A new phthalonitrile derivative (2), bearing diethylaminophenoxy - and chloro-substituents at peripheral positions was synthesized in this work. Cyclotetramerization of (2) in hexanol gave the desired metal-free (4) and metallophthalocyanines (5-8). These new phthalocyanines (4-8) were converted into water-soluble quaternized products by the reaction with methyl iodide (9-11). The novel compounds have been characterized by using elemental analysis, UV-Vis, FT-IR, (1)H NMR and MS spectroscopic data. The aggregation behaviors of the phthalocyanine complexes wet e studied in different solvents and concentrations. Electrochemical and spectroelectrochemical characterization of the complexes were also performed in solution. Cobalt phthalocyanine gives both metal-based and ring-based reduction processes in comparison to the complexes having 2H(+), Zn(2+), Ni(2+) and Cu(2+) metal center which give only ring-based reduction processes. Electrochemical and spectroelectrochemical measurements exhibit that all complexes oxidatively electro-polymerize on the Pt working electrode during repetitive cyclic voltammetry measurements. An in-situ electrocolorimetric method was applied to investigate the color of the electrogenerated anionic and cationic forms of the complexes for possible electrochromatic applications. (C) 2011 Elsevier Ltd. All rights reserved.