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<p>The nitration properties of <i>5</i>,<i>10</i>,<i>15</i>,<i>20</i>-tetra(1-naphthyl) porphyrin (TNP) were systematically investigated and compared with those of <i>5</i>,<i>10</i>,<i>15</i>,<i>20</i>-tetra(phenyl)porphyrin (TPP) using nitronium tetrafluoroborates and related nitrating agents. A thorough analysis, utilizing UV–Vis, <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR, ESR, mass spectrometry, and additional spectroscopic methods, was conducted to elucidate the nitration mechanism of tetra-aryl porphyrins and confirm the formation of the “sitting atop” NO<sub>2</sub>TPPBF<sub>4</sub> and NO<sub>2</sub>TNPBF<sub>4</sub> complexes. The <sup>1</sup>H NMR and mass spectrometry data suggest that nitration occurs with regioselectivity, predominantly at the para-position of the meso-substituted aryl groups relative to the porphyrin core. Furthermore, the spectroscopic results confirmed the successful synthesis of mono-, di-, and tri-nitro products in good to high yields using nitronium tetrafluoroborates.</p> Graphical abstract <p></p>

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Studies of electrophilic properties of aromatic porphyrin conjugates through intermediate mechanism

  • 期刊论文

  • 发表日期：

    2025年5月19日

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  • Anshu Dandia

摘要

The nitration properties of 5,10,15,20-tetra(1-naphthyl) porphyrin (TNP) were systematically investigated and compared with those of 5,10,15,20-tetra(phenyl)porphyrin (TPP) using nitronium tetrafluoroborates and related nitrating agents. A thorough analysis, utilizing UV–Vis, 1H NMR, 13C NMR, IR, ESR, mass spectrometry, and additional spectroscopic methods, was conducted to elucidate the nitration mechanism of tetra-aryl porphyrins and confirm the formation of the “sitting atop” NO2TPPBF4 and NO2TNPBF4 complexes. The 1H NMR and mass spectrometry data suggest that nitration occurs with regioselectivity, predominantly at the para-position of the meso-substituted aryl groups relative to the porphyrin core. Furthermore, the spectroscopic results confirmed the successful synthesis of mono-, di-, and tri-nitro products in good to high yields using nitronium tetrafluoroborates.

Graphical abstract