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Rigid three-dimensional (3D) polycyclic aromatic hydrocarbons (PAHs), in particular 3D nanographenes, have garnered interest due to their potential use in semiconductor applications and as models to study through-bond and through-space electronic interactions. Herein we report the development of a novel 3D-symmetric rylene imide building block, triperyleno[3,3,3]propellane triimides (), that possesses three perylene monoimide subunits fused on a propellane. This building block shows several promising characteristics, including high solubility, large π-surfaces, electron-accepting capabilities, and a variety of reactive sites. Further, the building block is compatible with different reactions to readily yield quasi-  symmetric nanostructures (, , and ) of varied chemistries. For the 3D nanostructures we observed red-shift absorption maxima and amplification of the absorption coefficients when compared to the individual subunits, indicating intramolecular electronic coupling among the subunits. In addition, the microplates of  exhibit comparable mobilities in different directions in the range of 10 cm V s, despite the rather limited intermolecular overlap of the π-conjugated moieties. These findings demonstrate that these quasi-  symmetric rylene imides have potential as 3D nanostructures for a range of materials applications, including in organic electronic devices.

Triperyleno[3,3,3]propellane triimides: achieving a new generation of quasi-D3h symmetric nanostructures in organic electronics

Triperyleno[3,3,3]propellane triimides: achieving a new generation of quasi-D_3h symmetric nanostructures in organic electronics