title: Oxatriphyrins(2.1.1) incorporating an ortho-phenylene motif.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50383 Wrocław (Poland) http://llg.chem.uni.wroc.pl/. milosz.pawlicki@chem.uni.wroc.pl.
authors.forename: Miłosz
authors.initials: M
authors.lastname: Pawlicki
authors.forename: Mateusz
authors.initials: M
authors.lastname: Garbicz
authors.forename: Ludmiła
authors.initials: L
authors.lastname: Szterenberg
authors.forename: Lechosław
authors.initials: L
authors.lastname: Latos-Grażyński
keywords: aromaticity; boron; density functional calculations; macrocycles; structure elucidation