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Direct organocatalytic enantioselective functionalization of SiOx surfaces
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dc.contributor.author | Parkin, John D. | |
dc.contributor.author | Chisholm, Ross | |
dc.contributor.author | Frost, Aileen B. | |
dc.contributor.author | Bailey, Richard G. | |
dc.contributor.author | Smith, Andrew D. | |
dc.contributor.author | Hähner, Georg | |
dc.date.accessioned | 2019-06-28T23:41:08Z | |
dc.date.available | 2019-06-28T23:41:08Z | |
dc.date.issued | 2018-07-20 | |
dc.identifier | 253279157 | |
dc.identifier | e38d9db3-bd9b-4571-b356-92e2a0aaa566 | |
dc.identifier | 85049996119 | |
dc.identifier | 85049996119 | |
dc.identifier | 000438712600026 | |
dc.identifier.citation | Parkin , 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.201804814 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/46569120 | |
dc.identifier.other | ORCID: /0000-0002-6765-344X/work/60426692 | |
dc.identifier.uri | https://hdl.handle.net/10023/18003 | |
dc.description | We 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.abstract | Traditional 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.extent | 5 | |
dc.format.extent | 742362 | |
dc.format.extent | 985390 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Chirality | en |
dc.subject | Heterogeneous catalysis | en |
dc.subject | Organocatalysis | en |
dc.subject | Scanning probe microscopy | en |
dc.subject | Surface chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | Catalysis | en |
dc.subject | Chemistry(all) | en |
dc.subject | DAS | en |
dc.subject | BDC | en |
dc.subject | R2C | en |
dc.subject.lcc | QD | en |
dc.title | Direct organocatalytic enantioselective functionalization of SiOx surfaces | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/anie.201804814 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-06-29 | |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | RPG-2015-109 | en |
dc.identifier.grantnumber | ep/k000411/1 | en |
dc.identifier.grantnumber | ep/l017008/1 | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | N/A | en |
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