Premium
18π‐Electron Tautomeric Benziphthalocyanine: A Functional Near‐Infrared Dye with Tunable Aromaticity
Author(s) -
Toriumi Naoyuki,
Muranaka Atsuya,
Hirano Keiichi,
Yoshida Kengo,
Hashizume Daisuke,
Uchiyama Masanobu
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.201404020
Subject(s) - tautomer , aromaticity , moiety , chemistry , resorcinol , infrared spectroscopy , solvent , photochemistry , computational chemistry , molecule , stereochemistry , organic chemistry
Abstract Dihydroxybenziphthalocyanine 1 , with bulky aryloxy groups, has been synthesized and characterized by X‐ray crystallography, NMR and UV/Vis‐NIR spectroscopy, and theoretical calculations. Macrocycle 1 is the first example of an aromatic benziphthalocyanine with an 18π‐electron structure, and was found to exist as an equilibrium mixture of weakly aromatic and strongly aromatic tautomers. The aromaticity and near‐IR absorption can be controlled by chemical modification at the reactive resorcinol moiety and by variation of the solvent.