Synthesis and characterization of functional phthalocyanines containing oxygen bridge

Phthalocyanines (Pcs) are 18 ?-electron aromatic macrocycles comprising four isoindole units linked together through their 1,3-positions by aza bridges. The particular two-dimensional electron delocalization over these macrocycles gives rise to a great number of unique physical properties. Thus, Phthalocyanines are chemically and thermally stable compounds that exhibit exceptional optical and electrical behavior. For these reasons, they find wide application in the area of materials science. Phthalocyanines are capable of incorporating more than 70 different metallic and nonmetallic cations in their ring cavity. It is also possible to attach a wide variety of substituents at the periphery of the macrocycle, which can alter the electronic structure of the system, and, when these groups are bulky or long chain hydrophobic moieties, can serve to increase the solubility?s of Phthalocyanines in common organic solvents. In the visible region, phthalocyanines are limited to blue, cyan and green colors. However, their absorption may be extended into the near infrared and by suitable chemical engineering it is possible to fingerprint the 700 - 1000 nm region.In the present work metallophtalocyanines {M[Pc(O-BzF4)]4 ( M=Cu(II), Zn(II), Co(II), Bz=Benzen} were obtain from cylotetramerization reaction of 4-(2,3,5,6-tetrafluorophenyl)phthalonitrile with corresponding appropriate [M(acac)2].nH2O in the presence of quinoline and 1,8-diazabicyclo[5,4,0] undec-7-ene (DBU) as a strong at reflux temperature.All of the phthalocyanines were purified by chromatography. The elemental analysis, IR, UV-Vis, 1H-NMR, 13C-NMR and MS (Mass) spectra confirm the proposed structures of the compounds