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Nested nanostructures direct fullerene functionalization

Supramolecular structure suggests a strategy for making single isomers of buckyball bis-adducts

by Bethany Halford
April 17, 2021 | A version of this story appeared in Volume 99, Issue 14

A buckyball surrounded by a nanohoop encased in a molecular cage.
Credit: Ernest Ubasart

For years, chemists have been kicking around plenty of ideas for adding groups to soccer ball–shaped C60. Some of the work has led to functionalized fullerenes that have applications in solar cells, for example. The challenge is that most syntheses produce a multitude of isomers that have to be painstakingly separated. Max von Delius’s group at Ulm University had been trying to make bis-adducts of C60—fullerenes with substituents added in just two locations—by surrounding the buckyballs with nanohoops. Xavi Ribas’s group at the University of Girona was working on a similar strategy with nanocages. When the chemists saw each other’s work during a scientific meeting, they decided to combine their efforts. Together, their teams made a molecular matryoshka, named for the Russian nesting dolls (Nat. Chem. 2021, DOI: 10.1038/s41557-021-00658-6). The supramolecular structure features a buckyball surrounded by a nanohoop, which is encased in a cage (shown). The structure limits reagents’ access to the fullerene. A cyclopropanation reaction produced a single isomer of a bis-adduct in 90% yield. The same reaction with naked buckyballs gives more than a dozen isomers. The authors suggest that the strategy could be used generally for making bis-adducts of buckyballs, although they note that streamlined reagents work better with the assembly than bulky ones.


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