Regeneration of β-Cyclodextrin Based Membrane by Photodynamic Disulfide Exchange — Steroid Hormone Removal from Water

Abstract

The occurrence of steroid hormones in water and their serious impact on human and ecosystem demand high performance materials for efficient removal of such micropollutants. Here, an affinity membrane is developed for hormone removal with regenerable binding sites. By using photodynamic disulfides as a linker, UV induced detachment of β-CD ligands from the membrane surface is demonstrated. The macroporous base membrane is first fabricated via a polymerization induced phase separation method using 2-hydroxyethyl methacrylate (HEMA) and ethylene dimethylacrylate (EDMA) monomers. Then the affinity membranes are prepared by immobilizing β-CD ligands to the poly(HEMA-co-EDMA) base membrane through the 2-carboxyethyl disulfide linker. The β-CD functionalized affinity membrane shows a 30% increase of E2 hormone uptake compared with the base membrane, attributed to the formation of CD-hormone host–guest inclusion complexes. The photodynamic disulfide linkers enable UV-induced detachment of blocked β-CD ligands from and reattachment of fresh β-CD ligands to the membrane surface after each adsorption cycle, thus conferring the affinity membrane with excellent regenerative properties. It is anticipated that the use of dynamic covalent bonds for binding ligands will be of interest for developing smart affinity membranes with regenerable and readjustable surface properties.