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2018•Angewandte ChemieRequires access

Benzonorcorrole NiII Complexes: Enhancement of Paratropic Ring Current and Singlet Diradical Character by Benzo‐Fusion

Takuya Yoshida, Kohtaro Takahashi, Yuki Ide, Ryohei Kishi, Jun‐ya Fujiyoshi, Sangsu Lee, Yuya Hiraoka, Dongho Kim, Masayoshi Nakano, Takahisa Ikeue, Hiroko Yamada, Hiroshi Shinokubo

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Abstract

Abstract Fused benzene rings to antiaromatic compounds generally improve their stability but attenuate their antiaromaticity. The opposite case is now reported. NiII 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.

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What this paper is about

Abstract Fused benzene rings to antiaromatic compounds generally improve their stability but attenuate their antiaromaticity. The opposite case is now reported. NiII 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.

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Available abstract

Abstract Fused benzene rings to antiaromatic compounds generally improve their stability but attenuate their antiaromaticity. The opposite case is now reported. NiII 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.

Key concepts: Antiaromaticity, Diradical, Chemistry, Singlet state, Ring (chemistry), Character (mathematics), Photochemistry, Stereochemistry

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