With the approach presented herein, a large aromatic pi-system is synthesized, which shows extraordinarily high solubility and an effective suppression of aggregation. This was due to a distortion of the aromatic core by bulky tert-butyl groups and the solubilizing effects of alkyl chains in the corona of the aromatic core. Therefore not only the processing and cleaning of the materials with standard laboratory techniques became possible, but moreover the first structure-rich UV/vis and a resolved (1)H NMR spectra for an aromatic system two times larger than hexa-peri-hexabenzocoronene were recorded. The bulk properties in an extruded fiber as well as on the surface showed a columnar self-assembly including a phase in which a homeotropic alignment on a substrate was observed, which turns the material into an interesting candidate for future applications in electronic devices.