Synthesis, Molecular Packing, and Thin Film Transistors of Dibenzo[a,m]rubicenes

We herein report an efficient synthesis of dibenzo­[a,m]­rubicene, a new member of nonplanar cyclopenta-fused polycyclic aromatic hydrocarbon, and its derivatives. It is found that the conformation and molecular packing of dibenzo­[a,m]­rubicenes in the solid state can be tuned by the substituting groups, and the silylethynylated derivatives of dibenzo­[a,m]­rubicenes function as p-type organic semiconductors in solution-processed thin film transistors with field effect mobility of up to 1.0 cm2 V–1 s–1.