Syntheses and dynamics of donor-acceptor [2]catenanes in water

Lei Fang*, Subhadeep Basu, Chi Hau Sue, Albert C. Fahrenbach, J Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

61 Scopus citations

Abstract

A subset of mechanically interlocked molecules, namely, donor-acceptor [2]catenanes, have been produced in aqueous solutions in good yields from readily available precursors. The catenations are templated by strong hydrophobic and [π⋯π] stacking interactions, which serve to assemble the corresponding supramolecular precursors, prior to postassembly covalent modification. Dynamic 1H NMR spectroscopic investigations performed on one of these [2]catenanes reveal that the pirouetting motion of the butadiyne-triethylene glycol chain occurs with a dramatically lower activation enthalpy, yet with a much higher negative activation entropy in water, compared to organic solvents. The preparations of mechanically interlocked molecules in water constitute the basis for the future development of complex functional molecular machinery in aqueous environments.

Original languageEnglish (US)
Pages (from-to)396-399
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number3
DOIs
StatePublished - Jan 26 2011

ASJC Scopus subject areas

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

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