Translational Isomerism in Some Two- and Three-Station [2]Rotaxanes

David B. Amabilino, Peter R. Ashton, Sue E. Boyd, Marcos Gómez-López, Wayne Hayes, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


The template-directed syntheses of three [2]rotaxanes are described. They all have dumbbell , components, with both hydroquinone and resorcinol rings inserted into polyether chains terminated by tetraarylmethane stoppers, that become encircled during the key self-assembly processes by the tetracationic cyclophane, cyclobis(paraquat-p-phenylene), with its two π-electron deficient bipyridinium units. It has been demonstrated by low-temperature 1H NMR spectroscopy that the π-electron deficient tetracationic cyclophane has a remarkably high preference to reside around the hydroquinone ring in these molecular shuttles. This observation illustrates how a very small constitutional difference-hydroquinone versus resorcinol recognition sites-can lead to the overwhelming preference for one translational isomer over another in this particular range of [2]rotaxanes.

Original languageEnglish (US)
Pages (from-to)3062-3075
Number of pages14
JournalJournal of Organic Chemistry
Issue number10
StatePublished - 1997

ASJC Scopus subject areas

  • Organic Chemistry


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