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.