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)  cm(2)  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.