The synthesis of novel, hexadeca-substituted metal-free and zinc(II) phthalocyanines bearing naphthoxy groups and chloro groups in peripheral positions and hexyloxy groups in non-peripheral positions is described. These phthalocyanines were characterized with elemental analyses, mass, proton nuclear magnetic resonance (H-1 NMR), fourier transform infrared spectroscopy (FT-IR) and ultraviolet-visible spectroscopy (UV-vis) techniques. Aggregation properties of these compounds were investigated in the different concentration range. The influences of the substituent on the hexadeca-substituted phthalocyanine framework and metal ion on the spectroscopic and photophysical properties have been investigated. The energy transfer to phthalocyanine core and radiative decays of the naphthol emission and phthalocyanine core were examined. (C) 2014 Elsevier B. V. All rights reserved.