Synthesis of perfluoroalkylated aromatic systems
Description
Different methods of introducing perfluoroalkyl groups onto aromatic systems have been investigated in the effort to achieve synthesis of novel ligands exhibiting unique chemical and physical properties. Techniques of facilitating the perfluoroalkylation of aromatic and heterocyclic organic molecules were investigated and used in the syntheses of perfluoroalkyl pyrazoles, perfluoroalkyl phthalonitriles, perfluoroalkyl phthalocyanines and boron subphthalocyanines. Alkyl-pyrazoles were perfluoroalkylated by perfluoroalkyl radicals, and perfluoroacyl acetylenes were condensed with hydrazine to form perfluoroalkyl-alkyl-pyrazoles. Perfluoroisopropylphthalonitriles were synthesized by the reaction of perfluoroisopropyl anion (generated in situ) and tetrafluorophthalonitrile. The reactions of 4,5-bis(perfluoroisopropyl)-3,6-difluorophthalonitrile with zinc, colbalt, and ruthenium salts at high temperature in the attempt to form metal complexes of 2,3,9,10,16,17,23,24-octakis(perfluoroisopropyl)-1,4,8,11,15,18, 22,25-octafluorophthalocyanine are described. The synthesis and attempted synthesis of some fluorinated and perfluoroalkylated subphthalocyanines and unsymmetrical phthalocyanines is included