Synthesis, Photophysical Properties, and Aromaticity of Pyrazine-Fused Tetrazapentalenes
Résumé
Pyrazine-fused 1,2,6,6a-tetrazapentalenes (PyTeAP) 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 scaffold of PyTeAP was confirmed by single-crystal X-ray diffraction analysis of one derivative. Examination of their photophysical properties in solution revealed blue fluorescence with λem = 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.
Domaines
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Décrit hal-03856904 Article Vincent 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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Cite hal-03856904 Article Vincent 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⟩
