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

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), phe...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2016-07, Vol.28 (7), p.562-568
Main Authors: Szemenyei, Balázs, Móczár, Ildikó, Pál, Dávid, Kocsis, Ivett, Baranyai, Péter, Huszthy, Péter
Format: Article
Language:English
Subjects:
anthracene
chiral crown ether
complexation
enantioselectivity
fluorescent sensor molecule
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Summary: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.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22614