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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| Format: | Article |
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MDPI AG
2017-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/8/1340 |
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| author | Marek Cigáň Miroslav Horváth Juraj Filo Klaudia Jakusová Jana Donovalová Vladimír Garaj Anton Gáplovský |
| author_facet | Marek Cigáň Miroslav Horváth Juraj Filo Klaudia Jakusová Jana Donovalová Vladimír Garaj Anton Gáplovský |
| author_sort | Marek Cigáň |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-14T02:52:06Z |
| format | Article |
| id | doaj.art-14c93bf71cc34001be8f8904ad24f27f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-14T02:52:06Z |
| publishDate | 2017-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-14c93bf71cc34001be8f8904ad24f27f2022-12-22T02:16:14ZengMDPI AGMolecules1420-30492017-08-01228134010.3390/molecules22081340molecules220813407-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic SolventsMarek Cigáň0Miroslav Horváth1Juraj Filo2Klaudia Jakusová3Jana Donovalová4Vladimír Garaj5Anton Gáplovský6Faculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, SlovakiaFaculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, SlovakiaFaculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, SlovakiaFaculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, SlovakiaFaculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, SlovakiaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, SK-832 32 Bratislava, SlovakiaFaculty of Natural Sciences, Institute of Chemistry, Comenius University, Ilkovičova 6, Mlynská dolina CH-2, SK-842 15 Bratislava, SlovakiaThe 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.https://www.mdpi.com/1420-3049/22/8/1340water sensingfluorescent probecoumarinoxime/oximate equilibriumdark excited statephotoinduced electron transfer |
| spellingShingle | Marek Cigáň Miroslav Horváth Juraj Filo Klaudia Jakusová Jana Donovalová Vladimír Garaj Anton Gáplovský 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents Molecules water sensing fluorescent probe coumarin oxime/oximate equilibrium dark excited state photoinduced electron transfer |
| title | 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents |
| title_full | 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents |
| title_fullStr | 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents |
| title_full_unstemmed | 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents |
| title_short | 7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents |
| title_sort | 7 dialkylaminocoumarin oximates small molecule fluorescent turn on chemosensors for low level water content in aprotic organic solvents |
| topic | water sensing fluorescent probe coumarin oxime/oximate equilibrium dark excited state photoinduced electron transfer |
| url | https://www.mdpi.com/1420-3049/22/8/1340 |
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