A phthalocyanine is a macrocyclic compound having an alternating nitrogen atom-carbon atom ring structure.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.
overview
The first known appearance of an unknown blue by-product (which we now know was metal-free phthalocyanine) was reported in 1907. 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.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.
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).
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| Strategy for the synthesis of phthalocyanines |
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| Typical starting materials for the synthesis of phthalocyanines. |
