New N,O-containing ligands for the biomimetic copper-catalyzed polymerization of 2,6-dimethylphenol |
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Authors: | Samuel J.A. Guieu, Anna Maria Manotti Lanfredi, Chiara Massera, Laura Dur n Pach n, Patrick Gamez,Jan Reedijk |
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Affiliation: | aLeiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands bUniversity of Parma, Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Parco Area delle Scienze 171A, I-43100 Parma, Italy |
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Abstract: | Poly(2,6-dimethyl-1,4-phenylene ether) (PPE), which is widely used in high-performance engineering plastics, is obtained by the copper-catalyzed oxidative coupling of 2,6-dimethylphenol. The oxidative polymerizations have been carried out in acetonitrile with structurally related [copper-(N,O-containing ligand)] complexes as the catalyst precursor compounds, which appeared to be of great interest for a better understanding of the factors influencing the catalytic activities. Steric effects (influence of a methyl group close to the metal center; ligands 4–7) or electronic effects (imino versus amino group; ligands 4, 5, 8 and 6, 7, 9, respectively) on the polymerization rates have been demonstrated. The use of mono- or dinucleating ligands has strengthened the proposed mechanism of the reaction involving dinuclear active species. |
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Keywords: | Copper catalysis N,O-ligands Phenol oxidative coupling Dinucleating ligands |
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