Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization
Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization
Authors
Julliard, Paul Gabriel
Pascal, Simon
Siri, Olivier
Cortes Arriagada, Diego
Sanhueza, Luis
Canard, Gabriel
Pascal, Simon
Siri, Olivier
Cortes Arriagada, Diego
Sanhueza, Luis
Canard, Gabriel
Authors
Date
Datos de publicaciĆ³n:
COMPTES RENDUS CHIMIE,Vol.24,27-45,2021
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Abstract
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-A(2)B(2)-porphyrins in reasonable yields. On the other hand, 5.15-diformyl-10,20-diarylporphyrin was directly obtained starting from the nano(dichloromethyDdipyrromethane, while traces of an unprecedented porphyrin bearing two mesa-aryl 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.