In this paper, novel two different chalcone compounds (E)-3-(5-chloro-2-hydroxyphenyl)-1-o-tolylprop-2-en-1-one (2a) and (E)-3-(5-bromo-2-hydroxyphenyl)-1-(2-methoxyphenyl)prop-2-en-1-one (2b) and their phthalonitrile compounds (3a and 3b) were synthesized in the first step. Then, metal-free (4a and 4b), cobalt (II) (5a and 5b), copper (II) (6a and 6b) and manganese (III) (7a and 7b) phthalocyanines containing chalcone groups at peripheral positions were synthesized. All novel compounds were characterized by general spectroscopic techniques. The electrochemical studies of cobalt (II) (5a and 5b), copper (II) (6a and 6b) and manganese (III) (7a and 7b) phthalocyanine complexes were determined by cyclic voltammetry (CV) and square-wave voltammetry (SWV). Electrochemical studies display that while the CuPc (6a and 6b) shows just Pc ring-based redox processes, the CoPc (5a and 5b), MnCIPc (7a and 7b) exhibit both metal-based and ring based redox reaction owing to the metal 3d orbitals lying among the Pc HOMO and LUMO. (C) 2019 Elsevier B.V. All rights reserved.