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Surface chemistry

Single handedness in flatland

Nature Chemistry volume 9, pages 195–196 (2017)Cite this article

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Planar molecules may break mirror symmetry when aligned on a surface, but both right- and left-handed forms will be created. Starting with a single-handed precursor, chiral adsorbates of planar hydrocarbons with a single handedness are formed in on-surface reactions.

It is not unusual for enantiomers of chiral molecules to have different biological activities, and so it can be important for pharmaceutical drugs — or even fragrances — to contain only the enantiomer that exhibits the desired properties. A significant challenge in chemistry, therefore, is the ability to resolve enantiomers or to produce only the required one through enantioselective chemical synthesis. Enantioselective syntheses require a chiral bias, which can be achieved by using readily available chiral starting materials, or chiral catalysts. Heterogeneous catalysed reactions — those that occur on an active solid surface — offer an efficient approach to the formation of chiral products because the catalyst remains in the solid state, which makes recovery of the often-expensive metal catalyst quite straightforward.

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Figure 1: A representation of the principle of chiral heterogeneous catalysis.
Figure 2: On-surface reaction of a dibenzoheptahelicene enantiomer to give a chiral adsorbate with a single handedness.

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Authors and Affiliations

  1. Karl-Heinz Ernst is at Empa, the Swiss Federal Laboratories for Materials Science and Technology, CH-8600 Dübendorf, Switzerland,

    Karl-Heinz Ernst

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  1. Karl-Heinz Ernst
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Correspondence to Karl-Heinz Ernst.

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Ernst, KH. Single handedness in flatland. Nature Chem 9, 195–196 (2017). https://doi.org/10.1038/nchem.2728

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