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The poly(3,4-alkylenedioxypyrrole) family of conjugated polymers (the PXDOPs) shows potential for widespread applications due to their unique electronic and optical properties; however, progress has been limited due to synthetic limitations. We report an optimized synthetic route for a new compound, 3,4-propyledioxypyrrole-N-acetic acid (ProDOP-N-AcOH), which utilizes inexpensive reagents, high yielding steps that require little or no purification (and no chromatography), and which can be converted, using either one or two facile synthetic transformations, to a variety of ester, alcohol, and ether derivatives. The derivatives were electropolymerized onto Pt button working electrodes, and it was found that the polymers containing ester N-pendant groups exhibited a peak monomer oxidation potential 100 mV higher than that of the ethers, suggesting an inductive effect. Polymer E12values were measured to be between −0.24 and 0.01 V and were highly dependent on polymer pendant group structure and electrochemical media. HOMO values measured by DPV were found to be relatively independent of polymer structure. All monomers were electropolymerized onto transparent ITO/glass anodes for the purpose of generating electrochromic films. The predominant electrochromic processes occurred in the near-IR and UV regions, suggesting that they may be candidate materials for electrochromic applications outside the visible spectrum. The polymer containing a hydroxyl pendant group exhibited a brilliant red color upon both light and heavy doping and was transmissive upon dedoping. The strong absorbance in the visible region, the high band gap of 3.40 eV, and the passivating electrochemistry may be due to the formation of a tight polymer network, cross-linked through hydrogen-bonding interactions. [ABSTRACT FROM AUTHOR]