Synthesis, Molecular Packing, and Thin Film Transistors of Dibenzo[<i>a</i>,<i>m</i>]rubicenes

We herein report an efficient synthesis of dibenzo­[<i>a</i>,<i>m</i>]­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[<i>a</i>,<i>m</i>]­rubicenes in the solid state can be tuned by the substituting groups, and the silylethynylated derivatives of dibenzo­[<i>a</i>,<i>m</i>]­rubicenes function as p-type organic semiconductors in solution-processed thin film transistors with field effect mobility of up to 1.0 cm<sup>2</sup> V<sup>–1</sup> s<sup>–1</sup>.