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- W2936512090 abstract "Deprotonated para-coumaric acid is commonly considered as a model for the chromophore in photoactive yellow protein, which undergoes E → Z isomerization following absorption of blue light. Here, tandem ion mobility mass spectrometry is coupled with laser excitation to study the photochemistry of deprotonated para-coumaric acid, to show that the E isomers of the phenoxide and carboxylate forms have distinct photochemical responses with maxima in their action spectra at 430 and 360 nm, respectively. The E isomer of the phenoxide anion undergoes efficient autodetachment upon excitation of its lowest ππ* transition. For the E isomer of the carboxylate deprotomer, a one-way photoinitiated proton transfer generates the phenoxide deprotomer through a mechanism postulated to involve an excited-state enol-keto tautomerism followed by a series of ground-state rearrangements including a second proton transfer. This mechanism is supported by experiments in which the relevant intermediate keto isomer is prepared and spectroscopically probed and through master equation modeling of possible ground-state isomerization processes. The Z isomer of the carboxylate deprotomer shows a weak Z → E photoisomerization response that occurs in competition with photodestruction (presumably electron detachment), demonstrating that the E and Z isomers undergo different processes in their excited states. The study highlights the utility of isomer-selective spectroscopy for characterizing the photochemistry of isolated anions possessing multiple deprotonation sites." @default.
- W2936512090 created "2019-04-25" @default.
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- W2936512090 date "2019-04-09" @default.
- W2936512090 modified "2023-10-17" @default.
- W2936512090 title "Photoinitiated Intramolecular Proton Transfer in Deprotonated <i>para</i>-Coumaric Acid" @default.
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- W2936512090 doi "https://doi.org/10.1021/acs.jpca.9b02023" @default.
- W2936512090 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30964682" @default.
- W2936512090 hasPublicationYear "2019" @default.
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