Novel helical poly(phenylacetylene)s bearing different sequences of l-proline dipeptide derivative pendants were prepared and used as CSPs in HPLC for enantioseparation.

Two novel helical poly(phenylacetylene) derivatives containing chiral phenylethyl carbamate residues in the end of each side chain (PPA-S and PPA-R) were synthesized by polymerization of the corresponding phenylacetylene monomers using Rh(nbd)BPh 4 as a catalyst in DMF. The enantioseparation properties of the polymers were evaluated as coated-type chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Under the same chromatographic conditions, PPA-S and PPA-R showed different enantioseparation properties, indicating that the different interactions between the analytes and the polymers, which result from the different chiral phenylethyl carbamate groups in the end of each side chains.Racemates 1, 7, and 8 could be better resolved on PPA-S, while racemate 6 was separated on PPA-R more efficiently. In addition, the coated-type CSPs showed good solvent tolerability and could work without any damage by introducing the polar solvents, such as CHCl 3 and THF, in eluent. Moreover, some racemates could be better resolved on these coated-type CSPs with the addition of THF to the eluent. K E Y W O R D S chiral phenylethyl carbamate, CSP, enantioseparation, helical poly(phenylacetylene), HPLC, solvent tolerability

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Novel one-handed helical copolymer (CPA) bearing L-proline tripeptide pendants and a handful of triethoxysilyl residues was synthesized, and hybridized into SiO2 porous microspheres (SiO2 PMS) during the growth process of...