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Triply Threaded [4]Rotaxanes.

Jonathan J Danon1, David A Leigh1,2, Paul R McGonigal2

  • 1School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, United Kingdom.

Journal of the American Chemical Society
|August 30, 2016
PubMed
Summary
This summary is machine-generated.

Researchers synthesized complex [4]rotaxanes with three axles threaded through a single ring using metal template synthesis. Larger macrocycles yielded more complex rotaxanes, demonstrating template control in molecular assembly.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in nanotechnology.
  • Template-directed synthesis is a key strategy for constructing complex molecular architectures.

Purpose of the Study:

  • To synthesize and characterize novel [4]rotaxanes with multiple axles threaded through a single macrocyclic ring.
  • To investigate the influence of macrocycle size on rotaxane formation.

Main Methods:

  • Active metal template synthesis utilizing nickel-catalyzed sp(3)-sp(3) homocouplings.
  • Preparation of alkyl bromide "half-threads" and 2,2':6',2"-terpyridyl macrocycles.
  • Characterization of products using Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry.

Main Results:

  • Successful synthesis of triply threaded [4]rotaxanes in up to 11% yield using 37- and 38-membered macrocycles.
  • No rotaxane products were formed with a 39-membered macrocycle under similar conditions.
  • Doubly threaded [3]rotaxanes were also obtained, indicating potential axle slippage in larger macrocycles.

Conclusions:

  • The size of the macrocycle is critical for the successful template synthesis of highly threaded [4]rotaxanes.
  • The results suggest that larger macrocycles may allow for axle slippage after demetalation, preventing the isolation of less threaded species.