Determination of the Enantiomeric Composition of Chiral Amines Based on the Quenching of the Fluorescence of a Chiral Calixarene

Autor:	Stephen J. Harris, Dermot Diamond, Teresa Grady, Malcolm R. Smyth, Perry Hailey
Rok vydání:	1996
Předmět:	chemistry.chemical_compound Tetramer Chemistry Computational chemistry Calixarene Fluorescence spectrometry Organic chemistry Enantiomer Enantiomeric excess Chiral derivatizing agent Fluorescence Analytical Chemistry Cyclophane
Zdroj:	Analytical Chemistry. 68:3775-3782
ISSN:	1520-6882 0003-2700
DOI:	10.1021/ac960383c
Popis:	The synthesis of three chiral calixarene derivatives is described. One of these, an (S)-di-2-naphthylprolinol tetramer, is shown to exhibit significant ability to discriminate between enantiomers of 1-phenylethylamine (PEA) and norephedrine on the basis of the quenching of the (S)-di-2-naphthylprolinol fluorescence emission in chloroform. The chiral discrimination appears to arise from preorganization of the four (S)-di-2-naphthylprolinol substituents on the calixarene, which define a three-dimensional chiral space. The ability to measure the enantiomeric composition of PEA and norephedrine to within an error of 4.1% and 2.6%, respectively, on the basis of a single fluorescence measurement is demonstrated.
Databáze:	OpenAIRE
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