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Abstract: This paper discusses the chiral discriminative gate effect of molecularly imprinted polymer (MIP) in organic solvents. We grafted l- (or d-) phenylalanine anilide (PAA) imprinted poly(ethylene glycol dimethacrylate-co-methacrylic acid) on an indium-tin oxide (ITO) in a number of organic solvents. Cyclic voltammetry of ferrocene with the grafted ITO electrode was carried out in several organic solvents and the effect of l- (or d-) PAA on an electric current of ferrocene was evaluated. As the result, the faradic current at the electrode grafted in the non-polar solvent was remarkably sensitive to the template in the voltammetry carried out in the non-polar solvent. However, it was insensitive to the enantiomer of the template. The results indicate that the gate effect of MIP can discriminate between the template and its analogue by stereochemical structure even if the difference in the chemical or physical property is omitted. They also indicate that the gate effect could have limited applications with the enantio-selective amperometric sensors working in non-polar solvents where biosensors cannot work
Template and target information: L-phenylalanine anilide, L-PAA, D-phenylalanine anilide, D-PAA
Author keywords: molecularly imprinted polymer, gate effect, phenylalanine anilide, chiral discrimination, biomimetic sensor