Galactodendritic porphyrinic conjugates as new biomimetic catalysts for oxidation reactions

Abstract

This work employed [5,10,15,20-tetrakis(pentafluorophenyl)porphyrin] ([H-2(TPPF20)], H(2)P1) as the platform to prepare a tetrasubstituted galactodendritic conjugate porphyrin (H(2)P3). After metalation with excess copper(II) acetate, H(2)P3 afforded a new solid porphyrin material, Cu(4)CuP3S. This work also assessed the ability of the copper(II) complex (CuP3) of H(2)P3 to coordinate with zinc(II) acetate, to yield the new material Zn4CuP3S. UVvisible, Fourier transform infrared, and electron paramagnetic resonance spectroscopies aided full characterization of the synthesized solids. (Z)-Cyclooctene epoxidation under heterogeneous conditions helped to evaluate the catalytic activity of Cu(4)CuP3S and Zn(4)CuP3S. The efficiency of Cu(4)CuP3S in the oxidation of another organic substrate, catechol, was also investigated. According to the results obtained in the heterogeneous process, Cu(4)CuP3S mimicked the activity of cytochrome P-450 and catecholase. In addition, Cu(4)CuP3S was reusable after recovery and reactivation. The data obtained herein were compared with the results achieved for the copper complex (CuP1) of [H-2(TPPF20)] and for CuP3 under homogeneous conditions

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