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Abstract: We report a novel quartz crystal microbalance sensor that provides enantioselectivity to dansylphenylalanine enantiomers by using a molecularly imprinted polymer film as a recognition element. The polymeric recognition thin film, imprinted with chiral dansyl-l-phenylalanine, was immobilised on a gold electrode modified with a photoactive precursor monolayer via a self-assembly process using photopolymerisation. The fabricated sensor was able to discriminate between l- and d- dansylphenylalanine enantiomers in solution owing to the enantioselectivity of the imprinted sites. The enantiomeric composition of l- and d-enantiomeric mixtures could be quantitatively determined by the fabricated sensor. The detection limit is 5 mug mL(-1) with a response range of 5-500 mug mL(-1) at pH 10.0. The influence of the template concentration on the sensitivity and selectivity of the synthesised polymer membranes was investigated and optimised. The surface characteristics of the polymer coating were studied by varying the pH value of the buffer solution, and a convenient regeneration process was proposed to increase the reproducibility and reusability of the sensor by flushing with pH 2.0 buffer. The selectivity and recognition mechanism of the imprinted polymer film were studied with compounds that are structurally related to the template. The method presented in this work provides a novel means of preparing highly selective and sensitive chemical sensors via self-assembly and molecularly imprinting techniques