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 III, J. Fraser Stoddart
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 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.
Spruell, J. M., Paxton, W. F., Olsen, J., Benítez, D., Tkatchouk, E., Stern, C. L., Trabolsi, A., Friedman, D. C., III, W. A. G., & Stoddart, J. F. (2009). A Push-Button Molecular Switch. *J. Am. Chem. Soc.*, *131*(32), 11571-11580. https://doi.org/10.1021/ja904104c