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Article: Amphiphilic bistable rotaxanes

TitleAmphiphilic bistable rotaxanes
Authors
KeywordsElectrochemistry
Molecular devises
Rotaxanes self-assembly
Tetrathiafulvalenes
Issue Date2003
Citation
Chemistry - A European Journal, 2003, v. 9, n. 13, p. 2982-3007 How to Cite?
AbstractTwo molecular shuttles/switches - a slow one and a fast one - in the shape of amphiphilic, bistable [2]rotaxanes have been synthesized and characterized. Both [2]rotaxanes contain a hydrophobic, tetraarylmethane and a hydrophilic, dendritic stopper. They are comprised of two π-electronrich stations - a monopyrrolotetrathiafulvalene unit and a 1,5-dioxynaphthalene moiety - which can act as recognition sites for the tetracationic cyclophane, cyclobis(paraquat-p-phenylene), to reside around. In addition, a model [2]rotaxane, incorporating only a monopyrrolotetrathiafulvalene unit in the rod section of the amphiphilic dumbbell component and cyclobis(paraquat-p-phenylene) as the ring component, has been investigated. The dumbbell-shaped components were constructed using conventional synthetic methodologies to assemble 1) the hydrophobic, tetraaryl-methane stopper and 2) the hydrophilic, dendritic stopper. Next, 3) the hydrophobic stopper was fused to the 1,5-dioxynaphthalene moiety and/or the monopyrrolotetrathiafulvalene unit by appropriate alkylations, followed by 4) attachment of the hydrophilic stopper, once again by alkylation to give the dumbbell-shaped compounds. Finally, 5) the [2]rotaxanes were self-assembled by using the dumbbells as templates for the formation of the encircling cyclobis-(paraquat-p-phenylene) tetracations. The two [2]rotaxanes differ in their arrangement of the π-electron-rich units, one in which the SMe group of the monopyrrolotetrathiafulvalene unit points toward the 1,5-dioxynaphthalene moiety (2.4PF6) and another in which it points away from the 1,5-dioxynaphthalene moiety (3·4PF6). This seemingly small difference in the orientation of the monopyrrolotetrathiafulvalene unit leads to profound changes in the physical properties of these rotaxanes. The bistable [2]rotaxanes were both isolated as brown solids. 1H NMR and UV-visible spectroscopy, and electrochemical investigations, reveal the presence of both possible translational isomers at ambient temperature. As a consequence of the existence of both possible translational isomers in these bistable [2]rotaxanes, they exhibit a complex electrochemical behavior, which is further complicated by the presence of folded.
Persistent Identifierhttp://hdl.handle.net/10722/332541
ISSN
2023 Impact Factor: 3.9
2023 SCImago Journal Rankings: 1.058
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorJeppesen, Jan O.-
dc.contributor.authorNielsen, Kent A.-
dc.contributor.authorPerkins, Julie-
dc.contributor.authorVignon, Scott A.-
dc.contributor.authorDi Fabio, Alberto-
dc.contributor.authorBallardini, Roberto-
dc.contributor.authorGandolfi, M. Teresa-
dc.contributor.authorVenturi, Margherita-
dc.contributor.authorBalzani, Vincenzo-
dc.contributor.authorBecher, Jan-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:12:19Z-
dc.date.available2023-10-06T05:12:19Z-
dc.date.issued2003-
dc.identifier.citationChemistry - A European Journal, 2003, v. 9, n. 13, p. 2982-3007-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/332541-
dc.description.abstractTwo molecular shuttles/switches - a slow one and a fast one - in the shape of amphiphilic, bistable [2]rotaxanes have been synthesized and characterized. Both [2]rotaxanes contain a hydrophobic, tetraarylmethane and a hydrophilic, dendritic stopper. They are comprised of two π-electronrich stations - a monopyrrolotetrathiafulvalene unit and a 1,5-dioxynaphthalene moiety - which can act as recognition sites for the tetracationic cyclophane, cyclobis(paraquat-p-phenylene), to reside around. In addition, a model [2]rotaxane, incorporating only a monopyrrolotetrathiafulvalene unit in the rod section of the amphiphilic dumbbell component and cyclobis(paraquat-p-phenylene) as the ring component, has been investigated. The dumbbell-shaped components were constructed using conventional synthetic methodologies to assemble 1) the hydrophobic, tetraaryl-methane stopper and 2) the hydrophilic, dendritic stopper. Next, 3) the hydrophobic stopper was fused to the 1,5-dioxynaphthalene moiety and/or the monopyrrolotetrathiafulvalene unit by appropriate alkylations, followed by 4) attachment of the hydrophilic stopper, once again by alkylation to give the dumbbell-shaped compounds. Finally, 5) the [2]rotaxanes were self-assembled by using the dumbbells as templates for the formation of the encircling cyclobis-(paraquat-p-phenylene) tetracations. The two [2]rotaxanes differ in their arrangement of the π-electron-rich units, one in which the SMe group of the monopyrrolotetrathiafulvalene unit points toward the 1,5-dioxynaphthalene moiety (2.4PF6) and another in which it points away from the 1,5-dioxynaphthalene moiety (3·4PF6). This seemingly small difference in the orientation of the monopyrrolotetrathiafulvalene unit leads to profound changes in the physical properties of these rotaxanes. The bistable [2]rotaxanes were both isolated as brown solids. 1H NMR and UV-visible spectroscopy, and electrochemical investigations, reveal the presence of both possible translational isomers at ambient temperature. As a consequence of the existence of both possible translational isomers in these bistable [2]rotaxanes, they exhibit a complex electrochemical behavior, which is further complicated by the presence of folded.-
dc.languageeng-
dc.relation.ispartofChemistry - A European Journal-
dc.subjectElectrochemistry-
dc.subjectMolecular devises-
dc.subjectRotaxanes self-assembly-
dc.subjectTetrathiafulvalenes-
dc.titleAmphiphilic bistable rotaxanes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.200204589-
dc.identifier.scopuseid_2-s2.0-0043027831-
dc.identifier.volume9-
dc.identifier.issue13-
dc.identifier.spage2982-
dc.identifier.epage3007-
dc.identifier.isiWOS:000184140700007-

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