New kinds of A3B-type unsymmetrical phthalocyanines

Phthalocyanine was first found as a byproduct of the synthesis of o-cyanobenzyl at 1907. Phthalocyanine Word is derived from Greek naphtha (mineral oil) and cyanine (dark blue). 20 years after this discovery, in 1927 by Diesbach and his friends synthesized 1,2-dibromobenzene from copper phthalocyanine. The synthesis method developed by Linstead, a plurality of metals in phthalocyanine synthesized and have shed light on the structure. X-ray diffraction analysis of phthalocyanines done by Robertson. In 1928 the first discovery of industrial phthalocyanines at Scottish Dyes Ltd. by phahthlimide assumption that occurred from phthalic anhydride and ammonia in the reactor in the company. Scottish Dyes Ltd. employees and Dunsworth Dnadrig have done preliminary work on the iron-containing material and have demonstrated that it has the potential of this product is extremely stable and insoluble pigments. They have proved that a phthalocyanine complex formed with iron metal leaked from the reactor of the substances which occur as a byproduct. In 1928, Scottish Dyes company Imperial Chemical Industries (ICI) have made the first patent application which has been associated with phthalocyanine in 1929. ICI awards article to learn the structure of the colored material and a sample Professor Jocelyn F. Thorpe. It's also the matter of the newly appointed lecturer Reginald P. Linstead gave to prove the relevance of research on behalf of the Academy (1902-1966). Thus ICI by defining the structure of the cooperation between Linstead and phthalocyanine contained in the synthesis of new metal phthalocyanine . Journal of Chemical Society began publishing the series published 6 pages. Imperial College for Science and Technology by employee Reginald P. Linstead organic compounds phthalocyanine used the first word in 1933 to define a new class. The advantages of phthalocyanine on a wide range of research is done. This is because the cytochrome and exhibit considerable similarities with the composition comprising macrocyclic structures such as chlorophyll. Phthalocyanines pigments and dyes are used commercially due to the high absorption properties they own. Because even a very small amount of saturated colors can vary. Also recently it phthalocyanines, since they have a high absorption function, many studies for use in photodynamic therapy is available. The heteroatomic phthalocyanines, thermal stability, chemical resistance, electrical, optical and fluid in both theoretical and application areas Because of the crystal properties are of great importance. Phthalocyanines are not at natural state and complete macrocyclic structures derived synthetically. Phthalocyanines, phthalimide as starting materials, phthalonitrile, phthalic anhydride, can be synthesized in the laboratory using diiminoizoindol and phthalic acid derivatives. Phthalocyanine ligands can form almost all metals complex. The number of square planar coordination of the phthalocyanine ring is four. phthalocyanine complexes with metal atoms of square pyramidal, octahedral and square planar prefer the result of the high number of co-ordination. Several methods are available which can be used for the synthesis of phthalocyanine. The choice of method is generally depends on the cost of synthesis. Phthalonitrile, phthalic acid, phthalic anhydride, phthalimide, and the starting material such as o-cyanobenzamide diiminoizoindol depends on the substituents. Synthesis with phthalonitrile provides a simple and clean process. The synthesis of phthalic anhydride although cheap needs catalysis such as ammonium molybdate or boric acid and urea, and productivity is low. Phthalocyanines can accommodate two hydrogen atoms or one metal atom in their central cavity. More than seventy different elements have been used to produce metallo phthalocyanines. Phthalocyanines coordinated by the metals having higher coordination number can result in square pyramidal, square planar or octahedral structures. In such cases central metal atom can be coordinated axially with ligands like Cl and H2O. Lanthanide and actinide metal ions form sandwich complexes, in which two Pc rings complex with the same metal ion. Phthalocyanines and metal containing phthalonitrile amines, phenols or alkali metal alcoholates are obtained as a result of reactions. The removal of metal from the metal phthalocyanine in the center with Elektrovalent to obtain metal-free phthalocyanine occurs. Phthalocyanines substituted depending on the number of groups of the starting materials can be separated as tetra or octa. In addition, according to the types of groups with the starting materials can be divided into symmetric and asymmetric. Tetrasubstitued phytalocyanines are generally obtained as a mixture of four structural isomers rarely be separated from one another. Tetrasubstitued phytalocyanines , have a much greater resolution than oktasubstitued Phytalocyanine. After synthesizing phthalocyanine, it is purified with UmAdIr most important method needs to be done. Once synthesized, the residue material to separate from product residues in the starting material is necessary. If the unwanted metal mixtures in the environment exists during the synthesis of phthalocyanine, phthalocyanine metal complex and affected by this synthesis may eventually lead to a defective product. It has been mentioned suitable methods for the synthesis of pure Pc. Symmetric and asymmetric synthesis of phthalocyanine are available. Although various methods of preparing substituted phthalocyanine symmetric, asymmetric substituted phthalocyanine preparation has quite a few methods. So recently attention has been paid to work on the expansion of the asymmetric synthesis of phthalocyanine. The reason is that this type phthalocyanines with unique physicochemical properties and structural capabilities. Valuable applications in material science of these compounds, especially for non-linear optics and optical limitations are available for use in photodynamic applications. This study was conducted studies on the asymmetric phthalocyanine. Asymmetric phthalocyanines is coming together as a mixture of isomers of two or more different but phthalonitrile derivative of these isomers is very difficult. Asymmetrical or symmetrical phthalocyanines low due to the inclusion of different substituents in peripheral positions are called asymmetrical phthalocyanines. Such phthalocyanines and porphyrazines attracts a lot of attention because of organized own properties. Most of the liquid is of asymmetric phthalocyanine crystal property. However, different types of phthalocyanine in the presence of the distillation of the mixture, and isolating the desired product is difficult. Generally, the yield is lower than others in the asymmetric synthesis of phthalocyanine. Three methods are available for the asymmetric synthesis of phthalocyanines. These statistical condensation method of synthesis of the polymer support and subphtalocyanine method. In this study, A3B type metals and metal-free phthalocyanines (3-5) with a dinitrile compound comprising Sudan IV compound and 4-nitrophthalonitrile compound was synthesized successfully. Statistical condensation method leads to a mixture of various substituted phthalocyanines. Thus, phthalonitrile in the selection of the starting materials of this group of resolutions. Cyclotetramerized the reaction of the intended synthesis, phthalocyanine compounds of different structure is 3: 1 type in the play an important role in the separation asymmetric phthalocyanine. Sudan which is a dinitrile compound containing group IV and 4-nitrophthalonitrile, n-pentanol in the after treatment by boiling under reflux and subsequently concentrated acid with dissolved lithium salt obtained asymmetric metal-free phthalocyanine. Then the metal-metal salts in the presence of zinc and cobalt phthalocyanine obtained when the phthalocyanine compound is provided. A3B phthalocyanine of the desired type (3-5) was obtained after purification medium efficiency. THF synthesized this compound 3 is dissolved in solvent such as dichloromethane. Compounds H-NMR, MALDI-TOF was characterized by FT-IR. A3B type phthalocyanine compounds (3-5) aggregation studies were examined in photophysical and photochemical properties. Compared to the non substituted zinc phthalocyanine is dissolved in THF low fluorescence quantum yield of compound 3 and 4 and show a shorter lifetime. 3 and 4 in compounds of the fluorescence was quenched effectively THF with 1,4 benzoquinone.