Microwave-assisted synthesis and characterization of the monomeric phthalocyanines containing naphthalene-amide group moieties and the polymeric phthalocyanines containing oxa-aza bridge

New naphthalene-amide substituted phthalocyanines and oxa-aza bridge polymeric phthalocyanines were prepared by conventional and microwave methods. The chlorides of Cu(I), Ni(II) and Co(II) were employed in order to synthesize the corresponding metal phthalocyanines and Zn(CH3COO)2 was used for the preparation of the zinc phthalocyanines. For the preparation of the Co-containing phthalocyanines, ammonium molybdate had to be added as catalyst. In the microwave-assisted synthesis, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or DMAE (dimethylaminoethanol) was used as a solvent. The solubility of the phthalocyanines containing naphthalene-amide group (1a–e, 3a–e) is low in ethanol, ethyl acetate, chloroform, DMF and DMSO. Polymeric phthalocyanines (2a–e) are not soluble in common organic solvents such as chloroform, DMF and DMSO but are soluble in dilute H2SO4.