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Three‐Stage Aromaticity Switching in Boron(III) and Phosphorus(V) N‐Fused p ‐Benziporphyrin
Author(s) -
Idec Aneta,
Pawlicki Miłosz,
LatosGrażyński Lechosław
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804983
Subject(s) - aromaticity , boron , stage (stratigraphy) , phosphorus , chemistry , medicinal chemistry , organic chemistry , molecule , geology , paleontology
Abstract Insertion of PCl 3 or PhBCl 2 into 5,10,15,20‐tetraaryl‐ p ‐benziporphyrin prompted an intramolecular fusion affording anti‐aromatic phosphorus(V) and non‐aromatic boron(III) complexes of two N‐fused dihydro‐ p ‐benziporphyrin isomers. These macrocycles are classified as carbatriphyrin due to the common [CNN] coordination. A sequence of direct transformations, triggered by protonation or two‐electron redox processes, afforded a set of three mutually convertible N‐fused p ‐benziporphyrinoids, with distinct anti‐aromatic, non‐aromatic, and aromatic spectroscopic features.