The synthesis and some properties of a novel type of phthalocycanine containing 4- substituted alkoxy group

In this work, the synthesis of new tetrahydrofurfuryl alcohol substituted metallo- phthalocyanines were described, heating without solvent methods.The first step in the synthetic procedure was to obtain phthalonitrile derivative containing tetrahidrofurfuryl alcohol group. This was accomplished by a base catalyzed nucleophilic aromatic nitro displacement of 4-nitrophthalonitrile with tetrahydroforfuryl alcohol. This reaction was carried out at 75-80 oC in DMF with K2CO3 as the base with good yield.The second step in the synthetic procedure was to obtain phthalocyanine compounds.The metallophthalocyanines were prepared from the corresponding phthalonitrile derivative and the metal salts (Co(II), Ni(II), Zn(II), Cu(II) acetates) by heating without solvent.The metal-free phthalocyanine (H2Pc) was also synthesized by heating a mixture of the phthalonitrile compound with DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) in the absence of solvent.Pcs were characterized using different spectroscopic techniques (FT-IR, UV?Vis, and 1H-NMR).Key Words: Phthalocyanine, Metal phthalocyanines, Synthesis