Enantioseparation of enantiomers is of great significance for the study of life sciences, medicinal chemistry and human health. Among the separation methods, the high performance liquid chromatography (HPLC) method using stereoregular synthetic or natural polymers as chiral stationary phases (CSPs) has been used as one of the most popular and effective ways for both the analytical and preparative separations of chiral compounds. Although polysaccharide derivatives with high chiral recognition abilities have been widely developed as popular CSPs, optically-active synthetic polymers as CSPs have also attracted significant interest by researchers around the world. Poly(phenylacetylene) derivatives possessing helical conformation in main chains have good optical activity and unique properties, and have potential applications in enantioseparation. In this study, a novel phenylacetylene monomer bearing 3,5-dimethylphenylcarbamate residue of L-cyclohexylglycinol was synthesized and then was polymerized in DMF using Rh(nbd)BPh4 as a catalyst to obtain a poly(phenylacetylene) derivative (PPAA-Chg-3,5DMPC). The structure analyses of PPAA-Chg-3,5DMPC by 1H nuclear magnetic resonance (NMR), infrared (IR), optical rotation, and circular dichroism (CD) spectra indicated that the polymer possesses a stereoregular cis-transoidal configuration and dynamic helical conformation in the main chain. The chiral recognition ability of PPAA-Chg-3,5DMPC was evaluated as the CSP in HPLC, and it showed an efficient chiral recognition for some racemates, such as racemic binaphthol and racemic trans-1,2-cyclohexanedicarboxylic acid dianilide. Furthermore, PPAA-Chg-3,5DMPC showed a high solvent tolerability, and tetrahydrofuran (THF)-containing eluents could be used to improve its chiral recognition ability. 

Synthesis and chiral recognition of helical poly(phenylacetylene)s bearing 3,5-dimethylphenylcarbamate residue of <i>L</i>-cyclohexylglycinol

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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Synthesis and chiral recognition of helical poly(phenylacetylene)s bearing 3,5-dimethylphenylcarbamate residue of L-cyclohexylglycinol