Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization
Date
Authors
SANHUEZA FRIGOLETT, JUAN MANUEL
Julliard, Paul Gabriel
Pascal, Simon
Siri, Olivier
Cortés-Arriagada, Diego
Sanhueza, Luís Manuel
Canard, Gabriel
Julliard, Paul Gabriel
Pascal, Simon
Siri, Olivier
Cortés-Arriagada, Diego
Sanhueza, Luís Manuel
Canard, Gabriel
Authors
Date
Datos de publicación:
10.5802/crchim.97
Keywords
Acyl Fluoride - Dipyrromethanes - Formylation - Photophysics - Porphyrins
Collections
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-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.
Description
Keywords
Acyl Fluoride , Dipyrromethanes , Formylation , Photophysics , Porphyrins
Citation
10.5802/crchim.97