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

Schapiro, Igor ; Gueye, Moussa ; Paolino, Marco ; Fusi, Stefania ; Marchand, Gabriel ; Haacke, Stefan ; Martin, M. Elena ; Huntress, Mark ; Vysotskiy, Victor P. LU and Veryazov, Valera LU orcid , et al. (2019) In Photochemical and Photobiological Sciences 18(9). p.2259-2269
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... (More)

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 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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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Photochemical and Photobiological Sciences
volume
18
issue
9
pages
11 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85072056461
  • pmid:31347633
ISSN
1474-9092
DOI
10.1039/c9pp00223e
language
English
LU publication?
yes
id
0b9d0834-deda-4fea-8898-a5f2ada53c4f
date added to LUP
2019-09-17 14:32:58
date last changed
2024-05-15 20:34:10
@article{0b9d0834-deda-4fea-8898-a5f2ada53c4f,
  abstract     = {{<p>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 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.</p>}},
  author       = {{Schapiro, Igor and Gueye, Moussa and Paolino, Marco and Fusi, Stefania and Marchand, Gabriel and Haacke, Stefan and Martin, M. Elena and Huntress, Mark and Vysotskiy, Victor P. and Veryazov, Valera and Léonard, Jérémie and Olivucci, Massimo}},
  issn         = {{1474-9092}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{2259--2269}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Photochemical and Photobiological Sciences}},
  title        = {{Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor}},
  url          = {{http://dx.doi.org/10.1039/c9pp00223e}},
  doi          = {{10.1039/c9pp00223e}},
  volume       = {{18}},
  year         = {{2019}},
}