2,7,11,16‐Tetra‐tert‐Butyl Tetraindenopyrene Revisited by an “Inverse” Synthetic Approach

A new synthetic route to tetraindenopyrene (TIP)—a bowl‐shaped cut‐out structure of C(70)—is reported. The key step in this approach is a fourfold palladium‐catalyzed C−H activation that increases the yield more than 50 times in comparison to the approach originally described by Scott and co‐workers. Besides examination of its optoelectronic properties and study of its aggregation in solution, TIP was also re‐investigated by dispersion‐corrected DFT methods, which showed that dispersion interactions significantly increase the bowl‐to‐bowl inversion barrier. Furthermore, TIP was used as a semiconductor in p‐channel thin‐film transistors (TFTs).