Synthesis, spectroscopy and QM/MM simulations of a biomimetic ultrafast light-driven molecular motor
(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.
(Less)
- author
- organization
- publishing date
- 2019
- 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
-
- pmid:31347633
- scopus:85072056461
- 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
- 2024-09-04 08:35:42
@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}}, }