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Applications of fluorescent sensor based on 1H-pyrazolo[3,4-b]quinoline in analytical chemistry.

Mac M, Uchacz T, Danel A, Musiolik H - J Fluoresc (2013)

Bottom Line: This process can be retarded upon complexation of the receptor moiety by inorganic cations.However, upon addition of some amounts of water the selectivity of this sensor has been enhanced (especially towards lead cation).The preliminary results in analytical application of the sensor are discussed.

View Article: PubMed Central - PubMed

Affiliation: Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060, Krakow, Poland.

ABSTRACT
Fluorescent dye 2-[(2-Hydroxyethyl)-(1,3-diphenyl-1H-pyrazolo[3,4-b]quinolin-6-ylmethyl)-amino]ethanol (LL1) was examined for its efficiency in the detection of small inorganic cations (lithium, sodium, barium, calcium, magnesium, cadmium, lead and zinc). The dye was synthesized in the laboratory and investigated by means of both, steady-state and time-resolved fluorescence techniques. This compound acts as a fluorescent sensor suitable for detection of small inorganic cations (lithium, sodium, barium, calcium, magnesium, cadmium, lead and zinc) in strongly polar solvent (acetonitrile). An electron transfer from the electro-donative part (receptor) of the molecule to the acceptor part (fluorophore) is thought to be the main mechanism that underlies functionality of the compound as a sensor. This process can be retarded upon complexation of the receptor moiety by inorganic cations. Relatively high sensitivity but poor selectivity of the amino alcohol that contains indicator towards the two-valued cations was observed. However, upon addition of some amounts of water the selectivity of this sensor has been enhanced (especially towards lead cation). The preliminary results in analytical application of the sensor are discussed.

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a 180–190 °C; b NBS/AIBN/CCl4, c diethanol-amine/K2CO3
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Sch2: a 180–190 °C; b NBS/AIBN/CCl4, c diethanol-amine/K2CO3

Mentions: The synthesis reaction steps of LL1 are depicted in Scheme 2. 6-methyl-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline 1 was obtained from the respective pyrazole and aniline precursors [11]. The resulting compound 2 was brominated with NBS (N-bromosuccinimide) in the presence of catalytic amount of AIBN (2,2′-azoisobutyronitrile). The nucleophilic substitution of the bromomethyl group with diethanolamine in acetonitrile gave the compound LL1. A more detailed description of the synthesis of this sensor was given in previous publication [12].Scheme 2


Applications of fluorescent sensor based on 1H-pyrazolo[3,4-b]quinoline in analytical chemistry.

Mac M, Uchacz T, Danel A, Musiolik H - J Fluoresc (2013)

a 180–190 °C; b NBS/AIBN/CCl4, c diethanol-amine/K2CO3
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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getmorefigures.php?uid=PMC3824276&req=5

Sch2: a 180–190 °C; b NBS/AIBN/CCl4, c diethanol-amine/K2CO3
Mentions: The synthesis reaction steps of LL1 are depicted in Scheme 2. 6-methyl-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline 1 was obtained from the respective pyrazole and aniline precursors [11]. The resulting compound 2 was brominated with NBS (N-bromosuccinimide) in the presence of catalytic amount of AIBN (2,2′-azoisobutyronitrile). The nucleophilic substitution of the bromomethyl group with diethanolamine in acetonitrile gave the compound LL1. A more detailed description of the synthesis of this sensor was given in previous publication [12].Scheme 2

Bottom Line: This process can be retarded upon complexation of the receptor moiety by inorganic cations.However, upon addition of some amounts of water the selectivity of this sensor has been enhanced (especially towards lead cation).The preliminary results in analytical application of the sensor are discussed.

View Article: PubMed Central - PubMed

Affiliation: Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060, Krakow, Poland.

ABSTRACT
Fluorescent dye 2-[(2-Hydroxyethyl)-(1,3-diphenyl-1H-pyrazolo[3,4-b]quinolin-6-ylmethyl)-amino]ethanol (LL1) was examined for its efficiency in the detection of small inorganic cations (lithium, sodium, barium, calcium, magnesium, cadmium, lead and zinc). The dye was synthesized in the laboratory and investigated by means of both, steady-state and time-resolved fluorescence techniques. This compound acts as a fluorescent sensor suitable for detection of small inorganic cations (lithium, sodium, barium, calcium, magnesium, cadmium, lead and zinc) in strongly polar solvent (acetonitrile). An electron transfer from the electro-donative part (receptor) of the molecule to the acceptor part (fluorophore) is thought to be the main mechanism that underlies functionality of the compound as a sensor. This process can be retarded upon complexation of the receptor moiety by inorganic cations. Relatively high sensitivity but poor selectivity of the amino alcohol that contains indicator towards the two-valued cations was observed. However, upon addition of some amounts of water the selectivity of this sensor has been enhanced (especially towards lead cation). The preliminary results in analytical application of the sensor are discussed.

Show MeSH