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Abstract: Four kinds of N-dansyl-amino acid-modified β-cyclodextrins (β-CDs) were prepared as fluorescent chemosensors for chiral discrimination. The use of an amino acid as a spacer improved binding affinities and chiral discrimination abilities of the chemosensors. N-dansyl-l-Phe-modified β-CD showed high d-selectivity for norbornane derivatives and N-dansyl-d-Phe-modified β-CD showed high l-selectivity for menthol. Microcalorimetric titration results indicate that the chemosensors selectively accommodate the enantiomer that induces the least unfavorable entropy change on making an inclusion complex. [Copyright &y& Elsevier]

Discusses the synthesis and characterization of fluorophore-amino acid-cyclodextrin (CD) triad systems as fluorescent indicators of molecular recognition. Structural analyses of beta-CD derivatives; Difference in the enantiomeric configuration of the leucine residue; Guest-responsive variations of fluorescence intensity.