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An acid-base switchable [2]rotaxane.

Arkadij M Elizarov1, Sheng-Hsien Chiu, J Fraser Stoddart

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, USA.

The Journal of Organic Chemistry
|December 21, 2002
PubMed
Summary
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Chemists created a bistable [2]rotaxane molecule with a movable ring component. Deprotonation of a specific site on the molecule causes the ring to shift between two recognition sites.

Area of Science:

  • Supramolecular Chemistry
  • Molecular Machines
  • Organic Chemistry

Background:

  • Rotaxanes are molecular assemblies with a ring threaded onto an axle.
  • Bistable molecular systems can exist in two distinct states, crucial for molecular switches.
  • Controlling the position of the ring component is key to designing functional molecular devices.

Purpose of the Study:

  • To synthesize and characterize a chemically addressable, bistable [2]rotaxane.
  • To demonstrate controllable movement of the ring component between recognition sites.
  • To investigate the potential of this system as a molecular switch.

Main Methods:

  • Chemical synthesis of a [2]rotaxane incorporating dialkylammonium and bis(pyridinium) recognition sites.
  • Assembly with dibenzo[24]crown-8 (DB24C8) as the ring component.

Related Experiment Videos

  • Analysis using proton nuclear magnetic resonance ((1)H NMR) spectroscopy in CDCl(3) solution.

    • Main Results:

    • Successful assembly of the target [2]rotaxane structure.
    • Demonstration of discrete, reversible ring movement upon deprotonation/reprotonation of the dialkylammonium site.
    • Confirmation of ring translocation from the dialkylammonium site to the bis(pyridinium)ethane site and back.

    Conclusions:

    • The synthesized [2]rotaxane exhibits chemically controllable bistability.
    • This system serves as a functional molecular shuttle, demonstrating discrete positional control.
    • The findings contribute to the development of advanced molecular machines and switches.