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5,20-Diheterohexaphyrins: metal-template-free synthesis and aromaticity switching

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Abstract

As the first example of expanded heteroporphyrins with heteroatoms at meso-positions, 5,20-dithiahexaphyrins and 5,20-diazahexaphyrins were synthesized via nucleophilic substitution reactions of α,α′-dibromotripyrrin as the key step. While 5,20-dithiahexaphyrins are practically nonaromatic, 5,20-[28]diazahexaphyrins show weakly antiaromatic characters and can be cleanly converted into aromatic 5,20-[26]diazahexaphyrins upon oxidation with PbO2, demonstrating distinct aromaticity switching with maintenance of dumbbell-like conformations.

Graphical abstract: 5,20-Diheterohexaphyrins: metal-template-free synthesis and aromaticity switching

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Publication details

The article was received on 19 Jul 2019, accepted on 07 Aug 2019 and first published on 08 Aug 2019


Article type: Communication
DOI: 10.1039/C9CC05580K
Chem. Commun., 2019, Advance Article

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    5,20-Diheterohexaphyrins: metal-template-free synthesis and aromaticity switching

    M. Umetani, J. Kim, T. Tanaka, D. Kim and A. Osuka, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC05580K

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