Direct growth of boronate based shikimic acid imprinted polymer on porous substrate surface: A stable membrane for specific molecular separation

Abstract

Identifiable separation of shikimic acid (SA) compound is important for antiviral drug production. Current separation methods used for shikimic acid remain unsatisfied due to lack of specificity that can accurately and instantly anchor the target molecular from interfering impurities. Membrane separation seems to be feasible with the advantages of low energy consumption and operating convenience. Herein, benefiting from the characteristic cis-diol group in SA, a smart and simple poly(vinylidene fluoride) (PVDF) based molecular imprinted membrane (MIM) is synthesized by using 4-vinylbenzeneboronic acid as functional monomer to form prepolymers with SA. The resulting SA-imprinted boronate affinity molecular imprinted membranes (SA-imprinted-BAMIMs) show enhanced adsorption capacity (51.99 mg g⁻¹) compared with reported material. It should be noted that the formation of boronate ester bond between functional monomer and SA can help to specifically capture the target, and the release of combined SA on the membrane becomes easy due to the reversible bind characteristic of boronate ester under different pH condition. Moreover, SA-imprinted-BAMIMs exhibit acceptable stability after ultrasonic for 5 h and satisfactory regeneration performance after 8 cycles of adsorption–desorption experiments (93.02%). This convenient MIMs display great potential in the following work on rapid and specific separation of SA for commercial synthesis of antiviral.