1-Chloro-9,10-bis(phenylethynyl)anthracene

1-Chloro-9,10-bis(phenylethynyl)anthracene is a chemical compound that belongs to the class of organic compounds known as anthracenes. It is a synthetic compound that is primarily used in the field of organic chemistry and material science.

Structure and Properties

• 1-Chloro-9,10-bis(phenylethynyl)anthracene is a polycyclic aromatic hydrocarbon (PAH) that consists of three fused benzene rings with a chlorine atom and two phenylethynyl groups attached. The compound is characterized by its planar structure and extended pi-conjugation, which contribute to its unique optical properties.

• The molecular formula of 1-Chloro-9,10-bis(phenylethynyl)anthracene is C30H16Cl, and its molecular weight is 405.90 g/mol. It is a solid at room temperature and exhibits strong fluorescence under UV light.

Synthesis

The synthesis of 1-Chloro-9,10-bis(phenylethynyl)anthracene involves the reaction of 9,10-dichloroanthracene with phenylacetylene in the presence of a palladium catalyst. This reaction is an example of a Sonogashira coupling, a type of cross-coupling reaction commonly used in organic chemistry to form carbon-carbon bonds.

Applications

Due to its strong fluorescence, 1-Chloro-9,10-bis(phenylethynyl)anthracene is often used as a fluorescent dye in various applications, including optical microscopy, fluorescence spectroscopy, and bioimaging. It is also used in the synthesis of organic light-emitting diodes (OLEDs) and other optoelectronic devices.

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Safety and Precautions

As with many chemical compounds, handling 1-Chloro-9,10-bis(phenylethynyl)anthracene requires caution. It should be used only in a well-ventilated area and with appropriate personal protective equipment (PPE), including gloves and eye protection. In case of exposure, seek immediate medical attention.

See Also

• Anthracene
• Polycyclic aromatic hydrocarbon
• Sonogashira coupling