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dc.contributor.authorChisholm, Ross
dc.contributor.authorParkin, John David
dc.contributor.authorSmith, Andrew David
dc.contributor.authorHähner, Georg
dc.identifier.citationChisholm , R , Parkin , J D , Smith , A D & Hähner , G 2016 , ' Isothiourea-mediated organocatalytic Michael addition-lactonization on a surface : modification of SAMs on silicon oxide substrates ' , Langmuir , vol. 32 , no. 13 , pp. 3130–3138 .
dc.identifier.otherPURE: 241582990
dc.identifier.otherPURE UUID: 103a3f68-0e99-476c-be29-f338d98d4ca5
dc.identifier.otherScopus: 84964327245
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567490
dc.identifier.otherORCID: /0000-0002-6765-344X/work/60426710
dc.identifier.otherWOS: 000373656000006
dc.descriptionFinancial support from the EPSRC (EP/K000411/1 and EP/L017008/1) is gratefully acknowledged.en
dc.description.abstractTailoring the functionality of self-assembled monolayers (SAMs) can be achieved either by depositing prefunctionalized molecules with the appropriate terminal groups or by chemical modification of an existing SAM in situ. The latter approach is particularly advantageous to allow for diversity of surface functionalization from a single SAM and if the incorporation of bulky groups is desired. In the present study an organocatalytic isothiourea-mediated Michael addition–lactonization process analogous to a previously reported study in solution is presented. An achiral isothiourea, 3,4-dihydro-2H-pyrimido[2,1-b]benzothiazole (DHPB), promotes the intermolecular Michael addition–lactonization of a trifluoromethylenone terminated SAM and a variety of arylacetic acids affording C(6)-trifluoromethyldihydropyranones tethered to the surface. X-ray photoelectron spectroscopy, atomic force microscopy, contact angle, and ellipsometry analysis were conducted to confirm the presence of the substituted dihydropyranone. A model study of this approach was also performed in solution to probe the reaction diastereoselectivity as it cannot be measured directly on the surface.
dc.rights(c) 2016 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.en
dc.subjectQD Chemistryen
dc.titleIsothiourea-mediated organocatalytic Michael addition-lactonization on a surface : modification of SAMs on silicon oxide substratesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.description.statusPeer revieweden

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