Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties

[Image: see text] A strategy for the synthesis of dibenz[a,j]anthracenes (DBAs) from cyclohexa-2,5-diene-1-carboxylic acids is presented. Our approach involves sequential C–H olefination, cycloaddition, and decarboxylative aromatization. In the key step for DBA skeleton construction, the bis-C–H ole...

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Autores principales: Wu, Yan-Ying, Wu, Yi-Lin, Lin, Cheng-Lan, Chen, Hung-Cheng, Chuang, Yao-Yuan, Chen, Chih-Hsien, Chou, Chih-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10630963/
https://www.ncbi.nlm.nih.gov/pubmed/37622587
http://dx.doi.org/10.1021/acs.orglett.3c02306
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author Wu, Yan-Ying
Wu, Yi-Lin
Lin, Cheng-Lan
Chen, Hung-Cheng
Chuang, Yao-Yuan
Chen, Chih-Hsien
Chou, Chih-Ming
author_facet Wu, Yan-Ying
Wu, Yi-Lin
Lin, Cheng-Lan
Chen, Hung-Cheng
Chuang, Yao-Yuan
Chen, Chih-Hsien
Chou, Chih-Ming
author_sort Wu, Yan-Ying
collection PubMed
description [Image: see text] A strategy for the synthesis of dibenz[a,j]anthracenes (DBAs) from cyclohexa-2,5-diene-1-carboxylic acids is presented. Our approach involves sequential C–H olefination, cycloaddition, and decarboxylative aromatization. In the key step for DBA skeleton construction, the bis-C–H olefination products, 1,3-dienes, are utilized as substrates for [4 + 2] cycloaddition with benzyne. This concise synthetic route allows for regioselective ring formation and functional group introduction. The structural features and photophysical properties of the resulting DBA molecules are discussed.
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spelling pubmed-106309632023-11-15 Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties Wu, Yan-Ying Wu, Yi-Lin Lin, Cheng-Lan Chen, Hung-Cheng Chuang, Yao-Yuan Chen, Chih-Hsien Chou, Chih-Ming Org Lett [Image: see text] A strategy for the synthesis of dibenz[a,j]anthracenes (DBAs) from cyclohexa-2,5-diene-1-carboxylic acids is presented. Our approach involves sequential C–H olefination, cycloaddition, and decarboxylative aromatization. In the key step for DBA skeleton construction, the bis-C–H olefination products, 1,3-dienes, are utilized as substrates for [4 + 2] cycloaddition with benzyne. This concise synthetic route allows for regioselective ring formation and functional group introduction. The structural features and photophysical properties of the resulting DBA molecules are discussed. American Chemical Society 2023-08-25 /pmc/articles/PMC10630963/ /pubmed/37622587 http://dx.doi.org/10.1021/acs.orglett.3c02306 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Wu, Yan-Ying
Wu, Yi-Lin
Lin, Cheng-Lan
Chen, Hung-Cheng
Chuang, Yao-Yuan
Chen, Chih-Hsien
Chou, Chih-Ming
Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties
title Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties
title_full Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties
title_fullStr Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties
title_full_unstemmed Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties
title_short Butterfly-Shaped Dibenz[a,j]anthracenes: Synthesis and Photophysical Properties
title_sort butterfly-shaped dibenz[a,j]anthracenes: synthesis and photophysical properties
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10630963/
https://www.ncbi.nlm.nih.gov/pubmed/37622587
http://dx.doi.org/10.1021/acs.orglett.3c02306
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