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Azoniadibenzo[ a , j ]phenalenide: A Polycyclic Zwitterion with Singlet Biradical Character
Author(s) -
Arikawa Shinobu,
Shimizu Akihiro,
Shintani Ryo
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902006
Subject(s) - zwitterion , delocalized electron , singlet state , character (mathematics) , charge (physics) , excited state , singlet fission , chemistry , photochemistry , homo/lumo , computational chemistry , physics , atomic physics , molecule , quantum mechanics , organic chemistry , geometry , mathematics
A polycyclic zwitterion, azoniadibenzo[ a , j ]phenalenide, having a singlet biradical character, was synthesized and isolated for the first time. The negative charge was found to be delocalized over the periphery of the main core of the zwitterion and the positive charge was localized near the nitrogen atom. Its singlet biradical character was confirmed by a small HOMO–LUMO energy gap with their spatial overlap, and observation of thermally excited triplet species together with DFT calculations.