First reported in 1963, metal dithiolenes are a class of metal complexes in which alkenyl units bridge two dithiolate donors to provide bidentate ligands surrounding a metal core. A subset of these complexes incorporates the alkenyl unit into an aromatic ring like benzene or thiophene to provide further electronic delocalization. Such aryl-fused metal dithiolenes are attractive as components of conjugated materials due to strong π-electron delocalization through both dithiolene ligands and the square-planar metal center. The presence of a low-energy intervalence charge transfer (IVCT) band provides the potential for NIR absorption, which is unique and coveted for materials such as dyes and liquid crystal matrices. In addition, tuning of the electronic and photonic properties can be accomplished via synthetic modification in the same manner as conventional conjugated materials. The Rasmussen group has previously developed planar, metal thiophenedithiolenes as new building blocks for conjugated materials. Inserting these units into conjugated backbones via the coupling of additional conjugated units to the exterior of the metal thiophenedithiolene core allows greater electron delocalization across the molecule and a red-shift of the IVCT band into the NIR. While a promising class of materials, metal thiophenedithiolenes are very electron-rich and suffer from a high HOMO energy level, which limits environmental stability and applications to electronic devices. Current efforts are focusing on the development of a new family of dithiolene analogues based on the thiazole heterocycle. The thiazole ring is more electron-deficient than thiophene and has been theorized to stabilize the HOMO without significantly shifting the unique NIR absorbance. Using previously developed techniques, two thiazole-based analogues were synthesized and characterized via UV-vis-NIR spectroscopy, cyclic voltammetry, and X-ray crystallography. The data show that the addition of nitrogen into the nickel thiophenedithiolene core stabilizes the HOMO while preserving the optical properties of the current thiophene analogues.