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

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 synthesi...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (21), p.13653-13662
Main Authors: Gutierrez, Vincent S., Arnault, Axel, Ferreira, Véronique, Artigas, Albert, Hagebaum-Reignier, Denis, Carissan, Yannick, Coquerel, Yoann, Hiebel, Marie-Aude, Suzenet, Franck
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01308