Tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane
[CAS# 929203-02-1]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: Tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane
• Synonyms: Tri[3-(3-pyridyl)mesityl]borane; Tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane; Tris(2,4,6-trimethyl-3-(pyridine-3-yl)phenyl)borane; Tris[3-(3-pyridyl)-2,4,6-trimethylphenyl]borane; Tris[3-(3-pyridyl)mesityl]borane; 3TPYMB
• Molecular Formula: C₄₂H₄₂BN₃
• Molecular Weight: 599.61
• CAS Registry Number: 929203-02-1
• SMILES: B(C1=C(C(=C(C=C1C)C)C2=CN=CC=C2)C)(C3=C(C(=C(C=C3C)C)C4=CN=CC=C4)C)C5=C(C(=C(C=C5C)C)C6=CN=CC=C6)C

Properties

• Solubility: Insoluble (1.5E^-6 g/L) (25 °C), Calc.^*
• Density: 1.13±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.636, Calc.^*
• Boiling Point: 697.4±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 375.6±31.5 °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

Tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane is a boron-based organic compound that has garnered significant attention in the fields of organic electronics, catalysis, and materials science. The structure of this compound consists of a boron atom centrally coordinating three 2,4,6-trimethyl-3-(3-pyridyl)phenyl groups, each of which contains both a pyridine and a phenyl ring. The presence of these functional groups imparts distinctive properties to the compound, making it useful in a variety of applications.

The discovery of tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane was part of an ongoing effort to design novel organic boron compounds for use in electronic and catalytic applications. Researchers have long been interested in boron-containing molecules due to their unique electronic properties, including their ability to interact with other chemical species through coordination. The pyridine group, in particular, offers a site for coordination with metal centers, while the trimethylphenyl groups provide stability and solubility in various solvents.

One of the most significant applications of tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane is in organic light-emitting diodes (OLEDs). OLEDs are widely used in display technologies, and their efficiency depends heavily on the materials used in the active layers. The incorporation of boron into the structure of OLED materials allows for enhanced charge transport properties and more efficient light emission. Tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane has been found to be particularly effective as a hole-transport material in OLED devices, improving both the brightness and stability of the resulting displays.

Additionally, the compound plays a crucial role in catalysis. The pyridine groups attached to the phenyl rings make tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane an excellent ligand for metal centers, facilitating the formation of metal-ligand complexes. These complexes are valuable in a wide range of catalytic processes, such as cross-coupling reactions and other organic transformations. The compound has been used in the development of new catalytic systems that are both efficient and selective, enabling reactions that were previously difficult or impractical to perform.

In the field of materials science, tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane is also being investigated for its potential use in the synthesis of new polymers and organic semiconductors. The compound’s ability to act as a building block for the design of more complex materials is of particular interest in the development of next-generation electronic devices. Its stability and versatility make it a promising candidate for the fabrication of high-performance materials for a variety of applications, including solar cells and sensors.

The compound’s use in energy applications extends beyond organic photovoltaics. The electronic properties of tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane also make it an attractive material for energy storage devices, such as organic batteries and supercapacitors. Its ability to undergo reversible electron transfer reactions enhances the efficiency of energy storage systems, which is crucial for the development of sustainable energy technologies.

In summary, tri[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane is a highly versatile and functional compound with a wide range of applications across various fields. Its electronic properties make it particularly useful in OLED technology, catalysis, and energy applications. Ongoing research into its properties and potential uses continues to uncover new applications, ensuring its place as a valuable material in the development of advanced technologies.

References

2024. In situ energetics modulation enables high-efficiency and stable inverted perovskite solar cells. Nature Photonics, 18(10).
DOI: 10.1038/s41566-024-01542-8

2024. Regulation of photophysical and electronic properties of I-III-VI quantum dots for light-emitting diodes. Science China Materials, 67(7).
DOI: 10.1007/s40843-024-2943-0

2024. Exciplex-driven blue OLEDs: unlocking multifunctionality applications. Applied Physics A, 130(5).
DOI: 10.1007/s00339-024-07520-9