ArticleMolecules (Basel, Switzerland)2018
Electrochemically Triggered Co-Conformational Switching in a [2]catenane Comprising a Non-Symmetric Calix[6]arene Wheel and a Two-Station Oriented Macrocycle.
Article in Molecules (Basel, Switzerland), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Stereoselective Synthesis of Topologically Chiral Knots and Links: Synthesis and Applications.Molecules (Basel, Switzerland) · 2026Review
- Synthesis and Characterization of a Two-Station Two-Gate Calix[6]arene-Based [2]Catenane.Molecules (Basel, Switzerland) · 2025Article
- The End of the Beginning of Mechanical Stereochemistry.Accounts of chemical research · 2024Article
- Facial Selectivity in Mechanical Bond Formation: Axially Chiral Enantiomers and Geometric Isomers from a Simple Prochiral Macrocycle.Journal of the American Chemical Society · 2024Article
- The Final Stereogenic Unit of [2]Rotaxanes: Type 2 Geometric Isomers.Journal of the American Chemical Society · 2024Article
- Calix[6]arene-Based [3]Rotaxanes as Prototypes for the Template Synthesis of Molecular Capsules.Molecules (Basel, Switzerland) · 2023Article
- Selective access to constitutionally identical, orientationally isomeric calix[6]arene-based [3]rotaxanes by an active template approach.Chemical science · 2021Article
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Authors and funding
7 authors.
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Abstract
Catenanes with desymmetrized ring components can undergo co-conformational rearrangements upon external stimulation and can form the basis for the development of molecular rotary motors. We describe the design, synthesis and properties of a [2]catenane consisting of a macrocycle-the 'track' ring-endowed with two distinct recognition sites (a bipyridinium and an ammonium) for a calix[6]arene-the 'shuttle' ring. By exploiting the ability of the calixarene to thread appropriate non-symmetric axles with directional selectivity, we assembled an oriented pseudorotaxane and converted it into the corresponding oriented catenane by intramolecular ring closing metathesis. Cyclic voltammetric experiments indicate that the calixarene wheel initially surrounds the bipyridinium site, moves away from it when it is reduced, and returns in the original position upon reoxidation. A comparison with appropriate model compounds shows that the presence of the ammonium station is necessary for the calixarene to leave the reduced bipyridinium site.
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