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 diisocy anates at 100-degrees-C in anisole or dimethyl sulfoxide. The obtained polyurethanes were applied to the stationary phase of high performanc e liquid chromatography to separate chiral compounds. The polyurethane s derived from (1S,3S)-diphenylpropanediol and aliphatic diisocyanates resolved several pairs of enantiomers of 2,2'-dihydroxy-1,1'-dinaphth yl derivatives, while those from aromatic diisocyanates showed only po or chiral recognition abilities. The wide angle X-ray diffraction stud ies revealed that the chiral recognition abilities were dependent on c rystallinity of the polymers.