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 journalArticle

Abstract

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 Cu2+-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
Volume131
Issue number32
DOIs
StatePublished - Aug 19 2009

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Switches
Molecules
catenane
tetrathiafulvalene

ASJC Scopus subject areas

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

Cite this

Spruell, J. M., Paxton, W. F., Olsen, J. C., Benítez, D., Tkatchouk, E., Stern, C. L., ... Stoddart, J. F. (2009). A push-button molecular switch. Journal of the American Chemical Society, 131(32), 11571-11580. https://doi.org/10.1021/ja904104c

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

In: Journal of the American Chemical Society, Vol. 131, No. 32, 19.08.2009, p. 11571-11580.

Research output: Contribution to journalArticle

Spruell, JM, Paxton, WF, Olsen, JC, Benítez, D, Tkatchouk, E, Stern, CL, Trabolsi, A, Friedman, DC, Goddard, WA & Stoddart, JF 2009, 'A push-button molecular switch', Journal of the American Chemical Society, vol. 131, no. 32, pp. 11571-11580. https://doi.org/10.1021/ja904104c
Spruell JM, Paxton WF, Olsen JC, Benítez D, Tkatchouk E, Stern CL et al. A push-button molecular switch. Journal of the American Chemical Society. 2009 Aug 19;131(32):11571-11580. https://doi.org/10.1021/ja904104c
Spruell, Jason M. ; Paxton, Walter F. ; Olsen, John Carl ; Benítez, Diego ; Tkatchouk, Ekaterina ; Stern, Charlotte L. ; Trabolsi, Ali ; Friedman, Douglas C. ; Goddard, William A. ; Stoddart, J. Fraser. / A push-button molecular switch. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 32. pp. 11571-11580.
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