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dc.contributor.authorSenge, Mathias
dc.date.accessioned2021-02-23T12:06:22Z
dc.date.available2021-02-23T12:06:22Z
dc.date.issued2020
dc.date.submitted2020en
dc.identifier.citationGrover, N., Locke. G.M., Flanagan, K. J., Beh, M.H.R., Thompson, A., Senge, M.O., 'Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds', Chemistry - A European Journal, 2020, 26, 11, 2405-2416en
dc.identifier.otherY
dc.identifier.urihttp://hdl.handle.net/2262/95305
dc.description.abstractConnecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally diverse multi‐porphyrin arrays that incorporate the non‐traditional rigid linker groups cubane and bicyclo[1.1.1]pentane (BCP) is described. A robust, reliable, and versatile synthetic procedure was employed to access porphyrin‐cubane/BCP‐porphyrin arrays, representing the largest non‐polymeric structures available for cubane/BCP derivatives. These reactions demonstrate considerable substrate scope, from utilization of small phenyl moieties to large porphyrin rings, with varying lengths and different angles. To control conformational flexibility, amide bonds were introduced between the bridgehead carbon of BCP/cubane and the porphyrin rings. Through varying the orientation of the substituents around the amide bond of cubane/BCP, different intermolecular interactions were identified through single crystal X‐ray analysis. These studies revealed non‐covalent interactions that are the first‐of‐their‐kind including a unique iodine‐oxygen interaction between cubane units. These supramolecular architectures indicate the possibility to mimic a protein structure due to the sp3 rigid scaffolds (BCP or cubane) that exhibit the essential conformational space for protein function while simultaneously providing amide bonds for molecular recognitionen
dc.format.extent2405-2416en
dc.language.isoenen
dc.relation.ispartofseriesChemistry - A European Journal;
dc.relation.ispartofseries26;
dc.relation.ispartofseries11;
dc.rightsYen
dc.subjectPorphyrin Unitsen
dc.subjectNon‐Traditional Rigid Scaffoldsen
dc.subjectBicyclo[1.1.1]pentaneen
dc.subjectCubaneen
dc.subjectMolecular tweezersen
dc.subjectPorphyrin arraysen
dc.subjectSupramolecular chemistryen
dc.titleBridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffoldsen
dc.typeJournal Articleen
dc.contributor.sponsorScience Foundation Irelanden
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/sengem
dc.identifier.rssinternalid224223
dc.identifier.doihttp://dx.doi.org/10.1002/chem.201904199
dc.rights.ecaccessrightsopenAccess
dc.contributor.sponsorGrantNumberIvP 13/IA/1894en


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