Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains

We synthesized n-type polymers poly{[N,N′-bis(2-octyldodecyl)-naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)} [P(NDI2OD-T2)] and poly{[N,N′-bis(3-(4-cardanol)propyl)-naphthalene-1,4,5,8-tetracarboxylic diimide]-alt-[5,5′-bis(2-thienyl)-2,2′-bithiophene]} [P(NDICL-T2)] w...

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Main Authors: Jin Cheng, Hongyu Fu, Yifan Qiao, Xuming Xue, Pirada Sudprasert, Kenji Ogino
Format: Article
Language:English
Published: MDPI AG 2024-12-01
Series:Micromachines
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Online Access:https://www.mdpi.com/2072-666X/15/12/1475
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author Jin Cheng
Hongyu Fu
Yifan Qiao
Xuming Xue
Pirada Sudprasert
Kenji Ogino
author_facet Jin Cheng
Hongyu Fu
Yifan Qiao
Xuming Xue
Pirada Sudprasert
Kenji Ogino
author_sort Jin Cheng
collection DOAJ
description We synthesized n-type polymers poly{[N,N′-bis(2-octyldodecyl)-naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)} [P(NDI2OD-T2)] and poly{[N,N′-bis(3-(4-cardanol)propyl)-naphthalene-1,4,5,8-tetracarboxylic diimide]-alt-[5,5′-bis(2-thienyl)-2,2′-bithiophene]} [P(NDICL-T2)] with cardanol-based side chains via Stille coupling to enhance electron mobility. Replacing the 2-octyldodecyl side chain with cardanol in P(NDICL-T2) improved electron mobility due to increased chain flexibility and ordered packing. Lower glass transition temperature (<i>t</i><sub>g</sub>), red-shifted UV-vis absorption, results from crystalline structure analysis, indicating tighter lamellar spacing and enhanced molecular ordering, and smoother surface morphology confirmed the enhanced intermolecular interactions and uniform film formation.
format Article
id doaj-art-0e764a5fa71b4ffab2d6fa6b1fcc2f4f
institution Kabale University
issn 2072-666X
language English
publishDate 2024-12-01
publisher MDPI AG
record_format Article
series Micromachines
spelling doaj-art-0e764a5fa71b4ffab2d6fa6b1fcc2f4f2024-12-27T14:40:47ZengMDPI AGMicromachines2072-666X2024-12-011512147510.3390/mi15121475Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side ChainsJin Cheng0Hongyu Fu1Yifan Qiao2Xuming Xue3Pirada Sudprasert4Kenji Ogino5Department of Chemical Engineering and Pharmaceutical Engineering, Changzhou Vocational Institute of Engineering, Changzhou 213164, ChinaGraduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, JapanGraduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, JapanDepartment of Chemical Engineering and Pharmaceutical Engineering, Changzhou Vocational Institute of Engineering, Changzhou 213164, ChinaFaculty of Science and Technology, Rajamangala University of Technology Tawan-OK, Chonburi 20110, ThailandGraduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, JapanWe synthesized n-type polymers poly{[N,N′-bis(2-octyldodecyl)-naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)} [P(NDI2OD-T2)] and poly{[N,N′-bis(3-(4-cardanol)propyl)-naphthalene-1,4,5,8-tetracarboxylic diimide]-alt-[5,5′-bis(2-thienyl)-2,2′-bithiophene]} [P(NDICL-T2)] with cardanol-based side chains via Stille coupling to enhance electron mobility. Replacing the 2-octyldodecyl side chain with cardanol in P(NDICL-T2) improved electron mobility due to increased chain flexibility and ordered packing. Lower glass transition temperature (<i>t</i><sub>g</sub>), red-shifted UV-vis absorption, results from crystalline structure analysis, indicating tighter lamellar spacing and enhanced molecular ordering, and smoother surface morphology confirmed the enhanced intermolecular interactions and uniform film formation.https://www.mdpi.com/2072-666X/15/12/1475cardanol-basedn-type polymerelectron-transporting properties
spellingShingle Jin Cheng
Hongyu Fu
Yifan Qiao
Xuming Xue
Pirada Sudprasert
Kenji Ogino
Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains
Micromachines
cardanol-based
n-type polymer
electron-transporting properties
title Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains
title_full Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains
title_fullStr Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains
title_full_unstemmed Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains
title_short Synthesis and Electron-Transporting Properties of N-Type Polymers with Cardanol-Based Side Chains
title_sort synthesis and electron transporting properties of n type polymers with cardanol based side chains
topic cardanol-based
n-type polymer
electron-transporting properties
url https://www.mdpi.com/2072-666X/15/12/1475
work_keys_str_mv AT jincheng synthesisandelectrontransportingpropertiesofntypepolymerswithcardanolbasedsidechains
AT hongyufu synthesisandelectrontransportingpropertiesofntypepolymerswithcardanolbasedsidechains
AT yifanqiao synthesisandelectrontransportingpropertiesofntypepolymerswithcardanolbasedsidechains
AT xumingxue synthesisandelectrontransportingpropertiesofntypepolymerswithcardanolbasedsidechains
AT piradasudprasert synthesisandelectrontransportingpropertiesofntypepolymerswithcardanolbasedsidechains
AT kenjiogino synthesisandelectrontransportingpropertiesofntypepolymerswithcardanolbasedsidechains