Microwave-Assisted Synthesis and Characterization of the Monomeric Phthalocyanines Containing Naphthalene-Amide Group Moieties and the Polymeric Phthalocyanines Containing Oxa-Aza Bridge

Abstract

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(CH<inf>3</inf>COO)<inf>2</inf> 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 H<inf>2</inf>SO<inf>4</inf>. © 2006 Elsevier Ltd. All rights reserved.