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Butterfly-shaped Dibenz[a,j]anthracenes: Synthesis and photophysical properties

Wu, Yan-Ying, Wu, Yi-Lin ORCID:, Lin, Cheng-Lan, Chen, Hung-Cheng, Chuang, Yao-Yuan, Chen, Chih-Hsien and Chou, Chih-Ming 2023. Butterfly-shaped Dibenz[a,j]anthracenes: Synthesis and photophysical properties. Organic Letters 25 (43) , pp. 7763-7768. 10.1021/acs.orglett.3c02306

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 1523-7060
Funders: EPSRC
Date of First Compliant Deposit: 28 September 2023
Date of Acceptance: 22 August 2023
Last Modified: 28 Nov 2023 15:54

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