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1,10‑Phenanthroline powder is a vital organic compound with the molecular formula C₁₂H₈N₂ and CAS registry number 66‑71‑7, with a molecular weight of 180.21. This compound exhibits a broad spectrum of chemical and biological activities, making it widely applied in multiple research and industrial fields. In its solid state, 1,10‑phenanthroline usually appears as colorless or pale yellow crystalline powder, with stable physical properties that facilitate storage and experimental operation.
This compound demonstrates favorable solubility in a variety of common solvents. It is readily soluble in polar organic solvents including ethanol, acetone, and dimethyl sulfoxide (DMSO), and also dissolves in certain inorganic solvents such as water and benzene. In contrast, it is almost insoluble in non‑polar solvents like petroleum ether. Notably, its hydrated and anhydrous forms show distinct physical characteristics: the monohydrate exists as a white crystalline powder with a melting point of 93–94 °C, while the anhydrous form has a higher melting point of 117 °C. Such well‑defined solubility and thermal properties greatly improve its operability in routine chemical experiments, analytical testing, and large‑scale industrial production.
In synthetic chemistry, 1,10‑phenanthroline is frequently used as a key structural building block for the construction of metal macrocyclic complexes. Through coordination and self‑assembly with diverse metal ions and auxiliary ligands, it can participate in the formation of metal macrocyclic compounds with well‑defined structures and specific functions. These functional complexes show promising application prospects in important fields such as homogeneous catalysis, chemical sensing, biological imaging, and controlled drug delivery systems.
As a classic bidentate chelating ligand, 1,10‑phenanthroline can form stable coordination complexes with many transition metal ions. Among these, the complexes formed with copper ions and their derivatives have attracted particular attention due to their unique biological activities. Studies have shown that such copper‑phenanthroline complexes possess obvious DNA cleavage activity and can act as non‑oxidative nucleolytic mimetic enzymes, thereby endowing them with potential anticancer properties.
In addition, 1,10‑phenanthroline functions as an effective metal chelating agent, which can regulate the intracellular metal ion balance and reduce oxidative stress. It has been reported to inhibit chromosomal aberrations induced by streptozotocin, suggesting a protective effect on genetic stability. These biological properties further expand its application value in biochemical research and pharmaceutical development.
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Chemical Formula |
C12H8N2 |
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Exact Mass |
180 |
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Molecular Weight |
180 |
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m/z |
180 (100.0%), 181 (13.0%) |
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Elemental Analysis |
C, 79.98; H, 4.47; N, 15.55 |
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1,10-Phenanthroline, with the chemical formula C ₁₂ H ₈ N ₂, is a nitrogen-containing bidentate ligand. The two nitrogen atoms in its molecular structure can form stable chelates with various metal ions. Since its artificial synthesis, this compound has demonstrated extensive application value in fields such as chemical analysis, organic synthesis, drug design, materials science, and environmental science due to its unique electronic properties and coordination ability.
1. Spectral analysis and metal detection
1,10-Phenanthroline powder is a classic reagent for detecting metal ions in spectroscopic analysis. The orange red complex formed between it and Fe ² ⁺ exhibits the maximum absorption peak at a wavelength of 510nm, with a stability constant of lgK=21.3 (20 ℃). This characteristic makes it a standard method for the determination of trace iron by visible light spectrophotometry. For example, in environmental monitoring, the iron content in water samples can be detected through this colorimetric reaction, with a sensitivity of 0.1 μ g/L.
In addition, the ligand can also be used for the detection of metal ions such as copper, palladium, and vanadium. The complex formed with copper ions exhibits a characteristic quenching effect in fluorescence spectra, which can be used for quantitative analysis of copper ions. The detection range covers 4.0 × 10 ⁻⁷ to 4.0 × 10 ⁻⁵ mol/L.
2. Redox indicator
In titration analysis, it has significant advantages as an oxidation-reduction indicator. For example, in the process of titrating iron salts with cerium sulfate, the ortho phenanthroline Fe (II) indicator (prepared from 1.485g of ortho phenanthroline monohydrate and 0.695g of FeSO ₄· 7H ₂ O) can accurately indicate the titration endpoint through color change. When Fe ² ⁺ is oxidized to Fe ³ ⁺, the solution color changes from orange red to colorless, and the endpoint judgment error is less than 0.1%.
3. Catalytic photometry and kinetic analysis
Based on the catalytic effect of 1,10-phenanthroline, catalytic photometry can achieve analysis within the concentration range of 0-1.0 × 10 ⁻ ³ mol/L. For example, in the molybdate catalytic system, the ligand can accelerate the reaction of potassium bromate oxidizing orange IV, and trace amounts of molybdenum can be determined by monitoring changes in absorbance. The kinetic method utilizes the change in reaction rate for analysis, with a detection range of 1.0 × 10 ⁻⁸ to 6.0 × 10 ⁻⁶ mol/L, suitable for the detection of ultra-low concentration samples.
Catalytic and Coordination Functions in Organic Synthesis
1. Transition metal catalyzed reactions
As a bidentate ligand, 1,10-Phenanthroline powder plays a crucial role in transition metal catalysis. In the organic boronic acid crosslinking reaction catalyzed by Cu (II), its coordination ability can stabilize the active intermediate and improve the reaction selectivity. For example, in the construction of carbon nitrogen bonds within guanidine derivatives, a system using cuprous iodide as a catalyst, 1,10-phenanthroline as a ligand, and cesium carbonate as a base can increase the yield from 58% to 89%.
In the field of carbon sulfur bond construction, this ligand also exhibits outstanding performance. Taking the cross coupling reaction between phenylthiophenol and iodobenzene as an example, in the CuI/1,10-phenanthroline catalytic system, trifluoromethyltrimethylsilane can be used as a trifluoromethyl source to achieve trifluoromethylation or trifluoromethylthiolation of the benzene ring with a yield of 75% to 82%.
2. C-H bond activation reaction
In the copper catalyzed cross coupling reaction between diazole and pentafluorobenzene, acting as a ligand can significantly enhance the reaction efficiency. The experiment showed that after adding 0.1 equiv ligand, the reaction time was shortened from 24 hours to 8 hours, and the yield of the target product increased from 63% to 91%. Its mechanism of action lies in stabilizing the copper active center through coordination, promoting the activation and coupling of C-H bonds.
3. Analysis of alkyl lithium compounds
In the determination of organic lithium reagent content, it can be used as a color reagent. The specific operation is to take 1mg of sample and react with ortho phenanthroline to form a dark colored complex, and then titrate with alcohol until the colorless endpoint. This method can accurately determine the concentration of alkyl lithium with an error of less than 2%, and is widely used for lithium reagent calibration in drug synthesis.
1. DNA cleavage activity
The complex formed with copper ions exhibits non oxidative nuclease properties. Experiments have shown that Cu (II) - phenanthroline complexes can cleave DNA double strands at specific sequences, and the cleavage efficiency is positively correlated with ligand concentration. When the ligand concentration is 50 μ M, the DNA cleavage rate reaches 87%, providing a theoretical basis for the development of new anti-cancer drugs.
Cytotoxicity study:
In the screening of anti-tumor drugs, phenanthroline metal complexes exhibit significant activity.
For example, the dichloroplatinum (II) complex formed by 3,4,7,8-tetramethyl-1,10-phenanthroline and platinum has an IC50 value of 12.3 μ M for human liver cancer cell HepG2, significantly lower than cisplatin's 28.7 μ M. Its mechanism of action may involve ligands promoting platinum drugs to penetrate cell membranes and target DNA.
3. Chromosomal aberration suppression
As a metal chelating agent, it can prevent chromosome aberrations induced by streptozotocin. In vitro experiments showed that treatment with 10 μ M phenanthroline can reduce chromosome breakage frequency by 68%, indicating its potential genetic protective effect.
Organic Light Emitting Diodes (OLEDs):
1,10-Phenanthroline and its derivatives can serve as hole transport layers for OLED materials due to their conjugated π - electron system. For example, the iridium complex with 3,4,7,8-tetramethyl-1,10-phenanthroline as the ligand has an electroluminescence efficiency of 18.7cd/A and an external quantum efficiency of 7.2%, significantly better than traditional aluminum quinone ligand systems.
Organic solar cells:
In organic solar cells, 1,10-phenanthroline derivatives can serve as hole transport materials.
Experiments have shown that the open circuit voltage of the polymer P3HT: PCBM system containing ortho phenanthroline units increases from 0.58V to 0.65V, the filling factor increases from 62% to 71%, and the energy conversion efficiency reaches 6.8%.
Development of fluorescent probes:
Based on the fluorescence properties of 1,10-phenanthroline, its derivatives can be used for metal ion detection. For example, 2-hydroxy-1,10-phenanthroline forms a 1:1 complex with Zn ² ⁺ in a pH 7.4 buffer solution, which enhances fluorescence intensity by 12 times and has a detection limit of 0.8 nM. It can be used for intracellular zinc ion imaging.
Iron content detection in water:
A rapid detection method for iron content in water samples can be established by utilizing the color reaction of ortho phenanthroline Fe (II) complex. Under the condition of pH=2-9, this method has a linear range of 0.05-5.0mg/L for the detection of Fe ² ⁺, with a recovery rate of 98% -102%. It is widely used for monitoring surface water and industrial wastewater.
Activation and degradation of pollutants by persulfate:
1,10-Phenanthroline powder can be used as a catalyst to activate persulfate (PMS) and generate reactive oxygen species (ROS) to degrade organic pollutants.At 25 ℃, the 0.1mM phenanthroline and 2mM PMS system can completely degrade 10mg/L bisphenol A within 30 minutes, with a degradation efficiency 4.2 times higher than that of the PMS system alone.
Monitoring of heavy metal pollution:
Surface enhanced Raman spectroscopy (SERS) technology can be used for sensitive detection of heavy metal ions in water. For example, on the nano silver aggregate substrate, the complex formed by ortho phenanthroline and Cd ² ⁺ exhibits a characteristic Raman peak at 1450 cm ⁻¹, with a detection limit of 0.1 nM, providing a new method for environmental heavy metal monitoring.
Animal fiber staining:
Can be used as a dye additive for animal fibers. The complex formed with metal ions can be fixed on the surface of protein fibers such as wool and silk, improving color fastness. Experiments have shown that the addition of 5% phenanthroline increases the wash fastness of wool fibers from level 3 to level 4-5.
Electroplating additives:
In the electroplating industry, it can be used as a brightener. For example, adding 0.2g/L phenanthroline to the zinc nickel alloy electroplating solution can reduce the surface roughness of the coating from Ra1.2 μ m to Ra0.3 μ m, while improving corrosion resistance.
Capillary chromatography column modification:
A mixed mode chromatography column with π - π interactions, hydrogen bonding, and electrostatic interactions can be prepared by modifying the surface of a silica gel monolithic column with 1,10-phenanthroline using chemical bonding technology. The separation efficiency of this column for polycyclic aromatic hydrocarbons is 3.2 times higher than that of traditional C18 columns, making it suitable for the analysis of complex samples.
The method of detecting 1,10-Phenanthroline by surface-enhanced Raman spectroscopy includes the following steps:
(1) Preparation of o-phenanthroline standard solution system: add 50~650 to each of five graduated tubes in turn μ L 20 mg/L nano-silver solution, 50-200 μ L 0.2 mol/L disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution with pH 5.8 ～ 7.8, mix well; Add 2.5 respectively μ L,5 μ L,10 μ L,30 μ L,40 μ L,50 μ L 1.0 × 10 ⁻ ⁷ mol/L phenanthroline standard solution, and then add 20~150 to each test tube μ L 2.0 mol/L NaCl solution, mix evenly, place for reaction for 15 min, dilute to 2.0 mL with secondary distilled water, and mix well;
(2) Prepare the blank control solution without o-phenanthroline standard solution according to the method in step;
(3) Take the above standard solution and blank control solution and put them into a quartz colorimetric dish respectively. On the Raman spectrometer, set the instrument parameters, scan to obtain the surface-enhanced Raman spectrum, and measure 1450 cm ⁻ ¹ The intensity value of the surface-enhanced Raman scattering peak at is I, and the intensity value of the surface-enhanced Raman scattering peak of the blank solution is I0 Δ I = I - I0;
(4) With Make a working curve for the concentration relationship of o-phenanthroline;
(5) Prepare the analytical solution of the sample to be tested according to the method in step (1), and replace the standard solution of o-phenanthroline with the sample to be tested, and determine the surface-enhanced Raman emission intensity value of the analytical solution of the sample to be tested as I sample according to the method in step (3), and calculate Δ I sample=I sample - I0;
(6) Calculate the content of o-phenanthroline in the tested sample according to the working curve in step.
The determination methods of o-phenanthroline mainly include catalytic spectrophotometry, fluorescence spectrometry and kinetic methods. The catalytic spectrum method uses the catalytic effect of o-phenanthroline, and the analysis range is 0~1.0 × 10⁻ ³ Mol/L; Phosphorescence quenching of o-phenanthroline by fluorescence spectrometry can increase the analysis range to 4.0 × 10⁻⁷～4.0 × 10⁻⁵ mol/L; The kinetic method is based on the change of reaction rate, and its analysis range is 1.0 × 10⁻⁸～6.0 × 10 ⁻ ⁶ mol/L. CN201210363302.6 provides a method for the detection of o-phenanthroline by surface-enhanced Raman spectroscopy.This method has the advantages of good selectivity, simplicity, rapidity and low cost, and has a good application prospect in the determination of o-phenanthroline. The technical solution for realizing the invention is:
Under the conditions of the present invention, the nano-silver solution is in the sodium dihydrogen phosphate-sodium hydrogen phosphate buffer solution, and the sodium chloride solution can make it aggregate to form the active base of the nano-silver aggregate. When the o-phenanthroline solution is added, the 1,10-Phenanthroline powder is adsorbed on the surface of the nano-silver aggregate and is 1450 cm thick ¹ There is a strong surface-enhanced Raman scattering peak at, and there is a good linear relationship between the concentration of o-phenanthroline and the intensity enhancement value of surface-enhanced Raman scattering peak. Based on this, a quantitative analysis method for the determination of o-phenanthroline can be established.
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