4,10-Dibromoanthanthrone as a new building block for p-type, n-type, and ambipolar π-conjugated materials.

New p-type, n-type, and ambipolar molecules were synthesized from commercially available 4,10-dibromoanthanthrone dye. Substitution at the 4,10- and 6,12-positions with different electron-rich and electron-poor units allowed the modulation of the optoelectronic properties of the molecules. A bis(dicyanovinylene)-functionalized compound was also prepared with a reduction potential as low as -50 mV versus Ag(+) with a crystalline two-dimensional lamellar packing arrangement. These characteristics are important prerequisites for air-stable n-type organic field-effect transistor applications.