Development of self-indicating resin

Osamu Ichihara, David Sampson, Mark Whittaker, Mark Bradley, Jin Ku Cho

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)261-267
Number of pages7
JournalCombinatorial Chemistry and High Throughput Screening
Volume10
Issue number4
Publication statusPublished - May 2007

Keywords

  • ORGANIC-SYNTHESIS
  • REAGENTS

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