From helical to planar chirality by on-surface chemistry
| Autor: | Andrej Jančařík, Martin Švec, Jana Vacek Chocholoušová, Irena G. Stará, Jaroslav Vacek, Oleksandr Stetsovych, Krzysztof Kosmider, Pavel Jelínek, Ivo Starý, Jiří Rybáček |
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| Rok vydání: | 2016 |
| Předmět: |
General Chemical Engineering
02 engineering and technology General Chemistry Planar chirality 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Crystallography Scanning probe microscopy chemistry.chemical_compound Adsorption Enantiopure drug Helicene chemistry Molecule 0210 nano-technology Chirality (chemistry) Mirror symmetry |
| Zdroj: | Nature chemistry. 9(3) |
| ISSN: | 1755-4349 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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