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A Stable Antiaromatic 5,20‐Dibenzoyl [28]Hexaphyrin(1.1.1.1.1.1): Core Au III Metalation and Subsequent Peripheral B III Metalation
Author(s) -
Ishida Shinichiro,
Soya Takanori,
Osuka Atsuhiro
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.201808513
Subject(s) - metalation , antiaromaticity , chemistry , core (optical fiber) , stereochemistry , physics , molecule , organic chemistry , aromaticity , optics
5,20‐Dibenzoyl [28]hexaphyrin(1.1.1.1.1.1) was synthesized as the first hexaphyrin bearing meso ‐aroyl substituents. The meso ‐dibenzoyl substituents are hydrogen‐bonded with the pyrrolic protons to stabilize an antiaromatic dumbbell conformer. Core metalation of this hexaphyrin with Au III afforded rectangular and aromatic [26]hexaphyrin bis‐Au III complexes, the major isomer of which was reduced with NaBH 4 to give its antiaromatic 28π bis‐Au III complex. This complex allowed facile peripheral metalation with B III owing to the peripheral benzoyl substituents.