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Synthesis and chromatographic evaluation of new polymeric chiral stationary phases based on three (1S,2S)-(−)-1,2-diphenylethylenediamine derivatives in HPLC and SFC

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Abstract

Three new polymeric chiral stationary phases were synthesized based on (1S,2S)-1,2-bis(2,4,6-trimethylphenyl)ethylenediamine, (1S,2S)-1,2-bis(2-chlorophenyl)ethylenediamine, and (1S,2S)-1,2-di-1-naphthylethylenediamine via a simple free-radical-initiated polymerization in solution. These monomers are structurally related to (1S,2S)-1,2-diphenylethylenediamine which is the chiral monomer used for the commercial P-CAP-DP polymeric chiral stationary phase (CSP). The performance of these three new chiral stationary phases were evaluated in normal phase high-performance liquid chromatography (HPLC) and supercritical fluid chromatography and the results were compared with those of the P-CAP-DP column. All three new phases showed enantioselectivity for a large number of racemates with a variety of functional groups, including amines, amides, alcohols, amino acids, esters, imines, thiols, and sulfoxides. In normal phase, 68 compounds were separated with 28 baseline separations (Rs ≥ 1.5) and in SFC, 65 compounds were separated with 24 baseline separations. In total 72 out of 100 racemates were separated by these CSPs with 37 baseline separations. Complimentary separation capabilities were observed for many analytes. The new polymeric CSPs showed similar or better enantioselectivities compared with the commercial column in both HPLC and SFC. However, faster separations were achieved on the new stationary phases. Also, it was shown that these polymeric stationary phases have good sample loading capacities while maintaining enantioselectivity.

Faster separations on new polymeric chiral stationary phases in HPLC

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Acknowledgments

We gratefully acknowledge the support of this work by the Robert A. Welch foundation (Y-0026).

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX, 76019, USA

    Tharanga Payagala, Eranda Wanigasekara & Daniel W. Armstrong

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  1. Tharanga Payagala
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  2. Eranda Wanigasekara
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  3. Daniel W. Armstrong
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Correspondence to Daniel W. Armstrong.

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Payagala, T., Wanigasekara, E. & Armstrong, D.W. Synthesis and chromatographic evaluation of new polymeric chiral stationary phases based on three (1S,2S)-(−)-1,2-diphenylethylenediamine derivatives in HPLC and SFC. Anal Bioanal Chem 399, 2445–2461 (2011). https://doi.org/10.1007/s00216-010-4615-6

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  • DOI: https://doi.org/10.1007/s00216-010-4615-6

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