Pumping a Ring-Sliding Molecular Motion by a Light-Powered Molecular Motor

Designing artificial molecular machines to execute complex mechanical tasks, like coupling rotation and translation to accomplish transmission of motion, continues to provide important challenges. Herein, we demonstrated a novel molecular machine comprising a second-generation light-driven molecular...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-05, Vol.84 (9), p.5790-5802
Main Authors: Yu, Jing-Jing, Zhao, Li-Yang, Shi, Zhao-Tao, Zhang, Qi, London, Gabor, Liang, Wen-Jing, Gao, Chuan, Li, Ming-Ming, Cao, Xiao-Ming, Tian, He, Feringa, Ben L, Qu, Da-Hui
Format: Article
Language:English
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Summary:Designing artificial molecular machines to execute complex mechanical tasks, like coupling rotation and translation to accomplish transmission of motion, continues to provide important challenges. Herein, we demonstrated a novel molecular machine comprising a second-generation light-driven molecular motor and a bistable [1]­rotaxane unit. The molecular motor can rotate successfully even in an interlocked [1]­rotaxane system through a photoinduced cis-to-trans isomerization and a thermal helix inversion, resulting in concomitant transitional motion of the [1]­rotaxane. The transmission process was elucidated via 1H NMR, 1H–1H COSY, HMQC, HMBC, and 2D ROESY NMR spectroscopies, UV–visible absorption spectrum, and density functional theory calculations. This is the first demonstration of a molecular motor to rotate against the appreciably noncovalent interactions between dibenzo-24-crown-8 and N-methyltriazolium moieties comprising the rotaxane unit, showing operational capabilities of molecular motors to perform more complex tasks.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00783