Catenanes that are chiral owing to the relative orientation of their rings have always been referred to as ‘topologically chiral’. It is now shown that although in specific cases the stereochemistry is a topological property of the structure, the underlying stereogenic unit itself is not inherently topological in nature.
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Jamieson, E. M. G., Modicom, F. & Goldup, S. M. Chirality in rotaxanes and catenanes. Chem. Soc. Rev. 47, 5266–5311 (2018). A review article that provides an intellectual framework for the discussion of stereochemistry in interlocked molecules.
Heard, A. W. & Goldup, S. M. Synthesis of a mechanically planar chiral rotaxane ligand for enantioselective catalysis. Chem 6, 994–1006 (2020). An example of enantioselective catalysis mediated by a mechanically planar chiral rotaxane.
Hirose, K. et al. The asymmetry is derived from mechanical interlocking of achiral axle and achiral ring components – syntheses and properties of optically pure rotaxanes. Symmetry 10, 20 (2018). An example of enantioselective sensing using a mechanically planar chiral rotaxane.
Wang, Y. et al. Multistate circularly polarized luminescence switching through stimuli-induced co-conformation regulations of pyrene-functionalized topologically chiral catenane. Angew. Chem. Int. Ed. 61, e202210542 (2022). An example of circularly polarized luminescence from a mechanically planar chiral catenane.
Zhang, S., Rodríguez-Rubio, A., Saady, A., Tizzard, G. J. & Goldup, S. M. A chiral macrocycle for the stereoselective synthesis of mechanically planar chiral rotaxanes and catenanes. Chem https://doi.org/10.1016/j.chempr.2023.01.009 (2023). Recent methodology that enables both mechanically planar chiral catenanes and rotaxanes to be synthesized using a common approach.
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This is a summary of: Pairault, N. et al. A catenane that is topologically achiral despite being composed of oriented rings. Nat. Chem. https://doi.org/10.1038/s41557-023-01194-1 (2023).
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Not all catenanes with oriented rings are topologically chiral. Nat. Chem. 15, 753–754 (2023). https://doi.org/10.1038/s41557-023-01197-y