Here describe the design, synthesis, and characterization of maleimide-functionalized 3,4-ethylenedioxythiophene (EDOT) monomers, and their corresponding polymers (PEDOT) and copolymers. The maleimide functionality can be readily reacted with a number of other moieties and provides access to a wide variety of potentially useful variants of EDOT. Several novel varieties of functionalized 3,4-ethylenedioxythiophene (EDOT+) monomers were developed and investigated, including EDOT-maleimide, EDOT-maleimide-cholesterol, EDOT-maleimide-adamantane, and EDOT-maleimide-cysteine. The corresponding polymers PEDOT+ were prepared by electrochemical deposition onto metallic electrodes. The physical and chemical properties of the resulting polymer films were characterized using optical and electron microscopy, vibrational spectroscopy, cyclic voltammetry, and electrochemical impedance spectroscopy. Post processing of the PEDOT-maleimide films was done using a electrochemical quartz crystal microbalance with dissipation along with X-ray photoelectron spectroscopy. The biocompatibility of the materials was examined using cell viability testing. These materials make it possible to precisely tailor the electrical and biological properties of poly(alkylthiophenes) that are of considerable current interest for a variety of applications including bioelectronic deivces.