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Light-controllable cucurbit[7]uril-based molecular shuttle.

Liangliang Zhu¹, Hong Yan, Xiao-Jun Wang

¹Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.

The Journal of Organic Chemistry

|November 2, 2012

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Researchers developed a novel photoresponsive [3]rotaxane molecular machine. This artificial machine uses cucurbit[7]uril rings and azobenzene units to control molecular movement with light.

Area of Science:

Supramolecular Chemistry
Molecular Machines
Photochemistry

Background:

Artificial molecular machines are a key area in modern chemistry.
Rotaxanes are mechanically interlocked molecules with potential applications in nanotechnology.

Purpose of the Study:

To design and construct a novel photoresponsive [3]rotaxane.
To investigate light-induced control over the movement of cucurbit[7]uril rings on a dumbbell component.

Main Methods:

Synthesis of a novel [3]rotaxane incorporating cucurbit[7]uril and azobenzene units.
Photoisomerization studies using UV and visible light.
Characterization using 1H NMR spectroscopy and fluorescence changes.

Main Results:

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A photoresponsive [3]rotaxane with two cucurbit[7]uril rings and an azobenzene dumbbell component was successfully synthesized.
UV light induced trans-to-cis photoisomerization of azobenzene restricted the shuttling of cucurbit[7]uril rings.
Visible light induced cis-to-trans photoisomerization restored the macrocycle's shuttling ability.
The controllable shuttling process was confirmed by NMR spectroscopy and fluorescence monitoring.

Conclusions:

A novel photoresponsive [3]rotaxane was developed, demonstrating light-controllable molecular motion.
This work advances the field of artificial molecular machines with potential for light-responsive materials and devices.