New Fluorescent Sensors Based on 1H-pyrazolo[3,4-b]quinoline Skeleton |
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Authors: | Marek Mac Tomasz Uchacz Tomasz Wróbel Andrzej Danel Ewa Kulig |
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Affiliation: | 1.Faculty of Chemistry,Jagiellonian University,Krakow,Poland;2.Student of Faculty of Chemistry,Jagiellonian University,Krakow,Poland;3.Department of Chemistry,University of Agriculture,Kraków,Poland |
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Abstract: | Novel fluorescing dyes 1,3,4-triphenyl-6-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-ylmethyl)-1H-pyrazolo[3,4-b]quinoline (K1) and 2-[(2-hydroxyethyl)-(1,3,4-triphenyl-1H-pyrazolo[3,4-b]quinolin-6-ylmethyl)-amino]ethanol (L1) have been synthesized and investigated by the means of steady state and time-resolved fluorescence techniques. These compounds act as sensors for the fluorescence detection of small inorganic cations (lithium, sodium, barium, magnesium and calcium) in solvents of different polarities (THF and acetonitrile). The mechanism, which allows application of these compounds as sensors, is an electron transfer from the electro-donative part of molecule to the acceptor part (fluorophore), which is retarded upon complexation of the electro-donative part by inorganic cations. We found that crown ether-containing compound is very sensitive to the addition of any investigated ions but amino alcohol-containing one exhibits better selectivity to the addition of two-valued cations. Two kinds of the complexes (LM+ and L2M+) were found in the investigated systems. In addition, the dyes may be used as fluorescence indicators in solvents of lower polarity like tetrahydrofuran. |
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