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<p>In this study, a new magnesium(II) porphyrazine derivative tetrasubstituted with dicarboxypyrrolyl moieties was synthesized. Two different approaches were used, utilizing conventional heating and microwave irradiation. The developed three-step processes were compared showing the superior performance of the microwave-assisted organic synthesis. The new macrocycle and the novel maleonitrile derivatives were characterized using spectral techniques (mass spectrometry, NMR spectroscopy, UV-Vis spectrophotometry) and the ability of the porphyrazine to generate singlet oxygen assessed using the method with 1,3-diphenylisobenzofuran. The singlet oxygen generation quantum yields were found to be moderate (Φ<sub>Δ</sub> = 0.23 and 0.22 in DMF and DMSO, respectively) and no aggregation behavior was noted in a series of dilutions. Additionally, the acute toxicity test using Microtox was performed showing almost no toxicity at the concentration of 10<sup>− 5</sup> mol/L. The electrochemical studies revealed three redox processes of targeted porphyrazine with low first oxidation peak, whereas the spectroelectrochemistry showed the formation of both cationic and anionic species at proper potentials.</p>

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Pyrrole dicarboxylate substituted porphyrazine, microwave assisted synthesis and properties

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月14日

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  • Wojciech Szczolko,
  • Michal Kryjewski,
  • Tomasz Koczorowski,
  • Eunice Zuchowska,
  • Lukasz Popenda,
  • Dariusz T. Mlynarczyk

摘要

In this study, a new magnesium(II) porphyrazine derivative tetrasubstituted with dicarboxypyrrolyl moieties was synthesized. Two different approaches were used, utilizing conventional heating and microwave irradiation. The developed three-step processes were compared showing the superior performance of the microwave-assisted organic synthesis. The new macrocycle and the novel maleonitrile derivatives were characterized using spectral techniques (mass spectrometry, NMR spectroscopy, UV-Vis spectrophotometry) and the ability of the porphyrazine to generate singlet oxygen assessed using the method with 1,3-diphenylisobenzofuran. The singlet oxygen generation quantum yields were found to be moderate (ΦΔ = 0.23 and 0.22 in DMF and DMSO, respectively) and no aggregation behavior was noted in a series of dilutions. Additionally, the acute toxicity test using Microtox was performed showing almost no toxicity at the concentration of 10− 5 mol/L. The electrochemical studies revealed three redox processes of targeted porphyrazine with low first oxidation peak, whereas the spectroelectrochemistry showed the formation of both cationic and anionic species at proper potentials.