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

Igor Schapiro, Moussa Gueye, Marco Paolino, Stefania Fusi, Gabriel Marchand, Stefan Haacke, M. Elena Martin, Mark Huntress, Victor P. Vysotskiy, Valera Veryazov, Jérémie Léonard, Massimo Olivucci*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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 CC 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.

Original languageAmerican English
Pages (from-to)2259-2269
Number of pages11
JournalPhotochemical and Photobiological Sciences
Volume18
Issue number9
DOIs
StatePublished - 2019

Bibliographical note

Publisher Copyright:
© 2019 The Royal Society of Chemistry and Owner Societies.

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