Recent efforts in our group to apply molecular motors in various areas have prompted us to explore the possibility to modify the stereogenic centre responsible for unidirectionality of the rotary motion into a quaternary stereocentre. We envisioned that such change would account for increased chemical and photochemical stability and potentially allow for asymmetric synthesis of the motor in order to access a single enantiomer for the purpose of asymmetric catalysis.1Therefore, a fluorine atom has been installed at the stereogenic centre to preserve sufficient steric difference between the two substituents, which is crucial for unidirectionality of the molecular motors. Influence of this structural change on the motor function has been studied. It has been found that this relatively minor change results in dramatic increase of the thermal helix inversion barrier compared to the original motors.Eventually, these findings have been applied to the developement of the next generation of meso- molecular motors with two units rotating in the same direction governed by a pseudoasymmetric centre.1. Wang, J.; Feringa, B. L.: Science, 2011  , 331, 1429-1432

Fluorine substituted motors with a quaternary stereogenic centre

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.