β-Disubstituted Pentacene Derivatives: Thin Film Structural Properties and Four-Probe Field Effect Mobility

2,9- and 2,10-diphenylpentacene were synthesized by direct C-H borylation of ketal-protected pentacene, followed by halodeboronation, resolution of the dihalo isomers, Suzuki arylation, cleavage of the ketals and decarbonylation in the solid state. They were studied as main active components in organic field effect transistors (OFETs). Diphenyl substitution of pentacene affects the unit cell dimensions only slightly, preserving a face to edge molecular packing in the first layers of thin films evaporated on SiO₂ substrates. Both isomers self-assemble into nanoribbons during the thin film growth upon vapor deposition. The similarity between the surface induced phases of the 2,9-isomer and unsubstituted pentacene leads to similar 4-probe hole mobilities, i. e. 0.13 cm² V^-1 s^-1 for the former. Whereas 2,9-disubstitution thus does essentially preserve the thin film characteristics of unsubstituted pentacene, 2,10-disubstitution is detrimental to the molecular ordering in the thin films and therefore to the field effect mobility which is only 0.07 cm² V^-1 s^-1. The known strong enhancement of field effect mobility observed upon diphenyl substitution of anthracene can thus not be emulated analogously with pentacene.