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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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%. |
format | Online Article Text |
id | pubmed-9053906 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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