ArticleNature chemistry2023
A catenane that is topologically achiral despite being composed of oriented rings.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Circularly polarized electroluminescence from topologically chiral [2]catenane-based neutral radicals with tunable deep-red emission.Nature communications · 2026Article
- Tangled Tail of Mechanically Interlocked Peptides.Journal of the American Chemical Society · 2026Review
- 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
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Authors and funding
6 authors.
Funding
Abstract
Catenanes-molecules comprising two interlocking rings held together like links in a chain-are topologically non-trivial: a catenane is a topological isomer of its separated rings, but the rings cannot be disconnected without bond scission. Catenanes can exist as topological enantiomers if both rings have directionality conferred by a defined atom sequence, but this has led to the assumption that the stereochemistry of chiral catenanes composed of oriented rings is inherently topological in nature. Here we show that this assumption is incorrect by synthesizing an example that contains the same fundamental stereogenic unit but whose stereochemistry is Euclidean. One ring in this chiral catenane is oriented by the geometry of an exocyclic double rather than determined by atom sequence within the ring. Isomerization of the exocyclic double bond results in racemization of the catenane, confirming that the stereochemistry is not topological in nature. Thus, we can unite the stereochemistry of catenanes with that of their topologically trivial cousins, the rotaxanes, enabling a more unified approach to their discussion.
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37169983What OpenQuestion holds
Registered trials
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