1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene
[CAS# 78525-36-7]

Identification

• Name: 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene
• Molecular Formula: C₂₆H₁₆Cl₄
• Molecular Weight: 470.22
• CAS Registry Number: 78525-36-7
• SMILES: C1=CC(=CC=C1C(=C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC=C(C=C4)Cl)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.653, Calc.^*
• Boiling Point: 526.8±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 261.7±26.1 ºC, Calc.^*

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

Discovory and Applicatios

1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene is a chemical compound known for its intricate structure, featuring multiple chlorinated aromatic rings connected through an ethenyl bridge. The molecular formula of this compound is C26H15Cl4, indicating the presence of four chlorine atoms within its structure, each attached to a phenyl ring.

The discovery of 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene is part of a broader effort in organic chemistry to explore and synthesize novel polyaryl ethylenes, which are compounds characterized by the presence of multiple aromatic rings connected by an ethenyl group. The introduction of chlorine atoms into these structures is particularly significant, as chlorinated aromatic compounds are known for their unique chemical and physical properties, including increased stability, resistance to degradation, and specific electronic characteristics.

The synthesis of 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene typically involves the reaction of chlorinated benzene derivatives with an appropriate ethenyl precursor under controlled conditions. The process is designed to ensure that the chlorination occurs selectively, leading to the formation of the desired product without unwanted by-products. This compound's structure, with its multiple chlorinated phenyl rings, gives it a high degree of rigidity and planarity, which can be advantageous in various applications.

One of the primary applications of 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene is in the field of advanced materials, particularly in the development of high-performance polymers and specialty chemicals. The presence of chlorine atoms in the compound contributes to its chemical inertness and resistance to oxidative degradation, making it a valuable component in the formulation of materials that require durability under harsh conditions. For example, polymers incorporating this compound can exhibit enhanced thermal stability and resistance to chemical attack, making them suitable for use in coatings, adhesives, and other industrial applications.

In addition to its use in materials science, 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene has been investigated for its potential applications in the field of organic electronics. The compound's structure allows for efficient π-π stacking interactions between the aromatic rings, which can facilitate charge transport in organic semiconductors. This property makes it a candidate for use in the active layers of organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs), where efficient charge transport is crucial for device performance.

Furthermore, the unique electronic properties of this compound, influenced by the electron-withdrawing effects of the chlorine atoms, make it an interesting subject for research in the design of novel organic molecules with specific optoelectronic characteristics. Researchers are exploring how modifications to the core structure of 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene can lead to new materials with tailored properties for applications in sensors, transistors, and other electronic devices.

The study of 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene also contributes to our understanding of the broader class of polyaryl ethylenes and their derivatives. By examining how the introduction of different substituents, such as chlorine atoms, affects the compound's properties, chemists can develop a deeper understanding of structure-property relationships in organic molecules. This knowledge is essential for the rational design of new materials with desired characteristics.

In summary, 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethenyl]benzene is a notable compound in the field of organic chemistry, with applications ranging from materials science to organic electronics. Its discovery and ongoing research highlight the importance of chlorinated aromatic compounds in developing advanced materials and technologies.