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Oxidative Polymerization of 3,6-Phenylenediamino-2,5-dichlorobenzoquinone

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Abstract

The oxidative polymerization of 3,6-phenylenediamino-2,5-dichlorobenzoquinone is studied for the first time, and the monomer is shown to exhibit a high reactivity in this process. The rate of its polymerization is much higher than that of aniline and 3,6-dianiline-2,5-dichlorobenzoquinone, and the induction period of oxidation is absent. The kinetic features of the oxidative polymerization of 3,6-phenylenediamino-2,5-dichlorobenzoquinone are investigated by measuring variation in the redox potential of the reaction mixture in the course of time. It is found that the kinetic curves of 3,6-phenylenediamino-2,5-dichlorobenzoquinone polymerization do not follow the S-shaped pattern typical of aniline polymerization. The mechanism of polymerization proceeding through a number of successive tautomeric rearrangements is advanced. The structure of the polymers is studied by FTIR and X-ray photoelectron spectroscopy. During the reaction of oxidative polymerization, cyclization processes occur to form phenazine and phenoxazine rings which give rise to a ladder polyconjugated polymer. The effect of reaction conditions, such as the concentration of reagents, their ratio, and the pH of the reaction medium, on the process is investigated.

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Funding

This work was performed within the framework of the State Task for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.

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Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991, Moscow, Russia

    A. V. Orlov, S. G. Kiseleva, G. N. Bondarenko & G. P. Karpacheva

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  1. A. V. Orlov
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  2. S. G. Kiseleva
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  3. G. N. Bondarenko
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  4. G. P. Karpacheva
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Correspondence to S. G. Kiseleva.

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Translated by T. Soboleva

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Orlov, A.V., Kiseleva, S.G., Bondarenko, G.N. et al. Oxidative Polymerization of 3,6-Phenylenediamino-2,5-dichlorobenzoquinone. Polym. Sci. Ser. B 61, 519–529 (2019). https://doi.org/10.1134/S1560090419050129

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