Abstract

Dual-stimuli pseudorotaxane switches: Threaded complexes dissociate upon deprotonation or oxidation. A mechanical bond changes the influence of a ‘speed bump’ on the outcome of a switching event.

Highlights

  • Artificial molecular switches[1] are controlled by external chemical,[2,3] light,[4,5] or electrochemical[6] stimuli

  • The redox-active wheel TTFC8 used in this study was synthesized as reported earlier.[29]

  • The naphthalene-substituted side of TTFC8 only shows a minor elongation in the central CvC bond (1.44 Å compared to 1.41 Å for dibenzo[24]crown-8 ether (DB24C8)), the C–O bond lengths and CvC–O angles are virtually the same (1.37 Å and 115°)

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Summary

Introduction

Artificial molecular switches[1] are controlled by external chemical,[2,3] light,[4,5] or electrochemical[6] stimuli. In mechanically interlocked molecules (MIMs) such as rotaxanes and catenanes, stimuli-induced switching manipulates the interactions of the wheels with their binding sites on the other component in a controlled manner.[7,8] Pseudorotaxanes are non-interlocked, but threaded axle-wheel complexes able to dissociate without breaking a covalent bond.

Results
Conclusion

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