This study reports the 3 new phthalonitrile derivatives, namely 4, 5 Bis-[4-(4-bromophenoxy) phenoxy] phthalonitrile (1), 4,5 Bis-[4-(4-chlorophenoxy) phenoxy]phthalonitrile (2), and 4, 5 Bis[4-(4-fluorophenoxy) phenoxy] phthalonitrile (3). Their octasubstituted zinc phthalocyanines (4, 5, 6) are reported for the first time in this study. The resulting compounds were characterized by utilizing some spectroscopic methods, such as UV-Vis, 1 HNMR, FT-IR spectroscopy, as well as mass spectraand elemental analysis. To show photosynthesizer’s potential, emission (FF ), singlet oxygen (1 O2 ), and photodegradation quantum yields (F∆, Fd ) of octaperipherally phthalocyanines (Pcs) were performed in the solutions, such as biocompatible solvent DMSO (dimethyl sulfoxide) as well as DMF (dimethylformamide) and THF (tetrahydrofuran). | Turkish Journal of Chemistry Turk J Chem 2020 44 1556-1564 http chem TÜBİTAK Research Article doi kim-2007-56 Newly synthesized peripherally octa-substituted zinc phthalocyanines carrying halogen terminated phenoxy-phenoxy moiety comparative photochemical and photophysical features Erkan KIRBAÇ Ali ERDOĞMUŞ Department of Chemistry Yıldız Technical University İstanbul Turkey Received Accepted Published Online Final Version Abstract This study reports the 3 new phthalonitrile derivatives namely 4 5 Bis- 4- 4-bromophenoxy phenoxy phthalonitrile 1 4 5 Bis- 4- 4-chlorophenoxy phenoxy phthalonitrile 2 and 4 5 Bis 4- 4-fluorophenoxy phenoxy phthalonitrile 3 . Their octa- substituted zinc phthalocyanines 4 5 6 are reported for the first time in this study. The resulting compounds were characterized by utilizing some spectroscopic methods such as UV-Vis 1HNMR FT-IR spectroscopy as well as mass spectraand elemental analysis. To show photosynthesizer s potential emission FF singlet oxygen 1O2 and photodegradation quantum yields F Fd of octa- peripherally phthalocyanines Pcs were performed in the solutions such as biocompatible solvent DMSO dimethyl sulfoxide as well as DMF dimethylformamide and THF tetrahydrofuran . Solvent and octa-peripherally binding effect of the halogen Br Cl F terminated phenoxy-phenoxy groups on phthalocyanine rings for photophysicochemical properties 4 5 and 6 were compared with the tetra-peripherally and tetra nonperipherally substituted derivatives. The new dyes 4 to 6 may be evaluated in photodynamic therapy PDT of cancer as photosensitizers due to efficient 1O2 from to . Key words Photochemistry photophysics zinc phthalocyanine octa-substituted halogen substitution 1. Introduction Phthalocyanines Pcs are known as macrocyclic compounds with different blue-green colors and unique spectroscopic properties. After being discovered in 1927 accidentally Pcs have since found use in
