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 journalArticle

29 Scopus citations

Abstract

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
Volume134
Issue number41
DOIs
StatePublished - Oct 17 2012

ASJC Scopus subject areas

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

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    Forgan, R. S., Gassensmith, J. J., Cordes, D. B., Boyle, M. M., Hartlieb, K. J., Friedman, D. C., Slawin, A. M. Z., & Stoddart, J. F. (2012). Self-assembly of a [2]Pseudorota[3]catenane in water. Journal of the American Chemical Society, 134(41), 17007-17010. https://doi.org/10.1021/ja3085115