Synthesis and computational studies of new metallo-phthalocyanines bearingdibenzoxanthenes and evaluation of their optical properties in solution and solidPMMA/ZnPc/Al nanocomposite films

Abstract

New thermally stable metallo-phthalocyanines bearing dibenzoxanthenes as highly organo-solubilizing aro-matic hydrocarbon substituents were successfully prepared by cyclotetramerization of corresponding phthalonitriles withanhydrous metal salts [Zn(CH3COO)2and NiCl2] in the presence of a catalytic amount of DBU in 2-(dimethylamino)ethanol. All of these phthalocyanines are soluble in some organic solvents such as DMF, DMSO, THF, CH2Cl2,and CHCl3. Then we successfully prepared the poly(methyl methacrylate) (PMMA)/ZnPc/Al nanocomposite lms byincorporating Al nanoparticles into a transparent PMMA/ZnPc matrix. The structure and morphology of nanocom-posite lms were studied using X-ray diffraction and scanning electron microscopy. The optical absorption spectra ofPMMA/ZnPc/Al nanocomposite lms showed red shifting in the Q-band in the polymeric matrix. The geometricalstructure of two phthalocyanines was investigated at the RHF/3-21G* computational level.