title: 18π-Electron tautomeric benziphthalocyanine: a functional near-infrared dye with tunable aromaticity.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Toriumi
authors.forename: Atsuya
authors.initials: A
authors.lastname: Muranaka
authors.forename: Keiichi
authors.initials: K
authors.lastname: Hirano
authors.forename: Kengo
authors.initials: K
authors.lastname: Yoshida
authors.forename: Daisuke
authors.initials: D
authors.lastname: Hashizume
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D004583:Electrons; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001562:Benzimidazoles; D009942:Organometallic Compounds; C526992:m-benziphthalocyanine
keywords: aromaticity; dyes/pigments; phthalocyanines; structure elucidation; tautomerism