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- W2097111450 abstract "Six water-soluble spiropyran derivatives have been characterized with respect to the thermal and photoinduced reactions over a broad pH-interval. A comprehensive kinetic model was formulated including the spiro- and the merocyanine isomers, the respective protonated forms, and the hydrolysis products. The experimental studies on the hydrolysis reaction mechanism were supplemented by calculations using quantum mechanical (QM) models employing density functional theory. The results show that (1) the substitution pattern dramatically influences the pKa-values of the protonated forms as well as the rates of the thermal isomerization reactions, (2) water is the nucleophile in the hydrolysis reaction around neutral pH, (3) the phenolate oxygen of the merocyanine form plays a key role in the hydrolysis reaction. Hence, the nonprotonated merocyanine isomer is susceptible to hydrolysis, whereas the corresponding protonated form is stable toward hydrolytic degradation." @default.
- W2097111450 created "2016-06-24" @default.
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- W2097111450 date "2013-10-21" @default.
- W2097111450 modified "2023-10-06" @default.
- W2097111450 title "Characterization of the Thermal and Photoinduced Reactions of Photochromic Spiropyrans in Aqueous Solution" @default.
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- W2097111450 doi "https://doi.org/10.1021/jp408781p" @default.
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