Stereochemistry of Molecular Figures-of-Eight

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dc.contributor.authorBoyle, Megan M.ko
dc.contributor.authorGassensmith, Jeremiah J.ko
dc.contributor.authorWhalley, Adam C.ko
dc.contributor.authorForgan, Ross S.ko
dc.contributor.authorSmaldone, Ronald A.ko
dc.contributor.authorHartlieb, Karel J.ko
dc.contributor.authorBlackburn, Anthea K.ko
dc.contributor.authorSauvage, Jean-Pierreko
dc.contributor.authorStoddart, James Fraserko
dc.date.accessioned2013-03-12T09:03:24Z-
dc.date.available2013-03-12T09:03:24Z-
dc.date.created2012-09-27-
dc.date.created2012-09-27-
dc.date.issued2012-08-
dc.identifier.citationCHEMISTRY-A EUROPEAN JOURNAL, v.18, no.33, pp.10312 - 10323-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10203/101849-
dc.description.abstractA trans isomer of a figure-of-eight (Fo8) compound was prepared from an electron-withdrawing cyclobis(paraquat-p-phenylene) derivative carrying trans-disposed azide functions between its two phenylene rings. Copper(I)-catalyzed azidealkyne cycloadditions with a bispropargyl derivative of a polyether chain, interrupted in its midriff by an electron-donating 1,5-dioxynaphthalene unit acting as the template to organize the reactants prior to the onset of two click reactions, afforded the Fo8 compound with Ci symmetry. Exactly the same chemistry is performed on the cis-bisazide of the tetracationic cyclophane to give a Fo8 compound with C2 symmetry. Both of these Fo8 compounds exist as major and very minor conformational isomers in solution. The major conformation in the trans series, which has been characterized by X-ray crystallography, adopts a geometry which maximizes its C?H...O interactions, while maintaining its p...p stacking and C?H...p interactions. Ab initio calculations at the M06L level support the conformational assignments to the major and minor isomers in the trans series. Dynamic 1H NMR spectroscopy, supported by 2D 1H NMR experiments, indicates that the major and minor isomers in both the cis and trans series equilibrate in solution on the 1H NMR timescale rapidly above and slowly below room temperature.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.subjectTEMPLATE-DIRECTED SYNTHESIS-
dc.subjectDENSITY-FUNCTIONAL THEORY-
dc.subjectCHEMICAL TOPOLOGY-
dc.subjectINTERLOCKED MOLECULES-
dc.subjectINCLUSION COMPLEXES-
dc.subjectCLICK CHEMISTRY-
dc.subjectKNOTS-
dc.subjectCATENANES-
dc.subjectRINGS-
dc.subject2>-
dc.subjectCATENANE-
dc.titleStereochemistry of Molecular Figures-of-Eight-
dc.typeArticle-
dc.identifier.wosid000307108100023-
dc.identifier.scopusid2-s2.0-84864599212-
dc.type.rimsART-
dc.citation.volume18-
dc.citation.issue33-
dc.citation.beginningpage10312-
dc.citation.endingpage10323-
dc.citation.publicationnameCHEMISTRY-A EUROPEAN JOURNAL-
dc.identifier.doi10.1002/chem.201202070-
dc.contributor.nonIdAuthorBoyle, Megan M.-
dc.contributor.nonIdAuthorGassensmith, Jeremiah J.-
dc.contributor.nonIdAuthorWhalley, Adam C.-
dc.contributor.nonIdAuthorForgan, Ross S.-
dc.contributor.nonIdAuthorSmaldone, Ronald A.-
dc.contributor.nonIdAuthorHartlieb, Karel J.-
dc.contributor.nonIdAuthorBlackburn, Anthea K.-
dc.contributor.nonIdAuthorSauvage, Jean-Pierre-
dc.type.journalArticleReview-
dc.subject.keywordAuthorclick chemistry-
dc.subject.keywordAuthordonor-acceptor systems-
dc.subject.keywordAuthorrotaxane-
dc.subject.keywordAuthortopology-
dc.subject.keywordAuthorX-ray diffraction-
dc.subject.keywordPlusTEMPLATE-DIRECTED SYNTHESIS-
dc.subject.keywordPlusDENSITY-FUNCTIONAL THEORY-
dc.subject.keywordPlusCHEMICAL TOPOLOGY-
dc.subject.keywordPlusINTERLOCKED MOLECULES-
dc.subject.keywordPlusINCLUSION COMPLEXES-
dc.subject.keywordPlusCLICK CHEMISTRY-
dc.subject.keywordPlusKNOTS-
dc.subject.keywordPlusCATENANES-
dc.subject.keywordPlusRINGS-
dc.subject.keywordPlus2>-
dc.subject.keywordPlusCATENANE-
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