Synthesis of Amphiphilic meso-Aryl­porphyrins in Organic Solvents and Aqueous Micellar Medium

Improved Method of 5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrins Synthesis

“…Later it was succeeded to increase to 43 % using a columnar chromatography on the silica gel. [10] The purpose of this work consisted in finding effective purification conditions for symmetric tetraarylporphyrins. The porphyrins synthesis was carried out by well-known methods using the monopyrrole condensation (Scheme 1).…”

New Pegylated Unsymmetrical meso-Arylporphyrins as Potential Photosensitizers

“…[14] We used an alternative strategy for the synthesis of such compounds -mixed aldehyde monopyrrole condensation using benzaldehydes functionalized by polyethylene oxide residues. To optimize the obtaining of target A 3 B-and AB 3 -meso-arylporphyrins two strategies of pyrrole and substituted benzaldehydes condensation were examined: in a mixture of organic solvents [15,16] and in an aqueous micellar medium. [16,17] Earlier [16] we have shown the efficiency of the monopyrrole condensation method in a solvent mixture for the synthesis of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin and its asymmetrically substituted analogs with higher alkyl substituents, worked out the methods of obtaining and picked up the conditions for isolation of such porphyrins.…”

“…To optimize the obtaining of target A 3 B-and AB 3 -meso-arylporphyrins two strategies of pyrrole and substituted benzaldehydes condensation were examined: in a mixture of organic solvents [15,16] and in an aqueous micellar medium. [16,17] Earlier [16] we have shown the efficiency of the monopyrrole condensation method in a solvent mixture for the synthesis of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin and its asymmetrically substituted analogs with higher alkyl substituents, worked out the methods of obtaining and picked up the conditions for isolation of such porphyrins. Previously the use of aqueous micellar medium allowed us to obtain not only the meso-tetrasubstituted porphyrins with polar groups, but also unsymmetrical amphiphilic porphyrins with higher alkyl substituents at the phenyl rings.…”

“…Pyrrole, benzaldehydes 3-5, p-hydroxybenzaldehyde in ratio 4:1:3 were used for synthesis of oligo-and PEGsubstituted meso-hydroxyphenylporphyrins according known approach [16] (Scheme 2). 3 % HCl was used as a catalyst, and DDQ -as an oxidant.…”

“…The target substituted meso-hydroxyphenylporphyrins were prepared by mixed aldehyde monopyrrole condensation by modified Adler method [16] in the mixture of organic solvents nitrobenzenepropionic acid/acetic acid in volume ratio 1:2:1 (Scheme 2). Products of reaction were precipitated from hexane, filtered and chromatographed using column chromatography on silica gel in dichloromethane increasing the polarity of the eluent system to dichloromethane/ ethylacetate 4:1.…”