Chiral macrocyclic membranes for efficient enantioselective separation

Chiral separation membranes have become one of the most important methods for enantiomeric separation, especially in the pharmaceutical field. Herein, a binaphthol-based chiral macrocyclic molecule was well-designed as a chiral selective block, and an enantiomeric separation membrane was prepared by interfacial polymerization. This chiral membrane exhibits good selectivity in separating racemic chiral mixtures of 1-phenylethanol, α-phenylethylamine, and ibuprofen. Remarkably, it can also be used for the separation of high-value chiral pharmaceutical salbutamol. The R-TMC membrane demonstrated high-resolution separation (ee = 97.2%) of S-salbutamol from R-salbutamol. It demonstrated high resolution (ee = up to 92%) and high flux (1.66 × 10−2 mol m−2 h−1) toward 1-phenylethanol under cross-flow filtration conditions. Density functional theory calculations and molecular dynamics simulations further verify that highly efficient enantioselective separation may be attributable to an impeded transport mechanism. This study demonstrates the potential of this polyester chiral separation membrane in the field of chiral drug separation and provides inspiration for the enantiomeric separation of chiral drugs.