The Suzuki cross-coupling reaction for the synthesis of porphyrazine possessing bulky 2,5-(biphenyl-4-yl)pyrrol-1-yl substituents in the periphery

Szczołko, Wojciech; Wzgarda, Anna; Koczorowski, Tomasz; Wicher, Barbara; Sobotta, Łukasz; Gdaniec, Zofia; Gdaniec, Мaria; Mielcarek, Jadwiga; Tykarska, Ewa; Gośliński, Tomasz

doi:10.1016/j.poly.2015.09.068

Cited by 10 publications

(3 citation statements)

References 42 publications

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“…Other examples originate in our group. Over the past 15 years, our group has synthesized numerous Pzs bearing peripheral 2,5-dimethylpyrrol-1-yl, 2,5-dithienylpyrrol-1-yl, 2,5-di(biphenyl-4-yl)pyrrol-1-yl, 2-(1-adamantyl)-5-phenylpyrrol-1-yl, and 3,4-dihalide-2,5dimethylpyrrol-1-yl moieties [20,21]. These Pzs have been thoroughly assessed in terms of their spectral, electrochemical, and catalytic properties.…”

Section: Introductionmentioning

confidence: 99%

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents

Koczorowski,

Rębiś

2023

Molecules

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The present study investigates four iron(II/III) porphyrazines with extending pyrrolyl peripheral substituents to understand the impact of introduced phenyl rings on the macrocycle’s electrochemical and spectroelectrochemical properties as well as their activity in oxidation reactions. The electrochemical studies showed six well-defined redox processes and quasi-reversible one-electron transfers—two originating from the iron cation and four related to the ring. Adding phenyl rings to the periphery increased the electrochemical gap by 0.1 V. The UV–Vis spectra changes were observed at the applied potential of −1.3 V with the presence of additional red-shifted bands. The oxidizing studies showed increased efficiency in the oxidation reaction of the reference substrate in the cases of Pz1 and Pz2 in both studied oxygen atom donors. The calculated reaction rates in t-BuOOH were 12.0 and 15.0 mmol/min, respectively, for Pz1 and Pz2, compared to 6.4 for Pz3 and 1.8 mmol/min for Pz4. The study identified potential applications for these porphyrazines in mimicking cytochrome P450 prosthetic groups for oxidation and hydroxylation reactions in the future.

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Section: Introductionmentioning

confidence: 99%

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents

Koczorowski,

Rębiś

2023

Molecules

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“…Luo et al [16] synthesized binuclear Pzs with twelve peripheral trimethylthiophenyl groups, revealing interesting photochromic characteristics. For the last 15 years, our group obtained many examples of Pzs bearing peripheral 2,5-dimethylpyrrol-1-yl, 2,5dithienylpyrrol-1-yl, 2,5-di(biphenyl-4-yl)pyrrol-1-yl, 2-(1-adamantyl)-5-phenylpyrrol-1-yl, and 3,4-dihalide-2,5-dimethylpyrrol-1-yl moieties [17][18][19][20][21]. Lately, it was found that bulky 2,5-diphenylpyrrol-1-yl substituents on the periphery of iron(II) porphyrazine influence its physicochemical properties, which was confirmed by Mössbauer spectroscopy [22].…”

Section: Introductionmentioning

confidence: 99%

The Valence and Spin State Tuning of Iron(II/III) Porphyrazines with Bulky Pyrrolyl Periphery in Solution and Solid State

et al. 2022

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Iron(III) porphyrazines containing peripheral 2,5-dimethyl-, 2-methyl-5-phenyl-, and 2,3,5-triphenyl-1H-pyrrol-1-yl substituents were synthesized and subjected to physicochemical characterization. This was accomplished by high-resolution mass spectrometry, nuclear magnetic resonance (as diamagnetic Fe(II) derivatives), HPLC purity analysis, and UV-Vis spectroscopy, accompanied by the solvation study in dichloromethane and pyridine. X-ray structure analysis was performed for a single crystal of the previously obtained 2,5-diphenyl-substituted derivative of porphyrazine complex (5d). The octahedral geometries of iron cation, present in the porphyrazine core, influenced the packing mode of molecules in the crystals. Mössbauer studies, performed for solid samples of iron porphyrazines, indicated that low-spin reduced iron states might occupy low- or high-symmetry binding sites. It was found that the hyperfine parameters and the subsequent contribution of the iron cations depend on the number of phenyl groups surrounding the pyrrolyl moiety. For iron(II) porphyrazine 2,3,5-triphenylpyrrol-1-yl substituents (5b), a high-spin ferrous state fraction was observed. Temperature-dependent measurements showed that the freed rotation of the peripheral porphyrazine ligands and the increased flexibility of the macrocycle ring result in the Fe2+ ion being stabilized in a diamagnetic state at a binding site of high symmetry at room temperature in the solid state. This process is most probably stimulated by the range of collective motions of the polymeric ribbons consisting of iron(II) porphyrazines observed in the X-ray.

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“…Due to interesting optical and electrochemical properties, they have been widely researched for many potential applications in nanotechnology, materials and medicinal chemistry [11,15,16]. Lately, our group has studied porphyrazines substituted in the periphery with methyl(3-pyridylmethyl)amino, 2,5-dimethylpyrrolyl substituents, dimethylamino, 2,5-dimethylpyrrol-1-yl, 2,5-dithienylpyrrol-1-yl, 2,5-di(biphenyl-4-yl)pyrrol-1-yl and 2-(1-adamantyl)-5-phenylpyrrol-1-yl moieties [17][18][19][20][21][22][23]. Moreover, an earlier developed alkylation path [1,4,15] leading to tetraalkylated diaminomaleonitrile substrates for Pzs synthesis has been explored [6].…”

Section: Introductionmentioning

confidence: 99%

Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties

Wieczorek

Piskorz

Popenda

et al. 2019

Heterocyclic Communications

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Novel magnesium(II) porphyrazine with peripheral methyl(3,5-dibromophenylmethyl)amine groups was synthesized in a multi-step procedure starting from commercially available diaminomaleonitrile. All intermediates and the final macrocycle were characterized using UV–Vis, FT-IR, MS and various NMR techniques. The absorption and emission properties of the macrocycle were evaluated in N,N-dimethylformamide, dimethyl sulfoxide, and dichloromethane. The potential photosensitizing activity was evaluated by assessing the ability of the macrocycle to generate singlet oxygen in dimethyl sulfoxide and N,N-dimethylformamide.

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The Suzuki cross-coupling reaction for the synthesis of porphyrazine possessing bulky 2,5-(biphenyl-4-yl)pyrrol-1-yl substituents in the periphery

Cited by 10 publications

References 42 publications

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents

The Valence and Spin State Tuning of Iron(II/III) Porphyrazines with Bulky Pyrrolyl Periphery in Solution and Solid State

Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties

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