Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media

Dmitry Berezin; Boris Berezin; Pavel Razgovorov

doi:10.52957/27821900_2022_03_34

UDC 544.42 UDC 544.653.2/.3 UDC 544.332

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SPECIFIC FEATURES OF THE KINETICS OF DESTRUCTIVE DEGRADATION OF PORPHINE AND PHTHALOCYANINE DERIVATIVES IN OXIDIZING MEDIA Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media

АА Аа

Published in From Chemistry Towards Technology Step-By-Step · Volume 3, Issue 3 · Pages 34–47 · Rubric: Scientific articles

DOI: https://doi.org/10.52957/27821900_2022_03_34

Received: 29.08.2022 Accepted: 12.09.2022 Published: 23.09.2022

Authors

Dmitry Berezin

Boris Berezin

Pavel Razgovorov

Dmitry Berezin

Academic degree: doctor of chemical sciences

Science rang: academician author.academy_titles.37 ; professor

Ivanovo State University of Chemistry and Technology Ivanovo

Boris Berezin

Russian Federation

Pavel Razgovorov

Academic degree: doctor of technical sciences

Science rang: professor

Yaroslavl State Technical University Professor · Kafedra «Tehnologiya stroitel'nogo proizvodstva». · Yaroslavl

ABSTRACT

The paper presents the analysis on chemical, thermal and electrochemical stability of some aromatic macroheterocycles (MHC) of porphyrin (H2P) class as well as their benzo- and aza-analogues, establishes electronic and structural factors determining the rate of pigment destruction in the presence of oxidant. The values of redox potentials of porphyrin-, tetraaz-, tetrabenzo-porphyrin- and phthalocyanine-type MHCs correlate with the temperatures at which their thermo-oxidative degradation starts and the decomposition rates in oxidizing media. The combined benzo- and azamer substitution in H2P molecules leads to their destabilisation with respect to oxidants, the situation depending strongly on the nature of the oxidant (H2O2, S2O82- and NO3-), the solvent (H2SO4, HOAc) as well as the nature of the metal in the molecule. The polymer state or spatial distortion of the MHC has a significant influence on the resistance to oxidising agents. The reaction mechanisms of oxidation of label-free porphyrins and phthalocyanines by hydrogen peroxide are shown to be identical. In both cases, the reaction centres of MHCs are N H bonds, either in the meso-position (H2Ps) or in the coordination cavity of the H2N4 molecule (H2P), and the pigments are cleaved to colourless products.

KEYWORDS

tetrapyrrolemacroheterocyclic compounds; porphyrins; phthalocyanines; oxidative degradation, redox potentials

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Berezin D. B., Berezin B. D., Razgovorov P. B. Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media // From Chemistry Towards Technology Step-By-Step. 2024. no. 3. pp. 34-47. DOI: https://doi.org/10.52957/27821900_2022_03_34. (Date of access 25.10.2026).

MLA

Dmitry Berezin, Berezin B. D., Razgovorov P. B.. "Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media." From Chemistry Towards Technology Step-By-Step 3.3 (2024): 34-47. DOI: https://doi.org/10.52957/27821900_2022_03_34.

APA

Berezin D. B., Berezin B. D., Razgovorov P. B. (2024). Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media. From Chemistry Towards Technology Step-By-Step, 3(3), 34-47. https://doi.org/10.52957/27821900_2022_03_34

Chicago

Dmitry Berezin, Berezin B. D., Razgovorov P. B.. "Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media." From Chemistry Towards Technology Step-By-Step 3, no. 3 (2024): 34-47. https://doi.org/10.52957/27821900_2022_03_34.

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{{cite journal | author = Berezin D. B., Berezin B. D., Razgovorov P. B. | title = Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media | journal = From Chemistry Towards Technology Step-By-Step | year = 2024 | volume = 3 | issue = 3 | pages = 34-47 | doi = 10.52957/27821900_2022_03_34 }}

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SPECIFIC FEATURES OF THE KINETICS OF DESTRUCTIVE DEGRADATION OF PORPHINE AND PHTHALOCYANINE DERIVATIVES IN OXIDIZING MEDIA Specific features of the kinetics of destructive degradation of porphine and phthalocyanine derivatives in oxidizing media

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