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A Push-Button Molecular Switch

Spruell, Jason M. and Paxton, Walter F. and Olsen, John-Carl and Benítez, Diego and Tkatchouk, Ekaterina and Stern, Charlotte L. and Trabolsi, Ali and Friedman, Douglas C. and Goddard, William A., III and Stoddart, J. Fraser (2009) A Push-Button Molecular Switch. Journal of the American Chemical Society, 131 (32). pp. 11571-11580. ISSN 0002-7863.

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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.

Item Type:Article
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URLURL TypeDescription
Goddard, William A., III0000-0003-0097-5716
Stoddart, J. Fraser0000-0003-3161-3697
Additional Information:Copyright © 2009 American Chemical Society. Received May 20, 2009. Publication Date (Web): July 24, 2009. This work was supported by the Microelectronics Advanced Research Corporation and its Focus Center Research Program, the Center on Functional Engineered Nano-Architectonics, and the NSF-MRSEC Program through the Northwestern University Materials Research Science and Engineering Center. J.M.S. gratefully acknowledges the National Science Foundation for a Graduate Research Fellowship as well as Northwestern University for a Presidential Fellowship. Computational facilities were funded by grants from ARO-DURIP and ONR-DURIP. Supporting Information: Spectral characterization of all new compounds, VT and 2D ^1H NMR spectral data and reductive CV electrochemical data for 1·4PF_6, and crystallographic data (CIF) for 1·4PF_6. This material is available free of charge via the Internet at
Funding AgencyGrant Number
Microelectronics Advanced Research Corporation (MARCO)UNSPECIFIED
NSF Graduate Research FellowshipUNSPECIFIED
Nortwestern UniversityUNSPECIFIED
Army Research Office (ARO)UNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
Issue or Number:32
Record Number:CaltechAUTHORS:20090911-153600968
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Official Citation:A Push-Button Molecular Switch Jason M. Spruell, Walter F. Paxton, John-Carl Olsen, Diego Bentez, Ekaterina Tkatchouk, Charlotte L. Stern, Ali Trabolsi, Douglas C. Friedman, William A. Goddard III, J. Fraser Stoddart Journal of the American Chemical Society 2009 131 (32), 11571-11580
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15803
Deposited By: George Porter
Deposited On:07 Oct 2009 18:36
Last Modified:03 Oct 2019 01:03

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