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Cyclodextrin Rotaxane with Switchable Pirouetting.

Qi-Wei Zhang1, Jaroslav Zajíček1, Bradley D Smith1

  • 1Department of Chemistry and Biochemistry , University of Notre Dame , 236 Nieuwland Science Hall , Notre Dame , Indiana 46556 , United States.

Organic Letters
|March 16, 2018
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Summary

A novel rotaxane featuring two alpha-cyclodextrin wheels was synthesized efficiently. Chemical additives control the movement of these wheels, enabling switchable molecular machinery.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in molecular machines.
  • Controlling the movement of components within rotaxanes is crucial for developing functional molecular devices.

Purpose of the Study:

  • To synthesize a rotaxane with two alpha-cyclodextrin (α-CD) wheels threaded onto an alkyl chain.
  • To achieve switchable control over the pirouetting motion of the α-CD wheels.

Main Methods:

  • A one-pot synthesis was employed at room temperature in water.
  • Spontaneous threading of α-CD onto a 12-carbon alkyl chain was followed by oxime condensation.
  • Boronic acid-containing stoppers were attached, and boronate ester bond formation was used for control.

Main Results:

  • The rotaxane was synthesized in a high yield of 92%.
  • The pirouetting motion of the α-CD wheels was successfully switched 'ON' and 'OFF' using chemical additives.
  • Control was achieved by modulating boronate ester bond formation.

Conclusions:

  • A switchable rotaxane system using α-CD wheels has been developed.
  • This work demonstrates a method for controlling mechanical motion in supramolecular architectures.
  • The findings open avenues for the design of responsive molecular machines.