Electrochemical Properties and Electropolymerization of Tetrakis(para-aminophenyl)porphyrin in Dichloromethane

Tesakova, Mariya V.; Popov, Ivan A.; Sheinin, V. B.; Semeikin, А. S.; Parfenyuk, V. I.; Койфман, О. И.

doi:10.6060/mhc121195p

Cited by 16 publications

(8 citation statements)

References 33 publications

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“…In the case of tetraphenylporphin in a dichlo romethane solution, two reversible oxidation processes are observed in the anodic region resulting in oxidation of the porphyrin with formation of the π cation radical and dication. 5,10,15,20 tetrakis(4' hydroxyphenyl)porphyrin in ethanol is characterized by irreversible oxidation of porphyrin witrh formation of a polyporphyrin film on the electrode [2,20], similar to the case of 5,10,15,20 tetrakis(4' aminophenyl)porphyrin [21]. Here, the oxidation potential shifts towards negative potentials as compared to tetraphenylporphyrin (table).…”

Section: Resultsmentioning

confidence: 99%

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Electrochemical properties and antioxidant activity of tetraphenylporphyrin derivatives

2015

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The method of cyclic voltammetry is used to estimate antioxidant activity of tetraphenylporphyrin (H 2 TPhP), 5,10,15,20 tetrakis(4' hydroxyphenyl)porphyrin (H 2 T(4 OHPh)P), and 5,10,15,20 tetrakis(4' hydroxy 3'5' di tert butylphenyl)porphyrin (H 2 T(4 OH 3,5 di t BuPh)P) in the reaction with 2,2 diphe nyl 1 picrylhydrazyl (DPPH). It is found that two of the three studied compounds, i.e., 5,10,15,20 tet rakis(4' hydroxyphenyl)porphyrin and 5,10,15,20 tetrakis(4' hydroxy 3'5' di tert butylphenyl)porphyrin are characterized by antioxidant activity with respect to the stable 2,2 diphenyl 1 picryl hydrazyl radical that increases in the following series: H 2 TPhP < H 2 T(4 OH 3,5 di t BuPh)P < H 2 T(4 OHPh)P. At the same time, tetraphenylporphyrin possesses practically no antiradical properties. The results obtained in this work indicate that, similar to the mechanism for phenol antioxidants as substances with a mobile hydrogen atom (proton donors), one of the mechanisms of the antioxidant effect of the studied porphyrins is related to their interaction with free radicals, particularly with DPPH according to the following reaction: AH + DPPH • → A • + DPPH H. A change in the structure of the H 2 T(4 OH 3,5 di t BuPh)P molecule due to formation of a sterically hindered phenol fragment resulting from introduction of two tert butyl substituents causes a decrease in the antioxidant activity of the studied porphyrins.

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Section: Resultsmentioning

confidence: 99%

“…The general mechanism of one-electron oxidation and reduction of porphyrins is determined by their structure and stereochemistry [1][2][3]. The unique por phyrin structure provides ample opportunities for developing systems with the given electrochemical properties [4,5].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical properties and antioxidant activity of tetraphenylporphyrin derivatives

2015

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“…При этом oни могут испытывать три и более процесса переноса электрона. [1][2][3][4] Отмечаем, что в научной литературе имеется ряд работ, в которых показано, что порфирины-лиганды и их металлоком-плексы обладают активностью по отношению к супе-роксид анион-радикалу. [5][6] Указанные факты делают эти соединения привлекательными с точки зрения использо-вания в качестве потенциальных антиоксидантов и пока-зывают перспективы практического применения.…”

Section: Introductionunclassified

Synthesis, Electrochemical Properties and Antioxidant Activity of Hydroxy Substituted Tetraphenylporphyrins

Tesakova¹,

Semeikin²,

Parfenyuk³

2017

MHC

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“…At complex formation with metal ions and formation of anions, highly symmetrical particles are formed resulting in two-fold degeneracy of the electron levels and disappearance of two "visible" bands [8]. Therefore, the antioxidant properties of the synthesized porphyrins in the reaction with 2,2′-diphenyl-1-picrylhydrazyl were estimated by highly sensitive electrochemical method which allows to analyze the properties in both aqueous and nonaqueous media [9] Redox potentials are very important characteristics of antioxidant capacity of potential antioxidants [10,11]. The lower value of oxidation potential of a substance, the more efficient its antioxidant properties.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical determination of antioxidant properties of a series of tetraphenylporphyrin derivatives and their zinc complexes

Tesakova

Семейкин

Parfenyuk

2015

J. Porphyrins Phthalocyanines

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Zinc complexes of a series of substituted tetraphenylporphyrins containing OH-groups in the phenyl rings were synthesized. Their antioxidant capacity was estimated in reaction of the porphyrins with 2,2′-diphenyl-1-picrylhydrazyl (DPPH) by cyclic voltammetry. The electron absorption spectra of the all synthesized compounds before and after the reaction with 2,2′-diphenyl-1-picrylhydrazyl were recorded. The effect of structure of the porphyrins and zinc complexes on their antioxidant capacity was discussed.

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Electrochemical Properties and Electropolymerization of Tetrakis(para-aminophenyl)porphyrin in Dichloromethane

Cited by 16 publications

References 33 publications

Electrochemical properties and antioxidant activity of tetraphenylporphyrin derivatives

Electrochemical properties and antioxidant activity of tetraphenylporphyrin derivatives

Synthesis, Electrochemical Properties and Antioxidant Activity of Hydroxy Substituted Tetraphenylporphyrins

Electrochemical determination of antioxidant properties of a series of tetraphenylporphyrin derivatives and their zinc complexes

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