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- W2327661503 abstract "This paper deals with the interplay between solvent properties and isomerism of 2-(2′-hydroxyphenyl)imidazo[4,5-b]pyridine (1), and the proton and charge-transfer processes that the different isomers undergo in the first-excited singlet state. We demonstrate the strong influence of these processes on the fluorescence properties of 1. We studied the behavior of 1 in several neutral and acidified solvents, by UV–vis absorption spectroscopy and by steady-state and time-resolved fluorescence spectroscopy. The fluorescence of 1 showed a strong sensitivity to the environment. This behavior is the result of conformational and isomeric equilibria and the completely different excited-state behavior of the isomers. For both neutral and cationic 1, isomers with intramolecular hydrogen bond between the hydroxyl group and the benzimidazole N undergo an ultrafast excited-state intramolecular proton transfer (ESIPT), yielding tautomeric species with very large Stokes shift. For both neutral and cationic 1, isomers with the OH group hydrogen-bonded to the solvent behave as strong photoacids, dissociating in the excited state in solvents with basic character. The pyridine nitrogen exhibits photobase character, protonating in the excited state even in some neutral solvents. An efficient radiationless deactivation channel of several species was detected, which we attributed to a twisted intramolecular charge-transfer (TICT) process, facilitated by deprotonation of the hydroxyl group and protonation of the pyridine nitrogen." @default.
- W2327661503 created "2016-06-24" @default.
- W2327661503 creator A5003169619 @default.
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- W2327661503 creator A5031527063 @default.
- W2327661503 creator A5046352274 @default.
- W2327661503 creator A5080919131 @default.
- W2327661503 date "2013-01-10" @default.
- W2327661503 modified "2023-10-16" @default.
- W2327661503 title "Photoinduced Proton and Charge Transfer in 2-(2′-Hydroxyphenyl)imidazo[4,5-<i>b</i>]pyridine" @default.
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- W2327661503 doi "https://doi.org/10.1021/jp311709c" @default.
- W2327661503 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23256779" @default.
- W2327661503 hasPublicationYear "2013" @default.
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