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

doi:10.1002/chir.22614

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

Chirality. 2016 Jul;28(7):562-8. doi: 10.1002/chir.22614.

Authors

Balázs Szemenyei¹, Ildikó Móczár¹, Dávid Pál¹, Ivett Kocsis¹, Péter Baranyai², Péter Huszthy¹

Affiliations

¹ Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary.
² "Lendület" Supramolecular Chemistry Research Group, Institute of Organic Chemistry, Research Centre of Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary.

PMID: 27349957
DOI: 10.1002/chir.22614

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. © 2016 Wiley Periodicals, Inc.

Keywords: anthracene; chiral crown ether; complexation; enantioselectivity; fluorescent sensor molecule.

Publication types

Research Support, Non-U.S. Gov't