Literature DB >> 24898757

18π-Electron tautomeric benziphthalocyanine: a functional near-infrared dye with tunable aromaticity.

Naoyuki Toriumi1, Atsuya Muranaka, Keiichi Hirano, Kengo Yoshida, Daisuke Hashizume, Masanobu Uchiyama.   

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.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aromaticity; dyes/pigments; phthalocyanines; structure elucidation; tautomerism

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Substances:

Year:  2014        PMID: 24898757     DOI: 10.1002/anie.201404020

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  2 in total

1.  Temperature-dependent changes in the molecular orientation and visible color of phthalocyanine films.

Authors:  Taniyuki Furuyama; Shiori Uchiyama; Tatsuki Chikamatsu; Takafumi Horikawa; Hajime Maeda; Masahito Segi; Hiromi Takahashi; Tetsuya Taima
Journal:  RSC Adv       Date:  2020-08-24       Impact factor: 3.361

2.  Low-Symmetry Phthalocyanines Bearing Carboxy-Groups: Synthesis, Spectroscopic and Quantum-Chemical Characterization.

Authors:  Dmitry A Bunin; Nobuhle Ndebele; Alexander G Martynov; John Mack; Yulia G Gorbunova; Tebello Nyokong
Journal:  Molecules       Date:  2022-01-14       Impact factor: 4.411

  2 in total

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