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Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films

Soluble precursor materials of organic semiconductors are employed for fabricating solution-processable thin film devices. While the so-called precursor approach has already been tried for various organic electronic devices such as transistors and solar cells, understanding of the conversion process...

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Autores principales: Shioya, Nobutaka, Fujii, Masamichi, Shimoaka, Takafumi, Eda, Kazuo, Hasegawa, Takeshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8924201/
https://www.ncbi.nlm.nih.gov/pubmed/35292720
http://dx.doi.org/10.1038/s41598-022-08505-5
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author Shioya, Nobutaka
Fujii, Masamichi
Shimoaka, Takafumi
Eda, Kazuo
Hasegawa, Takeshi
author_facet Shioya, Nobutaka
Fujii, Masamichi
Shimoaka, Takafumi
Eda, Kazuo
Hasegawa, Takeshi
author_sort Shioya, Nobutaka
collection PubMed
description Soluble precursor materials of organic semiconductors are employed for fabricating solution-processable thin film devices. While the so-called precursor approach has already been tried for various organic electronic devices such as transistors and solar cells, understanding of the conversion process in the film lags far behind. Here, we report that molecular aggregation of the precursor compound significantly influences the thermal conversion reaction in the film. For this study, two stereoisomers of a dinaphthothienothiophene (DNTT) precursor that are the endo- and exo-DNTT-phenylmaleimide monoadducts are focused on. The structural change during the thermal conversion process has been investigated by a combination of infrared spectroscopy and X-ray diffraction techniques. The results show that the endo-isomer is readily converted to DNTT in the film by heating, whereas the exo-isomer exhibits no reaction at all. This reaction suppression is found to be due to the self-aggregation property of the exo-isomer accompanying the intermolecular C–H[Formula: see text] O interactions. This finding shows a new direction of controlling the on-surface reaction, as well as the importance of analyzing the film structure at the initial stage of the reaction.
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spelling pubmed-89242012022-03-17 Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films Shioya, Nobutaka Fujii, Masamichi Shimoaka, Takafumi Eda, Kazuo Hasegawa, Takeshi Sci Rep Article Soluble precursor materials of organic semiconductors are employed for fabricating solution-processable thin film devices. While the so-called precursor approach has already been tried for various organic electronic devices such as transistors and solar cells, understanding of the conversion process in the film lags far behind. Here, we report that molecular aggregation of the precursor compound significantly influences the thermal conversion reaction in the film. For this study, two stereoisomers of a dinaphthothienothiophene (DNTT) precursor that are the endo- and exo-DNTT-phenylmaleimide monoadducts are focused on. The structural change during the thermal conversion process has been investigated by a combination of infrared spectroscopy and X-ray diffraction techniques. The results show that the endo-isomer is readily converted to DNTT in the film by heating, whereas the exo-isomer exhibits no reaction at all. This reaction suppression is found to be due to the self-aggregation property of the exo-isomer accompanying the intermolecular C–H[Formula: see text] O interactions. This finding shows a new direction of controlling the on-surface reaction, as well as the importance of analyzing the film structure at the initial stage of the reaction. Nature Publishing Group UK 2022-03-15 /pmc/articles/PMC8924201/ /pubmed/35292720 http://dx.doi.org/10.1038/s41598-022-08505-5 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Shioya, Nobutaka
Fujii, Masamichi
Shimoaka, Takafumi
Eda, Kazuo
Hasegawa, Takeshi
Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
title Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
title_full Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
title_fullStr Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
title_full_unstemmed Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
title_short Stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
title_sort stereoisomer-dependent conversion of dinaphthothienothiophene precursor films
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8924201/
https://www.ncbi.nlm.nih.gov/pubmed/35292720
http://dx.doi.org/10.1038/s41598-022-08505-5
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