Synthesis and Solid‐State Structures of 6,13‐Bis(trifluoromethyl)‐ and 6,13‐Dialkoxypentacene

Abstract

Abstract6,13‐Disubstituted pentacenes were synthesized. Their electrochemical and optical properties, in addition to their packing motifs in the solid state, were determined. Treatment of pentacenequinone with TMSCF3 (Ruppert's reagent) and deprotection led to 6,13‐bis(trifluoromethyl)pentacene‐6,13‐diol, which was aromatized to 6,13‐bis(trifluoromethyl)pentacene by using PBr3. 6,13‐Dialkoxypentacenes were accessible by alkylation of the corresponding hydroquinopentacenes by using dialkyl sulfates. 6,13‐Bis(trifluoromethyl)pentacene and 6,13‐dimethoxypentacene exhibit slipped face‐to‐face π stacking in the solid state, whereas 6,13‐diethoxypentacene forms pairs of π‐stacking molecules in the solid state.