CHIRAL RECOGNITION ABILITIES OF NEW OPTICALLY-ACTIVE POLYURETHANES DERIVED FROM CHIRAL 1,3-DIOLS AND DIISOCYANATES

Optically active polyurethanes were synthesized by the polyaddition of (1S,3S)-diphenylpropanediol or (2R,4R)-pentanediol to various diisocyanates at 100-degrees-C in anisole or dimethyl sulfoxide. The obtained polyurethanes were applied to the stationary phase of high performance liquid chromatography to separate chiral compounds. The polyurethanes derived from (1S,3S)-diphenylpropanediol and aliphatic diisocyanates resolved several pairs of enantiomers of 2,2'-dihydroxy-1,1'-dinaphthyl derivatives, while those from aromatic diisocyanates showed only poor chiral recognition abilities. The wide angle X-ray diffraction studies revealed that the chiral recognition abilities were dependent on crystallinity of the polymers.