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Synthetic Molecular Motors: Thermal N Inversion and Directional Photoinduced CN Bond Rotation of Camphorquinone Imines
Author(s) -
Greb Lutz,
Eichhöfer Andreas,
Lehn JeanMarie
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506691
Subject(s) - isomerization , molecular motor , imine , thermal , inversion (geology) , chemistry , kinetic energy , photochemistry , computational chemistry , materials science , physics , nanotechnology , thermodynamics , organic chemistry , quantum mechanics , paleontology , structural basin , biology , catalysis
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 CN 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.