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Article: Molecular Meccano. 2 Self-Assembly of [n]Catenanes

TitleMolecular Meccano. 2 Self-Assembly of [n]Catenanes
Authors
Issue Date1995
Citation
Journal of the American Chemical Society, 1995, v. 117, n. 4, p. 1271-1293 How to Cite?
AbstractThe mutual molecular recognition between different structural components in large rings has led to the template-directed synthesis of a wide range of catenanes composed of from two to five interlocked rings. The molecular self-assembly processes rely upon the recognition between (i) π-electron rich and π-electron deficient aromatic units and (ii) hydrogen bond donors and acceptors, in the different components. In order to increase our knowledge of the factors involved in such molecular self-assembly processes, a homologous series of [2]catenanes has been constructed using macrocyclic polyethers of the bis(p-phenylene)-(3n+4)-crown-n (n = 9—14) type as templates for the formation of the tetracationic cyclophane, cyclobis(paraquat-p-phenylene). Increasing the size of the tetracationic cyclophane to cyclobis(paraquat-4,4’-bitolyl) allows the simultaneous entrapment of two hydroquinone ring-containing macrocyclic polyethers affording a series of [3]catenanes, and one [4]catenane incorporating a cyclic dimer of the expanded cyclophane and three bis(p-pheny!ene)-34-crown-10 components. By analogy, increasing the number of hydroquinone rings in the macrocyclic polyether permits the self-assembly of more than one tetracationic cyclophane around the templates present in the macrocyclic polyether. In this context, the template-directed synthesis of two [3]catenanes, incorporating two cyclobis(paraquat-p-phenylene) components and either (i) tris(p-phenylene)-51-crown-15 or (ii) tetrakis(p-phenylene)-68-crown-20, has been achieved and is reported. A combination of these two approaches has led to the successful self-assembly, in two steps, of a linear [4]catenane, together with a small amount of a [5]catenane. The creation of these intricate molecular compounds lends support to the contention that self-assembly is a viable paradigm for the construction of nanometer-scale molecular architectures incorporating a selection of simple components. © 1995, American Chemical Society. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/332580
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAmabilino, David B.-
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorBrown, Christopher L.-
dc.contributor.authorNewton, Simon P.-
dc.contributor.authorPietraszkiewicz, Marek-
dc.contributor.authorPhilp, Douglas-
dc.contributor.authorRaymo, Francisco M.-
dc.contributor.authorReder, Anatoli S.-
dc.contributor.authorRutland, Marcus T.-
dc.contributor.authorSpencer, Neil-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorCórdova, Emilio-
dc.contributor.authorGodínez, Luis A.-
dc.contributor.authorGoodnow, Timothy T.-
dc.contributor.authorKaifer, Angel E.-
dc.contributor.authorSlawin, Alexandra M.Z.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:12:37Z-
dc.date.available2023-10-06T05:12:37Z-
dc.date.issued1995-
dc.identifier.citationJournal of the American Chemical Society, 1995, v. 117, n. 4, p. 1271-1293-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/332580-
dc.description.abstractThe mutual molecular recognition between different structural components in large rings has led to the template-directed synthesis of a wide range of catenanes composed of from two to five interlocked rings. The molecular self-assembly processes rely upon the recognition between (i) π-electron rich and π-electron deficient aromatic units and (ii) hydrogen bond donors and acceptors, in the different components. In order to increase our knowledge of the factors involved in such molecular self-assembly processes, a homologous series of [2]catenanes has been constructed using macrocyclic polyethers of the bis(p-phenylene)-(3n+4)-crown-n (n = 9—14) type as templates for the formation of the tetracationic cyclophane, cyclobis(paraquat-p-phenylene). Increasing the size of the tetracationic cyclophane to cyclobis(paraquat-4,4’-bitolyl) allows the simultaneous entrapment of two hydroquinone ring-containing macrocyclic polyethers affording a series of [3]catenanes, and one [4]catenane incorporating a cyclic dimer of the expanded cyclophane and three bis(p-pheny!ene)-34-crown-10 components. By analogy, increasing the number of hydroquinone rings in the macrocyclic polyether permits the self-assembly of more than one tetracationic cyclophane around the templates present in the macrocyclic polyether. In this context, the template-directed synthesis of two [3]catenanes, incorporating two cyclobis(paraquat-p-phenylene) components and either (i) tris(p-phenylene)-51-crown-15 or (ii) tetrakis(p-phenylene)-68-crown-20, has been achieved and is reported. A combination of these two approaches has led to the successful self-assembly, in two steps, of a linear [4]catenane, together with a small amount of a [5]catenane. The creation of these intricate molecular compounds lends support to the contention that self-assembly is a viable paradigm for the construction of nanometer-scale molecular architectures incorporating a selection of simple components. © 1995, American Chemical Society. All rights reserved.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleMolecular Meccano. 2 Self-Assembly of [n]Catenanes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja00109a011-
dc.identifier.scopuseid_2-s2.0-1242348325-
dc.identifier.volume117-
dc.identifier.issue4-
dc.identifier.spage1271-
dc.identifier.epage1293-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:A1995QE73000011-

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