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Issue 71, 2019

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

Author affiliations

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

Supplementary files

Article information


Submitted
19 Jul 2019
Accepted
07 Aug 2019
First published
08 Aug 2019

Chem. Commun., 2019,55, 10547-10550
Article type
Communication

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

M. Umetani, J. Kim, T. Tanaka, D. Kim and A. Osuka, Chem. Commun., 2019, 55, 10547 DOI: 10.1039/C9CC05580K

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