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

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 quench...

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Bibliographic Details
Main Authors: Marek Cigáň, Miroslav Horváth, Juraj Filo, Klaudia Jakusová, Jana Donovalová, Vladimír Garaj, Anton Gáplovský
Format: Article
Language:English
Published: MDPI AG 2017-08-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/22/8/1340
Description
Summary: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.
ISSN:1420-3049