Abstract
A molecular motor potentially performing a continuous unidirectional rotation is studied by a multidisciplinary approach including organic synthesis, transient spectroscopy and excited state trajectory calculations. A stereogenic center was introduced in the N-alkylated indanylidene–pyrroline Schiff base framework of a previously investigated light-driven molecular switch in order to achieve the unidirectional C=C rotary motion typical of Feringa’s motor. Here we report that the specific substitution pattern of the designed chiral molecule must critically determine the unidirectional efficiency of the light-induced rotary motion. More specifically, we find that a stereogenic center containing a methyl group and a hydrogen atom as substituents does not create a differential steric effect large enough to fully direct the motion in either the clockwise or counterclockwise direction especially along the E → Z coordinate. However, due to the documented ultrafast character and electronic circular dichroism activity of the investigated system, we find that it provides the basis for development of a novel generation of rotary motors with a biomimetic framework and operating on a picosecond time scale.
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Dedicated to the memory of Professor Ugo Mazzucato of the University of Perugia, Italy.
Electronic supplementary information (ESI) available: Two trajectory movies (echiral.006.md.xyz and zchiral.004.md.xyz). See DOI: 10.1039/c9pp00223e
These authors have equally contributed to the research.
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Schapiro, I., Gueye, M., Paolino, M. et al. Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor. Photochem Photobiol Sci 18, 2259–2269 (2019). https://doi.org/10.1039/c9pp00223e
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DOI: https://doi.org/10.1039/c9pp00223e