Porphyrazines with bulky peripheral pyrrolyl substituents – Synthesis via microwave-assisted Suzuki-Miyaura cross-coupling reaction, optical and electrochemical properties

Szczołko, Wojciech; Koczorowski, Tomasz; Wicher, Barbara; Kryjewski, Michał; Krakowska, Zuzanna; Tykarska, Ewa; Gośliński, Tomasz

doi:10.1016/j.dyepig.2022.110607

Cited by 3 publications

(3 citation statements)

References 42 publications

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“…Apart from ferrocene-based redox peaks (labeled as II A ), 4 exhibited additional features due to the electroactivity of the macrocyclic core [ 21 , 43 , 44 ]. It can be seen in Figure 6 A,B that two additional peaks at 0.13 (labeled as I A ) and 0.60 V (labeled as III A ) are visible.…”

Section: Resultsmentioning

confidence: 99%

“…In the case of 1, where only one oxohexyl group was anchored to the ferrocene, we observed a 0.28 V shift towards more positive potentials, exhibiting that oxohexyl groups possess moderate electronwithdrawing properties. Apart from ferrocene-based redox peaks (labeled as IIA), 4 exhibited additional features due to the electroactivity of the macrocyclic core [21,43,44]. It can be seen in Figure 6A,B that two additional peaks at 0.13 (labeled as IA) and 0.60 V (labeled as IIIA) are visible.…”

Section: Electrochemical Characterization Of Studied Compounds In Tba...mentioning

confidence: 97%

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Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents

et al. 2023

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Ferrocene is useful in modern organometallic chemistry due to its versatile applications in material sciences, catalysis, medicinal chemistry, and diagnostic applications. The ferrocene moiety can potentially serve many purposes in therapeutics and diagnostics. In the course of this study, (6-bromo-1-oxohexyl)ferrocene was combined with dimercaptomaleonitrile sodium salt to yield a novel maleonitrile derivative. Subsequently, this compound was subjected to an autocyclotetramerization reaction using the Linstead conditions in order to obtain an octaferrocenyl-substituted magnesium(II) sulfanyl porphyrazine. Following that, both compounds—the maleonitrile derivative and the porphyrazine derivative—were subjected to physicochemical characterization using UV-Vis, ES-TOF, MALDI-TOF, and one-dimensional and two-dimensional NMR spectroscopy. Moreover, the sulfanyl porphyrazine was subjected to various photophysical studies, including optical absorption and emission measurements, as well as the evaluation of its photochemical properties. Values of singlet oxygen generation quantum yields were obtained in different organic solvents. The electrochemical properties of the synthesized compounds were studied using cyclic voltammetry. According to the electrochemical results, the presence of electron-withdrawing oxohexyl groups attached to ferrocene afforded significantly more positive oxidation potentials of the ferrocene-based redox process up to 0.34 V vs. Fc+/Fc.

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Section: Resultsmentioning

confidence: 99%

Section: Electrochemical Characterization Of Studied Compounds In Tba...mentioning

confidence: 97%

Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents

et al. 2023

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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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Magnesium(II) porphyrazine with peripherally overloaded pyrrolyl substituents – Synthesis, optical and electrochemical characterization

Szczolko,

Koczorowski,

Bakun

et al. 2024

Journal of Molecular Structure

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Porphyrazines with bulky peripheral pyrrolyl substituents – Synthesis via microwave-assisted Suzuki-Miyaura cross-coupling reaction, optical and electrochemical properties

Cited by 3 publications

References 42 publications

Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents

Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents

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

Magnesium(II) porphyrazine with peripherally overloaded pyrrolyl substituents – Synthesis, optical and electrochemical characterization

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