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Phthalocyanine
[CAS# 574-93-6]

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Identification
Classification Biochemical >> Biochemical reagent >> Biological dye
Name Phthalocyanine
Synonyms 29H,31H-Phthalocyanine
Molecular Structure CAS # 574-93-6, Phthalocyanine, 29H,31H-Phthalocyanine
Molecular Formula C32H18N8
Molecular Weight 514.54
CAS Registry Number 574-93-6
EC Number 209-378-3
SMILES C1=CC=C2C(=C1)C3=NC4=NC(=NC5=C6C=CC=CC6=C(N5)N=C7C8=CC=CC=C8C(=N7)N=C2N3)C9=CC=CC=C94
Properties
Density 1.5±0.1 g/cm3, Calc.*
Melting point 300 ºC (decomp.) (Expl.)
Index of Refraction 1.932, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H315-H319-H335    Details
Precautionary Statements P261-P280-P305+P351+P338-P304+P340-P405-P501    Details
SDS Available
up Discovory and Applicatios
Phthalocyanine is a synthetic, organic compound known for its vibrant color and remarkable chemical properties. It is a macrocyclic compound that has found wide application in industries ranging from pigments to electronics, due to its stability, intense color, and conductive properties. The discovery of phthalocyanine and its subsequent applications have made it one of the most important chemical substances in modern material science.

Phthalocyanine was first synthesized in 1907 by the chemist L. S. McCay while attempting to create a new blue pigment. McCay’s work led to the formation of the first phthalocyanine pigment, which was initially a deep blue color. This compound was later identified as a metal complex, which includes a central metal atom coordinated to the nitrogen atoms in a macrocyclic structure. The term “phthalocyanine” derives from its structure, which is based on phthalic acid, a common aromatic compound. Over time, various metal derivatives of phthalocyanine, such as copper, cobalt, and aluminum phthalocyanines, were developed, each offering unique properties and applications.

One of the most significant applications of phthalocyanine is as a pigment. The deep blue color of copper phthalocyanine, in particular, became widely popular in the paint, ink, and textile industries. The pigment is prized for its exceptional lightfastness, chemical stability, and resistance to heat and weathering. It is used in a range of products, including automotive paints, printing inks, plastics, and cosmetics. The versatility of phthalocyanine pigments is largely due to the stability provided by the complexed metal ion at the center of the phthalocyanine ring, which prevents degradation and fading over time.

Phthalocyanines have also found important roles in the field of electronics and photonics. Certain phthalocyanine compounds exhibit semiconducting properties, making them useful in organic light-emitting diodes (OLEDs), solar cells, and photodetectors. Their ability to conduct electricity and their sensitivity to light has led to their application in organic photovoltaic cells, which are being developed as alternatives to traditional silicon-based solar panels. The high stability of phthalocyanines also contributes to the longevity and performance of these devices. Research into phthalocyanines as electron-accepting materials in organic solar cells continues to expand, with new metal-doped phthalocyanines showing promising results for improving efficiency.

In the field of catalysis, phthalocyanines are utilized as catalysts in various chemical reactions, particularly in reactions that involve oxidation processes. Metal-phthalocyanine complexes have been found to be effective catalysts in the conversion of hydrocarbons and other organic compounds, making them useful in industrial processes such as the production of fine chemicals and petrochemical refining. The ability of phthalocyanines to stabilize metal centers and facilitate electron transfer is key to their catalytic activity.

Phthalocyanines are also being investigated for use in medical applications. As photosensitizers in photodynamic therapy (PDT), certain phthalocyanine derivatives have shown effectiveness in treating cancer and other diseases. PDT involves the use of a photosensitizer, which is activated by light to produce reactive oxygen species that can destroy cancerous cells. The ability of phthalocyanine compounds to absorb light in the red to near-infrared region of the spectrum makes them suitable for this application, as these wavelengths penetrate deeper into tissue compared to shorter wavelengths.

In addition, the use of phthalocyanines in environmental applications, such as the removal of pollutants and the degradation of toxic substances, is an area of active research. Their strong affinity for metal ions and their ability to form stable complexes with various substances make them candidates for use in water purification and soil remediation.

Phthalocyanines also have potential applications in biotechnology and sensor technologies. Due to their ability to interact with biological molecules and their stability under various conditions, they are being explored as components in biosensors and diagnostic devices.

In conclusion, phthalocyanine is a versatile and highly functional chemical substance with a range of applications across several industries. From its discovery as a pigment to its use in electronics, catalysis, and medical treatments, the potential of phthalocyanine continues to be explored. Its unique combination of chemical stability, color properties, and electrical conductivity makes it an indispensable material in many modern technologies.
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