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Updated: Apr 28, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
18π-Electron tautomeric benziphthalocyanine: a functional near-infrared dye with tunable aromaticity
Naoyuki Toriumi1, Atsuya Muranaka, Keiichi Hirano
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
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.
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