Abstract
Optically active polyurethanes were synthesized by the polyaddition of (1S,3S)-diphenylpropanediol or (2R,4R)-pentanediol to various diisocyanates at 100°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.
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Kobayashi, T., Kakimoto, Ma. & Imai, Y. Chiral Recognition Abilities of New Optically Active Polyurethanes Derived from Chiral 1,3-Diols and Diisocyanates. Polym J 25, 969–975 (1993). https://doi.org/10.1295/polymj.25.969
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DOI: https://doi.org/10.1295/polymj.25.969