Synthesis and Characterization of Contorted Pentabenzo-Fused Coronenes as Semiconducting Materials

Here, we report the synthesis and characterization of a series of contorted, yet noncentrosymmetrical, polycyclic aromatic hydrocarbons with a pentabenzo-fused coronene as the core framework. The parent pentabenzo­[a,d,g,j,m]­coronene (PBC) compound is shown to exhibit a shifted and rotated type of π–π stacking interactions, which render this series a semiconducting material. Single-crystal-based field-effect transistor devices of PBC exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.42 cm2 V–1 s–1 and an on/off ratio of 105.