A detailed electrochemical characterization of the Ni(II) and Cu(II) complexes of the new ligand, 5,7,12,14-tetraphenyldibenzo[b,i][1,4,8,11]tetraaza[14]annulene, has been carried out in an effort to more fully understand the mechanism of electropolymerization of the tetramethyl analog of the macrocycle. Evidence has been obtained to support a radical mechanism for the electropolymerization of the nickel(II) complex of 5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraaza[14]annulene at the surface of an electrode at 0.97 V. The electrochemical properties of this new macrocyclic ligand system were also investigated. Metal complexes of a series of complexes with varying substituents were prepared and characterized. A linear relationship between the Hammett σ constants of the substituents and redox properties of the complexes was obtained. The redox potentials of the metal complexes of this new ligand were compared to those of the tetramethyl analog of the macrocycle. The new ligand system brings about a shift of the redox potentials by at least 0.3 V (in the positive direction). This shift is large in comparison to the shift in redox potential of tetraphenyl versus tetramethyl porphyrins. In order to determine of the nature of the redox shift is purely an inductive effect, the spin Hamiltonian parameters for the Cu(II) complexes of this new system are compared to that of the tetramethyl analog and it was determined that the inductive effect alone of the phenyl rings controls the large change in redox potentials of the ligand and the metal centers. The UV-Vis spectra of the copper(II) and the nickel(II) complexes, along with the free ligand, are also presented.