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.

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(R,R)- and (S,S)-enantiomers of anthracene-containing pyridino-18-crown-6 ether having tert-butyl groups at the stereogenic centers were prepared with the aim of achieving higher enantioselectivity than for the reported (S,S)-analogue having isobutyl groups. The enantiomeric recognition abilities of the new sensor molecules toward chiral protonated primary amines and amino acid esters were studied in acetonitrile by UV–vis and fluorescence spectroscopies. The pKa values of these pyridino-crown ethers and their reported (S,S)-analogues having methyl or isobutyl groups have also been determined in acetonitrile.

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Fluorescent chemosensors containing differently connected 1,2,3-triazole units for enantiomeric recognition studies of chiral protonated primary amines and amino acid esters.