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Domino Dehydrative π-Extension: A Facile Path to Extended Perylenes and Terrylenes.

ABSTRACT: Herein, we report a new method for synthesis of extended perylenes and terrylenes. The technique is based on the cascade dehydrative π-extensions (DPEX) of aryl aldehydes, in which stepwise annulations activate previously "dormant" substituents. Two- and fourfold cyclizations of 3-aryl-biphenyl-2,2'-dicarbaldehydes offer a rapid path to unsymmetrical perylenes and elusive terrylene derivatives, respectively. DPEX of 3,3''-(phenanthrene-1,8-diyl)bis (([1,1'-biphenyl]-2,2'-dicarbaldehyde)) leads to the biradical structure, which proceeds in situ into oxidative electrocyclization at room temperature. The described domino process complements and expands DPEX approach to a large family of fused acenes and related PAHs.

SUBMITTER: Feofanov M

PROVIDER: S-EPMC9299636 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Domino Dehydrative π-Extension: A Facile Path to Extended Perylenes and Terrylenes.

Feofanov Mikhail M Akhmetov Vladimir V Amsharov Konstantin K

Chemistry (Weinheim an der Bergstrasse, Germany) 20211110 69

Herein, we report a new method for synthesis of extended perylenes and terrylenes. The technique is based on the cascade dehydrative π-extensions (DPEX) of aryl aldehydes, in which stepwise annulations activate previously "dormant" substituents. Two- and fourfold cyclizations of 3-aryl-biphenyl-2,2'-dicarbaldehydes offer a rapid path to unsymmetrical perylenes and elusive terrylene derivatives, respectively. DPEX of 3,3''-(phenanthrene-1,8-diyl)bis (([1,1'-biphenyl]-2,2'-dicarbaldehyde)) leads t ...[more]

PMID: 34553791

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