Document Type

Article

Publication Date

2026

DOI

10.1039/d5ra08492j

Publication Title

RSC Advances

Volume

16

Issue

2

Pages

1443-1456

Abstract

Sulfhydryl group (SH) plays important roles in reactions with various functional groups, especially in biologically active systems. Photoswitchable diarylethene (DAE) derivatives have demonstrated applications in many research fields. Among the many classes of diarylethene derivatives, thiol derivatives have not been extensively explored. In this study, we systematically synthesized and characterized a series of bis-thiol functionalized dithienylethene derivatives. The thiol groups in this series are attached directly to the thiophene, or through a phenyl or methylene linker. Each series incorporated both dithienyl cyclopentene and hexafluorocyclopentene bridges and total six thiol substituted diarylethenes were synthesized. Among the six sulfhydryl DAE derivatives, four compounds were synthesized for the first time. Due to the reactivity of the thiol, they were prepared and stored as the corresponding thiol acetates. The photoswitching properties of the acetylated thiol derivatives were characterized. Three new thiol derivatives exhibited intriguing ‘turn-on’ fluorescence behavior, where the open isomers are non-fluorescent, while the closed isomers display fluorescence. These compounds represent a new class of fluorescent diarylethenes that do not require additional fluorophores. The thiol functional group offers potential for biological conjugation reactions and application as fluorescent probes.

Rights

© 2025 The Authors.

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported (CC BY-NC 3.0) License.

Data Availability

Article states: Data availability: "The data supporting this article have been included in the experimental section and also as part of the supplementary information (SI). The experimental section in the main text included characterization and NMR data for all new compounds. Supplementary information: additional experimental details for the synthesis of intermediates, ¹H, ¹³C, some ¹⁹F and 2D NMR spectra, additional photoswitching experiments and UV-vis spectra and fluorescence spectra. See DOI: https://doi.org/10.1039/d5ra08492j."

Original Publication Citation

Aryal, P., Bietsch, J., Grandhi, G. S., Choi, J., & Wang, G. (2026). Sulfhydryl-functionalized diarylethenes: Synthesis, photoswitching, and fluorescent properties. RSC Advances, 16(2), 1443-1456. https://doi.org/10.1039/d5ra08492j

ORCID

0009-0007-8137-1370 (Aryal), 0000-0002-9013-6926 (Choi), 0000-0001-7473-0004 (Wang)

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