Calix[4]arene-Based Chromogenic Chemosensor for the α-Phenylglycine Anion: Synthesis and Chiral Recognition

Calix[4]arene-based two-armed chiral anion receptors 3a and 3b have been synthesized and examined for their chiral anion-binding abilities by UV/Vis absorption and 1H NMR spectroscopy. The results of nonlinear curve fitting indicate that 3a and 3b form 1:1 stoichiometric complexes with the L- or D-α-phenylglycine anion by multiple hydrogen-bonding interactions and exhibit good enantioselective recognition for the enantiomers of the α-phenylglycine anions (3a: Kass(L)/Kass(D) = 4.76; 3b: Kass(D)/Kass(L) = 2.84). The marked colour changes observed for the complexation of 3a with the chiral anions and the good enantioselective recognition reveal that receptor 3a could be used as a good chiral chromogenic chemosensor for the enantiomers of the α-phenylglycine anion. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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