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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/218246
Substituent Effects in the Photophysical and Electrochemical Properties of Meso-Tetraphenylporphyrin Derivatives
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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.
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MILLHEIM, Alexandra c., PONZANO, Enric, MOYANO I BALDOIRE, Albert. Substituent Effects in the Photophysical and Electrochemical Properties of Meso-Tetraphenylporphyrin Derivatives. _Molecules_. 2024. Vol. 29. [consulta: 19 de gener de 2026]. ISSN: 1420-3049. [Disponible a: https://hdl.handle.net/2445/218246]