Issue 7, 2001

Enantioselective molecular sensing of aromatic amines using tetra-(S)-di-2-naphthylprolinol calix[4]arene

Abstract

This paper presents new analytical data, and evidence of the fluorescence quenching mechanism involved in enantioselective signals obtained with the chiral host tetra-(S)-di-2-naphthylprolinol calix[4]arene. Excellent selectivity is obtained with phenylglycinol and norephidrine in methanol, and samples of unknown enantiomeric composition have been determined with an average error of 1.08 and 0.62%, respectively (n = 6), on the basis of a single fluorescence measurement. The absence of any quenching observed with the related amines of phenylalaninol is attributed to a methylene spacer which inhibits efficient interaction between the aryl group of the guest and the naphthyl group of the host. The importance of the phenyl group of the guest in the quenching mechanism is confirmed by the complete absence of any quenching effect with cyclohexylethylamine.

Article information

Article type
Paper
Submitted
09 Jan 2001
Accepted
18 Apr 2001
First published
15 Jun 2001

Analyst, 2001,126, 1063-1067

Enantioselective molecular sensing of aromatic amines using tetra-(S)-di-2-naphthylprolinol calix[4]arene

K. Jennings and D. Diamond, Analyst, 2001, 126, 1063 DOI: 10.1039/B100378J

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