A Thermoresponsive Membrane for Chiral Resolution

Authors


  • The National Natural Science Foundation of China (50373029, 20674054), the Key Project of the Ministry of Education of China (106131), and the Specialized Research Fund for the Doctoral Program of Higher Education by the Ministry of Education of China (20040610042) are acknowledged for supporting this research. The authors are grateful to X.-Y. Zhang at the Analytical and Testing Center of Sichuan University for her help in the SEM observations, and also thank the Kohjin Co., Ltd., Japan, for kindly supplying the N-isopropylacrylamide.

Abstract

A novel thermoresponsive membrane for chiral resolution with high performance has been developed. The membrane exhibits chiral selectivity based on molecular recognition of beta-cyclodextrin (β-CD) and thermosensitivity based on the phase transition of poly(N-isopropylacrylamide) (PNIPAM). Linear PNIPAM chains were grafted onto porous nylon-6 membrane substrates by using a plasma-graft pore-filling polymerization method; the chains thus acted as microenvironmental adjustors for β-CD molecules. β-CD moieties were introduced into the linear PNIPAM chains by a chemical grafting polymerization method and acted as chiral selectors. The phase transition of grafted PNIPAM chains affects the microenvironment of β-CD molecules and, thus, the association between β-CD and guest molecules. The chiral selectivity of the prepared thermoresponsive membranes in chiral resolution operated at temperature below the lower critical solution temperature (LCST) of PNIPAM is higher than that of membranes with no thermosensitivity. Furthermore, the decomplexation ratio of enantiomer-loaded thermoresponsive membranes in decomplexation at temperatures above the LCST is much higher than that of membranes with no thermosensitivity. Thus, by simply changing the operation temperature, high, selective chiral resolution and efficient membrane regeneration are achieved. The proposed membrane provides a new and efficient way to solve the difficult decomplexation problem of chiral solid membranes, which is highly attractive for chiral resolution.

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