Our group has recently demonstrated that fullerenes, which are well-known electron acceptors, can also act as electron-pair acceptors: nucleophilic N-heterocyclic carbenes (NHCs) add readily to fullerenes by forming a C-C single bond (Figure A).This adduct formation significantly increases the electron density within the fullerene unit and facilitates its oxidation. The single-point attachment of the fullerene leads to a wheel-like structure. Its rotational flexibility along the NHC-carbene axis has been analyzed by variable-temperature X-ray diffraction (Figure B).

Electronic properties and molecular dynamics of fullerene-carbene adducts

245th National Meeting (2013)

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