Khashab, Niveen M.
Fahrenbach, Albert C.
Friedman, Douglas C.
Colvin, Michael T.
Coti, Karla K.
Benítez, Diego S.
Olsen, John Carl
Belowich, Matthew E.
Khatib, Hussam A.
Goddard, William Andrew III
Wasielewski, Michael R.
Stoddart, Fraser Fraser Raser
KAUST DepartmentPhysical Sciences and Engineering (PSE) Division
Chemical Science Program
Advanced Membranes and Porous Materials Research Center
Smart Hybrid Materials (SHMs) lab
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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.
- Solution-phase mechanistic study and solid-state structure of a tris(bipyridinium radical cation) inclusion complex.
- Authors: Fahrenbach AC, Barnes JC, Lanfranchi DA, Li H, Coskun A, Gassensmith JJ, Liu Z, Benítez D, Trabolsi A, Goddard WA 3rd, Elhabiri M, Stoddart JF
- Issue date: 2012 Feb 15
- Design and Synthesis of Nonequilibrium Systems.
- Authors: Cheng C, McGonigal PR, Stoddart JF, Astumian RD
- Issue date: 2015 Sep 22
- Mechanically induced intramolecular electron transfer in a mixed-valence molecular shuttle.
- Authors: Barnes JC, Fahrenbach AC, Dyar SM, Frasconi M, Giesener MA, Zhu Z, Liu Z, Hartlieb KJ, Carmieli R, Wasielewski MR, Stoddart JF
- Issue date: 2012 Jul 17
- Organogel formation by a cholesterol-stoppered bistable rotaxane and its dumbbell precursor.
- Authors: Zhao YL, Aprahamian I, Trabolsi A, Erina N, Stoddart JF
- Issue date: 2008 May 21
- An Electrochromic Tristable Molecular Switch.
- Authors: Sun J, Wu Y, Wang Y, Liu Z, Cheng C, Hartlieb KJ, Wasielewski MR, Stoddart JF
- Issue date: 2015 Oct 28