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Synthesis of Bis-Thioacid Derivatives of Diarylethene and Their Photochromic Properties. | LitMetric

AI Article Synopsis

  • Diarylethenes (DAEs) are versatile compounds that switch between open and closed forms when exposed to UV or visible light, and this study focuses on enhancing their properties by adding thioacid groups.
  • The researchers synthesized four thioacid-functionalized DTE derivatives, achieving high yields over 90% through a specific chemical activation method that involves hydroxysuccinimide and sodium hydrosulfide.
  • These new derivatives displayed reversible photoswitching behaviors, were characterized using UV-vis and NMR spectroscopy, and can be used as colorimetric sensors in agarose hydrogels, benefiting from their water solubility.

Article 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 -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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11618401PMC
http://dx.doi.org/10.1021/acsomega.4c05945DOI Listing

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