3-Bromo-11,11-dimethyl-11H-benzo[b]fluorene
[CAS# 1674334-59-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Fluorenes
• Name: 3-Bromo-11,11-dimethyl-11H-benzo[b]fluorene
• Molecular Formula: C₁₉H₁₅Br
• Molecular Weight: 323.23
• CAS Registry Number: 1674334-59-8
• SMILES: CC1(C2=C(C=C(C=C2)Br)C3=CC4=CC=CC=C4C=C31)C

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.671, Calc.^*
• Boiling Point: 435.5±24.0 °C (760 mmHg), Calc.^*
• Flash Point: 213.0±17.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

3-Bromo-11,11-dimethyl-11H-benzo[b]fluorene is a polycyclic aromatic hydrocarbon (PAH) that has attracted significant interest in the fields of organic chemistry and material science. With the molecular formula C16H15Br, this compound is characterized by its distinctive structure, which consists of a fluorene core modified by bromine and two methyl groups at the 11-position. The unique arrangement of its aromatic rings confers both interesting chemical properties and potential applications in various domains.

The discovery of 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene is rooted in the broader research efforts to synthesize and characterize brominated PAHs. These compounds have been extensively studied due to their significance in environmental chemistry, organic electronics, and materials science. The synthesis of 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene typically involves bromination reactions on the fluorene structure, providing a straightforward pathway to obtain the desired brominated derivative.

One of the primary applications of 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene lies in the field of organic electronics. The compound's unique electronic properties make it suitable for use in organic semiconductors, where it can be employed as a building block in the design of organic light-emitting diodes (OLEDs) and organic photovoltaic (OPV) devices. The presence of bromine enhances the material's solubility and allows for better film-forming properties, which are crucial for device fabrication. Moreover, the electronic structure of 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene facilitates charge transport, improving the overall performance of organic electronic devices.

Additionally, 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene is explored for its potential use in dye-sensitized solar cells (DSSCs). The compound's robust light absorption properties can be leveraged to enhance the efficiency of these solar cells. By integrating 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene into the dye sensitizers used in DSSCs, researchers aim to improve energy conversion rates and develop more efficient solar energy harvesting technologies.

In the realm of chemical sensing, 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene has shown promise as a sensing material due to its ability to interact with various analytes. Its structure allows for the detection of specific ions or molecules, making it a valuable candidate for the development of selective chemical sensors. This application has implications in environmental monitoring, where detecting pollutants or hazardous substances is crucial for public safety.

Furthermore, the compound has been investigated for its biological activities, particularly in the context of its potential as an anticancer agent. Preliminary studies suggest that 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene may exhibit cytotoxic effects against certain cancer cell lines. Ongoing research aims to explore its mechanism of action and optimize its efficacy as a therapeutic agent.

In summary, 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene is a versatile compound with promising applications in organic electronics, solar energy conversion, chemical sensing, and medicinal chemistry. Its unique structural features and electronic properties make it an attractive candidate for ongoing research and development. As the scientific community continues to explore its potential, 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene may contribute significantly to advancements in technology and therapeutic applications.

References

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