Designing Microparticle-Impregnated Polyelectrolyte Composite: The Combination of ATRP, Fast Azidation, and Click Reaction Using a Single-Catalyst, Single-Pot Strategy

Int J Mol Sci. 2019 Nov 8;20(22):5582. doi: 10.3390/ijms20225582.

Abstract

Polystyrene microparticles were covalently impregnated into the networks of functional polyelectrolyte chains designed via a tandem run of three reactions: (i) synthesis of water-soluble polyelectrolyte, (ii) fast azidation and (iii) a 'click' reaction, using the single-catalyst, single-pot strategy at room temperature in mild aqueous media. The model polyelectrolyte sodium polystyrenesulfonate (NaPSS) was synthesized via the well-controlled atom transfer radical polymerization (ATRP) whose halogen living-end was transformed to azide and subsequently coupled with an alkyne carboxylic acid through a 'click' reaction using the same ATRP catalyst, throughout. Halogen to azide transformation was fast and followed the radical pathway, which was explained through a plausible mechanism. Finally, the success of microparticle impregnation into the NaPSS network was evaluated through Kaiser assay and imaging. This versatile synthetic procedure, having a reduced number of discrete reaction steps and eliminated intermediate work-ups, has established a fast and simple pathway to design functional polymers required to fabricate stable polymer-particle composites where the particles are impregnated covalently and controllably.

Keywords: composite design; functionalization; microparticle; polymer.

MeSH terms

  • Azides / chemistry*
  • Bromides / chemistry
  • Catalysis
  • Click Chemistry / methods*
  • Copper / chemistry
  • Methanol / chemistry
  • Microspheres*
  • Polyelectrolytes / chemistry*
  • Polymerization*
  • Polystyrenes / chemistry
  • Proton Magnetic Resonance Spectroscopy
  • Solvents / chemistry
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry

Substances

  • Azides
  • Bromides
  • Polyelectrolytes
  • Polystyrenes
  • Solvents
  • Water
  • polystyrene sulfonic acid
  • Copper
  • Methanol