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Article: Catenated Cyclodextrins

TitleCatenated Cyclodextrins
Authors
Keywordscatenanes
cyclodextrins
macrocycles
orientational isomerism
Issue Date1995
Citation
Chemistry – A European Journal, 1995, v. 1, n. 1, p. 33-55 How to Cite?
AbstractA novel synthetic approach is described for the construction of catenanes in aqueous solution from a partially methylated cyclodextrin (CD)‐namely, heptakis(2,6‐di‐O‐methyl‐β‐cyclodextrin) (DM‐β‐CD)‐and a range of substrate molecules that contain a hydrophobic central core in the form of a 4,4′‐disubstituted biphenyl unit (usually bitolyl) carrying two hydrophilic polyether side chains terminated by primary amine functions. In water, the amphiphilic catenane precursors form 1:1 complexes with β‐CD and DM‐β‐CD and 2:1 (guest: host) complexes with the larger γ‐CD. Macrocyclizations of the biphenyl‐containing substrates with aromatic diacid chlorides in aqueous solution and in the presence of DM‐β‐CD under Schotten‐Baumann conditions afforded‐in low yields‐a range of [2]‐ and [3]catenanes. When a consitutionally asymmetrical diamine was employed as the substrate, orientational isomers of a [2]catenane were obtained. A [3]catenene incorporating a macrocyclic tetralactam was found to exist as a mixture of head‐to‐head and head‐to‐tail isomers, which could be separated by high pressure liquid chromatography and identified unambiguously by nuclear magnetic resonance spectroscopy. One of the [2]catenanes afforded good single crystals from which the solid state structure was determined by X‐ray crystallography. Other techniques which aided the characterization of these novel compounds included ultraviolet/visible and luminescence spectroscopy, dynamic nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. Generally speaking, the catenated cyclodextrins are soluble in halogenated and aromatic hydrocarbons as well as in hydroxylic solvents. The existence of these new compounds gives us a unique insight into the nature of the noncovalent bonding interactions that cyclodextrins employ in binding substrate molecules. Copyright © 1995 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Persistent Identifierhttp://hdl.handle.net/10722/333223
ISSN
2023 Impact Factor: 3.9
2023 SCImago Journal Rankings: 1.058
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorArmspach, Dominique-
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorBallardini, Roberto-
dc.contributor.authorBalzani, Vincenzo-
dc.contributor.authorGodi, Anna-
dc.contributor.authorMoore, Christopher P.-
dc.contributor.authorProdi, Luca-
dc.contributor.authorSpencer, Neil-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorTolley, Malcolm S.-
dc.contributor.authorWear, Trevor J.-
dc.contributor.authorWilliams, David J.-
dc.contributor.authorStoddart, J. F.-
dc.date.accessioned2023-10-06T05:17:39Z-
dc.date.available2023-10-06T05:17:39Z-
dc.date.issued1995-
dc.identifier.citationChemistry – A European Journal, 1995, v. 1, n. 1, p. 33-55-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/333223-
dc.description.abstractA novel synthetic approach is described for the construction of catenanes in aqueous solution from a partially methylated cyclodextrin (CD)‐namely, heptakis(2,6‐di‐O‐methyl‐β‐cyclodextrin) (DM‐β‐CD)‐and a range of substrate molecules that contain a hydrophobic central core in the form of a 4,4′‐disubstituted biphenyl unit (usually bitolyl) carrying two hydrophilic polyether side chains terminated by primary amine functions. In water, the amphiphilic catenane precursors form 1:1 complexes with β‐CD and DM‐β‐CD and 2:1 (guest: host) complexes with the larger γ‐CD. Macrocyclizations of the biphenyl‐containing substrates with aromatic diacid chlorides in aqueous solution and in the presence of DM‐β‐CD under Schotten‐Baumann conditions afforded‐in low yields‐a range of [2]‐ and [3]catenanes. When a consitutionally asymmetrical diamine was employed as the substrate, orientational isomers of a [2]catenane were obtained. A [3]catenene incorporating a macrocyclic tetralactam was found to exist as a mixture of head‐to‐head and head‐to‐tail isomers, which could be separated by high pressure liquid chromatography and identified unambiguously by nuclear magnetic resonance spectroscopy. One of the [2]catenanes afforded good single crystals from which the solid state structure was determined by X‐ray crystallography. Other techniques which aided the characterization of these novel compounds included ultraviolet/visible and luminescence spectroscopy, dynamic nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. Generally speaking, the catenated cyclodextrins are soluble in halogenated and aromatic hydrocarbons as well as in hydroxylic solvents. The existence of these new compounds gives us a unique insight into the nature of the noncovalent bonding interactions that cyclodextrins employ in binding substrate molecules. Copyright © 1995 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim-
dc.languageeng-
dc.relation.ispartofChemistry – A European Journal-
dc.subjectcatenanes-
dc.subjectcyclodextrins-
dc.subjectmacrocycles-
dc.subjectorientational isomerism-
dc.titleCatenated Cyclodextrins-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.19950010109-
dc.identifier.scopuseid_2-s2.0-84989509373-
dc.identifier.volume1-
dc.identifier.issue1-
dc.identifier.spage33-
dc.identifier.epage55-
dc.identifier.eissn1521-3765-
dc.identifier.isiWOS:A1995RW85700006-

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