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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

Chimie organique

Dates et versions

hal-03856911 , version 1 (17-11-2022)

Licence

Domaine public

Identifiants

  • HAL Id : hal-03856911 , version 1

Citer

Vincent Gutierrez, Axel Arnault, Véronique Ferreira, Albert Artigas, Denis Hagebaum-Reignier, et al.. Synthesis, Photophysical Properties, and Aromaticity of Pyrazine-Fused Tetrazapentalenes. France. 2022. ⟨hal-03856911⟩
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