Phthalocyanine-copper complex

The insolubilities of phthalocyanines made their analysis difficult and it took some time before a satisfactory structure was elucidated. Initial work was undertaken by the Linstead group at Imperial College in the 1930s that culminated in a series of six back to back papers published in 1934 [14], It was also Linstead who named the compounds in recognition of their synthesis from phthalic anhydride and similarity to the blue cyanine dyes. Definitive characterization of the nickel, platinum and copper phthalocyanine complexes, together with the metal-free compound, was revealed in 1935 following the publication of their X-ray structures by Robertson [15] the copper and metal-free compounds are illustrated in Fig. 7.5. 

INCORPORATION OF ANIONIC COPPER PHTHALOCYANINE COMPLEXES INTO THE INTERGALLERY OF Mg-AI LAYERED DOUBLE HYDROXIDES... 

In contrast to the copper phthalocyanine complex, magnetic exchange in the copper dipivaloil methanate complex is significant in all directions and averages not only the hyperfine but also the Zeeman part of interactions of all ions in a given direction. The resulting g-factor has a three-axis anisotropy and its main frame coincides with the axes of a crystalline lattice frame. 

Of all the metal complexes evaluated, copper phthalocyanines give the best combination of color and properties and consequentiy the majority of phthalocyanine dyes are based on copper phthalocyanine Cl Direct Blue 86 [1330-38-7] (Cl 74180) (68) is a typical dye. 

Although the substitution of a preformed phthalocyanine always leads to a complex mixture of more- or less-substituted products, the reaction is of major industrial importance. Besides the chloro- and bromocopper phthalocyanines, also polysulfonated phthalocyanines, which are used as water-soluble dyes, are produced by the reaction of copper phthalocyanine with the respective reactant. While typical aromatic reactions of the Friedel-Crafts type are also possible,333 direct nitration of the macrocycle commonly results in oxidation of the phthalocyanine. However, under mild conditions it is possible to introduce the nitro group directly into several phthalocyanines.334... 

However, there are metal complex pigments. Without doubt the most important metal complex pigment is copper phthalocyanine (4). The phthalocyanines were discovered by accident in 19286 and now represent the second most important class of colorants after the azo colorants. Copper phthalocyanine itself exists in several polymorphic forms and gives beautiful blue and cyan colors with outstanding fastness properties.5-7 Halogenated copper phthalocyanines provide green pigments (see Section 9.12.4.3). 

Organic semiconductors are becoming increasingly important in the fabrication of electronic devices. For electron transport, metal complex pigments, such as hexa-deca-fluoro copper phthalocyanine (76), are showing potential.79... 

Copper, and occasionally silver, have been used as catalysts for hydroformylation of a-olefins. Phosphite complexes of copper(I) chloride have been claimed as catalysts (126). Phthalocyanine complexes of Group IB metals have been stated to show a low degree of catalytic activity (127). One of the more interesting examples of copper catalysis was disclosed by McClure (128). Copper powder, with a controlled amount of water (0.2-4.0 moles H20/mole Cu), gave a slow conversion of pro-... 

Two processes have been used for making copper phthalocyanine, but neither yields a form suitable for immediate use as a pigment since the physical form and size distribution of the resulting particles are far from the optimum. The product is generally referred to as crude blue and requires purification and a sometimes complex series of finishing processes before it is in a form ready for use as a pigment. 

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