Isoindigo-based compounds have attracted attention for their application in both organic field effect transistors (OFETs) and organic photovoltaic devices (OPVs). Herein, the synthesis of an expanded, highly planar, ring-fused bis-isoindigo compound will be presented. The enforced planarity of the ring-fused structure lowers the band gap of this n-type organic semiconductor, such that it absorbs well into the near-infrared region of the spectrum. The modular synthetic approach allows for easy incorporation of halogen atoms that can be used to cross-couple organic donor groups (e.g., bithiophene) to yield donor-acceptor compounds. The narrow band gap of the resulting compounds makes them interesting materials for OPV applications; their highly planar geometry lends itself to aggregation in the solid state, making them potentially useful as semiconducting materials in OFETs. The synthesis of both bis-isoindigo and a bis-isoindigo-based donor-acceptor compound will be discussed, along with their performance in optoelectronic devices.