A new class of nitrogen-containing arene organic semiconductors incorporating fused indolizine units is described. This system, though having a zigzag shape, mimics the electronic properties of its linear analogue pentacene as a result of nitrogen lone pair incorporation into the π-electron system. Solubilizing trialkylsilylethynyl groups were employed to target crystal packing motifs appropriate for field-effect transistor devices. The triethylsilylethynyl derivative yielded hole mobilities of 0.1 cm V s and on/off current ratios of 10.