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 journalArticle

20 Scopus citations

Abstract

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
Volume62
Issue number10
DOIs
StatePublished - Jan 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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    Amabilino, D. B., Ashton, P. R., Boyd, S. E., Gómez-López, M., Hayes, W., & Stoddart, J. F. (1997). Translational Isomerism in Some Two- and Three-Station [2]Rotaxanes. Journal of Organic Chemistry, 62(10), 3062-3075. https://doi.org/10.1021/jo9612584