Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto–Enol Tautomerism of a β-Ketoester
Andrey G. Lvov, Anton V. Yadykov, Konstantin А. Lyssenko, Frank W. Heinemann, Валерий З. Ширинян, Marat M. Khusniyarov
Abstract
Manipulating the equilibrium between a ketone and an enol by light opens up ample opportunities in material chemistry and photopharmacology. By incorporating β-ketoester into the ethene bridge of a photoactive diarylethene, we achieved reversible light-induced tautomerization to give thermally stable enol. In a pristine state, the tautomeric equilibrium is almost completely shifted toward the ketone. Photocyclization of diarylethene results in a new equilibrium containing a significant fraction of the enol tautomer.
Topics & Concepts
TautomerChemistryEnolKeto–enol tautomerismKetonePhotochemistryDiaryletheneComputational chemistryOrganic chemistryPhotochromismCatalysisPhotochromic and Fluorescence ChemistryRadical Photochemical ReactionsPhotoreceptor and optogenetics research