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Direct amination of the antiaromatic NiII norcorrole

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Abstract

We have discovered a facile amination reaction of NiII dimesitylnorcorrole, which is an antiaromatic porphyrinoid with a 16π-electron conjugation system. The amination reaction proceeded at the β-positions of the norcorrole with high regioselectivity upon treatment with various amines used as solvents. The reaction requires neither catalysts nor pre-functionalization of the norcorrole. The optical and electrochemical properties of the amino norcorroles were substantially modulated by electron-donating nitrogen atoms. According to theoretical studies, the regioselectivity of amination can be accounted for by molecular orbitals of the norcorrole.

Graphical abstract: Direct amination of the antiaromatic NiII norcorrole

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Publication details

The article was received on 21 Apr 2017, accepted on 09 May 2017 and first published on 10 May 2017


Article type: Research Article
DOI: 10.1039/C7QM00176B
Citation: Mater. Chem. Front., 2017, Advance Article
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    Direct amination of the antiaromatic NiII norcorrole

    T. Yoshida and H. Shinokubo, Mater. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QM00176B

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