SANHUEZA FRIGOLETT, JUAN MANUEL
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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) 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. © 2021 Elsevier B.V., All rights reserved.
Two-step access to bis-meso-perfluoroalkyl-corroles towards meso-perfluoroacyl-ABC-corroles
A solventless and acid-catalyzed condensation of meso-perfluoroalkyl-dipyrromethanes with selected benzaldehydes was used to prepare ten different bilanes that were isolated before their oxidation into trans-A2B-corroles bearing two meso-perfluoroalkyl groups. Macrocycles bearing long chains (C3F7 or C7F15) are key precursors to afford ABC-corroles having a meso-acyl substituent when subjected to a mild and basic hydrolysis affecting one of the alkyl substituents. © 2024 Elsevier B.V., All rights reserved.