Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization
Starting from pyrrole-carbinol derivatives, a set of three optimized experimental conditions was used to prepare six dipyrromethanes (DPM) bearing meso-poly-halogeno-alkyl chains. On the one hand, the condensation of $p$-anisaldehyde and the DPMs bearing a perfluoroalkyl chain (CF3, C3F7 or C7F15) p...
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| Format: | Article |
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Académie des sciences
2021-07-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.97/ |
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| author | Julliard, Paul-Gabriel Pascal, Simon Siri, Olivier Cortés-Arriagada, Diego Sanhueza, Luis Canard, Gabriel |
| author_facet | Julliard, Paul-Gabriel Pascal, Simon Siri, Olivier Cortés-Arriagada, Diego Sanhueza, Luis Canard, Gabriel |
| author_sort | Julliard, Paul-Gabriel |
| collection | DOAJ |
| description | Starting from pyrrole-carbinol derivatives, a set of three optimized experimental conditions was used to prepare six dipyrromethanes (DPM) bearing meso-poly-halogeno-alkyl chains. On the one hand, the condensation of $p$-anisaldehyde and the DPMs bearing a perfluoroalkyl chain (CF3, C3F7 or C7F15) produced, after oxidation, the expected trans-A2B2-porphyrins in reasonable yields. On the other hand, 5,15-diformyl-10,20-diarylporphyrin was directly obtained starting from the meso-(dichloromethyl)dipyrromethane, while traces of an unprecedented porphyrin bearing two meso-acyl fluoride groups were isolated from the use of the meso-(chlorodifluoromethyl)dipyrromethane. The straightforward formation of bis-formyl porphyrins is competitive compared to previously reported methods and has been extended to other benzaldehydes. The electron-withdrawing character of the different substituents appended to porphyrins is enlightened through a combination of photophysical, electrochemical, structural and theoretical studies. |
| first_indexed | 2024-03-11T16:13:56Z |
| format | Article |
| id | doaj.art-1a9369cccc854737b9eb000902d45bbf |
| institution | Directory Open Access Journal |
| issn | 1878-1543 |
| language | English |
| last_indexed | 2024-03-11T16:13:56Z |
| publishDate | 2021-07-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj.art-1a9369cccc854737b9eb000902d45bbf2023-10-24T14:23:03ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432021-07-0124S3274510.5802/crchim.9710.5802/crchim.97Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterizationJulliard, Paul-Gabriel0https://orcid.org/0000-0001-6961-2986Pascal, Simon1https://orcid.org/0000-0001-8387-494XSiri, Olivier2https://orcid.org/0000-0001-9747-3813Cortés-Arriagada, Diego3https://orcid.org/0000-0002-6709-1723Sanhueza, Luis4https://orcid.org/0000-0002-3763-6948Canard, Gabriel5https://orcid.org/0000-0002-3572-9091Aix Marseille Univ, CNRS, CINaM, UMR 7325, Campus de Luminy, 13288 Marseille Cedex 09, FranceAix Marseille Univ, CNRS, CINaM, UMR 7325, Campus de Luminy, 13288 Marseille Cedex 09, FranceAix Marseille Univ, CNRS, CINaM, UMR 7325, Campus de Luminy, 13288 Marseille Cedex 09, FrancePrograma Institucional de Fomento a la Investigación, Desarrollo e Innovación, Universidad Tecnológica Metropolitana, Ignacio Valdivieso 2409, San Joaquín, Santiago, ChileDepartamento de Ciencias Biológicas y Químicas, Facultad de Recursos Naturales, Universidad Católica de Temuco, Temuco, Chile; Núcleo de Investigatión en Bioproductos y Materiales Avanzados (BioMA), Universidad Católica de Temuco, Av. Rudecindo Ortega 02950, Temuco, ChileAix Marseille Univ, CNRS, CINaM, UMR 7325, Campus de Luminy, 13288 Marseille Cedex 09, FranceStarting from pyrrole-carbinol derivatives, a set of three optimized experimental conditions was used to prepare six dipyrromethanes (DPM) bearing meso-poly-halogeno-alkyl chains. On the one hand, the condensation of $p$-anisaldehyde and the DPMs bearing a perfluoroalkyl chain (CF3, C3F7 or C7F15) produced, after oxidation, the expected trans-A2B2-porphyrins in reasonable yields. On the other hand, 5,15-diformyl-10,20-diarylporphyrin was directly obtained starting from the meso-(dichloromethyl)dipyrromethane, while traces of an unprecedented porphyrin bearing two meso-acyl fluoride groups were isolated from the use of the meso-(chlorodifluoromethyl)dipyrromethane. The straightforward formation of bis-formyl porphyrins is competitive compared to previously reported methods and has been extended to other benzaldehydes. The electron-withdrawing character of the different substituents appended to porphyrins is enlightened through a combination of photophysical, electrochemical, structural and theoretical studies.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.97/DipyrromethanesPorphyrinsFormylationAcyl fluoridePhotophysics |
| spellingShingle | Julliard, Paul-Gabriel Pascal, Simon Siri, Olivier Cortés-Arriagada, Diego Sanhueza, Luis Canard, Gabriel Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization Comptes Rendus. Chimie Dipyrromethanes Porphyrins Formylation Acyl fluoride Photophysics |
| title | Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization |
| title_full | Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization |
| title_fullStr | Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization |
| title_full_unstemmed | Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization |
| title_short | Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization |
| title_sort | functionalized porphyrins from meso poly halogeno alkyl dipyrromethanes synthesis and characterization |
| topic | Dipyrromethanes Porphyrins Formylation Acyl fluoride Photophysics |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.97/ |
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