Arranging Fullerenes through Hydrogen Bonding

作者：Kraft Andreas; Gsaenger Marcel; Beuerle Florian^*

来源：European Journal of Organic Chemistry, 2014, 2014(3): 523-528.

DOI：10.1002/ejoc.201301298

• Fullerenes
• Hydrogen bonds
• Structure elucidation
• Carboxylic acids

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.

• 出版日期2014-1