Organic semiconductors are useful for several industrially relevant, cutting edge products, including display technologies (LED), photovoltaic cells, sensors, thermoelectric energy materials, memory devices and energy storing batteries. They possess several advantages over inorganic counterparts because their chemical, physical and charge transport properties can be readily tuned in a predictable manner through standard organic chemistry transformations. Most importantly, organic semiconducting materials offer the opportunity to be processed via solution deposition techniques, opening the door to low cost, high throughput production methods and integration into a diverse array of products.

This dissertation focuses on efforts to enhance sustainability in organic semiconductors through a molecular design and synthetic approach. Chapter one details our research to combine the attractive properties of conjugated polyelectrolytes and narrow band gap conjugated polymers to generate narrow band gap conjugated polyelectrolytes, which were amongst the first examples of molecules combining these structural features, and discusses some of the interesting modifications in optoelectronic properties that were observed. Chapter two describes a modular D1-A-D2-A-D 1 small molecule semiconductor architecture and the structure/property relationships of thirteen chromophores that showcase the utility of this architecture to tailor properties for specific applications. Chapter three extends the investigation of D1-A-D2-A-D1 small molecules and identifies two structural features that enable solution processing from environmentally friendly media, including ethyl acetate and water.