A push-button molecular switch

Jason M. Spruell, Walter F. Paxton, John Carl Olsen, Diego Benítez, Ekaterina Tkatchouk, Charlotte L. Stern, Ali Trabolsi, Douglas C. Friedman, William A. Goddard, J Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

94 Scopus citations


The preparation, characterization, and switching mechanism of a unique single-station mechanically switchable hetero[2]catenane are reported. The facile synthesis utilizing a "threading-followed-by-clipping" protocol features Cu 2+ -catalyzed Eglinton coupling as a mild and efficient route to the tetrathiafulvalene-based catenane in high yield. The resulting mechanically interlocked molecule operates as a perfect molecular switch, most readily described as a "push-button" switch, whereby two discrete and fully occupied translational states are toggled electrochemically at incredibly high rates. This mechanical switching was probed using a wide variety of experimental techniques as well as quantum-mechanical investigations. The fundamental distinctions between this single-station [2]catenane and other more traditional bi- and multistation molecular switches are significant.

Original languageEnglish (US)
Pages (from-to)11571-11580
Number of pages10
JournalJournal of the American Chemical Society
Issue number32
StatePublished - Aug 19 2009

ASJC Scopus subject areas

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


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