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    Fullerene Building Blocks with Tailor-Made Solubility and New Insights into Their Hierarchical Self-Assembly

    Year: 2018

    Journal: Chem.-Eur. J., Volume 24, SEP 20, page 14088–14100

    Authors: Perez-Ojeda, M. Eugenia; Wabra, Isabell; Boettcher, Christoph; Hirsch, Andreas

    Organizations: Deutsche Forschungsgemeinschaft (DFG) [SFB 953]; Marie Sklodowska-Curie IF European Actions [747734]; Core Facility BioSupraMol (FU-Berlin)

    Keywords: building-blocks; fullerenes; hydrophobic; hydrophilic behavior; selective functionalization; supramolecular assembly

    Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The synthetic strategy relies on a selective protection with an isoxazoline moiety. The remaining octahedral positions were further functionalized with the desired groups to tune their solubility, yielding mixed [5:1] hexakisadducts. The subsequent deprotection by clean photolytic reaction led to fullerene pentakisadducts with an incomplete octahedral addition pattern, which are useful forerunners for the synthesis of building blocks. Their hydrophobic/hydrophilic behavior has been characterized both in solution and surface through octanol/water partition coefficients (log P) and contact angle measurements. Furthermore, these derivatives can form supramolecular constructions which have been studied by dynamic light scattering (DLS) and cryo-TEM.
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