A photochemically inactive diarylethene derivative with a naphthol group bridging through the imidazole unit (DIN) was synthesized to characterize a multifunctional switch. Upon stimulation by radiation (UV and visible light), the target diarylethene derivative DIN was not photochemically inactive but photo-active, it could be photo-converted into a keto compound. Moreover, the photochromic reaction of DIN was observed when it was stimulated by the addition of acid or methylation. Fluorescence quenching and the bathochromic effect occurred when DIN was stimulated by the addition of copper ions and a base, respectively. Its optical properties could be regulated by various chemical stimuli. Thus, it can potentially be utilized as a multiresponsive molecular switch.
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http://dx.doi.org/10.1039/c4pp00093e | DOI Listing |
Chemphyschem
January 2025
Keio University Faculty of Science and Technology Graduate School of Science and Technology: Keio Gijuku Daigaku Rikogakubu Daigakuin Rikogaku Kenkyuka, Applied Physics and Physico-Informatics, 3-14-1 Hiyoshi, Kohoku-ku, 223-8522, Yokohama, JAPAN.
Understanding the reversible transformation between two isomeric states of organic molecules under external stimulation is essential for advancing single-molecule device development. Photochromic diarylethene (DAE) derivatives are promising candidates for single molecular switching elements. This study investigates the single-molecule reactions of the closed-form isomer of a DAE derivative on Cu(111) using scanning tunneling microscopy (STM).
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December 2024
Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia 23529, United States.
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%.
View Article and Find Full Text PDFChem Sci
December 2024
Key Laboratory for Advanced Material, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology Shanghai 200237 China
Chemphyschem
January 2025
Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara, 630-0192, Japan.
Two novel diarylethene-fused subporphyrinoids were prepared and characterized. A mono diarylethene derivative was obtained via a statistical condensation reaction with 2 eq. of 1,2-dicyanobenzene and 1 eq.
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December 2024
Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo, 171-8501, Japan.
As a new molecular scaffold of photoswitchable fluorophore, we developed a photochromic diarylethene containing a betaine structure based on pyridinium N-enolate. A facile reaction of a pyridyl-substituted dithienylperfluorocyclopentene derivative with octafluorocyclopentene constructed the betaine structure. The introduction of the betaine moiety provided the diarylethene molecule with bathochromically shifted optical absorption and fluorescing ability, thus enabling the molecule to function as a visible-light-responsive turn-off mode photoswitchable fluorophore.
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