DOI: 10.1002/anie.202309393 ISSN:

Synthesis of C60/[10]CPP‐Catenanes by Regioselective, Nanocapsule‐Templated Bingel Bis‐Addition

Fabian M. Steudel, Ernest Ubasart, Luigi Leanza, Míriam Pujals, Teodor Parella, Giovanni M. Pavan, Xavi Ribas, Max von Delius
  • General Chemistry
  • Catalysis

The addition of two unsymmetric malonate esters to the Buckminster fullerene C60 can lead to 22 spectroscopically distinguishable isomeric products and therefore represents a formidable synthesis challenge. In this work, we achieve 87% selectivity for the formation of a single (in,out‐trans‐3) isomer by combining three approaches: (i) we use a starting material, in which the two malonates are covalently connected (tether approach); (ii) we form the strong supramolecular complex of C60 with the shape‐persistent [10]CPP macrocycle (template approach) and (iii) we embed this complex further within a self‐assembled nanocapsule (shadow mask approach). Variation of the spacer chain shed light on the limitations of the approach and the ring dynamics in the unusual [2]catenanes were studied in silico with atomistic resolution. This work significantly widens the scope of mechanically interlocked architectures comprising cycloparaphenylenes (CPP).

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