Nature utilises self-assembly for the formation of new functioning structures. In an attempt to mimic this process synthetically, attention has been turned to the use of functionalised C60-fullerenes due to their size, interesting photophysical properties and ability to act as electron acceptors. The possibility of modifying these properties further by enabling C60-fullerenes to self-assemble into dimers or ordered arrays makes them interesting building blocks.The synthesis of novel C60-derivatives for a specific application is challenging, due to problems such as low solubility (impeding production of the final product) and an inability to control how key properties are affected by functionalisation. Thus, this integrated approach for designing new C60-derivatives with optimised properties uses computational modelling to identify the most appropriate candidates for synthesis from a larger set of modelled systems, based on a range of properties, calculated using density functional theory.A series of novel C60-fullerene derivatives that have the ability to self-assemble via hydrogen-bonding has been modelled. In addition, synthesis routes for a subset of the derivatives have been developed and the resultant molecules analysed, using a range of techniques. Calculated monomer formation energies in a variety of solvents are compared with the synthesis pathways tested. The thermodynamic stability and preferred orientation of the self-assembled fullerene dimers, which have implications for extended molecular architectures, are explored based on a comparison of the binding energies and electron density distributions of dumbbell and see-saw conformations, as well as experimental results of ordered arrays of fullerenes. The potential for these C60-derivatives to act as light absorbers in solar cells is highlighted based on calculations of the HOMO-LUMO energy gap and solubility. The database of calculated and measured properties for this subset of molecules is the first step to being able to design C60-fullerene derivatives with tailored properties.

Designing self-assembling nanomolecules: An integrated computational and experimental approach

248th National Meeting (2014)

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