This thesis details the synthesis and characterization of N-annulated perylene diimides (N-PDI) for the use in organic electronic devices. Herein, we present a study on the side chain engineering of N-PDI with the goal of altering the self-assembly, solubility and electronics of the N-PDI chromophore. Chapter one introduces the PDI chromophore and various examples from the literature of how side chain engineering has been utilized to impart desired characteristics. Chapter two details the design and synthesis of six N-PDI monomers functionalized with different functional moieties at the pyrrolic N-position. Chapter three delves into the electronic and solid-state characterization of the six N-PDI monomers through the use of UV-Vis spectroscopy, cyclic voltammetry and solubility determination. Finally, in chapter four the N-PDI core is modified with an electron withdrawing cyano group in order to tune the electronics through stabilization of the LUMO electronic level of N-PDI. Three compounds with varying lengths of alkyl chains were synthesized for this study and each was characterized via UV-Vis spectroscopy, cyclic voltammetry and solubility determination.