A series of novel functionalised dumbbell‐shaped bifullerenes in which two [5.0] pentakis‐adducts of C60 are covalently connected by cyclic bismalonates were synthesised. These dimeric compounds, carrying various combinations of hydrophilic and hydrophobic addends, self‐assemble in aqueous solution towards supramolecular architectures of different structural complexity as observed by cryogenic transmission electron microscopy (cryo‐TEM). The detailed analysis of the image data revealed an unprecedented hierarchical aggregation behaviour. Whereas completely hydrophilic substituted bifullerenes formed profoundly monodisperse populations of small oligomeric elementary micelles consisting of only three or four bifullerene molecules in a supposedly bent conformation, their amphiphilic equivalents underwent a hierarchical two‐step assembly process towards larger spherical and even rod‐like structures. The data suggest that the hierarchical assembly process is driven by hydrophobic interactions of preformed tetrameric elementary micelles.
A novel polycationic [60]fullerene hexakis-adduct has been synthesized and investigated by electrospray ionization and tandem mass spectrometry. The polycationic ligand system comprises 12 pre-formed positive charges, compensated in the neutral molecule by bromide anions. Stable quasi-molecular cations were obtained through the release of the anionic counter ions covering a charge-state envelope from 3+
A method for the sequential fullerenylation of bis‐malonates with parent C60 and C2v‐symmetric pentakis‐adducts is reported. This approach relies on the finding that (a) chloromalonates can be used for the nucleophilic cyclopropanation of [6,6] double bonds of C60, and (b) chloromalonates, in contrast to bromomalonates, do not undergo base‐catalyzed halogen exchange reactions. For the proof of concept, we synthesized a heptafullerene by using a divergent approach based on a fullerene hexakis‐adduct with six bis‐malonate addends in octahedral positions, each of which is suitable for an additional cyclopropanation of a fullerene building block.
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