Macrocycle-functionalized polystyrene beads as specific absorbers

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Abstract

Crosslinked polystyrene beads were first functionalized with phenacyl ester linkers, and a series of four macrocycles with different ring sizes were synthesized from these linkers. The macrocycles were built from amide-linked monomers coupled by conventional peptide-synthesis methods. Annulation was achieved by copper(I)-catalyzed intramolecular azide–alkyne cycloaddition to give triazole linked macrocycles. The macrocycles were cleaved from the polymer beads with hydrazinolysis or saponification. The structures of macrocycles were confirmed by high-resolution nuclear magnetic resonance (NMR) and liquid chromatography–mass spectrometry (LC–MS) analysis. The ability of the polymers to selectively bind compounds from a mixture of aromatic derivatives in ethanol was tested. The prepared polystyrene supported macrocycles were found to selectively bind bromophenol blue and bromocresol green non-covalently with an association constant of 160–490 M−1.
Original languageUndefined/Unknown
Pages (from-to)24–30
JournalReactive and Functional Polymers
Volume89
DOIs
Publication statusPublished - 2015
MoE publication typeA1 Journal article-refereed

Keywords

  • solid support
  • molecular recognition
  • sorbents

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