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

1-Chloro-9,10-bis(phenylethynyl)anthracene is an organic compound belonging to the anthracene family. It features an anthracene core substituted with two phenylethynyl groups at positions 9 and 10, and a chlorine atom at position 1. This specific substitution pattern significantly influences its chemical and physical properties.

Chemical Structure and Properties

The molecule possesses a planar, conjugated π-system extending across the anthracene core and the phenylethynyl substituents. This extensive conjugation contributes to its potential applications in optoelectronics and materials science. The presence of the chlorine atom introduces a degree of electron-withdrawing character, further modifying its electronic properties. The precise spectroscopic data (UV-Vis, fluorescence, etc.) would be dependent on the solvent and surrounding environment. Its solubility is likely to be influenced by the relatively non-polar nature of the phenylethynyl groups.

Synthesis

The synthesis of 1-Chloro-9,10-bis(phenylethynyl)anthracene likely involves Sonogashira coupling reactions, a common method for forming carbon-carbon bonds between aryl halides (in this case, a chloroanthracene) and terminal alkynes (phenylethyne). Specific reaction conditions (catalyst, solvent, base) would need to be optimized for optimal yield.

Applications

Due to its extended conjugation and the presence of the chlorine atom, 1-Chloro-9,10-bis(phenylethynyl)anthracene could potentially find applications in various fields. These may include:

• Organic Light-Emitting Diodes (OLEDs): The conjugated structure suggests potential as an emitter or charge-transporting material in OLED devices.
• Organic Field-Effect Transistors (OFETs): Its electronic properties might make it suitable for use in OFETs.
• Nonlinear Optics: Molecules with extended conjugation often exhibit nonlinear optical properties.
• Sensors: The interaction of the molecule with its environment might allow for its use in sensing applications.

Safety and Handling

As with most organic compounds, appropriate safety precautions should be taken when handling 1-Chloro-9,10-bis(phenylethynyl)anthracene. Specific safety data sheets (SDS) should be consulted for detailed information regarding its toxicity, flammability, and other hazards. Suitable personal protective equipment (PPE) should be worn at all times.