Phthalocyanine

Description

Phthalocyanine is an aromatic, intensely blue-green heterocyclic compound. Its structure is similar to that of porphine (the framework of molecules such as chlorophyll) with four fused benzene rings. It forms dye complexes with most metals in the periodic table, notably copper. A. Braun and J. Tcherniac reported the free molecule in 1907, but didn’t establish its structure. The copper form was made accidentally in 1927 when researchers were trying to make phthalonitrile.
Phthalocyanine dyes have been widely used for decades. But the molecule’s electronic properties make it potentially useful in the hi-tech world. Japanese researchers are devising ways to slow the tautomerization rate of phthalocyanine so that the molecule can exist in two electronically distinct states, corresponding to the binary system that has been the basis of computer technology. This development would give rise to “molecular memory” that could eventually be used in extremely fast computers. Phthalocyanine is also very compact: It may be able to store ≈13 terabytes of data on a 1-cm2?chip.

Chemical properties

Blue to purple powder

The Uses of Phthalocyanine

Phthalocyanine is a common macrocylic blue-green dye able to form coordination complexes with many elements on the periodic table.

What are the applications of Application

Phthalocyanine is a common macrocylic blue-green dye

Definition

ChEBI: A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.

Definition

phthalocyanine: A synthetic compoundhaving molecules with fourisoindole rings linked by –N= bridges.The structure is similar to that of theporphyrins. It can form complexeswith central metal ions. Copperphthalocyanines are used as dyes.

Flammability and Explosibility

Not classified

Agricultural Uses

Phthalocyanine is a group of benzoporphyrins which have strong pigmenting power, forming a family of dyes.
The basic structure of the molecule comprises four isoindole groups (C₆H₄,)C₂N, joined by four nitrogen atoms. Four commercially important modifications are: (a) metal free phthalocyanine (C₆H₄C₂N)₄, having a bluegreen color,(b copper phthalocyanine in which a copper atom is held by secondary valences of the isoindole nitrogen atoms, (c) chlorinated copper phthalocyanine, green, in which 15 to 16 hydrogen atoms are replaced by chlorine, and (d) sulphonated copper phthalocyanine, water-soluble and green, in which two hydrogens are replaced by sulphonic acid groups. It is used in decorative enamels and automotive finishes; chlorophyll and haems have basic phthalocyanine structures in their molecules.

Purification Methods

Purify phthalocyanine by sublimation (two to three times) in an argon flow at 300-400Pa; and similarly for the Cu(II), Ni(II), Pb(II), VO(II) and Zn(II) phthalocyanine complexes. [Beilstein 26 III/IV 4255.]