Chiral Heterogeneous Polymer for the Separation of Naproxen Enantiomers

Abstract

Chiral organic heterogeneous polymer materials have a wide range of applications, including asymmetric catalysis, enantiospecific recognition, and the resolution of enantiopure compounds. Those chiral polymers self-assemble into various shapes and sizes, allowing them to tune their activity and enantioselectivity. In this study, we report the synthesis of chiral alkaloid dinaccamate polymers separated by different spacers. The prepared materials exhibited a porous, wirelike morphology with a width of ∼230 nm and a pore diameter of ∼17 Å. The chiral materials provided the highest resolution of racemic naproxen into pure enantiomers (selectivity factor ∼ 1.87) in 180.0 min, isolating approximately 99% of each enantiomer. A typical open-tubular chiral polymer on the Al<inf>2</inf>O<inf>3</inf> column being continuously eluted by hexane/ethanol [1:1 (v/v)] at a flow rate of 0.66 mL min–1 afforded appreciable resolution (R ∼ 2.01) with retention times of 26.98 min (R) and 40.01 min (S) for 10 resolution cycles. © 2025 American Chemical Society