Preparation of PSEBS membranes bearing (S)-(−)-methylbenzylamine as chiral selector

Abstract Nowadays, there is a strong need for replacement of racemates by enantiomerically pure drugs. Enantioseparation on polymer membranes seems to be one of the promising and economically feasible technologies for this purpose. As a material for membrane construction, linear polymer molecules bearing covalently bonded chiral selectors are very promising according to recent reports. A membrane formed from chloromethylated polystyrene-block-poly(ethylene-ran-butylene)-block-polystyrene (PSEBS) was cast and subsequently functionalized with a chiral selector (S)-(−)-α-methylbenzylamine. In preferential sorption experiments with racemic tryptophan and ibuprofen, the prepared membrane exhibited a higher affinity to l -tryptophan and (R)-(−)-ibuprofen than to corresponding enantiomers. The significant change in peak ratio from 48:52 to 60:40 ( d -tryptophan: l -tryptophan) was observed. This indicates the high potential of the covalently bonded (S)-(−)-α-methylbenzylamine selector for the fabrication of membranes selective towards chiral acids and ampholytes.