Schiff base oligomer of 2-[(4-chlorophenyl) imino methylene] phenol (CPIMP) was synthesized via oxidative polycondensation reaction in an alkaline medium. Oligomer-metal complex compounds were synthesized from the reactions of oligo-2-[(4-chlorophenyl) imino methylene] phenol (OCPIMP) with Co+2, Ni+2 and Cu+2 ions. The synthesis was achieved by oxidative coupling based on air oxygen as an oxidant. While synthesized Schiff base oligomer was soluble in most common organic solvents, its metal complexes were only soluble in dimethylsulfoxide. Electrochemical HOMO and LUMO band gap (E,) of this oligomer and its metal complexes were found to be between -6.17, -5.28 and -2.91, -3.26 and 3.29 and 2.02 eV, respectively. However optical band gap (E,) of this oligomer and its metal complexes were calculated from their absorption edges and were found between 2.26 and 3.18 eV Conductivity measurements of doped and undoped Schiff base oligomer and its metal complexes were carried out by electrometer at room temperature and atmospheric pressure and were calculated from four-point probe technique. When iodine was used as doping agent, conductivity of this oligomer and its metal complexes were observed to be increased. (c) 2005 Elsevier B.V. All rights reserved.