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Molecules 2017, 22(8), 1340; doi:10.3390/molecules22081340

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

1
Faculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, SK-832 32 Bratislava, Slovakia
*
Author to whom correspondence should be addressed.
Received: 14 July 2017 / Revised: 9 August 2017 / Accepted: 11 August 2017 / Published: 12 August 2017
(This article belongs to the Section Photochemistry)
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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. View Full-Text
Keywords: water sensing; fluorescent probe; coumarin; oxime/oximate equilibrium; dark excited state; photoinduced electron transfer water sensing; fluorescent probe; coumarin; oxime/oximate equilibrium; dark excited state; photoinduced electron transfer
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Cigáň, M.; Horváth, M.; Filo, J.; Jakusová, K.; Donovalová, J.; Garaj, V.; Gáplovský, A. 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents. Molecules 2017, 22, 1340.

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