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American Chemical Society, Inorganic Chemistry, 9(54), p. 4382-4393, 2015

DOI: 10.1021/acs.inorgchem.5b00196

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Galactodendritic Porphyrinic Conjugates as New Biomimetic Catalysts for Oxidation Reactions

This paper is available in a repository.
This paper is available in a repository.

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Abstract

This work employed [5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin] ([H 2 (TPPF 20)], 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 Zn 4 CuP3S. UV− visible, 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 (TPPF 20)] and for CuP3 under homogeneous conditions.