Selective C70 encapsulation by a robust octameric nanospheroid held together by 48 cooperative hydrogen bonds

Grzegorz Markiewicz, Anna Jenczak, Michał Kołodziejski, Julian J. Holstein, Jeremy K. M. Sanders () and Artur R Stefankiewicz ()
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Grzegorz Markiewicz: Laboratory of Functional Nanostructures, Faculty of Chemistry, Adam Mickiewicz University in Poznań
Anna Jenczak: Laboratory of Functional Nanostructures, Faculty of Chemistry, Adam Mickiewicz University in Poznań
Michał Kołodziejski: Laboratory of Functional Nanostructures, Faculty of Chemistry, Adam Mickiewicz University in Poznań
Julian J. Holstein: Faculty of Chemistry and Chemical Biology TU Dortmund
Jeremy K. M. Sanders: University Chemical Laboratory
Artur R Stefankiewicz: Laboratory of Functional Nanostructures, Faculty of Chemistry, Adam Mickiewicz University in Poznań

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract Self-assembly of multiple building blocks via hydrogen bonds into well-defined nanoconstructs with selective binding function remains one of the foremost challenges in supramolecular chemistry. Here, we report the discovery of a enantiopure nanocapsule that is formed through the self-assembly of eight amino acid functionalised molecules in nonpolar solvents through 48 hydrogen bonds. The nanocapsule is remarkably robust, being stable at low and high temperatures, and in the presence of base, presumably due to the co-operative geometry of the hydrogen bonding motif. Thanks to small pore sizes, large internal cavity and sufficient dynamicity, the nanocapsule is able to recognize and encapsulate large aromatic guests such as fullerenes C60 and C70. The structural and electronic complementary between the host and C70 leads to its preferential and selective binding from a mixture of C60 and C70.

Date: 2017
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DOI: 10.1038/ncomms15109

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