A phenanthroimidazole schiff base iron ion fluorescent probe compound and synthesis and application thereof

Abstract

The application provides a phenanthroimidazole Schiff base iron ion fluorescent probe compound and synthesis and application thereof, and belongs to the fields of chemical synthesis and cation detection. The application uses 4,4',4''-methylene triphenol, ethyl chloroacetate, hydrazine hydrate, phenanthraquinone and 4,4'-diphenyl dimethyl formaldehyde as raw materials to synthesize the target product in three steps, and the process is simple, the reaction condition is mild, the reaction time is short, and the synthesis is rapid, efficient, safe, reliable, green and environment-friendly; in the synthesis, no mercury salt and other toxic substances are used, the toxic side effects in the reaction are reduced, the synthesis process is simplified, the comprehensive cost of synthesis is effectively reduced, the yield of the final product is high, and the purity is high; the compound can recognize Fe 3+ with high sensitivity and high selectivity, and has a good industrial analysis application prospect.

Description

Technical Field

[0001] The present invention relates to a Schiff base fluorescent probe compound, in particular to a phenanthroimidazole Schiff base iron ion fluorescent probe compound and its synthesis. The present invention also relates to the application of the phenanthroimidazole Schiff base iron ion compound in fluorescent identification of iron ions, belonging to the fields of chemical synthesis and cation detection technology. Background Art

[0002] Fe is a component of many key enzymes in organisms and participates in a variety of biochemical reactions. It is one of the most abundant trace elements in the human body and plays a vital role in many life processes of organisms, including nerve conduction, oxygen transport, cell metabolism, and the synthesis of DNA and RNA. Fe is one of the most important metals in industry and is widely used by humans in various industrial productions, such as automobile manufacturing, casting alloys, electronic devices, reinforced concrete, etc. 3+ Excessive intake of Fe will not only pollute the environment, but also cause excessive intake of Fe in the human body. 3+ , which can lead to a series of diseases, such as cirrhosis, liver fibrosis, diabetes, heart disease and other diseases. 3+ Insufficient intake will lead to anemia. Therefore, it is necessary to establish an accurate and rapid Fe 3+ Detection methods are of great significance in the fields of biomedicine and environmental quality monitoring. In comparison, fluorescence analysis has been widely used for the analysis and detection of metal ions due to its high sensitivity and simplicity. Therefore, it is necessary to develop a rapid detection method for Fe 3+ The fluorescent probe is of great significance. Schiff base has a -C=N- structure, and the N atom in its structure has a pair of lone electrons, which creates an electron-rich chemical environment, making Schiff base a good metal ion ligand. The Schiff base structure has a strong coordination ability with metal ions, and Schiff bases with large π bonds generally have good fluorescence properties. Based on the above reasons, the synthesis of Schiff base structure compounds for Fe 3+ The identification of this method has great research significance and application value.

[0003] Currently, Fe 3+ Commonly used methods include reagent method, flame staining method, UV-visible spectroscopy, electrochemical method, pH titration method and colorimetry. However, these methods all have disadvantages, such as requiring certain chemical knowledge and experimental operation skills, being easily interfered with by other ions, and expensive instrument maintenance. Although several Fe3+ fluorescent probes have been developed, the raw materials are expensive, the reaction conditions are harsh, and they are easily interfered with by other ions. The high cost greatly limits their practical application. Summary of the Invention

[0004] The purpose of the present invention is to provide a Schiff base Fe with low raw material cost, simple synthesis process, high reaction efficiency, high yield and easy reaction control. 3+ Fluorescent probe compounds and synthesis methods thereof.

[0005] Another object of the present invention is to provide a Schiff base Fe 3+ Fluorescent probe compounds in the fluorescence recognition of Fe 3+ application.

[0006] 1. Schiff base iron ion fluorescent probe compounds and their synthesis

[0007] .

[0008] The Schiff base iron ion fluorescent probe of the present invention is a new compound with the molecular formula C 109 H 76 N 12 O6, labeled T, has the following structure:

[0009] The synthesis method of the Schiff base iron ion fluorescent probe compound of the present invention comprises the following process steps:

[0010] (1) Using DMF as solvent, 4,4',4''-methylenetriphenol and ethyl chloroacetate as substrates, potassium carbonate and potassium iodide as catalysts, the mixture was stirred at 100-120°C for 9-12 hours, hydrazine hydrate was added, and the mixture was stirred at 80-100°C for 8-10 hours. The mixture was filtered, washed, and dried to obtain a white or white-gray powdery product, 4,4',4''-methylenetriphenyloxyacetylhydrazine.

[0011] The molar ratio of 4,4',4''-methylenetriphenol, ethyl chloroacetate and hydrazine hydrate is 1:4.2:5~1:4.6:6. The molar ratio of 4,4',4''-methylenetriphenol to potassium carbonate is 1:3~1:5; and the molar ratio of 4,4',4''-methylenetriphenol to potassium iodide is 1:0.1~1:1.

[0012] (2) Using acetic acid as solvent, phenanthrenequinone and 4,4'-biphenyldicarboxaldehyde as substrates, and ammonium acetate as catalyst, the reaction was refluxed at 120°C~140°C for 4~8 hours, filtered, washed, and dried to obtain a yellow powdery product 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde. The molar ratio of phenanthrenequinone to 4,4'-biphenyldicarboxaldehyde was 1:1, and the molar ratio of phenanthrenequinone to ammonium acetate was 1:4~1:10.

[0013] (3) Using DMF or DMSO as solvent, 4,4',4''-methylenetriphenyloxyacetic acid hydrazide and 4'-(phenanthroimidazole-2-yl)biphenyl-4-carboxaldehyde as substrates, and p-toluenesulfonic acid as catalyst, the reaction was carried out at 80℃~100℃ for 2~10h, and the mixture was filtered, washed, and dried to obtain a light yellow powdery phenanthroimidazole Schiff base iron ion fluorescent probe compound.

[0014] The molar ratio of 4,4',4''-methylenetriaminetetramine to 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde is 1:3; the molar ratio of 4,4',4''-methylenetriaminetetramine to p-toluenesulfonic acid is 1:0.1-1:1; and the drying is carried out at 30-60°C.

[0015] The synthetic route is as follows:

[0016]

[0017] The Schiff base iron ion fluorescent probe compound obtained by the present invention is characterized by nuclear magnetic hydrogen spectrum, nuclear magnetic carbon spectrum and mass spectrum, which proves that it is successfully synthesized.

[0018] 2. Schiff base iron ion fluorescent probe compound for Fe 3+ Recognition experiment

[0019] The DMSO solution of Schiff base iron ion fluorescent probe compound emits strong cyan fluorescence under ultraviolet light. 3 mL of DMSO solution of Schiff base iron ion fluorescent probe compound (1×10 -3 mol L -1 ) were added into a series of 5 mL colorimetric tubes, 0.5 mL of Zn 2+ 、Cd 2+ Cr 3+ 、Cu 2+ 、Hg 2+ , K + 、Co 3+ 、Ag + Mg 2+ 、Mn 2+ 、Na + 、Ni 2+ , Pb 2+ 、Fe 3+ 、Al 3+ Aqueous solution ((1×10 -4 mol L -1 ), and observed its fluorescence response. The results showed that only Fe 3+ The addition of quenches the bright cyan fluorescence (488 nm, λ ex=430nm), and the fluorescence intensity was significantly reduced, while the addition of other cations could not quench the fluorescence produced under ultraviolet light, nor could its fluorescence spectrum be significantly changed ( Figure 1 ). This indicates that the Schiff base iron ion fluorescent probe compound can specifically and selectively recognize Fe 3+ The ion competition experiment verified that the probe has a strong affinity for Fe in the presence of other interfering ions. 3+ The probe was found to be selectively 3+ After quenching, the fluorescence intensity of the probe cannot be restored to its original level when other ions are added ( Figure 2 ). Finally, by measuring the probe at different concentrations of Fe 3+ The change of fluorescence intensity under the condition of the probe was obtained by fitting the data to obtain the nonlinear regression equation. 3+ The detection limit is 0.035 mol / L ( Figure 3 ).

[0020] Compared with the prior art, the present invention has the following advantages:

[0021] The present invention uses 4,4',4''-methylenetriphenol, ethyl chloroacetate, hydrazine hydrate, phenanthrenequinone and 4,4'-biphenyldicarboxaldehyde as raw materials to synthesize the target product in three steps. The process is simple, the reaction conditions are mild, the reaction time is short, and the reaction is rapid and efficient. No mercury salts or other toxic substances are used in the synthesis, which reduces the toxic and side effects in the reaction. The method is safe, reliable, and environmentally friendly. The raw materials in the synthesis are low in price and the catalyst is extremely easy to remove, which simplifies the synthesis process and effectively reduces the overall cost of the synthesis. The yield of the final product is high.

[0022] This ion probe can identify Fe with high sensitivity and selectivity. 3+ , in Fe 3+ It has a good application prospect in the detection of BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 Different cations Zn were added to the DMSO solution of T 2+ 、Cd 2+ Cr 3+ 、Cu 2+ 、Hg 2+ , K + 、Co 3+ 、Ag + Mg 2+ 、Mn 2+ 、Na + 、Ni 2+ , Pb 2+ 、Fe 3+ 、Al 3+ Fluorescence spectrum of ex =431nm).

[0024] Figure 2 is the fluorescence intensity of the Schiff base iron ion fluorescent probe in the presence of various metal ions;

[0025] Figure 3 is the nonlinear fitting curve of the Schiff base iron ion fluorescence probe;

[0026] Figure 4 This is the hydrogen spectrum of the Schiff base iron ion fluorescent probe compound;

[0027] Figure 5 This is the carbon spectrum of the Schiff base iron ion fluorescent probe compound;

[0028] Figure 6 This is the mass spectrum of the Schiff base iron ion fluorescent probe compound. DETAILED DESCRIPTION

[0029] The synthesis method and application of the Schiff base iron ion fluorescent probe compound of the present invention are described in detail below through specific examples.

[0030] Example 1

[0031] (1) 4,4',4''-methylenetriphenol (3.0 g, 0.01 mol), ethyl chloroacetate (4 g, 0.033 mol), potassium carbonate (2.13 g, 0.015 mol) and potassium iodide (0.1 g, 0.616 mmol) were added to a 250 mL flask containing 50 mL of DMF. The mixture was stirred at 110 °C for 12 h and then cooled to 70 °C. Hydrazine hydrate (80%, 2.57 g, 0.051 mol) was added and stirred at 90 °C for 9 h. The mixture was allowed to stand and cooled to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring. The white product 4,4',4''-methylenetriphenyloxyacetylhydrazine was obtained after drying.

[0032] (2) Phenanthrenequinone (6.24 g, 0.03 mol), 4,4'-biphenyldicarboxaldehyde (6.3 g, 0.03 mol) and ammonium acetate (11.56 g, 0.15 mol) were added to a 500 mL flask containing 200 mL of acetic acid. The mixture was stirred at 130 °C for 7 h. The mixture was allowed to stand and cool to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring. After drying, a yellow powdery product, 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde, was obtained.

[0033] (3) The above-mentioned 4,4',4''-methylenetriphenyloxyacetylhydrazine (5.08 g, 0.01 mol), 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde (11.94 g, 0.03 mol) and p-toluenesulfonic acid (0.08 g, 0.46 mmol) were added to a 500 mL flask containing 100 mL of DMF. The mixture was stirred at 90 °C for 9 h. The mixture was allowed to cool to room temperature, diluted with water and filtered, and then washed with water three times. After drying, a pale yellow powder of phenanthroimidazol-based Schiff base iron ion fluorescent probe compound was obtained. The yield calculated by weight was 98.6%. Figure 2 、 Figure 3 and Figure 4 These are the hydrogen spectrum, carbon spectrum and mass spectrum of the molecule respectively.

[0034] Product characterization data: Anal. calcd forC 109 H 76 N 12 O6. C 79.35, H 4.64, N 10.19, O5.82. Found C 78.78, H 4.61, N 10.12, O 5.78. 1 H NMR (400 MHz, DMSO- d 6): δ(ppm)13.56 (d, J = 16.0 Hz, 3H, -NH-), 11.66 (d, J = 8.8 Hz, 3H, -NH-), 8.88 (dt, J =14.1, 7.6 Hz, 6H, Ar-H), 8.59 (dd, J = 17.4, 8.2 Hz, 6H, Ar-H), 8.49 – 8.43 (m,3H,-CH=), 8.41 (s, 3H, Ar-H), 8.09 (d, J = 16.3 Hz, 4H, Ar-H), 7.99 (s, 6H, Ar-H), 7.87 (dd, J = 21.3, 7.6 Hz, 9H, Ar-H), 7.76 (d, J = 6.1 Hz, 8H, Ar-H), 7.67(d, J = 7.8 Hz, 6H, Ar-H), 7.09 – 6.86 (m, 12H, Ar-H), 5.47 (s, 1H,-CH-), 5.16(s, 3H,-CH 2-), 4.67 (s, 3H,-CH2-). 13 C NMR (101 MHz, DMSO- d 6): δ(ppm) 169.61,164.85, 156.98, 156.52,149.14, 147.91, 143.82, 140.98, 140.14, 137.62,133.84, 130.69, 130.25, 128.28, 128.13, 128.06, 127.59, 127.41, 127.18,125.81, 124.59, 124.26, 122.84, 122.47,114.96, 114.78, 65.22.ESI-MS: m / z (T+Na) + :1672.16.

[0035] Example 2

[0036] (1) 4,4',4''-methylenetriphenol (3.0 g, 0.01 mol), ethyl chloroacetate (4 g, 0.033 mol), potassium carbonate (2.13 g, 0.015 mol) and potassium iodide (0.1 g, 0.616 mmol) were added to a 250 mL flask containing 50 mL of DMF. The mixture was stirred at 100 °C for 12 h and then cooled to 70 °C. Hydrazine hydrate (80%, 2.57 g, 0.051 mol) was added and stirred at 80 °C for 8 h. The mixture was allowed to stand and cooled to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring and dried to obtain a white product, 4,4',4''-methylenetriphenyloxyacetylhydrazine.

[0037] (2) Phenanthrenequinone (6.24 g, 0.03 mol), 4,4'-biphenyldicarboxaldehyde (6.3 g, 0.03 mol) and ammonium acetate (11.56 g, 0.15 mol) were added to a 500 mL flask containing 200 mL of acetic acid. The mixture was stirred under magnetic stirring at 120 °C for 8 h. The mixture was allowed to cool to room temperature, diluted with water and filtered, and then washed with water three times with stirring. After drying, a yellow powdery product, 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde, was obtained.

[0038] (3) The above-mentioned 4,4',4''-methylenetriphenyloxyacetylhydrazine (5.08 g, 0.01 mol), 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde (11.94 g, 0.03 mol) and p-toluenesulfonic acid (0.04 g, 0.23 mmol) were added to a 500 mL flask containing 100 mL of DMF and reacted with magnetic stirring at 80°C for 10 h. The mixture was allowed to cool to room temperature, diluted with water and filtered, and then washed with water three times with stirring. After drying, a pale yellow powder of a phenanthroimidazolium Schiff base iron ion fluorescent probe compound was obtained. The yield calculated by weighing was 97.7%. The characterization and detection application of the product were the same as in Example 1.

[0039] Example 3

[0040] (1) 4,4',4''-methylenetriphenol (3.0 g, 0.01 mol), ethyl chloroacetate (4 g, 0.033 mol), potassium carbonate (2.13 g, 0.015 mol) and potassium iodide (0.1 g, 0.616 mmol) were added to a 250 mL flask containing 50 mL of DMF. The mixture was stirred at 120 °C for 9 h and then cooled to 70 °C. Hydrazine hydrate (80%, 2.57 g, 0.051 mol) was added and stirred at 80 °C for 8 h. The mixture was allowed to stand and cooled to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring. The white product 4,4',4''-methylenetriphenyloxyacetylhydrazine was obtained after drying.

[0041] (2) Phenanthrenequinone (6.24 g, 0.03 mol), 4,4'-biphenyldicarboxaldehyde (6.3 g, 0.03 mol) and ammonium acetate (11.56 g, 0.15 mol) were added to a 500 mL flask containing 200 mL of acetic acid. The mixture was stirred at 130 °C for 7 h. The mixture was allowed to stand and cool to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring. After drying, a yellow powdery product, 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde, was obtained.

[0042] (3) The above-mentioned 4,4',4''-methylenetriphenyloxyacetylhydrazine (5.08 g, 0.01 mol), 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde (11.94 g, 0.03 mol) and p-toluenesulfonic acid (0.08 g, 0.46 mmol) were added to a 500 mL flask containing 100 mL of DMF and reacted with magnetic stirring at 100 °C for 2 h. The mixture was allowed to stand and cool to room temperature, diluted with water and filtered, and then washed with water three times with stirring. After drying, a pale yellow powder of a phenanthroimidazolium Schiff base iron ion fluorescent probe compound was obtained. The yield calculated by weighing was 95.5%. The characterization and detection application of the product were the same as in Example 1.

[0043] Example 4

[0044] (1) 4,4',4''-methylenetriphenol (3.0 g, 0.01 mol), ethyl chloroacetate (4 g, 0.033 mol), potassium carbonate (2.13 g, 0.015 mol) and potassium iodide (0.1 g, 0.616 mmol) were added to a 250 mL flask containing 50 mL of DMF. The mixture was stirred at 110 °C for 9 h and then cooled to 70 °C. Hydrazine hydrate (80%, 2.57 g, 0.051 mol) was added and stirred at 90 °C for 7 h. The mixture was allowed to stand and cooled to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring. The white product 4,4',4''-methylenetriphenyloxyacetylhydrazine was obtained after drying.

[0045] (2) Phenanthrenequinone (6.24 g, 0.03 mol), 4,4'-biphenyldicarboxaldehyde (6.3 g, 0.03 mol) and ammonium acetate (11.56 g, 0.15 mol) were added to a 500 mL flask containing 200 mL of acetic acid. The mixture was stirred at 130 °C for 7 h. The mixture was allowed to stand and cool to room temperature. The mixture was diluted with water and filtered. The mixture was then washed with water three times with stirring. After drying, a yellow powdery product, 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde, was obtained.

[0046] (3) The above-mentioned 4,4',4''-methylenetriphenyloxyacetylhydrazine (5.08 g, 0.01 mol), 4'-(phenanthroimidazole-2-yl)biphenyl-4-carboxaldehyde (11.94 g, 0.03 mol) and p-toluenesulfonic acid (0.08 g, 0.46 mmol) were added to a 500 mL flask containing 100 mL of DMF and reacted with magnetic stirring at 80°C for 9 h. The mixture was allowed to cool to room temperature, diluted with water and filtered, and then washed with water three times with stirring. After drying, a pale yellow powder of a phenanthroimidazole Schiff base iron ion fluorescent probe compound was obtained. The yield calculated by weighing was 95.1%. The characterization and detection application of the product were the same as in Example 1.

[0047] Example 5: Schiff base iron ion fluorescent probe compound identifies Fe 3+

[0048] 3 mL of the DMSO solution of the Schiff base iron ion fluorescent probe compound prepared in Example 1 (1×10 - 3 mol L -1 ) were added into a series of 5 mL colorimetric tubes, 0.5 mL of Zn 2+ 、Cd 2+ Cr 3+ 、Cu 2+ 、Hg 2+ , K + 、Co 3+ 、Ag+ Mg 2 + 、Mn 2+ 、Na + 、Ni 2+ , Pb 2+ 、Fe 3+ 、Al 3+ aqueous solution (concentrations of 1×10 -4 mol L -1 ), if the bright cyan fluorescence of the DMSO solution of the Schiff base iron ion fluorescent probe compound is quenched, it means that the added 3+ If the fluorescence of the DMSO solution of the Schiff base iron ion fluorescent probe compound does not change, it means that the added 3+ .

Claims

1. A phenanthroimidazole Schiff base iron ion fluorescent probe compound, the molecular formula is C 109 H 76 N 12 O6, whose structure is as follows: 。 2. The method for synthesizing the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 1, comprising the following steps: (1) Using DMF as solvent, 4,4',4''-methylenetriphenol and ethyl chloroacetate as substrates, potassium carbonate and potassium iodide as catalysts, stirring and reacting at 100-120°C for 9-12 hours, then adding hydrazine hydrate, stirring and reacting at 80-100°C for 8-10 hours, filtering, washing, and drying to obtain 4,4',4''-methylenetriphenyloxyacetylhydrazine; (2) Using acetic acid as solvent, phenanthrenequinone and 4,4'-biphenyldicarboxaldehyde as substrates, and ammonium acetate as catalyst, the reaction was refluxed at 120°C~140°C for 4~8h, filtered, washed, and dried to obtain 4'-(phenanthroimidazol-2-yl)biphenyl-4-carboxaldehyde; (3) Using DMF or DMSO as solvent, 4,4',4''-methylenetriphenyloxyacetylhydrazine and 4'-(phenanthroimidazole-2-yl)biphenyl-4-carboxaldehyde as substrates, and p-toluenesulfonic acid as catalyst, the reaction was carried out at 80℃~100℃ for 2~10h, and the mixture was filtered, washed, and dried to obtain a phenanthroimidazole Schiff base iron ion fluorescent probe compound.

3. The method for synthesizing the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 2, wherein: In step (1), the molar ratio of 4,4',4''-methylenetriphenol, ethyl chloroacetate and hydrazine hydrate is 1:4.2:5 to 1:4.6:

6.

4. The method for synthesizing the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 2, wherein: In step (1), the molar ratio of 4,4',4''-methylenetriphenol to potassium carbonate is 1:3-1:5; the molar ratio of 4,4',4''-methylenetriphenol to potassium iodide is 1:0.1-1:

1.

5. The method for synthesizing the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 2, wherein: In step (2), the molar ratio of phenanthrenequinone to 4,4'-biphenyldicarboxaldehyde is 1:

1.

6. The method for synthesizing the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 2, wherein: In step (2), the molar ratio of phenanthrenequinone to ammonium acetate is 1:4 to 1:

10.

7. The method for synthesizing the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 2, wherein: In step (3), the molar ratio of 4,4',4''-methylenetriaminetetrahydropyrrolidone to 4'-(phenanthroimidazole-2-yl)biphenyl-4-carboxaldehyde is 1:3; the molar ratio of 4,4',4''-methylenetriaminetetrahydropyrrolidone to p-toluenesulfonic acid is 1:0.1 to 1:

1.

8. Use of the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 1 in the preparation of a fluorescent iron ion recognition reagent.

9. Use of the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 8 in the preparation of a fluorescent iron ion recognition reagent, characterized in that: In the DMSO solution of phenanthroimidazole Schiff base iron ion fluorescent probe compound, Zn 2+ 、Cd 2+ Cr 3+ 、Cu 2+ 、Hg 2+ , K + 、Co 3+ 、Ag + Mg 2+ 、Mn 2+ 、Na + 、Ni 2+ , Pb 2+ 、Fe 3+ 、Al 3+ In aqueous solution, only Fe 3+ The addition of can quench the bright cyan fluorescence emitted by the probe compound solution under ultraviolet light.

10. Use of the phenanthroimidazole Schiff base iron ion fluorescent probe compound according to claim 8 in the preparation of a fluorescent iron ion recognition reagent, characterized in that: In the DMSO solution of Schiff base iron ion fluorescent probe compound, Zn 2+ 、Cd 2+ Cr 3+ 、Cu 2+ 、Hg 2+ , K + 、Co 3+ 、Ag + Mg 2+ 、Mn 2+ 、Na + 、Ni 2+ , Pb 2+ 、Fe 3+ 、Al 3+ In aqueous solution, only Fe 3+ The addition of can significantly reduce the fluorescence emission peak of the fluorescence spectrum of the probe compound solution at 488nm.

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