Synthesis and Enantiomeric Recognition Studies of Optically Active Pyridino-Crown Ethers Containing an Anthracene Fluorophore Unit

Balázs Szemenyei, Ildikó Móczár, Dávid Pál, Ivett Kocsis, Péter Baranyai, Péter Huszthy

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Novel enantiopure pyridino-18-crown-6 ether-based sensor molecules containing an anthracene fluorophore unit were synthesized. Their enantiomeric recognition abilities toward the enantiomers of 1-phenylethylamine hydrogen perchlorate (PhEt), 1-(1-naphthyl)ethylamine hydrogen perchlorate (NapEt), phenylglycine methyl ester hydrogen perchlorate (PhgOMe), and phenylalanine methyl ester hydrogen perchlorate (PheOMe) were examined in acetonitrile using fluorescence spectroscopy. The sensor molecules showed appreciable enantiomeric recognition toward the enantiomers of NapEt, PhEt, and PhgOMe. The highest enantioselectivity was found in the case of crown ether containing isobutyl groups in the macroring and the enantiomers of NapEt. Chirality 28:562–568, 2016.

Original languageEnglish
Pages (from-to)562-568
Number of pages7
JournalChirality
DOIs
Publication statusPublished - 2016

Keywords

  • anthracene
  • chiral crown ether
  • complexation
  • enantioselectivity
  • fluorescent sensor molecule

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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