Pyridino-18-crown-6 ether type chemosensors containing a benzothiazole fluorophore unit: Synthesis and enantiomeric recognition studies

Three new fluorescent enantiopure pyridino-18-crown-6 ethers containing a benzothiazole unit were prepared, and the enantiomeric discrimination of these sensor molecules toward the hydrogen perchlorate salts of 1-phenylethylamine, 1-(1-naphthyl)ethylamine, phenylglycine methyl ester and phenylalanin...

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 20; pp. 2900 - 2909
Main Authors Pál, Dávid, Móczár, Ildikó, Szemenyei, Balázs, Marczona, Dániel, Kocsis, Ivett, Prikler, Gergely, Vezse, Panna, Baranyai, Péter, Huszthy, Péter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.05.2019
Elsevier
Subjects
Benzothiazole
Chemistry
Chemistry, Organic
Complexation
Enantiomeric recognition
Fluorescent sensor molecule
Physical Sciences
Pyridino-crown ether
Science & Technology
Complexation
Enantiomeric recognition
Fluorescent sensor molecule
Benzothiazole
Pyridino-crown ether
HIGHLY ENANTIOSELECTIVE RECOGNITION
ORGANIC AMMONIUM-SALTS
CHIRAL PYRIDINO-18-CROWN-6
OPTICAL CHARACTERIZATION
PYRIDINO-CROWN ETHERS
PERCHLORATE
SUBSTITUTED PYRIDINO-18-CROWN-6
ENANTIOSEPARATION
FLUORESCENT RECOGNITION
AZACROWN ETHERS
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Summary:Three new fluorescent enantiopure pyridino-18-crown-6 ethers containing a benzothiazole unit were prepared, and the enantiomeric discrimination of these sensor molecules toward the hydrogen perchlorate salts of 1-phenylethylamine, 1-(1-naphthyl)ethylamine, phenylglycine methyl ester and phenylalanine methyl ester was studied in acetonitrile by fluorescence spectroscopy. The ligands revealed appreciable or moderate selectivity toward the enantiomers of hydrogen perchlorate salts of 1-phenylethylamine, 1-(1-naphthyl)ethylamine and phenylglycine methyl ester. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.04.024