This contribution describes the synthesis of a saddle-shaped [8]circulene derivative, namely tetrabenzo[8]circulene, utilizing a combination of Diels-Alder chemistry and palladium-catalyzed arylation reactions. The presentation will detail our motivation for targeting this structure in accordance with Clar's theory of aromatic sextets and the resulting high stability achieved through this approach. Structural data obtained from both DFT calculations (Figure 1A,B) and single crystal x-ray diffraction (Figure 1C,D) will be presented to confirm the existence of localized aromaticity within this highly-contorted, non-planar, polycyclic aromatic hydrocarbon. Furthermore, the propensity of the molecule to pack into a unique 3-dimensional p-stacking network in the solid-state will be demonstrated.

Design, synthesis, and properties of a stable [8]circulene derivative

247th National Meeting (2014)

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