Thiophene-based molecular imprinted polymers (MIPs) are being investigated for their potential application as chemical sensors. We hypothesize that the sensors will have important applications for the detection and monitoring of environmentally hazardous chemicals. A desirable MIP will be comprised of monomers that are readily synthesized, amiable to derivatization, and easily polymerized. Furthermore, the polymer must have conductive properties that will allow for detection of a quantifiable electrochemical signal upon binding of the target analyte. Although a number of analytes will be studied, our initial investigations have examined the organic compound benzene as the target of interest. To accomplish this, a molecular imprint that resembles the structural characteristics of benzene and similar aromatics has been appended to thiophene and cyclopentadithiophene. A total of six monomers have been synthesized and are being studied. Conjugation, tether length, and rigidity are among the variables being investigated as part of the optimization process. Our syntheses, polymerization conditions, polymer characterization, and polymer electrochemical properties will be discussed.