The chirality of molecular structures is paramount in many phenomena, including enantioselective reactions, molecular self-assembly, biological processes and light or electron-spin polarization. Flat prochiral molecules, which are achiral in the gas phase or solution, can exhibit adsorption-induced chirality when deposited on surfaces. The whole array of such molecular adsorbates is naturally racemic as spontaneous global mirror-symmetry breaking is disfavoured. Here we demonstrate a chemical method of obtaining flat prochiral molecules adsorbed on the solid achiral surface in such a way that a specific adsorbate handedness globally dominates. An optically pure helical precursor is flattened in a cascade of on-surface reactions, which enables chirality transfer. The individual reaction products are identified by high-resolution scanning-probe microscopy. The ultimate formation of globally non-racemic assemblies of flat molecules through stereocontrolled on-surface synthesis allows for chirality to be expressed in as yet unexplored types of organic–inorganic chiral interfaces.
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This work was financially supported by a Czech Science Foundation grant (14-29667S, 14-16963J) and by the Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences (RVO: 61388963).
The authors declare no competing financial interests.
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Stetsovych, O., Švec, M., Vacek, J. et al. From helical to planar chirality by on-surface chemistry. Nature Chem 9, 213–218 (2017). https://doi.org/10.1038/nchem.2662
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