Phthalocyanine

A phthalocyanine is a macrocyclic compound having an alternating nitrogen atom-carbon atom ring structure The Phthalocyanines - Vols 1-4 Edited by C. C.Leznoff and A.B.P.Lever, Wiley 1986-1993"Phthalocyanine Materials - Synthesis, Structure and Function", Neil B. mckeown, Cambridge University Press 1998The Porphyrin Handbook, Vols. 15-20; Karl Kadish, Kevin M. Smith, Roger Guilard (eds); Academic Press 2003.

The molecule is able to coordinate hydrogen and metal cations in its center by coordinate bonds with the four isoindole nitrogen atoms. The central atoms can carry additional ligands. Most of the elements have been found to be able to coordinate to the phthalocyanine macrocycle. Therefore, a variety of phthalocyanine complexes exist.

Contents 1 History 2 Overview 3 Synthesis 4 Applications 5 References 6 External links

History

The first known appearance of an unknown blue by-product (which we now know was metal-free phthalocyanine) was reported in 1907. A.Braun, J.Tcherniac, Berichte der Deutschen Chemischen Gesellschaft, 1907, 40, 2907 In 1927, two researchers from Switzerland accidentally synthesized copper phthalocyanine, copper naphthalocyanine and copper octamethylphthalocyanine when they tried to convert σ-dibromobenzene into phthalonitrile. They remarked the enormous stability of these complexes but failed to appreciate their discovery and to fully characterize these blue complexes. H. de Diesbach,E. von der Weid, Helevtica Chimica Acta, 1927, 10, 886. The real discovery also started as an accident, when a blue product was found in a reaction flask where only white product was expected. However, this accident occurred in a dye company, Scottish Dyes, Ltd., Grangemouth, Scotland (later ICI) and the discovery was followed on.

Overview

The structure of a phthalocyanine molecule is closely related to that of the naturally occurring porphyrin systems.

Relationship of the phthalocyanine with the porphyrin macrocycle

The phthalocyanine macrocycle is also related to some other macrocyclic complexes, as e.g., the subphthalocyanine, superphthalocyanine or hemiporphyrazine.

Synthesis

The figure below (left side) shows that a phthalocyanine macrocycle consists of four identical corners. A synthesis strategy, therefore, starts from molecules which correspond to these corners. Such molecules are derivatives of phthalic acid: e.g., phthalonitrile, o-cyanobenzamide, phthalanhydride, phthalimide or diiminoisoindole. Several of these starting materials are shown in the figure below (right side).

Strategy for the synthesis of phthalocyanines

Typical starting materials for the synthesis of phthalocyanines

Applications

Copper phthalocyanine dyes are produced by introducing solubilizing groups, such as one or more sulfonic acid functions in CPC structure. These dyes find extensive use in various areas of textile dyeing (Direct dyes for cotton), for spin dyeing and in the paper industry. Direct blue 86 is the sodium salt of CPC-sulfonic acid whereas direct blue 199 is the ammonium salt of the CPC-sulfonic acid.

The organic amine salts of these sulfonic acids used as solvent dyes because of their solubility in organic solvents, e.g. Solvent Blue 38 and Solvent Blue 48.

The dye derived from Cobalt PC and an organic amine is Phthalogen Dye IBN.

1,3 Diiminoisoindolene, the intermediate formed during phthalocyanine manufacture, used in combination with a copper salt affords the dye GK 161.

Phthalocyanine Blue BN.png Phthalocyanine Blue BN

Phthalocyanine Green G.png Phthalocyanine Green G

References

External links

• Society of Porphyrins and Phthalocyanines
• Sir Patrick Linstead: Phthalocyanines (Video)

This article is licensed under the GNU Free Documentation License. It uses material from Wikipedia