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New bifunctional amphiphilic oxyethylimidazolium derivatives of calix[4]arene containing alkynyl/azide fragments: regularities of aggregation and polymerization under azide/alkyne cycloaddition conditions

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Abstract

New bifunctional amphiphilic oxyethylimidazolium derivatives of calix[4]arene with terminal alkynyl or azide fragments in the polar moiety of the molecule were synthesized. The aggregation characteristics (critical aggregation concentrations, size, and zeta potential) of the synthesized macrocyclic azides, alkynes, and their mixtures were studied. Polymeric particles were obtained under the azide/alkyne cycloaddition conditions. Covalent cross-linking of the aggregate core was proved by IR spectroscopy. The size, molecular weight, and morphology of the polymerized particles were determined. The catalytic properties of the in situ formed Pd(OAc)2 complex with the prepared polymerized particles were studied in the model Suzuki cross-coupling reaction in an aqueous medium.

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Authors and Affiliations

  1. Kazan (Volga region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    V. A. Burilov, I. M. Bogdanov, R. I. Garipova, A. A. Volodina, D. A. Mironova & I. S. Antipin

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of Russian Academy of Sciences,”, 8 ul. Arbuzova, 420088, Kazan, Russian Federation

    S. E. Solovieva

  3. Interdisciplinary Center for Analytical Microscopy, Kazan (Volga region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    V. G. Evtugyn

Authors
  1. V. A. Burilov
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  2. I. M. Bogdanov
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  3. R. I. Garipova
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  4. A. A. Volodina
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  5. D. A. Mironova
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  6. V. G. Evtugyn
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  7. S. E. Solovieva
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  8. I. S. Antipin
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Corresponding author

Correspondence to V. A. Burilov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 131–138, January, 2022.

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00095).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Burilov, V.A., Bogdanov, I.M., Garipova, R.I. et al. New bifunctional amphiphilic oxyethylimidazolium derivatives of calix[4]arene containing alkynyl/azide fragments: regularities of aggregation and polymerization under azide/alkyne cycloaddition conditions. Russ Chem Bull 71, 131–138 (2022). https://doi.org/10.1007/s11172-022-3386-5

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  • DOI: https://doi.org/10.1007/s11172-022-3386-5

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