Primary-Colored Electrochromism of 1,4-Phenylenediamines

Ten 1,4-phenylenediamines were studied using electrochemical techniques (voltammetry and controlled potential electrolysis) and UV/Vis spectroscopy under ambient conditions. All compounds demonstrated vibrant color changes upon one-electron electrochemical oxidation in acetonitrile, with most displaying a primary color (red, green, blue, or yellow) in their oxidized state. The four electrochromes that exhibited the most intense color changes were examined by using a gold micromesh electrode laminated inside a polymer film to determine their electrochromic properties in solution (contrast ratios, chromatic efficiency, and cycle life). Their colored radical cations were also characterized by electron paramagnetic resonance spectroscopy as well as monitored for color retention over a period of 24 hours. Notably, only relatively small potentials were required to initiate the chromatic changes and the oxidized forms of the compounds were long-lived and unaffected by atmospheric oxygen or moisture.