Synthetic Molecular Motors: Thermal N Inversion and Directional Photoinduced CN Bond Rotation of Camphorquinone Imines |
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| Authors: | Dr. Lutz Greb Dr. Andreas Eichhöfer Prof. Dr. Jean‐Marie Lehn |
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| Affiliation: | 1. Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, 8 allée Gaspard Monge, Strasbourg 67000 (France);2. Institut für Nanotechnologie (INT), Karlsruhe Institut für Technologie, Hermann‐von‐Helmholtz‐Platz 1, 76344 Eggenstein‐Leopoldshafen (Germany) |
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| Abstract: | The thermal and photochemical E/Z isomerization of camphorquinone‐derived imines was studied by a combination of kinetic, structural, and computational methods. The thermal isomerization proceeds by linear N inversion, whereas the photoinduced process occurs through C?N bond rotation with preferred directionality as a result of diastereoisomerism. Thereby, these imines are arguably the simplest example of synthetic molecular motors. The generality of the orthogonal trajectories of the thermal and photochemical pathways allows for the postulation that every suitable chiral imine qualifies, in principle, as a molecular motor driven by light or heat. |
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| Keywords: | density functional calculations imines isomerization molecular motors photochemistry |
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