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Synthesis of Bis-Thioacid Derivatives of Diarylethene and Their Photochromic Properties
Aryal, Pramod ; Bietsch, Jonathan ; Grandhi, Gowri Sankar , et al. ACS Omega,2024,9(48):47489-47499. DOI: 10.1021/acsomega.4c05945
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Abstract: Diarylethenes (DAEs) are an important class ofphotoswitchable compounds that typically undergo reversiblephotochemical conversions between the open and closed cyclizedforms upon treatment with UV light or visible light. In this study,we introduced thioacid functional groups to several photochromicdithienylethene (DTE) derivatives and established a method thatcan be used to prepare these photoswitchable thioacids. Fourthioacid-functionalized diarylethene derivatives were synthesizedthrough the activation of carboxylic acids with N-hydroxysuccini-mide, followed by reactions with sodium hydrosulfide with yields over 90%. These derivatives exhibited reversible photoswitchingand photochromic properties upon treatment with ultraviolet (UV) and visible lights. The thioacid groups on these compounds canact as reaction sites for attaching other desirable functionalities. The photochromic properties of these new derivatives werecharacterized by using ultraviolet?visible (UV?vis) spectroscopy. The photocyclizations of one of the derivatives and its potassiumsalt 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.
Purchased from AmBeed: 4282-31-9 ; 5798-75-4 ; 14221-01-3 ; 1892-57-5
CAS No. : | 4282-31-9 | MDL No. : | MFCD00016896 |
Formula : | C6H4O4S | Boiling Point : | No data available |
Linear Structure Formula : | HOOCC4H2SCOOH | InChI Key : | YCGAZNXXGKTASZ-UHFFFAOYSA-N |
M.W : | 172.16 | Pubchem ID : | 20273 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
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