Sulfhydryl-functionalized diarylethenes: synthesis, photoswitching, and fluorescent properties
Pramod Aryal1, Jonathan Bietsch1, Gowri Sankar Grandhi1
1Department of Chemistry and Biochemistry, Old Dominion University 4501 Elkhorn Avene Norfolk VA 23529-0126 USA g1wang@odu.edu +1 757 683-4628 +1 757 683-3781.
RSC Advances
|January 7, 2026
Summary
Researchers synthesized novel thiol-functionalized photoswitchable diarylethene (DAE) derivatives. Four new compounds exhibited unique
Area of Science:
- Organic Chemistry
- Photochemistry
- Materials Science
Background:
- Sulfhydryl (thiol) groups are crucial in biological systems and chemical reactions.
- Photoswitchable diarylethene (DAE) derivatives have diverse applications.
- Thiol-functionalized DAEs remain underexplored.
Purpose of the Study:
- To synthesize and characterize novel bis-thiol functionalized dithienylethene derivatives.
- To investigate the photoswitching properties and fluorescence behavior of these new compounds.
- To explore the potential of thiol-functionalized DAEs as fluorescent probes.
Main Methods:
- Systematic synthesis of six bis-thiol substituted dithienylethene derivatives, including four novel compounds.
- Preparation and storage of reactive thiols as thiol acetates.
- Characterization of photoswitching properties and fluorescence behavior of acetylated thiol derivatives.
Main Results:
- Successful synthesis of six bis-thiol functionalized DAEs, with four reported for the first time.
- Characterization of photoswitching properties of the acetylated thiol derivatives.
- Discovery of 'turn-on' fluorescence in three new thiol derivatives, where closed isomers are fluorescent and open isomers are not.
Conclusions:
- Developed a new class of fluorescent diarylethenes without requiring additional fluorophores.
- Demonstrated 'turn-on' fluorescence behavior in novel thiol-substituted DAEs.
- Highlighted the potential of these compounds for biological conjugation and as fluorescent probes.
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