Eumelanin, the black to brown human pigment, is a nano-structured biomaterial that is intimately involved in skin cancer. Known to bind metals and organic compounds, eumelanin has fascinating properties that can be exploited for environmental applications, including the potential photo-degradation of organic pollutants. Structurally, eumelanin is a supramolecular assembly of semiconducting organic nanoparticles derived from mixtures of heterogeneous oligomers of four to eight dihydroxyindole units. We are investigating combinatorial polymerization methods to generate useful eumelanin-like materials for environmental remediation, as well as developing synthetic methods to generate well-defined dihydroxyindole oligomers via the Suzuki reaction. Self-assembly of these oligomers will be studied to address the question of how their molecular structure influences the eumelanin superstructure and resulting properties, both to inform the environmental remediation program and to further elucidate eumelanin's role in skin cancer. This poster will describe our initial results in these endeavors including the development of synthetic eumelanin filters for binding lead (probed by atomic absorption spectroscopy) and successful indole-indole Suzuki couplings.