Preparation of highly selective stationary phases for high-performance liquid chromatographic separation of enantiomers by direct copolymerization of monomers with single or twin chiral ligands

Mingcheng Xu, Enugurthi Brahmachary, Miroslav Janco, Frank H. Ling, Frantisek Svec, Jean Frechet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Uniformly sized macroporous polymer beads, which can be used as chiral stationary phase (CSP), have been prepared by the staged templated suspension polymerization process using chiral monomer as one of the copolymerization components. This approach enables the preparation of CSPs for which properties such as pore size, pore volume, surface area, chemistry, and chiral ligands can be tuned over a broad range. Several types of well-defined chiral monomers were prepared and allowed to assess synergistic effect of multiple selectors attached to a branched linker as well as the effect of the length and chemistry of the linker. Microscale batch screening was used for simple and rapid evaluation of selectivity. The most promising candidate CSPs were prepared on a larger scale and packed into HPLC columns. Their performance was demonstrated on the separation of racemic N-(3,5-dinitrobenzoyl)-α-amino acid alkylamides. The highest separation factors α of up to 27 were observed for CSPs prepared from monomers containing the branched spacer. These highly selective CSPs also enabled the separation of larger amounts of the target racemates upon column overload conditions.

Original languageEnglish (US)
Pages (from-to)25-40
Number of pages16
JournalJournal of Chromatography A
Volume928
Issue number1
DOIs
StatePublished - Aug 31 2001

Keywords

  • Chiral stationary phases, LC
  • Enantiomer separation
  • Monomers

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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