An artificial plastic receptor that discriminates axial asymmetry

An artificial plastic receptor that can discriminate axial asymmetry of opt ically active binaphthyldiamine derivatives was prepared by the 'molecular imprinting' technique. A light-radical polymerization in the presence of an axially asymmetric compound, (R)-2,2'-bis-methylcarbonylamino-1,1'-binapht hyl (binaphthyldiamine bis-acetamide (BINADA-ac)) as a template molecule wi th methacrylic acid (MA) as a functional monomer, and ethyleneglycol dimeth acrylate (EGDMA) as a crosslinker, at 4 degreesC. The obtained polymer exhi bited a superior enantioselectivity to the (R)-enantiomer by HPLC analyses. This plastic receptor should recognize the template molecule with its shap e and character of its functional groups. It should be useful in the develo pment of chiral stationary phases for the optical resolutions of axially as ymmetric compounds.