Molecular Meccano, 52. - Template-directed synthesis of a rotacatenane

David B. Amabilino, Peter R. Ashton, 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

A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable- temperature 1H-NMR spectroscopy.

Original languageEnglish (US)
Pages (from-to)1295-1302
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
StatePublished - Jun 1999

Keywords

  • Catenanes
  • Mechanically interlocked molecules
  • Molecular recognition
  • Rotaxanes
  • Template-directed synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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