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2024-07-03

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cc-by (c) Dardouri, N. E. et al., 2024
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/218389

<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span>

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https://doi.org/10.3390/molecules29153689

Abstract

Porphyrins were identified some years ago as a promising, easily accessible, and tunable class of organic photoredox catalysts, but a systematic study on the effect of the electronic nature and of the position of the substituents on both the ground-state and the excited-state redox potentials of these compounds is still lacking. We prepared a set of known functionalized porphyrin derivatives containing different substituents either in one of the meso positions or at a β-pyrrole carbon, and we determined their ground- and (singlet) excited-state redox potentials. We found that while the estimated singlet excited-state energies are essentially unaffected by the introduction of substituents, the redox potentials (both in the ground- and in the singlet excited-state) depend on the electron-withdrawing or electron-donating nature of the substituents. Thus, the presence of groups with electron-withdrawing resonance effects results in an enhancement of the reduction facility of the photocatalyst, both in the ground and in the excited state. We next prepared a second set of four previously unknown meso-substituted porphyrins, having a benzoyl group at different positions. The reduction facility of the porphyrin increases with the proximity of the substituent to the porphine core, reaching a maximum when the benzoyl substituent is introduced at a meso position.

Subject

Porfirines, Electroquímica

Subject (English)

Porphyrins, Electrochemistry

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Articles publicats en revistes (Química Inorgànica i Orgànica)

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DARDOURI, N. E., et al. Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived meso-Tetraarylporphyrin. Molecules. 2024. Vol. 29. ISSN 1420-3049. [consulted: 10 of August of 2026]. Available at: https://hdl.handle.net/2445/218389

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