In this study, donor-acceptor type thiophene-perylene-thiophene monomers were synthesized and polymerized by both oxidative polymerization using FeCl3 as catalyst and the electrochemical process. UV-vis, FTIR, H-1 NMR, and elemental analysis techniques were used for structural characterization. Thermal behaviors of these compounds were determined by using TGA system. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels and electrochemical and optical band gap values were calculated by using the results of cyclic voltammetry and UV-vis measurements, respectively. The number-average molecular weight (M-n), weight-average molecular weight (M-n), and polydispersity index (PDI) values of synthesized polymers were determined by size exclusion chromatography. Conductivity measurements of these polymers were carried out by electrometer by using a four-point probe technique. The conductivity was observed to be increased by iodine doping. (C) 2008 Wiley Periodicals, Inc.