{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Millheim AC"],"funding":["Ministerio de Ciencia, Innovación y Universidades"],"pagination":["3689"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11314014"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["29(15)"],"pubmed_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."],"journal":["Molecules (Basel, Switzerland)"],"pubmed_title":["Substituent Effects in the Photophysical and Electrochemical Properties of Meso-Tetraphenylporphyrin Derivatives."],"pmcid":["PMC11314014"],"funding_grant_id":["PID2020-116846GB-C21"],"pubmed_authors":["Ponzano E","Millheim AC","Moyano A"],"additional_accession":[]},"is_claimable":false,"name":"Substituent Effects in the Photophysical and Electrochemical Properties of Meso-Tetraphenylporphyrin Derivatives.","description":"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.","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Aug","modification":"2025-04-18T20:09:13.04Z","creation":"2025-04-07T07:56:32.217Z"},"accession":"S-EPMC11314014","cross_references":{"pubmed":["39125093"],"doi":["10.3390/molecules29153689"]}}