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Direct organocatalytic enantioselective functionalization of SiOx surfaces

Research output: Contribution to journalArticle

Author(s)

John D. Parkin, Ross Chisholm, Aileen B. Frost, Richard G. Bailey, Andrew D. Smith, Georg Hähner

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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.

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Original languageEnglish
Pages (from-to)9377-9381
Number of pages5
JournalAngewandte Chemie International Edition
Volume57
Issue number30
Early online date29 Jun 2018
DOIs
Publication statusPublished - 20 Jul 2018

    Research areas

  • Chirality, Heterogeneous catalysis, Organocatalysis, Scanning probe microscopy, Surface chemistry

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