A Push-Button Molecular Switch

作者:Spruell Jason M; Paxton Walter F; Olsen John Carl; Benitez Diego; Tkatchouk Ekaterina; Stern Charlotte L; Trabolsi Ali; Friedman Douglas C; Goddard William A III; Stoddart J Fraser*
来源:Journal of the American Chemical Society, 2009, 131(32): 11571-11580.
DOI:10.1021/ja904104c

摘要

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.