Synthesis, Photophysical Properties, and Aromaticity of Pyrazine-Fused Tetrazapentalenes - Aix-Marseille Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2022

Synthesis, Photophysical Properties, and Aromaticity of Pyrazine-Fused Tetrazapentalenes

Abstract

Pyrazine-fused 1,2,6,6a-tetrazapentalenes (Py-TeAP) are zwitterionic tricyclic compounds exhibiting an original pattern with four consecutive nitrogen atoms. They were obtained by a challenging cyclization through the formation of a N−N bond under thermolytic conditions. Ten derivatives were synthesized, and the original sca old of PyTeAP was confirmed by single-crystal X-ray di raction analysis of one derivative. Examination of their photophysical properties in solution revealed blue fluorescence with λ em = 416−426 nm. Theoretical investigations of the aromaticity in these compounds through magnetic criteria evidenced the presence of a dominant 14-electron circuit at the periphery. pubs.acs.org/joc Article
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Dates and versions

hal-03856904 , version 1 (17-11-2022)

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Vincent S Gutierrez, Axel Arnault, Véronique Ferreira, Albert Artigas, Denis Hagebaum-Reignier, et al.. Synthesis, Photophysical Properties, and Aromaticity of Pyrazine-Fused Tetrazapentalenes. Journal of Organic Chemistry, 2022, 87 (21), pp.13653-13662. ⟨10.1021/acs.joc.2c01308⟩. ⟨hal-03856904⟩
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