PREPARATION OF FUNCTIONALIZED POLYHALOGENATED TETRAARYL-PORPHYRINS BY SELECTIVE SUBSTITUTION OF THE PARA-FLUORINES OF MESO-TETRA-(PENTAFLUOROPHENYL)PORPHYRINS

Reaction of various nucleophiles, such as primary and secondary amines in refluxing DMF, alkoxides in alcohol or THF and thiols in the presence of NEt3 in DMF, with meso-tetra-(pentafluorophenyl)porphyrin (or its Zn(II) and Fe(III) complexes) led to the selective replacement of the p-fluorine substituents of the starting porphyrin by NR2 , OR or SR groups, in yields between 70 and 90%. The same regioselectivity was obtained by reaction of meso-tetra-(pentafluorophenyl) octabromoporphyrin with n-propylamine. Reaction with KCN gave a more complex reaction mixture.