Novel strategy for molecular imprinting of phenolic compounds utilizing disulfide templates

A molecularly imprinted polymer was synthesized by using allyl phenyl disulfide as a template. The mixture of allyl phenyl disulfide, divinylbenzene, and 2,2'-azobis(isobutyronitrile) in chloroform was polymerized by UV irradiation for 24 h at 5 degrees C and further 3 h at 80 degrees C. The disulfide bonds of the resulting polymer were reductively cleaved by NaBH(4) in methanol to give thiol groups in the binding sites. The polymer selectively recognized phenol rather than thiophenol. In chromatographic study using polymer-packed columns, the retention factor of the IP for phenol was 5.60 and that of a reference polymer was 4.20. The higher retention for phenol was supported by ab initio calculation.