Oligocatenanes made to order

David B. Amabilino, Peter R. Ashton, Vincenzo Balzani, Sue E. Boyd, Alberto Credi, Ju Young Lee, Stephan Menzer, J. Fraser Stoddart*, Margherita Venturi, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

133 Scopus citations

Abstract

The construction of catenanes, comprised of between two and seven interlocked rings, has been achieved. Two tris-1,5-naphtho-57-crown-15 macrocycles template the formation of cyclobis(paraquat-4,4'-biphenylene) to give a [3]catenane, which acts as a template for the construction of one and then another cyclobis(paraquat-p-phenylene) to give a [4]- and [5]catenane (Olympiadane). When high pressure was used in these templated syntheses, a [6]- and [7]catenane, as well as a [5]catenane that is topologically isomeric with Olympiadane, were also obtained. X-ray analyses of the [3]-, [5]-, and [7]catenanes reveal an optimum use of electrostatic, π-π stacking, [C- H···π] interactions, and [C-H···O] hydrogen bonds in the organization of the component rings within the molecules. Noteworthy in the [7]catenane structure is the location of four of the PF6/- anions within voids present in the 20+ ion. Temperature-dependent 1H NMR spectroscopic studies and electrochemical investigations have revealed the dynamic and redox behavior of these catenanes in solution.

Original languageEnglish (US)
Pages (from-to)4295-4307
Number of pages13
JournalJournal of the American Chemical Society
Volume120
Issue number18
DOIs
StatePublished - May 13 1998

ASJC Scopus subject areas

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

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