A new diarylethene-derived photochromic compound, with little cytotoxicity, plasma membrane-permeability, and efficient photoswitchability in cells upon alternative UV and visible light irradiation, was synthesized and applied to live cell imaging.
A series of "turn-on" fluorescence diarylethenes derived from 2,3-bis(2-methylbenzo[b]thiophen-3-yl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one (1) with alkyl and acetyl substituents were synthesized. The photochemical and photophysical properties of these derivatives, including the photoreaction of crystalline 1, were thoroughly investigated to reveal substituent effects on their properties. The results indicated that alkyl substituents did not significantly affect the absorption and emission spectra of the diarylethenes. However, large absorption and emission wavelength shifts were observed for the diarylethene with an acetyl substituent due to extension of π-π conjugation. Significantly, all of the fluorescent ring-closed forms of the compounds isomerized to their ring-open forms in the presence of Cu(2+) in the dark. EPR results provide clear evidence for the formation of the compound 1 radical cation intermediate that might be generated in the reaction between c-1 and Cu(2+) . DFT calculations found that the ground-state activation energy for ring-opening of 1(.+) was approximately 9.2 kcal mol(-1) lower than that of 1 without Cu(2+) , such that a Cu(2+) -catalyzed oxidative cycloreversion reaction at room temperature might be possible.
a series of diarylethene compounds with a thiophene bridging unit have been synthesized to investigate the relationship between molecular structure and photochromic properties. In particular, the fluorescence properties related to compound 1 were investigated. The results showed that a six-membered ring carrying an electron-donating sulfur atom and an electron-withdrawing carbonyl group is necessary to form a "push-pull" system for the fluorescence of 1.
A convenient, microwave-assisted, one-pot synthesis of the fulgimides (3) bearing reactive groups on N-substituents from the corresponding fulgides (1a-d) and amines (2a-e) is described. The synthesis provided the functionalized fulgimides (3) in yields of 50-84% under microwave irradiation within 25 min in the presence of 4-dimethylaminopyridine (DMAP) and dicyclohexylcarbodiimide (DCC).
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