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Tuning the Rotation Rate of Light-Driven Molecular Motors

Bauer, Jurica, Hou, Lili, Kistemaker, Jos C. M., Feringa, Ben L.
Journal of organic chemistry 2014 v.79 no.10 pp. 4446-4455
alkenes, ambient temperature, fluorenes, isomerization, kinesin, moieties, nanotechnology, organic chemistry, ultraviolet-visible spectroscopy
Overcrowded alkenes are among the most promising artificial molecular motors because of their ability to undergo repetitive light-driven unidirectional rotary motion around the central CC bond. The exceptional features of these molecules render them highly useful for a number of applications in nanotechnology. Many of these applications, however, would benefit from higher rotation rates. To this end, a new molecular motor was designed, and the isomerization processes were studied in detail. The new motor comprises a fluorene lower half and a five-membered-ring upper half; the upper-half ring is fused to a p-xylyl moiety and bears a tert-butyl group at the stereogenic center. The kinetics of the thermal isomerization was studied by low-temperature UV–vis spectroscopy as well as by transient absorption spectroscopy at room temperature. These studies revealed that the tert-butyl and p-xylyl groups in the five-membered-ring upper half may be introduced simultaneously in the molecular design to achieve an acceleration of the rotation rate of the molecular motor that is larger than the acceleration obtained by using either one of the two groups individually. Furthermore, the new molecular motor retains unidirectional rotation while showing remarkably high photostationary states.