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Oxatriphyrins(2.1.1) Incorporating an ortho ‐Phenylene Motif
Author(s) -
Pawlicki Miłosz,
Garbicz Mateusz,
Szterenberg Ludmiła,
LatosGrażyński Lechosław
Publication year - 2015
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.201410595
Subject(s) - delocalized electron , aromaticity , molecule , electron delocalization , structural motif , boron , ring (chemistry) , benzene , chemistry , crystallography , phenylene , motif (music) , crystal structure , stereochemistry , computational chemistry , organic chemistry , polymer , physics , acoustics , biochemistry
An understanding of fundamental aspects of archetypal organic structural motifs remains a key issue faced by the experimental and theoretical chemists. Two possible bonding modes for a disubstituted benzene ring, that is a meta and para, determines the π delocalization for oligomeric structures. When the less abundant ortho ‐substituted variant is introduced into a triphyrin(2.1.1) skeleton an aromatic molecule is obtained and the carbocyclic ring participates in the conjugation of the macrocycle. The two‐electron reduction and introduction of boron(III) changes the aromatic character and results in an anti‐aromatic structure which has been confirmed by single‐crystal analysis and supported by theoretical calculations.