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Synthesis of 1-amino-2,5-di(2-thienyl)benzenes as potential monomers for the preparation of hybrid polythiophene anionic sensors

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Abstract

A convenient method for the synthesis of 1-amino-2,5-di(2-thienyl)benzenes was proposed. The method involves in situ generation of aryne intermediates from 1-halo-2,5-di-(2-thienyl)benzenes in the presence of strong bases followed by reactions of the arynes with polyfunctional primary and secondary amines. The products obtained in 75–85% yields are promising monomers for the preparation of polythiophene anionic sensors. Polymerization of dibrominated 1-piperidino-2,5-di(2-thienyl)benzene gave the corresponding poly[(bithiophenediyl)(phenylene)].

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Authors and Affiliations

  1. B. N. El’tsin Ural Federal University, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    G. V. Zyryanov, I. S. Kovalev, I. N. Egorov, V. L. Rusinov & O. N. Chupakhin

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    G. V. Zyryanov & O. N. Chupakhin

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  1. G. V. Zyryanov
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  2. I. S. Kovalev
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  3. I. N. Egorov
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  4. V. L. Rusinov
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  5. O. N. Chupakhin
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Correspondence to G. V. Zyryanov.

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Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 302–306, February, 2012.

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Zyryanov, G.V., Kovalev, I.S., Egorov, I.N. et al. Synthesis of 1-amino-2,5-di(2-thienyl)benzenes as potential monomers for the preparation of hybrid polythiophene anionic sensors. Russ Chem Bull 61, 303–307 (2012). https://doi.org/10.1007/s11172-012-0042-5

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  • DOI: https://doi.org/10.1007/s11172-012-0042-5

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