Facile Synthesis of Azahelicenes and Diaza[8]circulenes through the Intramolecular Scholl Reaction.

Chemistry

Division of Applied Chemistry Graduate School of Natural Science and Technology, Okayama University Tsushima, Okayama, 700-8530, Japan.

Published: November 2021

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Article Abstract

Carbazole-based aza[7]helicenes and hetero[9]helicenes were successfully obtained via the intramolecular Scholl reaction of 3,6-bis(biphenyl-2-yl)carbazole congeners, while the reaction of 3,6-bis(naphthylphenyl)-appended carbazole gave a triple helicene via an unexpected simultaneous double aryl rearrangement. DFT calculations suggested that the rearrangement proceeded via an arenium cation intermediate. In addition, the reaction of methoxy-appended substrate gave an azahepta[8]circulene via the concurrent C-C bond formation. These helical dyes showed circularly polarized luminescence. The azahepta[8]circulene was further transformed into deeply saddle-distorted dibenzodiaza[8]circulenes as the first example of its solution-based synthesis and unambiguous structural determination.

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http://dx.doi.org/10.1002/chem.202102269DOI Listing

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