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Boron(III) Carbazosubphthalocyanines: Core‐Expanded Antiaromatic Boron(III) Subphthalocyanine Analogues
Author(s) -
Chan Joseph Y. M.,
Kawata Takahiro,
Kobayashi Nagao,
Ng Dennis K. P.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811420
Subject(s) - antiaromaticity , boron , chemistry , conjugated system , crystallography , ring (chemistry) , condensation , crystal structure , electron deficiency , molecule , stereochemistry , aromaticity , organic chemistry , polymer , physics , thermodynamics
Condensation of 1,8‐diamino‐3,6‐dichlorocarbazole with a series of disubstituted 1,3‐diiminoisoindolines, followed by treatment with BF 3 ⋅OEt 2 led to the formation of the corresponding core‐expanded boron(III) subphthalocyanine analogues. These air‐stable π‐conjugated boron(III) carbazosubphthalocyanines possess two boron‐containing seven‐membered‐ring units and a 16 π‐electron skeleton, and represent the first examples of antiaromatic boron(III) subphthalocyanine analogues as supported by spectroscopic and theoretical studies. The molecular structure of one of these compounds was unambiguously determined by single‐crystal X‐ray diffraction analysis. In contrast to typical boron(III) subphthalocyanines, which adopt a cone‐shaped structure, the π skeleton of this compound is almost planar.