A chiral stationary phase coated by surface molecularly imprinted polymer for separating 1,1'-binaphthalene-2,2'-diamine enantiomer by high performance liquid chromatography

J Chromatogr A. 2015 Jan 9:1376:172-6. doi: 10.1016/j.chroma.2014.12.009. Epub 2014 Dec 12.

Abstract

This report describes novel pathway for the development of a new type of CSP. A chiral stationary phase (CSP) prepared by coating a molecularly imprinted polymer (MIP) on the surface of silica gel (SMIP-CSP) showed a high separation factor (3.39) in separating racemic 1,1'-binaphthalene-2,2'-diamine (DABN) by high performance liquid chromatography (HPLC). Being the crosslinking agent, ethylene glycol dimethacrylate (EGDMA) was copolymerized with the monomer, methacrylic acid (MAA), in the presence of (R)-DABN as the template molecules on the surface of the silica gel particles to produce the SMIP-CSPs. The effects of the pretreatment temperature, the (R)-DABN content and the type of silica gel and monomer in the SMIP-CSPs on the separation of the racemic DABN were systematically investigated.

Keywords: 1,1′-Binaphthalene-2,2′-diamine; Chiral separation; Coating; Surface molecularly imprinted polymers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Cross-Linking Reagents / chemistry
  • Methacrylates / chemistry
  • Molecular Imprinting
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Polymethacrylic Acids / chemistry*
  • Silicon Dioxide
  • Stereoisomerism
  • Temperature

Substances

  • 2,2'-diamino-1,1'-binaphthalene
  • Cross-Linking Reagents
  • Methacrylates
  • Naphthalenes
  • Polymethacrylic Acids
  • polymethacrylic acid
  • Silicon Dioxide
  • ethylene dimethacrylate