High yielding template-directed syntheses of [2]rotaxanes

José A. Bravo, Françisco M. Raymo, J. Fraser Stoddart, Andrew J.P. White, David J. Williams

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

Three dumbbell-shaped compounds incorporating terminal triisopropylsilyl stoppers, connected to a central 1,5-dioxynaphthalene recognition site by [-CH2CH2O-]n spacers (n = 1-3), have been synthesized. These compounds have been employed as templates for the synthesis of [2]rotaxanes incorporating cyclobis(paraquat-p-phenylene) as the ring component. It was found that the length of the polyether chains of the templates influences the efficiencies of the template-directed syntheses. Rotaxane formation occurs only if n > 1 and, when n = 3 the corresponding [2]rotaxane can be isolated in a yield as high as 72 %. This remarkable yield is the highest ever obtained for the template-directed syntheses of [2]rotaxanes incorporating donor/acceptor Interactions.

Original languageEnglish (US)
Pages (from-to)2565-2571
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number11
DOIs
StatePublished - Nov 1998

Keywords

  • Molecular recognition
  • Rotaxanes
  • Self-assembly
  • Template-directed synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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