Source document Angewandte Chemie : international edition : a journal of the German Chemical Society. Vol. 57, no. 17 (2018), pp. 4797-4801. - Weinheim : Wiley-VCH, 2018 Keywords fotoprepínače - photoswitches   acidity   aromaticity   diarylethenes   fotochromizmus - photochromism   LanguageEnglish CountryGermany systematics 54 AnnotationPhotoswitchable acid-base pairs, whose pK(a) values can be reversibly altered, are attractive molecular tools to control chemical and biological processes with light. A significant, light-induced pK(a) change of three units in aqueous medium has been realized for two thermally stable states, which can be interconverted using UV and green light. The light-induced pK(a) modulation is based on incorporating a 3-H-thiazol-2-one moiety into the framework of a diarylethene photoswitch, which loses the heteroaromatic stabilization of the negatively charged conjugate base upon photochemical ring closure, and hence becomes significantly less acidic. In addition, the efficiency of the photoreactions is drastically increased in the deprotonated state, giving rise to catalytically enhanced photochromism. It appears that protonation has a significant influence on the shape of the ground- and excited-state potential energy surfaces, as indicated by quantum-chemical calculations. Public work category ADC No. of Archival Copy43297 Repercussion category LVOV, Andrey G. - KHUSNIYAROV, Marat M. - SHIRINIAN, Valerii Z. Azole-based diarylethenes as the next step towards advanced photochromic materials. In Journal of photochemistry and photobiology C : photochemistry reviews. ISSN 1389-5567, 2018, vol. 36, pp. 1-23.
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