Self-assembly of a [2]Pseudorota[3]catenane in water

Ross S. Forgan, Jeremiah J. Gassensmith, David B. Cordes, Megan M. Boyle, Karel J. Hartlieb, Douglas C. Friedman, Alexandra M.Z. Slawin, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Scopus citations


A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p- phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H⋯O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.

Original languageEnglish (US)
Pages (from-to)17007-17010
Number of pages4
JournalJournal of the American Chemical Society
Issue number41
StatePublished - Oct 17 2012

ASJC Scopus subject areas

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


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