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The well-established exohedral functionalization chemistry of fullerenes, with C 60 as the most prevalent example, provides easy access to a variety of functionalized carbon nanostructures with great structural diversity and unusual spatial orientation of the attached moieties. Therefore, such molecular nanostructures can be identified as promising building blocks for the design and synthesis of three-dimensionally cross-linked molecular architectures giving rise to novel topologies which would not be accessible from other organic building blocks. Within this perspective, we would like to give an overview on recent progress in the design and synthesis of metal–organic hybrid architectures composed of highly functionalized fullerene derivatives as organic connectivity centers and metal ions or clusters as cross-linking nodes. The ultimate goal of these investigations is the precise control of three-dimensional arrangements of fullerene units in the solid state and the implementation of such carbon derivatives as organic connectivity centers into porous functional materials such as metal–organic frameworks (MOFs). [ABSTRACT FROM AUTHOR]

Multivalent organic molecules possessing spherically well-arranged functionalities are promising building blocks for extended molecular networks. [60]Fullerene hexakisadducts are intriguing candidates allowing the organization of up to 12 functional groups within one molecule with high geometric precision. We have synthesized a hexakisadduct bearing 12 glycolic acid side-chains in good yield and with high regioisomeric purity and elucidated its solid-state structure from single crystals grown by the slow diffusion of dichloromethane into a methanol solution. Individual fullerene moieties are arranged in cubic close-packing mode and form an extended network by means of multiple supramolecular interactions. Each molecule forms 24 hydrogen bonds and is connected to six neighbouring fullerene derivatives. The crystal structure showcases the first example of a 3D arrangement of fullerene derivatives by directed hydrogen bonding in the solid state. These findings indicate the high potential of six-fold substituted fullerene derivatives as building blocks for crystalline frameworks. [ABSTRACT FROM AUTHOR]