Synthesis and Spectroscopic Properties of Diarylethene-Subporphyrinoid Hybrids

Taichi Muto; Nanari Tamiya; Akuto Takagi; Tadashi Mizutani; Didier Bourissou; Gwénaël Rapenne; Mihoko Yamada; Tsuyoshi Kawai

doi:10.1002/cphc.202400615

Synthesis and Spectroscopic Properties of Diarylethene-Subporphyrinoid Hybrids

Chemphyschem. 2024 Sep 20:e202400615. doi: 10.1002/cphc.202400615. Online ahead of print.

Authors

Taichi Muto¹, Nanari Tamiya², Akuto Takagi², Tadashi Mizutani², Didier Bourissou³, Gwénaël Rapenne^{1

4

5}, Mihoko Yamada¹, Tsuyoshi Kawai^{1

4

6}

Affiliations

¹ Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara, 630-0192, Japan.
² Department of Applied Chemistry, Graduate School of Science and Engineering, Doshisha University, 1-3 Tataramiyakodani, Kyotanabe, Kyoto, 610-0321, Japan.
³ Laboratoire Hétérochimie Fondamentale et Appliquée (UMR 5069), Université de Toulouse (UPS), CNRS, 118 route de Narbonne, F-31062, Toulouse, France.
⁴ International Collaborative Laboratory for Interfaces, Molecules and Materials, NAIST- Université de Toulouse (UPS), 118 route de Narbonne, 31062, Toulouse, Cedex 9, France.
⁵ CEMES, Université de Toulouse, CNRS, F-31055, Toulouse, Cedex 4, France.
⁶ Medilux Research Center, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara, 630-0192, Japan.

PMID: 39305012
DOI: 10.1002/cphc.202400615

Abstract

Two novel diarylethene-fused subporphyrinoids were prepared and characterized. A mono diarylethene derivative was obtained via a statistical condensation reaction with 2 eq. of 1,2-dicyanobenzene and 1 eq. of thiophene-disubstituted butenedinitrile. The symmetric triply diarylethene-fused subporphyrazine was synthesized via a cyclotrimerization reaction of the thiophene-disubstituted butenedinitrile derivative. These compounds were characterized by NMR spectroscopy and high-resolution mass spectrometry. The spectroscopic properties have been measured in hexane and in chloroform. The mono diarylethene-fused-type compound showed photochromism at 580 nm and >700 nm wavelength, accompanied by degradation. According to DFT calculations, photoreactivity likely depends on the contribution of aromatic feature of pyrrole ring bonded to two thiophene rings.

Keywords: DFT calculation; Diarylethene; Photochromism; Porphyrinoids; Subphthalocyanine.

Abstract

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