2026-04-18T06:14:15Zhttps://recercat.cat/oai/request

oai:recercat.cat:2445/2183892025-12-04T21:41:53Zcom_2072_1057col_2072_478917col_2072_478933

RECERCAT author Dardouri, N. E. author Hrichi, S. author Torres, Pol author Chaabane-Banoues, R. author Sorrenti, Alessandro author Roisnel, T. author Turowska-Tyrk, I. author Babba, I. author Crusats i Aliguer, Joaquim author Moyano i Baldoire, Albert author Nasri, H. 2025-01-31T18:59:50Z2025-01-31T18:59:50Z2024-07-032025-01-31T18:59:50Z 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. cc-by (c) Dardouri, N. E. et al., 2024 http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess Porfirines Electroquímica Porphyrins Electrochemistry Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived meso-Tetraarylporphyrin info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion