Fluorinated derivatives of meso-(aminophenyl)porphyrins: Synthesis and some transformation

Abstract

Condensation of amino groups in 5-(4-aminophenyl)-10,15,20-triphenylporphyrin and 5,10,15,20-tetrakis(4-aminophenyl)porphyrin with pentafluorobenzaldehyde resulted in corresponding Schiff bases and was shown to be a convenient route for the preparation of fluorinated porphyrin derivatives. Compounds thus obtained were easily transformed into the corresponding amines using sodium borohydride. Fluorinated carboranyl porphyrins were prepared via the nucleophilic substitution of the para-fluorine atom of pentafluorophenyl-substituted amine porphyrin derivatives with carborane S-nucleophiles. The alternative synthetic route to the fluorinated carboranyl porphyrins included the condensation of para-carboranyl-substituted tetrafluorobenzaldehyde with corresponding meso-aminoporphyrins. All prepared porphyrins were characterized by different spectroscopic techniques such as UV-vis, IR, 1H, 11B, 19F NMR and mass spectra.

BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies

“…49,50 Similar reactions are usually employed for the functionalization of macrocyclic compounds such as porphyrins, chlorins, phthalocyanines and BODIPYs. 15,37,[51][52][53] It was found that the reactions of BODIPYs 4, 5 and 7 with the corresponding mercaptocarboranes proceeded efficiently for 1 h in DMF in the presence of NaOAc for compounds 4 and 5 and in the presence of K 2 CO 3 for compound 7 providing the desired BODIPYs 8-10 decorated with three carborane clusters in 70-81% yields (Scheme 1).…”

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

“…To continue our ongoing efforts on the preparation of porphyrin-based photosensitizers [17–20], we present herein the synthesis of maleimide-subtituted porphyrins and chlorins based on 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin ( 1 ) as the starting compound. The presence of fluorine atoms on the four phenyl rings at the meso -positions of the porphyrin structure can make a strong influence on the hydrophobic interactions and lipophilicity, metabolic stability, thus modulating the biological efficiency of the photosensitizing agents [21–22].…”