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Phthalocyanines A synthetic compound having molecules with four isoindole rings linked by N= bridges. The structure is similar to that of the porphyrins. It can form complexes with central metal ions. Copper phthalocyanines are used as dyes.

(General structure of Phthalocyanine) Unsubstituted Phthalocyanine, abbreviated H2Pc, and many of its complexes have very low solubility in organic solvents. Benzene at 40 C dissolves less than a milligram of H2Pc or CuPc per liter. H2Pc or CuPc dissolve easily in sulfuric acid due to the protonation of the nitrogen atoms bridging the pyrrole rings. Many phthalocyanine compounds are thermally very stable, do not melt but can be sublimed, CuPc sublimes at >500 C under inert gases (nitrogen, CO2). Substituted phthalocyanine complexes often have much higher solubility. They are less thermally stable and often cannot be sublimed. Unsubstituted phthalocyanines strongly absorb light between 600 and 700 nm, thus these materials are blue or green. Substitution can shift the absorption towards longer wavelengths, changing the color from pure blue to green to colorless (when the absorption is in the near infrared). Phthalocyanines are structurally related to other macrocyclic pigments, especially the porphyrins. Both feature four pyrrole-like subunits linked to form a 16-membered ring. The pyrrole-like rings within H2Pc are closely related to isoindole. Both porphyrins and phthalocyanines function as planar tetradentate dianionic ligands that bind metals through four inwardly projecting nitrogen centers. Such complexes are formally derivatives of Pc2, the conjugate base of H2Pc. Many derivatives of the parent phthalocyanine are known, where either carbon atoms of the macrocycle are exchanged for nitrogen atoms or where the hydrogen atoms of the ring are substituted by functional groups like halogens, hydroxy, amino, alkyl, aryl, thiol, alkoxy, nitro, etc. groups.