1. Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor.
- Author
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Schapiro, Igor, Gueye, Moussa, Paolino, Marco, Fusi, Stefania, Marchand, Gabriel, Haacke, Stefan, Martin, M. Elena, Huntress, Mark, Vysotskiy, Victor P., Veryazov, Valera, Léonard, Jérémie, and Olivucci, Massimo
- Subjects
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MOLECULAR motor proteins , *SPECTRUM analysis , *SCHIFF bases , *CIRCULAR dichroism , *ORGANIC synthesis , *MOLECULAR switches - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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