Tetrasodium 1,3,6,8-pyrenetetrasulfonate
[CAS# 59572-10-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Tetrasodium 1,3,6,8-pyrenetetrasulfonate
• Synonyms: 1,3,6,8-Pyrenetetrasulfonic acid tetrasodium salt; Trasar 23299
• Molecular Formula: C₁₆H₁₉O₁₂S₄.₄Na
• Molecular Weight: 623.54
• CAS Registry Number: 59572-10-0
• EC Number: 626-424-1
• SMILES: O=S(=O)([O-])c1cc(S(=O)(=O)[O-])c2ccc3c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])c4ccc1c2c43.[Na+].[Na+].[Na+].[Na+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Tetrasodium 1,3,6,8-pyrenetetrasulfonate is a water-soluble organic compound that belongs to the class of pyrene derivatives. It is a sulfonated version of pyrene, a polycyclic aromatic hydrocarbon, where four sulfonate groups are attached at the 1, 3, 6, and 8 positions of the pyrene ring structure. Its chemical formula is C16H8Na4O8S4, and it is often used as a fluorescent probe in various scientific and industrial applications due to its distinct optical properties.

The compound is typically synthesized by sulfonating pyrene with concentrated sulfuric acid in the presence of suitable reagents that allow for the selective substitution of sulfonate groups at the specified positions on the pyrene ring. The resulting product is then neutralized to form the tetrasodium salt, which is highly soluble in water and can be easily handled in aqueous environments.

One of the most notable characteristics of tetrasodium 1,3,6,8-pyrenetetrasulfonate is its fluorescent properties. Pyrene and its derivatives are well known for their ability to absorb light at specific wavelengths and emit light at longer wavelengths. When excited by ultraviolet (UV) or visible light, tetrasodium 1,3,6,8-pyrenetetrasulfonate emits fluorescence that is used in various applications, particularly in the fields of analytical chemistry and biochemistry.

One major application of tetrasodium 1,3,6,8-pyrenetetrasulfonate is in fluorescence spectroscopy. The compound is used as a fluorescence probe to study the interactions between different molecules in solution. It is particularly useful in detecting hydrophobic environments and studying molecular interactions in biological systems, such as protein-ligand interactions, membrane studies, and drug binding studies. The distinctive fluorescence of this compound allows for sensitive detection and analysis of chemical or biological processes.

In addition to its use in fluorescence spectroscopy, tetrasodium 1,3,6,8-pyrenetetrasulfonate is often employed in surface chemistry and material science. It can be used to investigate the surface properties of nanoparticles and other materials. When adsorbed onto surfaces, the compound’s fluorescence properties can reveal information about the surface characteristics and interactions of materials, such as surface roughness, charge, and molecular organization. This makes it a valuable tool in the development of advanced materials for applications in sensors, electronics, and catalysis.

Tetrasodium 1,3,6,8-pyrenetetrasulfonate is also used in biological assays. Due to its water solubility and fluorescent properties, it can be utilized in the study of cellular processes, such as cellular uptake and transport mechanisms. It has been used in live-cell imaging, allowing researchers to track the movement and localization of molecules within cells. The compound’s fluorescence intensity and emission spectrum make it a useful tool in imaging applications, particularly in the context of cellular biology and drug discovery.

Furthermore, tetrasodium 1,3,6,8-pyrenetetrasulfonate has been employed in the development of biosensors and diagnostic assays. The compound’s fluorescence can be used to detect the presence of specific analytes or changes in the environment, providing a means for sensitive and rapid detection in clinical and research settings.

Despite its numerous applications, the compound should be handled with care, as with any chemical that has a significant biological or chemical reactivity. It is important to follow appropriate safety guidelines to avoid exposure to the compound, especially in concentrated forms. Additionally, proper disposal procedures must be followed to prevent environmental contamination.

In conclusion, tetrasodium 1,3,6,8-pyrenetetrasulfonate is a versatile and highly useful compound in various scientific fields, particularly in fluorescence spectroscopy, surface chemistry, and biological research. Its fluorescent properties make it a valuable tool for studying molecular interactions, cell behavior, and material properties.

References

1990. The influence of unusual counterions on the electrochemistry and physical properties of polypyrrole. Journal of Materials Science, 25(9).
DOI: 10.1007/bf00582447

2017. An electrochemical aptamer-based assay for femtomolar determination of insulin using a screen printed electrode modified with mesoporous carbon and 1,3,6,8-pyrenetetrasulfonate. Microchimica Acta, 185(1).
DOI: 10.1007/s00604-017-2570-z

2021. A Pyrene Fluorescent Probe for Rapid Detection of Ferric Ions. Journal of Fluorescence, 31(3).
DOI: 10.1007/s10895-021-02695-3