Role of chirality and macroring in imprinted polymers with enantiodiscriminative power

Jozsef Kupai, Eszter Rojik, Peter Huszthy, Gyorgy Szekely*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Scopus citations


Enantioselective discrimination of chiral amines is of great importance as their biological properties often differ. Therefore, here we report the development of synthetic receptors for their enantioselective recognition and pH-sensitive drug release. This paper reports the preparation of three pyridine and two benzene derivatives containing an allyloxy group [(S,S)-5, 6-9] as well as their evaluation as functional monomer anchors for chiral imprinting of amines. The enantiomeric enriching ability and controlled release of the imprinted polymers (IPs) were evaluated using racemic mixture of 1-(1-naphthyl)ethylamine hydrogen perchlorate (1). The effect of the enantiomeric purity of the template on the enantioseparation performance was investigated. Racemic template in combination with enantiomerically pure macrocyclic anchors and vice versa yields IPs with excellent enantiomeric recognition. In vitro drug delivery, enantiomeric enrichment and pH-sensitive release were investigated through kinetic models.

Original languageEnglish (US)
Pages (from-to)9516-9525
Number of pages10
JournalACS Applied Materials and Interfaces
Issue number18
StatePublished - May 13 2015


  • chirality
  • crown compounds
  • drug delivery
  • enantioselectivity
  • molecularly imprinted polymer

ASJC Scopus subject areas

  • Materials Science(all)


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