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Synthesis, acid-base interactions, and photostability of copper(ii) tetrakis(3,5-di-tert-butylbenzoyloxy)phthalocyanine

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Abstract

3,4-Dicyanophenyl 3,5-di-tert-butylbenzoate was synthesized for the first time. Copper tetrakis(3,5-di-tert-butylbenzoyloxy)phthalocyaninate was obtained also for the first time from this compound using template cyclotetramerization. Prepared compounds were identified by UV-vis, IR, 1H and 13C NMR spectroscopies. The features of the acid-base interaction and the acidity constants of the copper tetrakis(3,5-di-tert-butylbenzoyloxy)phthalocyaninate protonated forms, as well as copper tetra(4-tert-butyl)phthalocyaninate and its ligand in the system CH2Cl2—100% trifluoroacetic acid were studied. It was found that the macrocycles protonation includes two reversible stepwise reactions, namely, mono- and diprotonation at the meso nitrogen atoms. The acidity constants dependence on the chemical structure of molecules has been revealed. The phthalocyanines photocatalytic stability in benzene was also investigated. It was shown that an increase in the electron-donating properties of the macrocycle decreases the complex stability, and vise versa, a decrease of the electron density in the macrocycle increases the photostability.

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Funding

The work was performed in the framework of State task of the Ministry of Education and Research of Russian Federation (task No. FZZW-2020-0008).

The study was carried out using the resources of the Center for Shared Use of Scientific Equipment of Ivanovo State University of Chemistry and Technology with the support of the Ministry of Education and Science of Russian Federation (agreement No. 075-15-2021-671).

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Authors and Affiliations

  1. Ivanovo state university of chemistry and technology, 7 Sheremetievsky prosp., 153000, Ivanovo, Russia

    A. S. Malyasova, E. A. Kostrova, V. E. Maizlish & O. I. Koifman

  2. Yaroslavl State Technical University, 88 Moskovsky prosp., 150023, Yaroslavl, Russia

    I. G. Abramov

  3. G. A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1 ul. Akademicheskaya, 153045, Ivanovo, Russia

    O. I. Koifman

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  1. A. S. Malyasova
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Corresponding author

Correspondence to A. S. Malyasova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences R. Z. Sagdeev on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2405–2415, December, 2021.

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

The authors declare no competing interests.

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Malyasova, A.S., Kostrova, E.A., Abramov, I.G. et al. Synthesis, acid-base interactions, and photostability of copper(ii) tetrakis(3,5-di-tert-butylbenzoyloxy)phthalocyanine. Russ Chem Bull 70, 2405–2415 (2021). https://doi.org/10.1007/s11172-021-3360-7

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