2019The Journal of Organic ChemistryOpen access

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

Jingjing Yu, Liyang Zhao, Zhao‐Tao Shi, Qi Zhang, Gábor London, Wenjing Liang, Chuan Gao, Mingming Li, Xiaoming Cao, He Tian, Ben L. Feringa, Da‐Hui Qu

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Abstract

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 1 H NMR, 1 H– 1 H 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.

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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 1 H NMR, 1 H– 1 H 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.

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Available abstract

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 1 H NMR, 1 H– 1 H 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.

Key concepts: Molecular motor, Ring (chemistry), Motion (physics), Physics, Control theory (sociology), Materials science, Computer science, Chemistry

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