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Issue 9, 2019
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Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor

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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[double bond, length as m-dash]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 EZ 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.

Graphical abstract: Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor

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Publication details

The article was received on 14 May 2019, accepted on 16 Jul 2019 and first published on 25 Jul 2019


Article type: Paper
DOI: 10.1039/C9PP00223E
Photochem. Photobiol. Sci., 2019,18, 2259-2269

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    Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor

    I. Schapiro, M. Gueye, M. Paolino, S. Fusi, G. Marchand, S. Haacke, M. E. Martin, M. Huntress, V. P. Vysotskiy, V. Veryazov, J. Léonard and M. Olivucci, Photochem. Photobiol. Sci., 2019, 18, 2259
    DOI: 10.1039/C9PP00223E

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