Highly Organosoluble Metal‐Free Phthalocyanines and Metallophthalocyanines: Synthesis and Characterization

Abstract

Abstract The syntheses and characterization of metal‐free and metal‐containing (Zn and Ni) derivatives of a symmetrically octa‐substituted phthalocyanine derived from 4,5:12,13‐bis(4′‐ tert ‐butylbenzo)‐8,9‐(4″,5″‐dicyanobenzo)‐6,11‐ditosyl‐6,11‐diaza‐2,15‐dithiacyclohexadeca‐4,8,12‐triene and CuPc from 4,5:12,13‐bis(4′‐ tert ‐butylbenzo)‐8,9‐(4″,5″‐dibromobenzo)‐6,11‐ditosyl‐6,11‐diaza‐2,15‐dithiacyclohexadeca‐4,8,12‐triene were carried out. Pentanuclear silver(I) and palladium(II) complexes have also been prepared from nickel(II) phthalocyaninate derivatives. The prepared phthalocyanines were semiconducting materials in the range of 10 –5 to10 –10 S cm –1 in vacuo and under atmospheric pressure. The extraction abilities of NiPc and detosylated phthalocyanines were evaluated in chloroform/water by using several heavy‐metal picrates such as Ag + , Cd 2+ , Cu 2+ , Hg 2+ , Pb 2+ , Pd 2+ , and Zn 2+ . The extraction affinities of NiPc and detosylated phthalocyanines for Ag + were found to be the highest in solvent extraction experiments. The new compounds were characterized by using elemental analysis, UV/Vis, FTIR, NMR, MS spectroscopic data and DTA/TG. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)