Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative

Masaya Naito; Noriho Taniguchi; Shinobu Miyagawa; Hikaru Takaya; Yuji Tokunaga

Results in Chemistry (Dec 2023)

Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative

Masaya Naito,
Noriho Taniguchi,
Shinobu Miyagawa,
Hikaru Takaya,
Yuji Tokunaga

Affiliations

Masaya Naito: Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan; Corresponding authors.
Noriho Taniguchi: Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
Shinobu Miyagawa: Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
Hikaru Takaya: Department of Life and Health Sciences, Faculty of Life and Environmental Sciences, Teikyo University of Science, Adachi-ku, Tokyo 120-0045, Japan; Institute for Molecular Science, National Institute of Natural Science, Okazaki, Aichi 444-8585, Japan
Yuji Tokunaga: Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan; Corresponding authors.

Journal volume & issue: Vol. 6
p. 101164

Abstract

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A chromogenic trefoil-shaped salicylaldehyde azine derivative displayed solvent-dependent isomerism of the C3h and CS symmetries. An azine derivative was prepared from triformylphloroglucinol and 3,5-di-tert-butylsalicylaldehyde hydrazone. The trefoil structure was established using single-crystal X-ray diffraction. UV–vis absorption spectroscopy revealed that solvent-dependent isomerization was accompanied by a bathochromic shift. Isomerization was controlled by adjusting the strength of the intramolecular hydrogen bonding of the azine derivative by solvent polarity. This unusual solvent-dependent isomerization can be utilized for creation azine-based new solvatochromic materials.

Published in Results in Chemistry

ISSN: 2211-7156 (Online)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: https://www.journals.elsevier.com/results-in-chemistry/

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