[4-(3,6-Dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid
[CAS# 2747959-96-0]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: [4-(3,6-Dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid
• Synonyms: Me-4PACz
• Molecular Formula: C₁₈H₂₂NO₃P
• Molecular Weight: 331.35
• CAS Registry Number: 2747959-96-0
• EC Number: 954-313-0
• SMILES: CC1=CC2=C(C=C1)N(C3=C2C=C(C=C3)C)CCCCP(=O)(O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.621, Calc.^*
• Boiling Point: 525.8±60.0 ºC (760 mmHg), Calc.^*
• Flash Point: 271.8±32.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Discovory and Applicatios

[4-(3,6-Dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid is an important organic molecule that has drawn considerable interest in recent years due to its multifunctional properties and potential applications in advanced electronic and optoelectronic materials. This compound contains two critical functional units: a carbazole core and a phosphonic acid group, linked via a butyl chain. The combination of these structural components makes it useful for applications in organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and self-assembled monolayers (SAMs).

The carbazole core of the molecule, specifically the 3,6-dimethyl-substituted variant, provides excellent electron-donating properties and high thermal stability. Carbazole derivatives are widely recognized for their hole-transporting capabilities, making them valuable in electronic devices. The addition of methyl groups at the 3 and 6 positions enhances the stability and electronic properties of the carbazole unit, improving its ability to transport charge carriers. This structural modification is particularly advantageous in preventing undesired aggregation and improving film-forming properties, which are critical for the fabrication of high-performance devices.

The phosphonic acid group, attached to the molecule through a butyl linker, allows for strong binding to metal oxide surfaces such as indium tin oxide (ITO) and other transparent conducting oxides. This binding property makes [4-(3,6-dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid a promising candidate for use as a surface-modifying agent. By forming a self-assembled monolayer (SAM) on electrode surfaces, the molecule can improve the interface properties between the electrode and the organic layers in devices like OLEDs and OPVs. These SAMs help reduce surface energy, enhance charge injection efficiency, and improve overall device performance and stability.

The discovery of this compound emerged from efforts to improve the efficiency and lifetime of organic electronic devices through interface engineering. Researchers recognized the need for stable hole-transport materials that could be easily anchored to electrode surfaces. The synthesis of [4-(3,6-dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid typically involves a multi-step process. The initial step includes the preparation of 3,6-dimethylcarbazole, which is then alkylated with a butyl halide. Finally, the phosphonic acid group is introduced through a phosphonation reaction using appropriate reagents like triethyl phosphite followed by oxidation. Each step requires careful control to achieve high yields and purity of the final product.

One of the key applications of [4-(3,6-dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid is in OLED technology. In OLEDs, the compound can be used to modify the anode surface, improving hole injection from the electrode to the emissive organic layer. By enhancing hole injection efficiency, the molecule helps reduce operating voltage and improve luminance efficiency. This results in brighter displays and lower power consumption, which are critical for applications in display panels, smartphones, and televisions.

In the field of organic photovoltaics, the compound is utilized to enhance the performance of devices by improving the interface between the active layer and the electrode. The self-assembled monolayer formed by the phosphonic acid group ensures better energy level alignment, facilitating efficient charge extraction and reducing recombination losses. This leads to higher power conversion efficiencies and improved device stability, making the molecule valuable for developing next-generation solar energy technologies.

Furthermore, [4-(3,6-dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid has potential applications in the creation of hybrid organic-inorganic materials. By anchoring the carbazole unit to metal oxide surfaces, researchers can design materials that combine the advantages of organic semiconductors with the robustness of inorganic materials. These hybrid systems are being explored for use in sensors, light-harvesting systems, and other functional materials.

Research continues to focus on optimizing the synthesis, processing, and application of [4-(3,6-dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid to unlock its full potential. The combination of excellent hole-transport properties and strong surface-binding capabilities ensures that this compound remains a versatile tool in the advancement of organic electronics and optoelectronics.