Preparation of cellulose stilbene-4-carboxylate and its application to thin-layer chromatography

Abstract

Photoreactive cellulose stilbene-4-carboxylate (SB-cellulose) with degrees of substitution of up to 1.9 has been prepared by the reaction of regenerated amorphous microcrystalline cellulose with stilbene-4-carbonyl chloride. The stilbene moiety in the SB-cellulose was found to undergo an isomerization from trans to the more polar cis form under irradiation with UV light, resulting in an increase in the swelling ability of the SB-cellulose in water. Application of the SB-cellulose as an adsorbent in thin-layer Chromatography (TLC) was examined. The separation of the spots of appropriate hydrophobic dyes in the TLC was improved using the SB-cellulose as a component of the adsorbent, and more so by irradiation with UV light. Application of this method to the optical resolution of amino acids is suggested as a promising technique for some amino acids such as phenylalanine.