Synthetic Molecular Motors: Thermal N Inversion and Directional Photoinduced CN Bond Rotation of Camphorquinone Imines

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...

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Veröffentlicht in:Angewandte Chemie International Edition 2015-11, Vol.54 (48), p.14345-14348
Hauptverfasser: Greb, Lutz, Eichhöfer, Andreas, Lehn, Jean-Marie
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Eichhöfer, Andreas
Lehn, Jean-Marie
description 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. Naturally simple: The thermal and photochemical E/Z isomerization of camphorquinone‐derived imines was studied by a combination of kinetic, structural, and computational methods. Based on these studies of configurational switching in imine derivatives, chiral imines such as camphorquinone‐based imines are proposed to be the simplest example of synthetic molecular motors.
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subjects Computer applications
density functional calculations
Imines
Inversion
Isomerization
Molecular motors
Photochemicals
photochemistry
Rotation
title Synthetic Molecular Motors: Thermal N Inversion and Directional Photoinduced CN Bond Rotation of Camphorquinone Imines
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