A dinitrile precursor, 1,2-bis(3-hydroxypropylmercapto)-4,5-dicyanobenzene (3), was synthesized via base-catalyzed nucleophilic aromatic chlorine displacement of 4,5-dichlorophthalonitrile with 3-mercapto-1-propanol. A novel metal-free phthalocyanine (4) (M = 2H) and its metal complexes (5)-(8) (M = Zn, Ni, Cu and Co) were prepared by the cyclotetramerization reaction of (3) with the appropriate materials. The aggregation property of the zinc(II) phthalocyanine (5) was investigated in terms of concentration, Ag+, Hg2+, Pb2+ and Cd2+ cations and also different solvents, such as dimethylformamide and pyridine. Complexation of the peripheral dithia groups of (5) with Ag+ or Pd2+ yields the pentanuclear complex (9) or (10), respectively. The fluorescence spectrum of compound (5) was also studied. The electrical conductivities of (5)-(10) in air and under vacuum were found to be similar to 10(-9)-10(-5) S m(-1). All the novel compounds were characterized by elemental analysis, UV-Vis, FT-IR, NMR and MS spectral data and DSC techniques. (C) 2013 Elsevier Ltd. All rights reserved.