Synthesis and characterization of phthalocyanine derived with a new chalcone

Phthalocyanines set up by chance have been the subject of numerous inquiries and these (Leznoff and Lever, 1989b; McKeown, 1998). Phthalocyanine (Pc), which means"dark blue mineral oil painting" in Greek, was discovered at the morning of the twentieth century as an undoable and dark colored by product during the conflation of o-cyanobenzamide from phthalimide and acetic anhydride, but its molecular structure wasn't illustrated for further than a quarter of a century (De Diesbach and Von der Weid, 1927; Leznoff and Lever, 1989b). Although phthalocyanines are composed of pyrrole units and are structurally veritably analogous to motes set up spontaneously in nature, similar as chlorophyll a, hemoglobin and porphyrin, they're produced entirely synthetically (García-Sánchezetal.,2013). Phthalocyanines are veritably stable blue or green colors and colorings, an important class of commercially available chemicals in numerous fields of technology. The two hydrogen tittles in the patch's central depression are one of further than 70 central can be substituted with essence, and a variety of Substituents can be attached to both supplemental and axial positions. (De la Torre et al; Elemans et al, 2006; Engelkamp and Middelbeek, 1999) In particular, supplemental or list of different groups to thenon-peripheral positions and Pc depression, making it easier to synthesize motes. PCs are red photodynamic remedy in recent times because they absorb in the hereafter region (600- 800 nm). PDT) system, which can be used in the alternate generation print detectors class. Eldar et al, 1990; Haimovici et al, 2002; Spesia et al, 2009). The phthalocyanine emulsion, a tetrapyrrole outgrowth, was first synthesized in 1907 in the South Metropolitan- cyanobenzamidine by Braun and Tcherniac at the Gas Company (London) reported as a result of its accidental appearance as a colored byproduct during product. Braun and Tcherniac, 1907). Latterly, in 1927, the University of Fribourg By Diesbach and von Weid, o- dibromobenzene was synthesized from bobby cyanide and pyridine bobby (II) as a blue product formed by hotting at high temperature in the presence of phthalocyanine (Pc) was attained but its structure wasn't illustrated (De Diesbach and Von 2 der Weid, 1927) in 1934, a symmetric, 18 π, conforming of four iminoisoindoline units. The structure of sweet phthalocyanine (Pc) with electrons was delved by Linstead and Robertson's X-ray studies. (Linstead, 1934; Linstead and Lowe, 1934). Phthalocyanine, with its naturally being porphyrin structure similarity, with the differences arising from the four benzo groups and nitrogen tittles in each of the four meso positions (McKeown, 2003; Robertson,) Both metal-containing and metal-free phthalocyanines have been known for nearly a century and are in the same group as biologically occurring porphyrins, making them xxii perhaps one of the most extensively studied macrocyclic molecules. Due to their beneficial properties, such as optical, electronic, electrical, photoelectric and electrochemical properties, they have become among the most studied candidates for use in the production of new electronic devices, gas sensors and detectors, many catalytic reactions and solar cells. The intramolecular π-π interactions of phthalocyanines lead to strong intermolecular interactions, which in turn cause aggregation, which negatively affects the solubility of the molecules. Therefore, the utilization of the extraordinary properties of these structures is undermined. To avoid this, different functional groups or newly designed molecules are attached to phthalocyanines from peripheral or non-peripheral positions. These bonded groups or molecules confer different unique properties to phthalocyanines. Chalcones, which are aromatic ketones and enones, are the basis of many biological compounds and have important properties such as anti-cancer antioxidant, antimicrobial, cytotoxic, analgesic and antipyretic They are also known as precursors of flavonoids and isoflavonoids. The synthesis of a basic chalcone compound is carried out via aldol condensation and is formed by a sodium hydroxide-catalyzed reaction between an aldehyde and a ketone. Chalcones, which are compatible with their biological activity and have good solubility, can be easily used in biological systems. In areas such as electrocatalysis, photodynamic therapy, enzyme inhibitory effects, photodiode properties, photophysical and photochemical properties, metal sensing applications, DNA binding, enzyme inhibition synthesis of chalcone-substituted metallophthalocyanines, spectral, electrochemical and spectroelectrochemical properties are of increasing interest for both experimental and theoretical studies. In this study, the synthesis of a chalcone-derived phthalocyanine and its electrochemical and spectroelectrochemical behavior will be investigated and the experimental spectroscopic data will be compared with the theoretical data calculated by FTIR method. To synthesize my target Pc's, I first obtained chalcone 3 compound. For this, I synthesized chalcone 3 compound by adding 4-Methoxyacetophenone to 4- hydroxybenzyldehyde molecule in the presence of KOH catalyst for 24 hours. For this, starting from 4-hydroxybenzyldehyde and 4-Methoxyacetophenone, I obtained chalcone 3 compound with a yield of 28.4% in ethanol water mixture. I used my chalcone 3 compound as the main product to synthesize chalcone 5. I added potassium carbonate to my chalcone 3 compound by dissolving 4-nitrophthalonitrile in DSMO and continued my reaction for 24 hours and synthesized my chalcone 5 compound. This synthesized chalcone compound will be the starting material of phthalocyanine at room temperature with 4-nitrophthalonitrile in a yield of 52.1%. 1H and 13C NMR spectra were used to determine the structures of chalcone 3 and chalcone 5. The synthesized chalcone 3 and chalcone 5 molecules were confirmed by FT-IR spectra. The phthalonitrile compound 5 was used as starting material for metallophthalocyanines (MPc's). Chalcone 3 and chalcone 5 were successfully synthesized as tetrahedral metallophthalocyanines with "(E)-3-(4-hydroxyphenyl)-1- (4-methoxyphenyl) prop-2-en-1-one"attached at the peripheral positions of the phthalocyanines. This monomer was then reacted with Zn(OAc)2.2H2O, Co(OAc)2.4H2O salts and cadmium acetate dihydrate at 160 ⁰C under nitrogen atmosphere at 160 ⁰C using Zn+2 for Pc-6, Co+2 for Pc-7 and Cd+2 for Pc-8 as metal ion sources for the center of phthalocyanines. Metallophthalocyanines were obtained by reaction with zinc, cobalt and cadmium salts. After the cyclotetramerization reaction, an isomeric mixture of the desired MPc's was obtained as expected. The xxiii synthesized new phthalocyanines Pc-6, Pc-7, Pc-8 were characterized by 1H and 13C NMR, FTIR, HRMS and UV-Vis spectroscopy Keywords: Chalcone, Phthalocyanine, Redox, spectroelectrochemistry, Catalysis, UV Visible