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Bathophenanthroline is an organic compound with important physical and chemical properties. It is a colorless or light yellow crystalline powder. The molecular formula C24H16N2, CAS 1662-01-7, has a melting point between 215 and 216 ℃ and is insoluble in water, but can be slightly soluble in dilute acids. In organic solvents, it has good solubility and is easily soluble in organic solvents such as ethanol, acetone, benzene, isoamyl alcohol, hexanol, etc. Its structure contains two bipyridine groups, which are connected to each other through a naphthalene ring.
BathophenanthroL has good stability. When forming complexes with metal ions, their color changes, making them a commonly used complexing indicator. It is a complex indicator with multiple uses, widely used in analytical chemistry, material science, electrochemistry, pharmaceutical chemistry, and other fields, providing important tools and methods for scientific research.
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| C.F | C24H16N2 |
| E.M | 332 |
| M.W | 332 |
| m/z | 332 (100.0%), 333 (26.0%), 334 (2.7%) |
| E.A | C, 86.72; H, 4.85; N, 8.43 |
1. Applications in analytical chemistry:
It is widely used in analytical chemistry for complexometric titration. It is a highly sensitive metal indicator that can form colored complexes with various metal ions to indicate the titration endpoint. For example, Bathophenanthrolin can form a red complex with copper ions for titration of copper ions. At the same time, it can also form complexes with metal ions such as iron, cobalt, and nickel for titration analysis of these metal ions. By using metal indicators such as Bathophenanthrolin, precise determination of trace metal ions can be achieved.
2. Applications in Materials Science:
Bathophenanthrolin is also widely used in materials science. BathophenanthroL can form complexes with various metal ions, so it can be used as a metal ion doping agent to prepare composite materials with specific properties. For example, by doping Bathophenanthrolin with titanium ions into polymers, composite materials with specific conductivity can be prepared. In addition, Bathophenanthrolin can also be used as a catalyst to promote polymerization reactions.
3. Applications in electrochemistry:
Bathophenanthrolin also has important applications in the field of electrochemistry. BathophenanthroL can be used as an indicator in electrochemical sensors to monitor the concentration of metal ions in solutions. For example, modifying Bathophenanthrolin onto the electrode surface can create a copper ion sensor for monitoring the concentration of copper ions in biological samples such as serum and urine. This type of sensor has extensive applications in the biomedical field and can be used for disease diagnosis and treatment monitoring.
4. Application in Pharmaceutical Chemistry:
Bathophenanthrolin also has some special applications in pharmaceutical chemistry. BathophenanthroL can serve as a carrier for anticancer drugs for drug delivery and targeted therapy. For example, Bathophenanthrolin can be connected to tumor specific antibodies, and then drug molecules can be connected to Bathophenanthrolin to achieve precise drug delivery and tumor treatment. In addition, Bathophenanthrolin can also be used for drug activity screening and drug action mechanism research, providing assistance for new drug development.
5. It can form colorless or yellow complexes with various metal ions.
For example, bathophenanthroL can form colorless complexes with Cd, Zn, and Mn, as well as yellow complexes with Fe, Cu, and Cu. In addition, iron complexes can be extracted by some organic solvents such as isoamyl alcohol, trichloromethane, n-hexanol, nitrobenzene, ethanol, and amyl acetate. Its dissociation constant (pK) is 4.30 (I=0.3, KCl, 25 ℃, 50% dioxane).
Organic synthesis and catalytic reactions
As a derivative of 1,10-phenanthroline, the two nitrogen atoms in the 4,7-diphenyl-1,10-phenanthroline molecule can form stable complexes with transition metal ions such as Zn ² ⁺, Cd ² ⁺, Mn ² ⁺, Fe ² ⁺, Cu ² ⁺, etc. These complexes are often used as catalysts in organic chemical reactions, promoting key steps such as coupling reactions and isomerization reactions.
For example, in the reaction of diethylzinc with n-pentane, 4,7-diphenyl-1,10-phenanthroline as a ligand can significantly improve the reaction efficiency, providing an important tool for the synthesis of complex organic molecules. In addition, its derivatives (such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) can also be used as organic synthesis blocks for the modification and derivatization of bioactive molecules and optoelectronic materials.
Analytical Chemistry and Metal Ion Detection
Plays an important role in analytical chemistry. The yellow complex formed with Fe ² ⁺ and Cu ² ⁺ has high stability and can be quantitatively detected for metal ions by photometry or extraction photometry. For example, in environmental monitoring, this compound can be used to determine the iron and copper content in water or soil; In the biomedical field, bathophenanthroL can be used for the detection of plasma copper ions, providing a basis for the diagnosis of related diseases. In addition, the excellent extraction performance of its complex in organic solvents makes it an effective tool for metal separation and enrichment.
Optoelectronic materials and electronic devices
Bathophenanthroline has shown great potential in the field of optoelectronic materials. The conjugated system in its molecular structure endows bathophenanthroL with excellent fluorescence properties, with emission spectra located in the visible light region and high quantum yields, making bathophenanthroL widely used in fields such as fluorescent probes, chemical labeling, and organic light-emitting diodes (OLEDs).
For example, as an electronic transport layer material for OLED devices, bathophenanthroL has high conductivity and fast transmission rate, which can significantly improve device performance. However, its stability issues (such as easy crystallization) still need further optimization to achieve commercial applications. In addition, the compound can also serve as a light absorbing agent for organic solar cells, converting solar energy into electrical energy and providing new ideas for the development of renewable energy.
Coordination Chemistry and Catalyst Design
BathophenanthroL is an important ligand in coordination chemistry. The complex formed with transition metals not only has high stability, but also can achieve specific catalytic functions through structural regulation. For example, copper (I) complexes are used in photocatalytic reactions due to their unique luminescent properties; Metal complexes such as zinc and cadmium can serve as catalyst precursors and participate in highly selective conversion processes such as asymmetric synthesis and cycloaddition reactions. These studies provide theoretical support for the development of green chemistry and sustainable synthesis technologies.
Biomedical and Fluorescence Imaging
Based on its excellent fluorescence performance, 4,7-diphenyl-1,10-phenanthroline has potential application value in the biomedical field. For example, its complexes can be used as fluorescent probes for dynamic monitoring of intracellular metal ions or research on protein ligand interactions. In addition, through functional modification, the compound can also achieve targeted delivery, providing new strategies for disease diagnosis and treatment.
BathophenanthroL is a commonly used chelating indicator that can be prepared in the laboratory through different synthesis methods. The following are common laboratory synthesis methods:
Method 1:
2Fe(OH)2 + 3H2O +2HCl= 2FeCl3 + 4H2O
2FeCl3 + 3H2O + 3NH3 = 2Fe (OH)3↓+ 6NH4Cl
Add 10.6 g of 2,2 '- bipyridine and 9.2 g of iron powder to a 250 mL three necked bottle.
Add 300 mL of water, followed by 40 mL of concentrated hydrochloric acid (36%) and 10 mL of glacial acetic acid.
Place under stirring and heat until the reaction solution is slightly boiling and refluxed for 30 minutes.
Remove precipitates from the reaction solution using the decantation method to obtain a clear solution.
Add 100 mL of water to the clarified solution, followed by 35 mL of ammonia, and the solution will appear light red.
Remove the precipitate from the solution using the decantation method, and then wash the precipitate with ammonia water until the washing solution contains no ferrous ions.
Discard the ammonia solution, wash the precipitate with toluene, and then dry it with a vacuum dryer to obtain the product Bathophenanthrolin.
Method 2:
Cu + 4HNO3 = Cu (NO3)2 + 2NO2↑+ 2H2O
Cu (NO3)2 + 8NH3 = Cu(NH3)4(OH)2↓+ 6NH4NO3
Add 25 mL of 8M nitric acid and 2.0 g of copper shavings to a 250 mL three necked bottle.
Heat until the reaction solution is slightly boiling and refluxed for 1 hour.
Remove precipitates from the reaction solution using the decantation method to obtain a clear solution.
Add 45 mL of ammonia water, and the solution will appear dark blue.
Remove the precipitate from the solution using the decantation method, and then wash the precipitate with ammonia water until there are no copper ions in the washing solution.
Discard the ammonia solution, wash the precipitate with toluene, and then dry it with a vacuum dryer to obtain the product Bathophenanthrolin.
The above are two common laboratory synthesis methods for bathophenanthrol. BathophenanthroL should be noted that the chemical reagents involved in these methods have a certain degree of danger and need to be carried out in the laboratory, following laboratory safety operating standards. At the same time, in order to obtain purer products, operations such as filtration, washing, and drying are required. In addition, in order to ensure the accuracy of the experimental results, bathophenanthroL is necessary to accurately record and analyze the experimental process.
Bathophenanthrol (4,7-diphenyl-1,10-phenanthroline) was developed based on fundamental coordination chemistry research of the parent 1,10-phenanthroline scaffold. This compound was first chemically synthesized by Francis H.
Case at Temple University. Afterwards, the research group consisting of G. F. Smith, W. H. McCurdy and Harvey Diehl systematically characterized its analytical performance. They published their findings in The Analyst in 1952, establishing its utility as a chromogenic reagent for ferrous ions.
The research team coined the name Bathophenanthroline, deriving it from the bathochromic shift observed for its ferrous chelate relative to the parent compound.
Compared with 1,10-phenanthroline, phenyl substitutions at the 4- and 7-positions greatly raise its molar absorptivity. The resulting metal complex is extractable by organic solvents, and the reagent exhibits markedly improved resistance to interference from coexisting metal ions.
Subsequent researchers have continuously broadened its scope of applications. In 1959, this reagent was applied to the determination of trace iron in biological culture media. Water-soluble sulfonated derivatives were later developed to suit aqueous matrices such as serum and environmental water, making bathophenanthrol a standard ligand for trace ferrous ion analysis over time.
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