Olympiadane: Sir Fraser Stoddart’s playful interlocked molecule

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Olympiadane is a mind-blowing, mechanically interlocked structure composed of five interlocking macrocycles (not cyclodextrins, though) that resembles the Olympic rings. It was synthesized and named by Sir Fraser Stoddart and coworkers 30 years before the present Games of the XXXIII Olympiad, held in Paris [1]. The molecule (a [5]catenane which was assembled from eight components in two steps at ambient temperature and pressure) was designed actually without any practical use in mind at the time of the original publication. However, such synthetic approaches have built a whole new field of chemistry — namely, one in which the mechanical bond is a pre-eminent feature of molecular compounds. Professor Stoddart has pioneered the development of the use of molecular recognition and self-assembly processes in template-directed protocols for the syntheses of various two-state mechanically interlocked molecules. It was for this research that he was awarded, along with Jean-Pierre Sauvage (Strasbourg) and Ben Feringa (Groningen), the 2016 Nobel Prize in Chemistry for “The Design and Synthesis of Molecular Machines.” Professor Stoddart is also a very active contributor of cyclodextrin applications, especially Cyclodextrin Metal–Organic Frameworks [2].

[1] Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. (1994). “Olympiadane”. Angew. Chem. Int. Ed. Engl. 33 (12): 1286–1290. doi:10.1002/anie.199412861.

[2] Indranil Roy and J. Fraser Stoddart: Cyclodextrin Metal–Organic Frameworks and Their Applications Accounts of Chemical Research 2021 54 (6), 1440-1453. doi:10.1021/acs.accounts.0c00695

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