Many electronic devices, such as solar cells, light emitting diodes, and transistors depend on inorganic semiconductors.  Inorganic semiconducting materials such as silicon, gallium arsenide, and germanium, require processing techniques that are not only costly but environmentally virulent.  Organic semiconductors have the advantages of simple and low cost processing with mechanical flexibility. Organic materials have been extensively studied for the last 20 years; however, organic radical materials have not been as widely considered.  Molecules incorporating multiple benzotriazinyl radicals (molecular species that have an unpaired electron) have potential electronic applications due to their charge transport properties.  Benzotriazinyl radicals are extremely stable and do not decompose overtime, enabling investigation of their solid state properties.  The material’s properties can be tuned by introducing subtle structural changes at the molecular level. Command over their solid-state packing at the molecular level allows for further control of macroscopic properties.  Herein we disclose a range of novel benzotriazinyl radical materials. These novel materials exhibit interesting electronic properties, desirable for organic semiconductors. Further, the structure-property relationship among these novel materials will be explored to better understand organic radical materials on a fundamental level for future applications.