Compound 1 has been prepared by the reaction of 4-nitrophthalonitrile with triethanolamine. Compound 3 has been synthesized with quaternarization of compound 2 which prepared by cyclotetramerization of compound 1. The synthesized compounds have been characterized by elemental analysis, H-1 NMR, UV Vis, IR and MALDI-TOF MS spectral data. The interaction of compound 3 with calf thymus DNA was investigated spectrophotometrically. The phthalocyanine-DNA binding mechanism as well as the thermodynamic properties of binding was studied. The thermal denaturation profile, gel electrophoresis studies and the viscosity experiments were also conducted to clarify the mechanism. The replacement of ethidium bromide with phthalocyanine was monitored flourometrically to verify the binding mode. The Stern Volmer plot has nonlinear characteristic that implies both collisions of molecules and formation of ground state complexes which causes the fluorescence quenching. The experimental results indicate that the synthesized ball type water soluble phthalocyanine binds to calf thymus DNA via mainly intercalation. (C) 2015 Elsevier Ltd. All rights reserved.