A phthalonitrile precursor 4-(3-hydroxypropylmercapto)phthalonitrile (3) was synthesized via a base-catalyzed nucleophilic aromatic nitro displacement of 4-nitrophthalonitrile with the 3-mercapto-1-propanol. A novel tetrasubstituted metal-free phthalocyanine (4) (M = 2H) and its metal complexes (5-8) (M = Zn, Ni, Cu and Co) bearing 3-hydroxypropylmercapto moieties were prepared by the cyclotetramerization reaction of (3) with the appropriate materials. The visible spectra of the zinc(II) phthalocyanine (5) was recorded with different concentrations and different ions as Ag+, Hg2+ and Pb2+ in DMF and also with different solvents as dimethylformamide and pyridine. Fluorescence spectrum of the compound (5) was also studied. Temperature and frequency dependence of AC conductivity for (4-8) was investigated in air and under vacuum and were found to be similar to 10(-8)-10(-5) S.m(-1). Thermal properties of the phthalocyanines were examined by differential scanning calorimetry. All the novel compounds have been characterized by elemental analysis, UV-vis, FT-IR, NMR and MS spectral data and DSC techniques.