Azoniadibenzophenalenide: A Polycyclic Zwitterion with Singlet Biradical Character

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...

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Bibliographic Details
Published inAngewandte Chemie Vol. 131; no. 19; pp. 6481 - 6485
Main Authors Arikawa, Shinobu, Shimizu, Akihiro, Shintani, Ryo
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.05.2019
Subjects
Chemistry
Energy gap
Molecular orbitals
Zwitterions
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Summary: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.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201902006