%0 Journal Article %T Synthesis, Photophysical Properties, and Aromaticity of Pyrazine-Fused Tetrazapentalenes %+ Institut de Chimie Organique et Analytique (ICOA) %+ Institut des Sciences Moléculaires de Marseille (ISM2) %A Gutierrez, Vincent, S %A Arnault, Axel %A Ferreira, Véronique %A Artigas, Albert %A Hagebaum-Reignier, Denis %A Carissan, Yannick %A Coquerel, Yoann %A Hiebel, Marie-Aude %A Suzenet, Franck %< avec comité de lecture %@ 0022-3263 %J Journal of Organic Chemistry %I American Chemical Society %V 87 %N 21 %P 13653-13662 %8 2022 %D 2022 %R 10.1021/acs.joc.2c01308 %K Azapentalenes %K aromaticity %K fluorescence %K DFT %K N-heterocycles %Z Chemical Sciences/Organic chemistryJournal articles %X 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 %G English %2 https://hal.science/hal-03856904/document %2 https://hal.science/hal-03856904/file/2022JOC-1.pdf %L hal-03856904 %U https://hal.science/hal-03856904 %~ CEA %~ CNRS %~ UNIV-AMU %~ UNIV-ORLEANS %~ ICOA %~ EC-MARSEILLE %~ ISM2 %~ INC-CNRS %~ ANR %~ CTOM %~ TEST2-HALCNRS %~ LABOS-SYNORG