Bathocuproin
[CAS# 4733-39-5]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: Bathocuproin
• Synonyms: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
• Molecular Formula: C₂₆H₂₀N₂
• Molecular Weight: 360.46
• CAS Registry Number: 4733-39-5
• EC Number: 225-240-5
• SMILES: CC1=CC(=C2C=CC3=C(C=C(N=C3C2=N1)C)C4=CC=CC=C4)C5=CC=CC=C5

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 279-283 °C (Expl.)
• Index of Refraction: 1.686, Calc.^*
• Boiling Point: 531.9±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 231.0±21.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H413
• Safety Statements: P264-P270-P273-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Bathocuproine is a chemical substance that has garnered significant attention for its unique properties and applications in various scientific fields. It is a copper(I) complex, specifically a copper(I) chelate of 2,9-dimethyl-1,10-phenanthroline. Bathocuproine exhibits remarkable characteristics, such as strong coordination with copper ions, making it an excellent ligand for copper-based applications. The discovery of bathocuproine dates back to studies of transition metal coordination compounds, where it was identified as an effective ligand that forms stable complexes with copper.

Bathocuproine is primarily used in the field of chemistry for detecting and quantifying trace amounts of copper ions in various samples. Its ability to strongly bind copper ions has made it a popular reagent in analytical chemistry, particularly in the development of colorimetric assays. The binding of copper to bathocuproine results in a characteristic color change, which can be quantified using spectrophotometry. This property is useful in environmental monitoring, industrial processes, and biochemical assays where copper levels need to be measured precisely.

In addition to its analytical uses, bathocuproine has been explored for its potential applications in materials science, particularly in the field of organic electronics. It is used in the fabrication of copper-based organic light-emitting diodes (OLEDs), where its coordination with copper helps improve the stability and performance of the devices. Copper complexes in OLEDs are beneficial for their low-cost fabrication and efficient energy conversion. Bathocuproine's ability to stabilize the copper ion in such devices is crucial for enhancing their durability and overall efficiency.

Bathocuproine also plays a significant role in the study of copper redox chemistry. By forming stable copper complexes, it helps researchers investigate the behavior of copper in different oxidation states, which is important for understanding copper’s role in biological systems and industrial applications. Copper is an essential metal in many biological processes, and bathocuproine has been used in studies examining copper's role in enzymes, metalloproteins, and its interaction with other biological molecules.

Another notable application of bathocuproine is in the development of sensors for environmental and industrial monitoring. Its ability to specifically detect copper ions makes it a useful component in sensors that monitor water quality or industrial waste, ensuring that copper contamination is quickly identified and managed. This is particularly relevant in industries such as mining, where copper is often found in large quantities and must be carefully controlled.

In summary, bathocuproine is a versatile compound with applications spanning analytical chemistry, materials science, and environmental monitoring. Its strong coordination with copper ions has led to its widespread use in detecting copper in various settings, as well as enhancing the performance of copper-based materials in electronics. As research continues, bathocuproine is likely to find even more applications in fields where the interaction of metals and complex ligands plays a crucial role.

References

2024. Tailoring the π-conjugation in self-assembled hole-selective molecules for perovskite photovoltaics. Science China Materials.
DOI: 10.1007/s40843-024-3093-9

1965. Eine Methode zur spektralphotometrischen Bestimmung von Kupfer in hochgereinigtem Niob, Tantal, Molybdän und Wolfram mit Bathocuproin. Fresenius' Zeitschrift für analytische Chemie.
DOI: 10.1007/bf00514578