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Force-Induced Ring Flipping in a Threaded Pillar[5]Arene.

Lei Chen1, Tomás Nicolás-García1, Igor Rončević1

  • 1Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

Angewandte Chemie (International Ed. in English)
|August 26, 2025
PubMed
Summary
This summary is machine-generated.

Mechanical force enables control over pillar[5]arene conformations, accessing challenging structures. This controlled flipping acts as a mechanical damper, enhancing material toughness.

Keywords:
FlippingMechanical forcePillar[5]areneRotaxaneUnstoppering

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Mechanochemistry

Background:

  • Pillar[n]arenes are versatile macrocycles with unique host-guest properties and planar chirality due to their specific conformations.
  • Controlling intermediate conformations, like a single inverted ring, in pillar[n]arenes is synthetically challenging.

Purpose of the Study:

  • To investigate the use of mechanical force to control pillar[n]arene conformations.
  • To explore the force-induced flipping of a single hydroquinone ring in pillar[5]arene-based rotaxanes.
  • To understand the influence of rotaxane components and pillararene substituents on this flipping motion.

Main Methods:

  • Utilized mechanochemistry to apply controlled force to pillar[5]arene-based rotaxanes.
  • Investigated the effect of stopper and axle design on the flipping dynamics.
  • Analyzed the impact of pillar[5]arene substituents on the conformational changes.

Main Results:

  • Demonstrated force-induced flipping of a single hydroquinone ring in pillar[5]arene rotaxanes, accessing elusive conformations.
  • Showcased control over this flipping motion by varying rotaxane architecture and pillararene substituents.
  • Identified the flipping behavior as a mechanical damping mechanism that slows polymer scission under tension.

Conclusions:

  • Mechanical force provides a novel route to synthetically challenging supramolecular architectures.
  • The force-induced flipping mechanism acts as a mechanical damper, offering potential for creating tougher materials.