Our goal was to explore the properties and behavior of a cross-conjugated pentacene fused porphyrin system and its use as a molecular “on-off” switch. The use of a pentacenequinone bridging point allows for considerable extension of the aromatic system, increasing the system’s desirable properties. Upon excitation, this system can potentially form a diradical system, which has been seen in similar systems. These similar systems have shown that once excited, the diradicals can increase the effects of conjugation and the ability of the pi systems to interact with each other. This property is the basis of our research and as such, the synthesis of 7,8-dibromo-5,10,15,20-tetrakis(4-isopropylphenyl)porphyrin was necessary to continue the exploration of a pentacene-fused cross-conjugated system.