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Updated: Nov 10, 2025

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Sequential Tether-Directed Synthesis of New [3 : 2 : 1] Hexakis-Adducts of C60 with a Mixed Octahedral Addition
Michael Wachter1, Lisa Jurkiewicz1, Andreas Hirsch1
1Friedrich-Alexander Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany.
Abstract:
A new concept for the regioselective synthesis of [3 : 2 : 1] hexakis-adducts of fullerene C60 was developed. Based on sequential tether-directed remote functionalizations, chiral [3 : 2] pentakis-adducts with an incomplete octahedral addition pattern were synthesized via stepwise cyclopropanation of C60 with suitable macrocyclic tri- and bifunctional cyclomalonate tethers. The four resulting stereoisomers were isolated using chiral HPLC. The corresponding pairs of enantiomers show mirror image behavior in their CD-spectra. The pentakis-adducts served as suitable building blocks for the spatially controlled synthesis of mixed hexakis-adducts. Implementation of functional group-bearing monomalonates afforded octahedral [3 : 2 : 1] hexakis-adducts suitable for the construction of larger molecular and supramolecular fullerene architectures in excellent yield.
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