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Halogenation of Fluoro-Substituted Zinc(II) Tetraphenylporphyrins at the β-Position

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Abstract

[2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato]zinc(II) was synthesized by reaction of [5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato]zinc(II) with N-bromosuccinimide in chloroform–methanol, chloroform–dimethylformamide, and dimethylformamide. The reaction of [5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato]zinc(II) with N-chlorosuccinimide in chloroform–methanol or dimethylformamide gave [2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato]zinc(II). [2,3,7,8,12,13,17,18-Octachloro-5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrinato]zinc(II) was obtained by chlorination of [5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrinato]zinc(II) with excess N-chlorosuccinimide in dimethylformamide. The synthesized complexes were identified by electronic absorption spectroscopy, 1H NMR, and mass spectrometry.

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ACKNOWLEDGMENTS

This study was performed using the equipment of the joint center “Upper Volga Regional Center for Physicochemical Studies.”

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-03-00078A).

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Authors and Affiliations

  1. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045, Ivanovo, Russia

    N. V. Chizhova & N. Zh. Mamardashvili

  2. Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russia

    A. I. Rusanov & D. V. Tyurin

Authors
  1. N. V. Chizhova
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  2. A. I. Rusanov
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  3. D. V. Tyurin
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  4. N. Zh. Mamardashvili
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Correspondence to N. V. Chizhova.

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Chizhova, N.V., Rusanov, A.I., Tyurin, D.V. et al. Halogenation of Fluoro-Substituted Zinc(II) Tetraphenylporphyrins at the β-Position. Russ J Org Chem 56, 2132–2136 (2020). https://doi.org/10.1134/S1070428020120131

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  • DOI: https://doi.org/10.1134/S1070428020120131

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