Rotaxane or pseudorotaxane? That is the question!

Peter R. Ashton, Ian Baxter, Matthew C T Fyfe, Françisco M. Raymo, Neil Spencer, J. Fraser Stoddart, Andrew J P White, David J. Williams

Research output: Contribution to journalArticlepeer-review

253 Scopus citations

Abstract

A series of secondary dialkylammonium ions (RCH2)2NH2+ have been prepared, and their binding properties toward the macrocyclic polyether dibenzo[24]crown-8 (DB24C8) evaluated. By using this information, a route to a kinetically stable rotaxane-like entity - stabilized by noncovalent bonding interactions between the DB24C8 macroring and the ammonium center - was established, in which the crown ether slips over a dialkylammonium ion's stopper groups (R). However, we have found that the kinetic stability of this rotaxane-like entity is extremely dependent on the nature of the solvent in which it is dissolved, suggesting that pseudorotaxanes lie in the fuzzy domain between two sets of extremes, wherein a beadlike macrocycle and a dumbbell-like component may either (1) exist as a rotaxane or (2) be completely disassociated from one another.

Original languageEnglish (US)
Pages (from-to)2297-2307
Number of pages11
JournalJournal of the American Chemical Society
Volume120
Issue number10
DOIs
StatePublished - Mar 18 1998

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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