of Chemical Pollution and Environmental Safety & MOE Key Laboratory of Environmental Theoretical Chemistry School of Environment South China Normal University Guangzhou 510006 ChinaKey Laboratory of Optoelectronic Chemical Materials and Devices School of Optoelectronic Materials & Technology Ministry of Education Jianghan University Wuhan 430056 P. R. ChinaInstitute of Chemistry Chinese Academy of Sciences Beijing 100080 P. R. ChinaSCNU Environmental Research Institute Guangdong Provincial Key Laboratory of Chemical Pollution and Environmental Safety & MOE Key Laboratory of Environmental Theoretical Chemistry School of Environment South China Normal University Guangzhou 510006 ChinaKey Laboratory of Optoelectronic Chemical Materials and Devices School of Optoelectronic Materials & Technology Ministry of Education Jianghan University Wuhan 430056 P. R. ChinaInstitute of Chemistry Chinese Academy of Sciences Beijing 100080 P. R. ChinaAbstract Although the effects of electron‐deficient group substitution on isoindigo on the corresponding conjugated polymers are extensively studied, the modification of isoindigo core with electron‐rich groups has not been investigated. It is envisioned that the introduction of the methoxy group on isoindigo will not only tune the highest occupied molecular orbital (HOMO) energy level of the corresponding polymers but also introduce O···S “conformation lock” to increase the coplanarity of the polymers, which should facilitate hole transport. Herein, the syntheses of two methoxylated isoindigos and the investigations on the charge transport behaviors of their copolymers with bisthiophene (2T) and bisthiazole (2Tz) are reported. It is found that the substitution positions have a drastic influence on the UV–vis absorption and electrochemical properties for both monomers and polymers. Theoretical calculations and single crystal structure analysis confirm the existence of O···S “conformation lock”, however, both methoxy substitutions also change the aggregation behaviors of the corresponding polymers to a mixed face‐on/edge‐on orientation which has an adverse effect for charge transport. Among the four polymers, the polymer of 5,5'‐methoxylated isoindigo and 2T exhibit the best hole mobility of 1.9 × 10−1 cm2 V−1 s−1.https://doi.org/10.1002/mame.202200688isoindigo derivativesmethoxy substitutionorganic field‐effect transistors |
| spellingShingle | Zihan Xiong Wei Wen Yifei Zhu Youbing Mu Zhiyuan Zhao Zhenggang Lan Xiaobo Wan Yunqi Liu The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers Macromolecular Materials and Engineering isoindigo derivatives methoxy substitution organic field‐effect transistors |
| title | The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers |
| title_full | The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers |
| title_fullStr | The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers |
| title_full_unstemmed | The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers |
| title_short | The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers |
| title_sort | effects of methoxylated isoindigo on the optical and charge transport properties of the corresponding polymers |
| topic | isoindigo derivatives methoxy substitution organic field‐effect transistors |
| url | https://doi.org/10.1002/mame.202200688 |
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