Pyridino-18-crown-6 ether type chemosensors containing a benzothiazole fluorophore unit

Synthesis and enantiomeric recognition studies

Dávid Pál, Ildikó Móczár, Balázs Szemenyei, Dániel Marczona, Ivett Kocsis, Gergely Prikler, Panna Vezse, P. Baranyai, P. Huszthy

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)2900-2909
Number of pages10
JournalTetrahedron
Volume75
Issue number20
DOIs
Publication statusPublished - May 17 2019

Fingerprint

Crown Ethers
Phenethylamines
Fluorophores
Ether
Hydrogen
Salts
Ethers
Enantiomers
Fluorescence Spectrometry
Fluorescence spectroscopy
Ligands
Molecules
Sensors
perchlorate
18-crown-6
benzothiazole
methyl phenylglycine
1-(1-naphthyl)ethylamine
phenylalanine methyl ester
acetonitrile

Keywords

  • Benzothiazole
  • Complexation
  • Enantiomeric recognition
  • Fluorescent sensor molecule
  • Pyridino-crown ether

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Pyridino-18-crown-6 ether type chemosensors containing a benzothiazole fluorophore unit : Synthesis and enantiomeric recognition studies. / Pál, Dávid; Móczár, Ildikó; Szemenyei, Balázs; Marczona, Dániel; Kocsis, Ivett; Prikler, Gergely; Vezse, Panna; Baranyai, P.; Huszthy, P.

In: Tetrahedron, Vol. 75, No. 20, 17.05.2019, p. 2900-2909.

Research output: Contribution to journalArticle

Pál, Dávid ; Móczár, Ildikó ; Szemenyei, Balázs ; Marczona, Dániel ; Kocsis, Ivett ; Prikler, Gergely ; Vezse, Panna ; Baranyai, P. ; Huszthy, P. / Pyridino-18-crown-6 ether type chemosensors containing a benzothiazole fluorophore unit : Synthesis and enantiomeric recognition studies. In: Tetrahedron. 2019 ; Vol. 75, No. 20. pp. 2900-2909.
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