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 (F F ), 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 0.55 to 0.75.
Highlights
Phthalocyanines (Pcs) are known as macrocyclic compounds with different blue-green colors and unique spectroscopic properties
All the compounds were purified by column chromatography after thin layer chromatography studies
Their characterization were performed by using FTIR, 1H NMR and UV-Vis spectroscopic techniques, together with mass spectra and elemental analysis
Summary
Phthalocyanines (Pcs) are known as macrocyclic compounds with different blue-green colors and unique spectroscopic properties. The most versatile method of modifying a Pc’s properties comes from the Pc’s 16 different perimeter substitution points (α and β), as these allow the addition of substituents of almost any composition, electron affinity, polarity, and size. These substituents are what allow Pcs to perform the host of functions that they are used for in the modern industry [15]. Substituents that carry properties affecting the electron distribution of the Pc can, affect the Pc’s photophysical properties and are position sensitive [16]
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