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Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties
Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2...
Autores principales: | , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer US
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6472551/ https://www.ncbi.nlm.nih.gov/pubmed/31057182 http://dx.doi.org/10.1007/s10853-019-03551-3 |
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author | Knall, Astrid-Caroline Hoefler, Sebastian Franz Hollauf, Manuel Thaler, Ferula Noesberger, Sven Hanzu, Ilie Ehmann, Heike Hobisch, Mathias Spirk, Stefan Wen, Shuguang Yang, Renqiang Rath, Thomas Trimmel, Gregor |
author_facet | Knall, Astrid-Caroline Hoefler, Sebastian Franz Hollauf, Manuel Thaler, Ferula Noesberger, Sven Hanzu, Ilie Ehmann, Heike Hobisch, Mathias Spirk, Stefan Wen, Shuguang Yang, Renqiang Rath, Thomas Trimmel, Gregor |
author_sort | Knall, Astrid-Caroline |
collection | PubMed |
description | Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s10853-019-03551-3) contains supplementary material, which is available to authorized users. |
format | Online Article Text |
id | pubmed-6472551 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Springer US |
record_format | MEDLINE/PubMed |
spelling | pubmed-64725512019-05-03 Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties Knall, Astrid-Caroline Hoefler, Sebastian Franz Hollauf, Manuel Thaler, Ferula Noesberger, Sven Hanzu, Ilie Ehmann, Heike Hobisch, Mathias Spirk, Stefan Wen, Shuguang Yang, Renqiang Rath, Thomas Trimmel, Gregor J Mater Sci Polymers Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s10853-019-03551-3) contains supplementary material, which is available to authorized users. Springer US 2019-04-03 2019 /pmc/articles/PMC6472551/ /pubmed/31057182 http://dx.doi.org/10.1007/s10853-019-03551-3 Text en © The Author(s) 2019 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. |
spellingShingle | Polymers Knall, Astrid-Caroline Hoefler, Sebastian Franz Hollauf, Manuel Thaler, Ferula Noesberger, Sven Hanzu, Ilie Ehmann, Heike Hobisch, Mathias Spirk, Stefan Wen, Shuguang Yang, Renqiang Rath, Thomas Trimmel, Gregor Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
title | Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
title_full | Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
title_fullStr | Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
title_full_unstemmed | Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
title_short | Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
title_sort | synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties |
topic | Polymers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6472551/ https://www.ncbi.nlm.nih.gov/pubmed/31057182 http://dx.doi.org/10.1007/s10853-019-03551-3 |
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