Development of self-indicating resin

Comb Chem High Throughput Screen. 2007 May;10(4):261-7. doi: 10.2174/138620707780636592.

Abstract

Previously, we have reported the development and application of self-indicating resins (SIR), materials which can indicate presence or absence of amines in the reaction solution by the conspicuous color change of a phenolsulfophthalein type dye immobilized on resin beads [2a]. Although the functionality necessary for attaching the dye to the resins could be readily introduced by the Suzuki-Miyaura coupling during the synthesis of the SIR 1, this approach was only applicable to the dyes containing suitable functionality for the cross-coupling reaction. In this article we describe a new approach of immobilizing the indicating dyes onto the resin support. The dyes suitable for loading onto aminomethyl polystyrene (PS) resin were prepared by Friedel-Crafts reaction of 2-sulfoterephthalic anhydride with a wide range of phenols. Using this new route, the SIR 6c was readily prepared in >100g quantities. Use of the SIR 6c in the synthesis of a 144 member urea library was demonstrated and the SIR successfully indicated the endpoint of the reaction between amines and isocyanates.

MeSH terms

  • Indicators and Reagents / chemistry
  • Molecular Structure
  • Peptide Library
  • Polystyrenes / chemical synthesis*
  • Polystyrenes / chemistry
  • Resins, Synthetic / chemical synthesis*
  • Resins, Synthetic / chemistry

Substances

  • Indicators and Reagents
  • Peptide Library
  • Polystyrenes
  • Resins, Synthetic