Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate

Heptalene has a fused structure of two cycloheptatrienes which is one of the non-aromatic bicyclic molecules with a 12π-electronic structure. We report herein the synthesis of thiophene-fused heptalene derivatives from the corresponding azulenothiophenes via cycloaddition reaction with dimethyl acet...

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Autores principales: Shoji, Taku, Miura, Kota, Ariga, Yukino, Yamazaki, Akari, Ito, Shunji, Yasunami, Masafumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7385116/
https://www.ncbi.nlm.nih.gov/pubmed/32719442
http://dx.doi.org/10.1038/s41598-020-69425-w
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author Shoji, Taku
Miura, Kota
Ariga, Yukino
Yamazaki, Akari
Ito, Shunji
Yasunami, Masafumi
author_facet Shoji, Taku
Miura, Kota
Ariga, Yukino
Yamazaki, Akari
Ito, Shunji
Yasunami, Masafumi
author_sort Shoji, Taku
collection PubMed
description Heptalene has a fused structure of two cycloheptatrienes which is one of the non-aromatic bicyclic molecules with a 12π-electronic structure. We report herein the synthesis of thiophene-fused heptalene derivatives from the corresponding azulenothiophenes via cycloaddition reaction with dimethyl acetylenedicarboxylate. Their structure was clarified by single-crystal X-ray structural analysis. The electronic properties of the thiophene-fused heptalenes obtained by this study were characterized by UV/Vis and fluorescence spectroscopy measurements. The electrochemical features of these derivatives were also examined by voltammetry and spectroelectrochemical experiments.
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spelling pubmed-73851162020-07-28 Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate Shoji, Taku Miura, Kota Ariga, Yukino Yamazaki, Akari Ito, Shunji Yasunami, Masafumi Sci Rep Article Heptalene has a fused structure of two cycloheptatrienes which is one of the non-aromatic bicyclic molecules with a 12π-electronic structure. We report herein the synthesis of thiophene-fused heptalene derivatives from the corresponding azulenothiophenes via cycloaddition reaction with dimethyl acetylenedicarboxylate. Their structure was clarified by single-crystal X-ray structural analysis. The electronic properties of the thiophene-fused heptalenes obtained by this study were characterized by UV/Vis and fluorescence spectroscopy measurements. The electrochemical features of these derivatives were also examined by voltammetry and spectroelectrochemical experiments. Nature Publishing Group UK 2020-07-27 /pmc/articles/PMC7385116/ /pubmed/32719442 http://dx.doi.org/10.1038/s41598-020-69425-w Text en © The Author(s) 2020 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 license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license 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 license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Shoji, Taku
Miura, Kota
Ariga, Yukino
Yamazaki, Akari
Ito, Shunji
Yasunami, Masafumi
Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
title Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
title_full Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
title_fullStr Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
title_full_unstemmed Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
title_short Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
title_sort synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7385116/
https://www.ncbi.nlm.nih.gov/pubmed/32719442
http://dx.doi.org/10.1038/s41598-020-69425-w
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