Radically enhanced molecular recognition
Creators
- Trabolsi, Ali1, 2
- Khashab, Niveen1, 2
- Fahrenbach, Albert C.1
- Friedman, Douglas C.1
- Colvin, Michael T.1
- Cotí, Karla K.1, 3
- Benítez, Diego4
- Tkatchouk, Ekaterina4
- Olsen, John-Carl1, 3
- Belowich, Matthew E.1
- Carmielli, Raanan1
- Khatib, Hussam A.1, 2
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Goddard, William A., III4
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Wasielewski, Michael R.1
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Stoddart, J. Fraser1
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1.
Northwestern University
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2.
King Abdullah University of Science and Technology
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3.
University of California, Los Angeles
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4.
California Institute of Technology
Abstract
The 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 [2]rotaxanes can be switched by altering electrochemical potentials. In a tristable [2]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.
Additional Information
© 2010 Nature Publishing Group. Published online: 17 December 2009. The research was supported by the US Air Force Office of Scientific Research (AFOSR) under their Multidisciplinary University Research Initiative (MURI), award number FA9550-07-1-0534 and by the US National Science Foundation (NSF) under grant numbers CHE-0718928 (M.R.W.) and CHE-0924620 (J.F.S.). M.T.C thanks the Link Foundation for a fellowship. MSC facilities were funded by grants from ARO-DURIP and ONR-DURIP.Attached Files
Supplemental Material - nchem.479-s1.pdf
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nchem.479-s1.pdf
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Additional details
Identifiers
- Eprint ID
- 17198
- DOI
- 10.1038/nchem.479
- Resolver ID
- CaltechAUTHORS:20100115-112029668
Related works
- Describes
- 10.1038/nchem.479 (DOI)
Funding
- Air Force Office of Scientific Research (AFOSR)
- FA9550-07-1-0534
- NSF
- CHE-0718928
- NSF
- CHE-0924620
- Link Foundation
Dates
- Created
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2010-01-28Created from EPrint's datestamp field
- Updated
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2021-11-08Created from EPrint's last_modified field