1,3,5-Triphenylbenzene
[CAS# 612-71-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 1,3,5-Triphenylbenzene
• Molecular Formula: C₂₄H₁₈
• Molecular Weight: 306.40
• CAS Registry Number: 612-71-5
• EC Number: 210-318-3
• SMILES: C1=CC=C(C=C1)C2=CC(=CC(=C2)C3=CC=CC=C3)C4=CC=CC=C4

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 172-174 ºC (Expl.)
• Index of Refraction: 1.619, Calc.^*
• Boiling Point: 460.0±0.0 ºC (760 mmHg), Calc.^*
• Flash Point: 233.3±17.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

1,3,5-Triphenylbenzene is an organic compound consisting of a central benzene ring substituted with three phenyl groups at the 1, 3, and 5 positions. Its structure imparts unique physical and chemical properties, making it a compound of interest in various research and industrial applications. The compound is part of a larger class of molecules known as polyphenyls, and its synthesis and characterization have been studied extensively in the fields of organic chemistry and material science.

The discovery of 1,3,5-triphenylbenzene dates back to the early 20th century, with the first reports of its synthesis appearing in the chemical literature in the 1900s. The development of methods for synthesizing substituted benzene derivatives, including triphenylbenzene, was made possible by advances in the field of aromatic chemistry. The compound’s synthesis typically involves the Friedel–Crafts alkylation reaction, where a phenyl group is added to a benzene ring in the presence of a catalyst such as aluminum chloride. Over the years, researchers have developed more efficient synthetic routes, expanding the scope of its applications.

One of the primary areas of interest for 1,3,5-triphenylbenzene is in the study of organic materials, particularly in the development of organic semiconductors and light-emitting devices. Its unique structure, with three bulky phenyl groups attached to a central benzene ring, allows for specific interactions with other molecules, which can influence its electronic and optical properties. As such, 1,3,5-triphenylbenzene has been investigated for use in organic light-emitting diodes (OLEDs), organic solar cells, and other electronic devices where organic materials are used for their semiconducting properties. The molecule’s high thermal stability and its ability to form stable thin films make it an attractive candidate for these applications.

In addition to its role in organic electronics, 1,3,5-triphenylbenzene is also studied for its potential use in liquid crystal displays (LCDs). Its molecular structure allows it to interact with liquid crystals in ways that can be useful for tuning the properties of the display material, such as improving response times and enhancing the clarity of the image. This has led to the exploration of 1,3,5-triphenylbenzene as a potential component in liquid crystal devices.

Furthermore, 1,3,5-triphenylbenzene has been utilized in research related to supramolecular chemistry, which involves the study of non-covalent interactions between molecules. Its rigid structure and ability to interact with other molecules in a specific manner make it a useful tool in the design of molecular assemblies and materials. For instance, it can be used as a building block in the synthesis of molecular scaffolds and host-guest systems, where it can form complexes with other molecules. Such interactions can be explored for applications in sensors, catalysis, and drug delivery systems.

1,3,5-triphenylbenzene is also studied for its photophysical properties, particularly its fluorescence. Its ability to emit light upon excitation makes it a useful molecule in the development of fluorescent materials for various applications, including sensors, biological imaging, and dye-sensitized solar cells. The fluorescence properties of 1,3,5-triphenylbenzene are influenced by the environment in which it is placed, and research into these effects continues to provide valuable insights into the behavior of organic fluorescent materials.

In conclusion, 1,3,5-triphenylbenzene is a versatile and important chemical compound with numerous applications in materials science, organic electronics, and supramolecular chemistry. Its unique molecular structure and ability to interact with other molecules make it a valuable component in the development of advanced materials, including OLEDs, liquid crystal displays, and organic semiconductors. As research into its properties and applications continues, 1,3,5-triphenylbenzene is likely to play an increasingly important role in the development of next-generation electronic and optoelectronic devices.