In this study, 7-(diethyl 2-methylmalonatoxy)-3-[p-(3,4-dicyanophenoxy)phenyl]coumarin (3), 7-(diethyl 2-methylmalonatoxy)-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin (4) and their related peripheral and non-peripheral tetra substituted zinc(II) (3a and 4a) and indium(III) chloride (3b and 4b) phthalocyanine derivatives were prepared for the first time. The novel phthalonitrile (3 and 4) and phthalocyanine (3a-b and 4a-b) compounds were characterized by elemental analyses and different spectroscopic techniques such as FT-IR, UV-vis, H-1 NMR and MALDI-TOF mass. The spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of these novel phthalocyanines were investigated in dimethylsulfoxide solutions. The fluorescence quenching behaviors of the studied zinc(II) phthalocyanines (3a and 4a) by 1,4-benzoquinone were also determined. (C) 2016 Elsevier B.V. All rights reserved.