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Article: Bis[2]catenanes and a bis[2]rotaxane - Model compounds for polymers with mechanically interlocked components

TitleBis[2]catenanes and a bis[2]rotaxane - Model compounds for polymers with mechanically interlocked components
Authors
KeywordsCatenanes
Polycatenanes
Polyrotaxanes
Rotaxanes
Self-assembly
Issue Date1996
Citation
Chemistry - A European Journal, 1996, v. 2, n. 1, p. 31-44 How to Cite?
AbstractThe self-assembly of three bis[2]catenanes and a bis[2]rotaxane, by two complementary strategies, is reported. A synthetic route to derivatives of bis-para-phenylene[34]crown-10 (BPP34C10) and 1,5-naphtho-para-phenylene[36]- crown-10 (1/5NPP36C10) containing a fused five-membered ring with a secondary amine function is described. These intermediate N-allylimido macrocyclic polyethers undergo template-directed reactions with 1,1′-[1,4- phenylenebis-(methylene)]bis-4,4′-bipyridinium bis-(hexafluorophosphate) and 1,4-bis(bromomethyl)benzene to produce [2]catenanes containing an N-allyl functionality. The N-allylimido macrocyclic polyethers have also been reduced and deprotected to afford macrocycles possessing a free NH group, which are then linked through a 4,4′-biphenyldicarbonyl spacer to produce bis(crown ether)s, in which each crown ether moiety has two recognition sites. These ditopic BPP34C10 and 1/5NPP36C10 derivatives are capable of sustaining self-assembly reactions at both recognition sites to yield bis[2]catenanes. The self-assembly of a complementary bis[2]catenane, in which two tetracationic cyclophanes are linked together with a flexible hexyl chain, has also been achieved by treating 1,1′-[1,4-phenylene-bis(methylene)]bis-4,4′- bipyridinium bis-(hexafluorophosphate) with a compound containing two linked 1,4-bis(bromomethyl)benzene units in the presence of BPP34C10. Replacing BPP34C10 with a dumbbell-shaped compound containing a linear polyether unit intercepted by a naphthalene residue and terminated by two bulky adamantoyl groups has led to the self-assembly of a bis[2]rotaxane. The X-ray crystal structures of one of the catenanes and its associated crown ether component are reported, together with solution state dynamic 1H NMR spectroscopic studies, showing that there is substantial degree of order characterizing the molecular structure of the catenanes. © VCH Verlagsgesellschaft mbH, 1996.
Persistent Identifierhttp://hdl.handle.net/10722/332315
ISSN
2023 Impact Factor: 3.9
2023 SCImago Journal Rankings: 1.058
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorHuff, Jürgen-
dc.contributor.authorMenzer, Stephan-
dc.contributor.authorParsons, Ian W.-
dc.contributor.authorPreece, Jon A.-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorTolley, Malcolm S.-
dc.contributor.authorWhite, Andrew J.P.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:10:31Z-
dc.date.available2023-10-06T05:10:31Z-
dc.date.issued1996-
dc.identifier.citationChemistry - A European Journal, 1996, v. 2, n. 1, p. 31-44-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/332315-
dc.description.abstractThe self-assembly of three bis[2]catenanes and a bis[2]rotaxane, by two complementary strategies, is reported. A synthetic route to derivatives of bis-para-phenylene[34]crown-10 (BPP34C10) and 1,5-naphtho-para-phenylene[36]- crown-10 (1/5NPP36C10) containing a fused five-membered ring with a secondary amine function is described. These intermediate N-allylimido macrocyclic polyethers undergo template-directed reactions with 1,1′-[1,4- phenylenebis-(methylene)]bis-4,4′-bipyridinium bis-(hexafluorophosphate) and 1,4-bis(bromomethyl)benzene to produce [2]catenanes containing an N-allyl functionality. The N-allylimido macrocyclic polyethers have also been reduced and deprotected to afford macrocycles possessing a free NH group, which are then linked through a 4,4′-biphenyldicarbonyl spacer to produce bis(crown ether)s, in which each crown ether moiety has two recognition sites. These ditopic BPP34C10 and 1/5NPP36C10 derivatives are capable of sustaining self-assembly reactions at both recognition sites to yield bis[2]catenanes. The self-assembly of a complementary bis[2]catenane, in which two tetracationic cyclophanes are linked together with a flexible hexyl chain, has also been achieved by treating 1,1′-[1,4-phenylene-bis(methylene)]bis-4,4′- bipyridinium bis-(hexafluorophosphate) with a compound containing two linked 1,4-bis(bromomethyl)benzene units in the presence of BPP34C10. Replacing BPP34C10 with a dumbbell-shaped compound containing a linear polyether unit intercepted by a naphthalene residue and terminated by two bulky adamantoyl groups has led to the self-assembly of a bis[2]rotaxane. The X-ray crystal structures of one of the catenanes and its associated crown ether component are reported, together with solution state dynamic 1H NMR spectroscopic studies, showing that there is substantial degree of order characterizing the molecular structure of the catenanes. © VCH Verlagsgesellschaft mbH, 1996.-
dc.languageeng-
dc.relation.ispartofChemistry - A European Journal-
dc.subjectCatenanes-
dc.subjectPolycatenanes-
dc.subjectPolyrotaxanes-
dc.subjectRotaxanes-
dc.subjectSelf-assembly-
dc.titleBis[2]catenanes and a bis[2]rotaxane - Model compounds for polymers with mechanically interlocked components-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.19960020109-
dc.identifier.scopuseid_2-s2.0-0002259505-
dc.identifier.volume2-
dc.identifier.issue1-
dc.identifier.spage31-
dc.identifier.epage44-
dc.identifier.eissn1521-3765-
dc.identifier.isiWOS:A1996TV22300005-

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