Optically‐active polyurethanes containing coumarin dimer component: Synthesis, characterization, and chiral recognition ability

Yun Chen, Jiann‐Jang ‐J Lin

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15 Citations (Scopus)

Abstract

Optically‐active polyurethanes (2a‐2c) were prepared by polyaddition reaction of diamide (1a, 1b) and diester (1c) derivatives of chiral coumarin dimer with 4,4′‐diphenylmethane diisocyanate (MDI) in chloroform and methyl ethyl ketone, respectively. The inherent viscosity of the polyurethanes are between 0.13 and 0.21 dL/g in N,N‐dimethylacetamide (DMAc) at 30°C. Treated silica gels were absorbed with ca. 25 wt % of the polyurethanes, and packed as chiral stationary phases for direct optical resolution of 16 racemates with aromatic groups by high‐performance liquid chromatography (HPLC). Polyurethanes 2a and 2b, obtained from diamide derivatives, show efficient resolution ability to some of the racemates (α = 1.06‐1.79), especially the atropic (R5) and trans (R6‐R9) isomers. The recognition ability of the polyurethanes can be attributed to the simultaneous aromatic stacking and hydrogen‐bonding interactions with racemates. © 1992 John Wiley & Sons, Inc.

Original languageEnglish
Pages (from-to)2699-2707
Number of pages9
JournalJournal of Polymer Science Part A: Polymer Chemistry
Volume30
Issue number13
DOIs
Publication statusPublished - 1992 Dec

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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