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

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

Marek Cigáň, Miroslav Horváth, Juraj Filo, Klaudia Jakusová, Jana Donovalová, Vladimír Garaj, Anton Gáplovský

Molecules. 2017 Aug 12;22(8):1340.

PMID: 28805688

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR421139	Cations in Water - Low Level			Price

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