Synthesis of Bis-Thioacid Derivatives of Diarylethene and Their Photochromic Properties

Authors

Pramod Aryal, Old Dominion UniversityFollow
Jonathan Bietsch, Old Dominion UniversityFollow
Gowri Sankar Grandhi, Old Dominion UniversityFollow
Richard Chen, Old Dominion UniversityFollow
Surya B. Adhikari, Old Dominion UniversityFollow
Ephraiem S. Sarabamoun, Old Dominion University
Joshua J. Choi, University of Virginia
Guijun Wang, Old Dominion UniversityFollow

Document Type

Article

Publication Date

2024

DOI

10.1021/acsomega.4c05945

Publication Title

ACS Omega

Volume

9

Pages

47489-47499

Abstract

Diarylethenes (DAEs) are an important class of photoswitchable compounds that typically undergo reversible photochemical conversions between the open and closed cyclized forms upon treatment with UV light or visible light. In this study, we introduced thioacid functional groups to several photochromic dithienylethene (DTE) derivatives and established a method that can be used to prepare these photoswitchable thioacids. Four thioacid-functionalized diarylethene derivatives were synthesized through the activation of carboxylic acids with N-hydroxysuccinimide, followed by reactions with sodium hydrosulfide with yields over 90%. These derivatives exhibited reversible photoswitching and photochromic properties upon treatment with ultraviolet (UV) and visible lights. The thioacid groups on these compounds can act as reaction sites for attaching other desirable functionalities. The photochromic properties of these new derivatives were characterized by using ultraviolet-visible (UV-vis) spectroscopy. The photocyclizations of one of the derivatives and its potassium salt were also characterized by using nuclear magnetic resonance (NMR) spectroscopy. The anions of the thioacid formed water-soluble photochromic systems, and their applications as colorimetric sensors in agarose hydrogels were demonstrated.

Rights

© 2024 The Authors.

This publication is licensed under a Creative Commons Attribution 4.0 International (CC-BY 4.0) License.

Original Publication Citation

Aryal, P., Bietsch, J., Grandhi, G. S., Chen, R. C., Adhikari, S. B., Sarabamoun, E. S., Choi, J. J., & Wang, G. J. (2024). Synthesis of bis-thioacid derivatives of diarylethene and their photochromic properties. ACS Omega, 9, 47489−47499. https://doi.org/10.1021/acsomega.4c05945

ORCID

0009-0007-8137-1370 (Aryal)

Repository Citation

Aryal, Pramod; Bietsch, Jonathan; Grandhi, Gowri Sankar; Chen, Richard; Adhikari, Surya B.; Sarabamoun, Ephraiem S.; Choi, Joshua J.; and Wang, Guijun, "Synthesis of Bis-Thioacid Derivatives of Diarylethene and Their Photochromic Properties" (2024). Chemistry & Biochemistry Faculty Publications. 329.
https://digitalcommons.odu.edu/chemistry_fac_pubs/329