Khashab, Niveen M.
Fahrenbach, Albert C.
Friedman, Douglas C.
Colvin, Michael T.
Coti, Karla K.
Benítez, Diego S.
Olsen, John Carl
Belowich, Matthew E.
Goddard, William Andrew III
Wasielewski, Michael R.
Stoddart, Fraser Fraser Raser
KAUST DepartmentAdvanced Membranes and Porous Materials Research Center
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
End User Computing
Physical Science and Engineering (PSE) Division
Smart Hybrid Materials (SHMs) lab
Online Publication Date2009-12-17
Print Publication Date2010-01
Permanent link to this recordhttp://hdl.handle.net/10754/561443
MetadataShow full item record
AbstractThe tendency for viologen radical cations to dimerize has been harnessed to establish a recognition motif based on their ability to form extremely strong inclusion complexes with cyclobis(paraquat-p-phenylene) in its diradical dicationic redox state. This previously unreported complex involving three bipyridinium cation radicals increases the versatility of host-guest chemistry, extending its practice beyond the traditional reliance on neutral and charged guests and hosts. In particular, transporting the concept of radical dimerization into the field of mechanically interlocked molecules introduces a higher level of control within molecular switches and machines. Herein, we report that bistable and tristable rotaxanes can be switched by altering electrochemical potentials. In a tristable rotaxane composed of a cyclobis(paraquat-p-phenylene) ring and a dumbbell with tetrathiafulvalene, dioxynaphthalene and bipyridinium recognition sites, the position of the ring can be switched. On oxidation, it moves from the tetrathiafulvalene to the dioxynaphthalene, and on reduction, to the bipyridinium radical cation, provided the ring is also reduced simultaneously to the diradical dication. © 2010 Macmillan Publishers Limited. All rights reserved.
CitationTrabolsi, A., Khashab, N., Fahrenbach, A. C., Friedman, D. C., Colvin, M. T., Cotí, K. K., … Stoddart, J. F. (2009). Radically enhanced molecular recognition. Nature Chemistry, 2(1), 42–49. doi:10.1038/nchem.479
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