Synthesis, crystal packing, and ambipolar carrier transport property of twisted dibenzo[g,p]chrysenes
A versatile method for the synthesis of dibenzo[g,p]chrysene (DBC) derivatives based on regio- and stereoselective stannyllithiation to diarylacetylenes is described. This method affords a variety of DBCs possessing both electron-donating and electron-withdrawing functional groups. These twisted molecules take brickwork packing structures in single crystals. Thus, ambipolar carrier transport properties with mobility values of up to 10-3 cm2 V-1 s-1 in the amorphous state were achieved. Functional groups on DBC frameworks are considered to increase carrier mobility through the enhancement of intermolecular interactions in the brickwork packing structures. More than bricks and mortar: Dibenzo[g,p]chrysenes possessing a variety of substituents were synthesized. Single-crystal X-ray diffraction studies of these compounds revealed that they possess twisted molecular and brickwork packing structures. These structures are useful for their application to carrier transport materials.