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dc.contributor.authorParkin, John D.
dc.contributor.authorChisholm, Ross
dc.contributor.authorFrost, Aileen B.
dc.contributor.authorBailey, Richard G.
dc.contributor.authorSmith, Andrew D.
dc.contributor.authorHähner, Georg
dc.date.accessioned2019-06-28T23:41:08Z
dc.date.available2019-06-28T23:41:08Z
dc.date.issued2018-07-20
dc.identifier253279157
dc.identifiere38d9db3-bd9b-4571-b356-92e2a0aaa566
dc.identifier85049996119
dc.identifier85049996119
dc.identifier000438712600026
dc.identifier.citationParkin , J D , Chisholm , R , Frost , A B , Bailey , R G , Smith , A D & Hähner , G 2018 , ' Direct organocatalytic enantioselective functionalization of SiO x surfaces ' , Angewandte Chemie International Edition , vol. 57 , no. 30 , pp. 9377-9381 . https://doi.org/10.1002/anie.201804814en
dc.identifier.issn1433-7851
dc.identifier.otherORCID: /0000-0002-2104-7313/work/46569120
dc.identifier.otherORCID: /0000-0002-6765-344X/work/60426692
dc.identifier.urihttps://hdl.handle.net/10023/18003
dc.descriptionWe thank the Engineering and Physical Sciences Research Council (GH, ADS and JDP acknowledge EP/K000411/1 and EP/L017008/1, and ADS and ABF acknowledge EP/J018139/1) and the Leverhulme Trust (GH and RGB acknowledge RPG2015-109). This work was supported by the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractTraditional methods to prepare chiral surfaces involve either the adsorption of a chiral molecule onto an achiral surface, or adsorption of a species that forms a chiral template creating lattices with long range order. To date only limited alternative strategies to prepare chiral surfaces have been studied. In this manuscript a “bottom-up” approach is developed that allows the preparation of chiral surfaces by direct enantioselective organocatalytic reactions on a functionalized silicon oxide supported self-assembled monolayer (SAM). The efficient catalytic generation of enantiomerically enriched organic surfaces is achieved using a commercially available homogeneous isothiourea catalyst that promotes an enantioselective Michael-lactonization process upon a silicon-oxide supported SAM functionalized with a reactive trifluoroenone group. Chiral atomic force microscopy (χ-AFM) is used to probe the enantiomeric enrichment of the organic films by measurement of the force distributions arising from interaction of d- or l-cysteine-modified AFM tips and the organic films.
dc.format.extent5
dc.format.extent742362
dc.format.extent985390
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
dc.subjectChiralityen
dc.subjectHeterogeneous catalysisen
dc.subjectOrganocatalysisen
dc.subjectScanning probe microscopyen
dc.subjectSurface chemistryen
dc.subjectQD Chemistryen
dc.subjectCatalysisen
dc.subjectChemistry(all)en
dc.subjectDASen
dc.subjectBDCen
dc.subjectR2Cen
dc.subject.lccQDen
dc.titleDirect organocatalytic enantioselective functionalization of SiOx surfacesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.1002/anie.201804814
dc.description.statusPeer revieweden
dc.date.embargoedUntil2019-06-29
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberRPG-2015-109en
dc.identifier.grantnumberep/k000411/1en
dc.identifier.grantnumberep/l017008/1en
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberN/Aen


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