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Issue 35, 2019
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Influence of different sequences of l-proline dipeptide derivatives in the pendants on the helix of poly(phenylacetylene)s and their enantioseparation properties

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Abstract

Two novel phenylacetylenes containing L-proline dipeptide derivatives with different sequences were synthesized and polymerized in THF using Rh(nbd)BPh4 as a catalyst to obtain the corresponding one-handed helical poly(phenylacetylene) derivatives (PPA-1 and PPA-2). The effect of different sequences of L-proline dipeptide derivatives in the pendants on the helical conformation of the polymer main chain was mainly evaluated and the enantioseparation properties of PPA-1 and PPA-2 for eleven racemates were investigated as chiral stationary phases (CSPs) for HPLC. In N,N-dimethylacetamide, the CD signals of PPA-1 and PPA-2 were the opposite, and the CD intensity of PPA-1 was higher than that of PPA-2, indicating that the two polymers possess different main chain helical conformations and PPA-1 may have a higher screw-sense excess. PPA-1 and PPA-2 showed rather different enantioseparation properties depending on the different helical structures, induced by different coating solvents and the different sequences of L-proline dipeptide derivatives in the pendants. In addition, each of the two poly(phenylacetylene) derivatives has its own merits. PPA-1 showed a more extensive chiral selectivity, while PPA-2 showed a more specific recognition of certain enantiomers, such as racemates 8 and 9. These two racemates could be better resolved on PPA-2 with the separation factors being even higher than those on the well-known commercial chiral columns Chiralcel or Chiralpak AD, OD, AS and OJ-H.

Graphical abstract: Influence of different sequences of l-proline dipeptide derivatives in the pendants on the helix of poly(phenylacetylene)s and their enantioseparation properties

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Publication details

The article was received on 10 May 2019, accepted on 02 Aug 2019 and first published on 02 Aug 2019


Article type: Paper
DOI: 10.1039/C9PY00675C
Polym. Chem., 2019,10, 4810-4817

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    Influence of different sequences of L-proline dipeptide derivatives in the pendants on the helix of poly(phenylacetylene)s and their enantioseparation properties

    Y. Zhou, C. Zhang, Z. Zhou, R. Zhu, L. Liu, J. Bai, H. Dong, T. Satoh and Y. Okamoto, Polym. Chem., 2019, 10, 4810
    DOI: 10.1039/C9PY00675C

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