Radically enhanced molecular recognition

Handle URI:
http://hdl.handle.net/10754/561443
Title:
Radically enhanced molecular recognition
Authors:
Trabolsi, Ali; Khashab, Niveen M. ( 0000-0003-2728-0666 ) ; Fahrenbach, Albert C.; Friedman, Douglas C.; Colvin, Michael T.; Coti, Karla K.; Benítez, Diego S.; Tkatchouk, Ekaterina; Olsen, John Carl; Belowich, Matthew E.; Carmieli, Raanan; Khatib, Hussam A.; Goddard, William Andrew III; Wasielewski, Michael R.; Stoddart, Fraser Fraser Raser
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. © 2010 Macmillan Publishers Limited. All rights reserved.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Advanced Membranes and Porous Materials Research Center; Smart Hybrid Materials (SHMs) lab
Publisher:
Nature Publishing Group
Journal:
Nature Chemistry
Issue Date:
17-Dec-2009
DOI:
10.1038/nchem.479
PubMed ID:
21124379
Type:
Article
ISSN:
17554330
Appears in Collections:
Articles; Advanced Membranes and Porous Materials Research Center; Physical Sciences and Engineering (PSE) Division; Controlled Release and Delivery Laboratory; Chemical Science Program

Full metadata record

DC FieldValue Language
dc.contributor.authorTrabolsi, Alien
dc.contributor.authorKhashab, Niveen M.en
dc.contributor.authorFahrenbach, Albert C.en
dc.contributor.authorFriedman, Douglas C.en
dc.contributor.authorColvin, Michael T.en
dc.contributor.authorCoti, Karla K.en
dc.contributor.authorBenítez, Diego S.en
dc.contributor.authorTkatchouk, Ekaterinaen
dc.contributor.authorOlsen, John Carlen
dc.contributor.authorBelowich, Matthew E.en
dc.contributor.authorCarmieli, Raananen
dc.contributor.authorKhatib, Hussam A.en
dc.contributor.authorGoddard, William Andrew IIIen
dc.contributor.authorWasielewski, Michael R.en
dc.contributor.authorStoddart, Fraser Fraser Raseren
dc.date.accessioned2015-08-02T09:11:27Zen
dc.date.available2015-08-02T09:11:27Zen
dc.date.issued2009-12-17en
dc.identifier.issn17554330en
dc.identifier.pmid21124379en
dc.identifier.doi10.1038/nchem.479en
dc.identifier.urihttp://hdl.handle.net/10754/561443en
dc.description.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 [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. © 2010 Macmillan Publishers Limited. All rights reserved.en
dc.publisherNature Publishing Groupen
dc.titleRadically enhanced molecular recognitionen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentAdvanced Membranes and Porous Materials Research Centeren
dc.contributor.departmentSmart Hybrid Materials (SHMs) laben
dc.identifier.journalNature Chemistryen
dc.contributor.institutionDepartment of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, United Statesen
dc.contributor.institutionDepartment of Chemistry, Argonne-Northwestern Solar Energy Research (ANSER), Northwestern University, United Statesen
dc.contributor.institutionDepartment of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, United Statesen
dc.contributor.institutionMaterials and Process Simulation Center, California Institute of Technology, Pasadena, CA 91125, United Statesen
kaust.authorTrabolsi, Alien
kaust.authorKhashab, Niveen M.en
kaust.authorKhatib, Hussam A.en

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