Metalation of 6,13,20,21-tetrakis-aryl-22H-[14]tribenzotriphyrin(2.1.1) (TriPs) with PdCl2 provides Pd-II-TriP complexes in 45-56% yields. The complexes were characterized by mass spectrometry, and UV-visible absorption, magnetic circular dichroism, and H-1 NMR spectroscopy. A single crystal X-ray analysis reveals that the Pd-II-TriPs adopts a deeply saddled conformation. The palladium(II) ion is coordinated by two pyrrole nitrogen atoms and two chloride ions to form the square-planar coordination environment. The redox properties of the Pd-II-TriPs were studied by cyclic voltammetry. Each compound undergoes one irreversible and two reversible one-electron reductions. There is a marked red-shift of the main spectral bands, relative to those of the free-base TriP ligand, due to a marked relative stabilization of the LUMO upon coordination by PdCl2.