Novel phthalocyanines bearing four 4-phenyloxyacetic acid functionalities

Metal-free (2) and Co(II), Zn(II), Ni(II), Cu(II) metallophthalocyanines (2a–d) with four 4-phenyloxyacetic acid groups on the periphery were prepared by cyclotetramerization of new p-(3,4-dicyanophenoxy)phenylacetic acid (1) and the corresponding divalent metal salts. Further reactions of these products with thionylchloride and then benzylamine in tetrahydrofuran, and octanol in pyridine gave amide (3, 3a–d) and ester (4, 4a–d) derivatives, respectively. The new compounds have been characterized by elemental analyses, IR, UV–Vis, mass and 1H NMR spectroscopy. The redox properties of compounds 2 and 2a–d were identified by cyclic voltammetry.

Graphical abstractA metal-free phthalocyanine was synthesized from p-(3,4-dicyanophenoxy)phenylacetic acid. The metallo derivatives were prepared by its treatment with metal salts. Further reactions of these products with thionylchloride and then benzylamine and octanol gave amide and ester derivatives, respectively. The compounds were characterized and cyclic voltammetry of these compounds was also presented.Figure optionsDownload full-size imageDownload as PowerPoint slide