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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.