7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent 'Turn-On' Chemosensors for Low-Level Water Content in Aprotic Organic Solvents

Autor: Marek Cigáň, Miroslav Horváth, Juraj Filo, Klaudia Jakusová, Jana Donovalová, Vladimír Garaj, Anton Gáplovský
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Molecules, Vol 22, Iss 8, p 1340 (2017)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules22081340
Popis: The water sensing properties of two efficient two-component fluorescent “turn-on” chemo-sensors based on the 7-dialkylaminocoumarin oxime acid-base equilibrium were investigated. Interestingly, although simple frontier orbital analysis predicts an intramolecular photoinduced electron transfer quenching pathway in conjugated oximates, TD-DFT (Time-dependent density functional theory) quantum chemical calculations support non-radiative dark S1 excited state deactivation as a fluorescence quenching mechanism. Due to the acid-base sensing mechanism and sensitive “turn-on” fluorescent response, both studied coumarin aldoxime chemosensors exhibit rapid response to low-level water content in polar aprotic solvents, with detection limits comparable to chemodosimeters or chemosensors based on interpolymer π-stacking aggregation.
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