Novel phthalocyanines bearing four 4-phenyloxyacetic acid functionalities

Abstract

Metal-free (2) and Co(II), Zn(II), Ni(II), Cu(II) metalloplithalocyanines (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 H-1 NMR spectroscopy. The redox. properties of compounds 2 and 2a-d were identified by cyclic voltammetry. (C) 2007 Elsevier Ltd. All rights reserved.