Porphyrin light-harvesting systems have recently shown promising solar energy conversion properties in organic photovoltaic devices. Porphyrins, which absorb a broad portion of the solar spectrum and can be easily tuned with peripheral substituents, make them ideal candidates for solar energy conversion research. However, polymers and small molecule systems using porphyrins have been plagued by low hole mobilities. Thiazolothiazole is a fused bicyclic aromatic ring system that has been shown to produce materials with high hole mobilities. In efforts to synthesize porphyrin materials for organic solar cell applications with increased red light sensitivity and hole mobilities, a series of thiazolothiazole-functionalized porphyrins have been modeled computationally and pursued synthetically. Several porphyrin and thiazolothiazole precursors have been synthesized and characterized spectroscopically. Sonogashira cross-coupling of porphyrins and ethynyl containing symmetric thiazolothiazoles for small-molecule and polymer systems have been pursued. Preliminary data of a porphyrin-thiazolothiazole polymer system suggests increased red light sensitivity, characterized by a red-shifted Soret absorption peak relative to the porphyrin starting material, along with an enhanced Q band region.