Solid-phase approaches toward cyclic oligomers

David B. Shortell, Liam C. Palmer, James M. Tour*

*Corresponding author for this work

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Strategies were sought to effect cyclizations of oligo(m-phenylene ethynylene) by exploiting pseudo-high dilution effects on polymer supports. Using Pd/Cu-catalyzed coupling protocols, Merrifield's resin (1% crosslinked chloromethylated polystyrene) proved inadequate for site isolation; inter-site couplings ensued on the flexible support. Conversely, use of the Argopore resin, a more highly crosslinked polystyrene, inhibited inter-site interactions, and no identifiable final product could be separated from the resin. Spectroscopic and mass spectrometric methods indicated that the product from the Argopore resin might be a threaded catenane.

Original languageEnglish (US)
Pages (from-to)9055-9065
Number of pages11
JournalTetrahedron
Volume57
Issue number44
DOIs
StatePublished - Oct 29 2001

Keywords

  • Macrocycle
  • Pseudo-high dilution
  • Supramolecular

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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