Premium
Synthesis and Switching the Aromatic Character of Oxatriphyrins(2.1.1)
Author(s) -
Pawlicki Miłosz,
Hurej Karolina,
Szterenberg Ludmiła,
LatosGrażyński Lechosław
Publication year - 2014
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.201310129
Subject(s) - aromaticity , delocalized electron , porphyrin , thiophene , boron , molecule , character (mathematics) , annulene , ring (chemistry) , chemistry , materials science , computational chemistry , photochemistry , organic chemistry , mathematics , geometry
Triangularly shaped, contracted porphyrinoids belong to a group of molecules where the geometry significantly modifies the observed electronic properties. The need for a controllable, effective, and widely applicable approach to triphyrins drives extensive research towards macrocyclic materials that act as potential controlling motifs by switching their aromaticity. Two isomeric thiophene‐fused triphyrins(2.1.1) were synthesized by applying an innovative approach. Spectroscopic techniques (NMR, UV/Vis) show that both macrocycles are aromatic and quantitatively convert into anti‐aromatic structures after reduction with a zinc amalgam. The reduced forms were stabilized through boron(III) coordination, thereby allowing the observation of anti‐aromatic 16 π delocalization within a contracted porphyrin.