Functionalized pentacene: improved electronic properties from control of solid-state order.

Molecular order has proven to be a significant factor in the performance of devices based on organic semiconductors. Recent studies involving solubilized versus unsubstituted thiophene oligomers have demonstrated that modifications which increase orbital overlap in the solid state can improve device performance by more than an order of magnitude.1 Similar studies on pentacene, a compound which has already demonstrated remarkable potential for device applications,2 have also focused on maximizing orbital overlap by inducing order in films.3 However, these pentacene studies have thus far relied on substrate modification, rather than on pentacene functionalization,4 to achieve the desired goals. We report here the preparation of two functionalized pentacene derivatives, and the effect of this functionalization on both the solid-state ordering and the electronic properties of the resulting crystals.