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Benzonorcorrole Ni II Complexes: Enhancement of Paratropic Ring Current and Singlet Diradical Character by Benzo‐Fusion
Author(s) -
Yoshida Takuya,
Takahashi Kohtaro,
Ide Yuki,
Kishi Ryohei,
Fujiyoshi Junya,
Lee Sangsu,
Hiraoka Yuya,
Kim Dongho,
Nakano Masayoshi,
Ikeue Takahisa,
Yamada Hiroko,
Shinokubo Hiroshi
Publication year - 2018
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.201712961
Subject(s) - antiaromaticity , diradical , chemistry , singlet state , ring (chemistry) , character (mathematics) , photochemistry , stereochemistry , computational chemistry , aromaticity , organic chemistry , physics , molecule , atomic physics , geometry , mathematics , excited state
Abstract Fused benzene rings to antiaromatic compounds generally improve their stability but attenuate their antiaromaticity. The opposite case is now reported. Ni II benzonorcorroles were synthesized and the effect of benzo‐fusion on the antiaromaticity was elucidated. The benzo‐fusion resulted in significant decrease of the HOMO–LUMO gaps and enhancement of the paratropic ring current effect. Furthermore, the introduction of the benzo groups induced singlet diradical character in the antiaromatic porphyrinoid.