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Supramolecular Control: Strategic Uses of Carbon Nanohoops, Fluorinated Cyclohexanes and Organophosphates

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In this talk, I will present recent work by our group on the use of supramolecular chemistry to address challenges in synthesis, materials science and systems chemistry. Control over the selectivity of fullerene bis-addition reactions was achieved by encapsulating C60 in a three-shell complex (“Russian Doll”). Thanks to the combined template effects of a self-assembled cage and nanohoop [10]CPP, [1] the C60 trans-3 bis-adduct (Fig. 1 attached) was obtained with ideal chemo-, itero- and regioselectivity, [2] which has recently enabled the synthesis of unprecedented C60 /[10]CPP [2]catenanes. [3] Control over the length of self-assembled nanofibers was achieved by the living supramolecular polymerization of all-cis fluorinated cyclohexanes. [4] The exceptionally high dipole moment of the C6H6F5OR motif gave rise to folded monomers that only polymerized into nanofibers of double-helical topology upon addition of seeds. Control over the persistence of supramolecular assemblies over time was achieved in chemically-fuelled phosphoramidate5 and acylphosphate6 systems. Generating chemically driven steady states from organophosphates is far from trivial, but holds great promise for the creation of chemically-driven molecular machines and transient self-assemblies.

References 1 Y. Xu, M. von Delius, Angew. Chem. Int. Ed. 2020, 59, 559. 2 Y E . Ubasart, O. Borodin, M. von Delius, X. Ribas et al. Nat. Chem. 2021, 13, 420. 3 F. Steudel, G. Pavan, X. Ribas, M. von Delius et al. Angew. Chem. Int. Ed. 2023 pending minor revisions. 4 O. Shyshov, G. M. Pavan, M. von Delius et al. Nat. Commun. 2021, 12, 3134. 5 A. Englert, M. von Delius et al. J. Am. Chem. Soc. 2022, 144, 15266. 6 A. Englert, M. von Delius et al. ChemRXiv 2023, DOI : 10.26434/chemrxiv-2023-5j129

This talk is part of the Materials Chemistry Research Interest Group series.

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