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dc.contributor.authorMaugeri, Leonardo
dc.contributor.authorLebl, Tomas
dc.contributor.authorCordes, David Bradford
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorPhilp, Douglas
dc.date.accessioned2018-01-21T00:31:49Z
dc.date.available2018-01-21T00:31:49Z
dc.date.issued2017-02-17
dc.identifier249500204
dc.identifiera9a7e39d-f9e4-4eaa-a837-90f350e40500
dc.identifier85013155683
dc.identifier000394736000015
dc.identifier.citationMaugeri , L , Lebl , T , Cordes , D B , Slawin , A M Z & Philp , D 2017 , ' Cooperative binding in a phosphine oxide-based halogen bonded dimer drives supramolecular oligomerization ' , The Journal of Organic Chemistry , vol. 82 , no. 4 , pp. 1986–1995 . https://doi.org/10.1021/acs.joc.6b02822en
dc.identifier.issn0022-3263
dc.identifier.otherORCID: /0000-0002-0269-3221/work/48131697
dc.identifier.otherORCID: /0000-0002-5366-9168/work/32706766
dc.identifier.otherORCID: /0000-0002-9198-4302/work/56639220
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861338
dc.identifier.urihttps://hdl.handle.net/10023/12545
dc.descriptionThe authors thank the Marie Curie Initial Training Network on Replication and Adaption in Networks (ReAd) for financial support (early stage researcher funding to L.M.).en
dc.description.abstractTriphenylphosphine oxide forms halogen-bonded (XB) complexes with pentafluoroiodobenzene and a 1,4-diaryl-5-iodotriazole. The stability of these complexes is assessed computationally and by 31P NMR spectroscopy in d8-toluene solution, where both complexes are weakly associated. This knowledge is applied to the design and synthesis of two self-complementary phosphine oxide-iodotriazole hybrids that incorporate a phosphine oxide XB acceptor and a 1,4-diphenyl-5-iodotriazole XB donor within the same molecule. The self-complementary design of these modules facilitates their assembly in both d8-toluene and, surprisingly, d2-DCM into dimers, with significant stabilities, through the formation of halogen-bonded diads. The stability of these assemblies is a result of significant levels of cooperative binding that is present in both solvents. The connection of two of these hybrid units together, using a flexible spacer, facilitates the aggregation of these modules in d2-DCM solution, through halogen bonding, forming oligomeric assemblies.
dc.format.extent10
dc.format.extent7099605
dc.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleCooperative binding in a phosphine oxide-based halogen bonded dimer drives supramolecular oligomerizationen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doi10.1021/acs.joc.6b02822
dc.description.statusPeer revieweden
dc.date.embargoedUntil2018-01-20
dc.identifier.urlhttp://pubs.acs.org/doi/suppl/10.1021/acs.joc.6b02822en
dc.identifier.grantnumber289723en


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