The synthesis, characterization, and effects of functionalization on the inherent electronic properties and crystal structure of tetrabenzo[8]circulene is described. Over the past year a number of synthetic approaches towards the core structure of [8]circulene have been developed. Our synthetic strategy revolves around a Diels�Alder reaction and a palladium-catalyzed arylation reaction to provide a highly stabilized tetrabenzo[8]circulene structure. Crystal packing forces in the solid-state structure of the parent molecule introduce a unique pinwheel-like conformation (A) in contrast to the predicted saddle-shaped structure (B) derived from DFT calculations � leading away from a proposed columnar stacking motif and towards a more complex 3-dimensional packing arrangement.Employing the synthetic strategy developed for tetrabenzo[8]circulene, new functionalized derivatives of this structure have been developed. These novel compounds differ from the parent molecule in both the solid-state structure and the optoelectronic properties yet retain the high order of stability that was built into the molecule in our original synthesis. The synthetic strategy for functionalizing these structures, the physical and calculated structures, and the electronic properties are presented.

Functionalization of tetrabenzo[8]circulene and its effect on solid-state structure and electronic properties

248th National Meeting (2014)

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