Synthesis of non-peripherally and peripherally substituted zinc (II) phthalocyanines bearing pyrene groups via different routes and their photophysical properties

This work reports on photophysical properties of the non-peripherally and peripherally substituted zinc phthalocyanines (Pcs) prepared by two different synthetic routes. Tetra-substituted non-peripheral (5) and peripheral (6) zinc phthalocyanines containing 4-mercaptophenol groups were synthesized from novel phthalonitrile derivatives for the first time. Pyrene-containing phthalocyanine derivatives (7-8) were obtained by the reaction of compounds 5-6 with 1-bromoacetylpyrene. In the second route, compounds 7-8 were prepared by cyclotetramerization of pyrene-containing phthalonitrile derivatives (3a or 4a). The synthesized compounds were characterized by elemental analysis, FT-IR, UV-Vis, NMR spectroscopy and mass spectra. General trends were described for electronic absorption, fluorescence quantum yields, lifetimes, and fluorescence quenching by benzoquinone of these compounds. The effects of position of substituent on photophysical properties of the tetra-substituted zinc Pcs were also investigated. (C) 2013 Elsevier Ltd. All rights reserved.