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Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units

Donor–acceptor π-conjugated random copolymers based on regioregular poly(3-hexylthiophene), rr-P3HT, with unsymmetrical monothienoisoindigo moieties were obtained by direct arylation polycondensation of 2-bromo-3-hexylthiophene with unsymmetrical monothienoisoindigo motifs under the optimized condit...

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Autores principales: Uegaki, Kaoru, Nakabayashi, Kazuhiro, Yamamoto, Shin-ichi, Koizumi, Toshio, Hayashi, Shotaro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9053906/
https://www.ncbi.nlm.nih.gov/pubmed/35518285
http://dx.doi.org/10.1039/d0ra03557b
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author Uegaki, Kaoru
Nakabayashi, Kazuhiro
Yamamoto, Shin-ichi
Koizumi, Toshio
Hayashi, Shotaro
author_facet Uegaki, Kaoru
Nakabayashi, Kazuhiro
Yamamoto, Shin-ichi
Koizumi, Toshio
Hayashi, Shotaro
author_sort Uegaki, Kaoru
collection PubMed
description Donor–acceptor π-conjugated random copolymers based on regioregular poly(3-hexylthiophene), rr-P3HT, with unsymmetrical monothienoisoindigo moieties were obtained by direct arylation polycondensation of 2-bromo-3-hexylthiophene with unsymmetrical monothienoisoindigo motifs under the optimized conditions [palladium-immobilized on thiol-modified silica gel with chloride counter anions, PITS-Cl (2.5 mol%), PivOH (1.0 equiv.), K(2)CO(3) (3.0 equiv.), DMAc, 100 °C, 24 h]. Incorporation of unsymmetrical monothienoisoindigo electron-acceptor units into the polymers tuned their highest occupied and lowest unoccupied molecular orbital levels, which were close to those of the hole transport material (PEDOT) and electron transport material (PCBM), respectively, in thin-film organic solar cells. Alkyl chains of the unsymmetrical monothienoisoindigo units in the polymers tuned their macrostructural order, resulting in the observation of crystalline patterns and specific absorption peaks in thin films. An organic solar cell containing the most crystalline random copolymer showed an efficiency of 1.91%.
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spelling pubmed-90539062022-05-04 Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units Uegaki, Kaoru Nakabayashi, Kazuhiro Yamamoto, Shin-ichi Koizumi, Toshio Hayashi, Shotaro RSC Adv Chemistry Donor–acceptor π-conjugated random copolymers based on regioregular poly(3-hexylthiophene), rr-P3HT, with unsymmetrical monothienoisoindigo moieties were obtained by direct arylation polycondensation of 2-bromo-3-hexylthiophene with unsymmetrical monothienoisoindigo motifs under the optimized conditions [palladium-immobilized on thiol-modified silica gel with chloride counter anions, PITS-Cl (2.5 mol%), PivOH (1.0 equiv.), K(2)CO(3) (3.0 equiv.), DMAc, 100 °C, 24 h]. Incorporation of unsymmetrical monothienoisoindigo electron-acceptor units into the polymers tuned their highest occupied and lowest unoccupied molecular orbital levels, which were close to those of the hole transport material (PEDOT) and electron transport material (PCBM), respectively, in thin-film organic solar cells. Alkyl chains of the unsymmetrical monothienoisoindigo units in the polymers tuned their macrostructural order, resulting in the observation of crystalline patterns and specific absorption peaks in thin films. An organic solar cell containing the most crystalline random copolymer showed an efficiency of 1.91%. The Royal Society of Chemistry 2020-05-19 /pmc/articles/PMC9053906/ /pubmed/35518285 http://dx.doi.org/10.1039/d0ra03557b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Uegaki, Kaoru
Nakabayashi, Kazuhiro
Yamamoto, Shin-ichi
Koizumi, Toshio
Hayashi, Shotaro
Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
title Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
title_full Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
title_fullStr Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
title_full_unstemmed Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
title_short Donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
title_sort donor–acceptor random regioregular π-conjugated copolymers based on poly(3-hexylthiophene) with unsymmetrical monothienoisoindigo units
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9053906/
https://www.ncbi.nlm.nih.gov/pubmed/35518285
http://dx.doi.org/10.1039/d0ra03557b
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