Synthesis, Characterization, And Redox Properties Of Select 1,4-Diazocine-6,11-Diones Towards An Electrochromic Dye-Set

The daily consumption of personalized digital visual information depends on the current purview of electronic-based displays. Present manufacturers utilize modern technologies, such as LCD, OLED, QLED, and electronic ink, or "E Ink," in their devices to display text, pictures, and other forms of media to individual users. However, as modern society continues to rely on the use of digital displays, the demand for low-power alternatives will continue to rise as their application in varying scenarios is realized. Currently, "E Ink" technology continues to grow as the dominant solution in the e-readers and digital signage marketplace, and can even be seen in major retail store fronts. We therefore endeavored to create a novel set of organic molecules to act as redox-active dyes to be implemented in an electrochromic digital display. Based on the hypothesis that 8-membered ring diazocines can be reduced from a nonaromatic, colorless compound to a more conjugated aromatic structure, a set of "Chameleon Compounds" (named for their color-changing behavior) was synthesized and characterized via UV-Vis, NMR, and crystallographic techniques. Further insight into the color-shifting behavior of the model compound's core motif was investigated using DFT-based theoretical calculations and solution-phase electroanalytical techniques, such as cyclic voltammetry, spectroelectrochemistry, and electrochemical impedance spectroscopy. Upon evaluation of the data obtained, a call for further research towards diazocines, and other electrochromic materials, is made.