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Abstract
Oxidative polymerization of 2,6-disubstituted phenols has been performed by using iron(III)-salen complex and hydrogen peroxide as catalyst and oxidizing agent, respectively. The oxidative reaction of 2,6-dimethylphenol produced the polymer along with a byproduct dimer of 3,5,3',5'-tetramethyl-4,4'-dipheno-quinone. The addition of pyridine suppressed the formation of the dimer to mainly give the polymer with molecular weight of more than 1×104 in high yields. From NMR analysis, the polymer was found to consist of exclusively 1,4-oxyphenylene unit. Effects of the solvent composition, added amount and type of amine, and catalyst amount have been systematically investigated. 2-Allyl-6-methylphenol and 2,6-diphenylphenol produced the corresponding polymer under the similar polymerizaconditions, whereas the formation of C-C coupling dimer was observed in using 2,6-diisopropylphenol and 2,6-dimethoxyphenol as monomer.
ACKNOWLEDGEMENTS
This work was partly supported by a Grant-in-Aid for Specially Promoted Research (No. 08102002) from the Ministry of Education, Science, and Culture, Japan, and by NEDO of the project on Technology for Novel High-Functional Materials in Industrial Science and Technology Frontier Program, AIST.