Tetra-p-tolylethene
[CAS# 5831-43-6]

Identification

• Name: Tetra-p-tolylethene
• Synonyms: 1-methyl-4-[1,2,2-tris(4-methylphenyl)ethenyl]benzene
• Molecular Formula: C₃₀H₂₈
• Molecular Weight: 388.54
• CAS Registry Number: 5831-43-6
• SMILES: CC1=CC=C(C=C1)C(=C(C2=CC=C(C=C2)C)C3=CC=C(C=C3)C)C4=CC=C(C=C4)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.613, Calc.^*
• Boiling Point: 480.5±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 245.8±21.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

Tetra-p-tolylethene is an organic compound that belongs to the family of polyaryl ethylenes. Its molecular structure consists of four p-tolyl groups attached to a central ethene (ethylene) unit, which imparts a unique combination of rigidity, planarity, and electronic properties to the molecule. The chemical formula of Tetra-p-tolylethene is C30H28, reflecting its composition of carbon and hydrogen atoms, with each p-tolyl group contributing a methyl-substituted phenyl ring to the overall structure.

The discovery of Tetra-p-tolylethene can be traced back to the mid-20th century, during a period of intense research into the synthesis and properties of substituted ethylenes. These studies aimed to explore how different aryl substitutions affected the stability, reactivity, and electronic characteristics of the central ethene unit. The synthesis of Tetra-p-tolylethene typically involves the coupling of p-tolyl-substituted precursors under conditions that promote the formation of the central double bond, resulting in the assembly of the four aryl groups around the ethene core.

Tetra-p-tolylethene has garnered attention primarily for its application in materials science, particularly in the development of organic semiconductors and light-emitting materials. The planar structure of the molecule, combined with the presence of four p-tolyl groups, allows for efficient π-π stacking interactions, which are crucial for charge transport in organic electronic devices. This property makes Tetra-p-tolylethene a promising candidate for use in organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs), where high charge mobility and stability are essential for device performance.

In OLEDs, Tetra-p-tolylethene can be incorporated into the emissive layer, where it contributes to the efficient generation of light through the recombination of electrons and holes. Its molecular structure can be tuned to achieve specific emission wavelengths, making it possible to produce devices with tailored color outputs. The use of Tetra-p-tolylethene in OPVs, on the other hand, is based on its ability to facilitate charge separation and transport, leading to improved power conversion efficiencies in solar cells.

Beyond electronics, Tetra-p-tolylethene has also found applications in the development of advanced polymers and specialty materials. Its rigid, planar structure imparts mechanical strength and thermal stability to polymer matrices, making it a valuable component in high-performance coatings, adhesives, and other materials that require durability under challenging conditions. The methyl groups on the p-tolyl rings further enhance the hydrophobicity of the material, providing resistance to moisture and chemical degradation.

In addition to its practical applications, Tetra-p-tolylethene is of interest to researchers studying the fundamental aspects of organic chemistry. Its structure serves as a model system for understanding how aryl substitution patterns influence the electronic properties of ethylenes. By examining the effects of different substituents on the central ethene unit, chemists can gain insights into the design principles needed to create new materials with specific optical and electronic properties.

The study of Tetra-p-tolylethene also contributes to the broader field of conjugated organic molecules, where the interplay between molecular structure and function is a key focus. Researchers are particularly interested in exploring how variations in the substitution pattern, such as the introduction of electron-donating or electron-withdrawing groups, affect the material's performance in various applications.

In summary, Tetra-p-tolylethene is a notable compound in organic chemistry and materials science, with applications ranging from organic electronics to high-performance polymers. Its discovery and continued study provide valuable insights into the design and synthesis of advanced materials with tailored properties.