Disubstituted 4, 4 '-bipyridine derivative, preparation method thereof and electro-catalytic material

Abstract

The invention relates to a disubstituted 4, 4 '-bipyridine derivative as well as a preparation method and an electro-catalytic material thereof. The compound has the following structural general formula: in the formula, R1 is C2-6 alkyl, and R2 is C3-6 alkenyl. The preparation method comprises the following steps: mixing halogenated alkane and 4, 4 '-dipyridyl in an organic solvent for reaction, carrying out solid-liquid separation on a reaction system, and precipitating an intermediate compound from filtrate; redissolving the intermediate compound, and adding halogenated olefin for reaction; and collecting a precipitation product, and drying to obtain the 4, 4 '-bipyridine derivative. The electro-catalytic material is used for electro-catalytic oxygen evolution reaction and comprises foamed nickel and a disubstituted 4, 4 '-bipyridine derivative loaded on the foamed nickel. Compared with the prior art, the disubstituted 4, 4 '-bipyridine derivative and the electrocatalytic material prepared by the invention have relatively small overpotential voltage and resistance in an alkaline electrolyte environment, and can be used for an electrocatalytic oxygen evolution process of electrolyzed water.

Description

Technical Field

[0001] This invention belongs to the field of electrocatalytic materials technology, and in particular relates to a bisubstituted 4,4′-bipyridine derivative, its preparation method, and electrocatalytic materials. Background Technology

[0002] Electrocatalytic oxygen evolution reaction (OER) is a core process in energy conversion technologies such as water splitting, metal-air batteries, and renewable fuel cells. However, OER involves a four-electron transfer process with slow kinetics, requiring highly efficient electrocatalysts to reduce overpotential and improve reaction efficiency. Currently, noble metal-based materials are considered the benchmark catalysts for OER, but their high cost and scarcity limit large-scale application. Therefore, developing efficient, stable, and inexpensive non-noble metal OER catalysts has become a research hotspot.

[0003] Among numerous non-precious metal catalysts, organic molecular catalysts have attracted considerable attention due to their tunable structure and abundant redox active sites. Among these, viologen compounds, with their unique electron-accepting ability and reversible redox properties, exhibit great potential in the field of electrocatalysis. The basic chemical structure of viologen compounds is a 1,1'-disubstituted-4,4'-bipyridine salt, which can generate radical intermediates through electrochemical or chemical reduction. These active species may participate in electron transfer during the electrocatalytic oxygen evolution reaction, thereby enhancing catalytic efficiency.

[0004] However, research on traditional viologen derivatives in electrocatalytic materials is still in its early stages, mainly facing the following challenges: insufficient catalytic activity; most viologen derivatives exhibit poor stability under electrocatalytic reaction conditions, or insufficient exposure of catalytic active sites, resulting in low current density; viologen molecules typically exist in an insulating state, requiring combination with conductive supports (such as carbon materials or metal oxides) to function effectively. For example, CN104492501A discloses a viologen-modified non-covalent graphene fuel cell catalyst support material, employing a viologen-modified non-covalent graphene modification method, using graphene oxide and platinum precursors to react with viologen in a room-temperature aqueous solution to prepare a viologen-modified non-covalent graphene-supported Pt electrocatalyst. CN117327006A discloses a photochromic polyoxomolybdate, combining methyl viologen cations with polyoxomolybdate for oxygen evolution reactions in neutral electrolytes. However, the viologen molecules in the above-mentioned electrocatalytic materials all need to be combined with conductive supports such as graphene and polyoxomolybdate to work effectively, which increases the complexity of material design; and none of the above-mentioned electrocatalytic materials can achieve electrocatalytic oxygen evolution in an alkaline environment.

[0005] Therefore, a novel viologen compound and its corresponding electrocatalytic material for electrocatalytic oxygen evolution still need to be developed. Summary of the Invention

[0006] The purpose of this invention is to overcome at least one defect in the prior art by providing a bisubstituted 4,4′-bipyridine derivative, its preparation method, and an electrocatalytic material.

[0007] The objective of this invention can be achieved through the following technical solutions:

[0008] The first aspect of this invention provides a disubstituted 4,4′-bipyridine derivative having the following general structural formula:

[0009]

[0010] In the formula, R1 is C 2-6 Alkyl group, R2 is C 3-6 The alkenyl group.

[0011] Furthermore, the disubstituted 4,4′-bipyridine derivative has the following structural formula:

[0012]

[0013] A second aspect of the present invention provides a method for preparing a disubstituted 4,4′-bipyridine derivative, the method comprising the following steps:

[0014] S1: Haloalkanes and 4,4′-bipyridine are mixed in an organic solvent and reacted under heating conditions with stirring; the reaction system is separated into solid and liquid phases, and then an ether solvent is added to the filtrate to precipitate the intermediate compound;

[0015] S2: The intermediate compound is reconstituted and then added to the haloalkene. The reaction is carried out under heating and stirring. The precipitate is collected and dried to obtain the 4,4′-bipyridine derivative.

[0016] The general structural formulas of the haloalkanes and haloalkenes are X-R1 and X-R2, respectively, where X is any one of fluorine, chlorine, bromine, and iodine.

[0017] Further, in step S1, the molar ratio of 4,4′-bipyridine to haloalkanes is 1:(1 to 1.8).

[0018] Furthermore, in step S1, the heating temperature is 50-70°C, preferably 60°C.

[0019] Furthermore, in step S1, the reaction time is 12-36 hours, preferably 24 hours.

[0020] Further, in step S2, the molar ratio of the intermediate compound to the haloalkene is 1:(1 to 2.2).

[0021] Furthermore, in step S2, the heating temperature is 70-90℃, preferably 80℃.

[0022] Furthermore, in step S2, the reaction time is 24-72 hours, preferably 48 hours.

[0023] A third aspect of the present invention provides an electrocatalytic material. The electrocatalytic material is used for the electrocatalytic oxygen evolution reaction under alkaline conditions, and comprises nickel foam and a disubstituted 4,4′-bipyridine derivative supported on the nickel foam.

[0024] Furthermore, the mass ratio of the disubstituted 4,4′-bipyridine derivative to nickel foam is (1-2):6.

[0025] Furthermore, the area of ​​the nickel foam is 1–10 cm². 2 .

[0026] Furthermore, the electrocatalytic material is prepared by the following method: adding a disubstituted 4,4′-bipyridine derivative to a naphthol solution until it is completely dissolved to obtain a precursor solution; dropping the precursor solution onto nickel foam and drying it to obtain the electrocatalytic material.

[0027] Furthermore, the mass ratio of the disubstituted 4,4′-bipyridine derivative to naphthol is (5-10):1.

[0028] Furthermore, the naphthol solution is an aqueous solution of naphthol in ethanol, with a volume ratio of water to ethanol of 1:(1-2). The role of naphthol is to bind the disubstituted 4,4′-bipyridine derivative onto the nickel foam without compromising its conductivity.

[0029] This invention introduces alkyl and alkenyl groups at the N ends of 4,4'-bipyridine, respectively. Through the synergistic effects of electronic effects, steric hindrance, and the conjugated system, its electrocatalytic performance can be precisely controlled. This structural design not only enhances reaction activity and selectivity but also improves catalyst stability and interfacial mass transfer efficiency, providing a new paradigm for the construction of highly efficient electrocatalytic systems.

[0030] The disubstituted 4,4'-bipyridine derivatives of this invention achieve a significant improvement in the electrocatalytic activity for oxygen evolution through four major mechanisms: electronic state regulation (optimization of N atom adsorption energy), accelerated electron transport (expansion of the conjugated system), steric optimization (exposure of active sites and O2 escape), and synergistic metal coordination. Among these, the electron migration effect of the disubstituents is key to regulating the electron density of the active sites, while the synergy between the conjugated system and steric hindrance ensures both electron transport efficiency and the reactivity of the active sites.

[0031] Compared with the prior art, the present invention has the following beneficial effects:

[0032] (1) The bis-substituted 4,4′-bipyridine derivatives obtained by this invention have a small energy level gap, and the final electrocatalytic material has a small overpotential voltage and resistance in an alkaline electrolyte environment, which can be used for the electrocatalytic oxygen evolution process of water electrolysis.

[0033] (2) The disubstituted 4,4′-bipyridine derivatives of this invention exhibit reversible redox activity at the molecular level, promoting efficient charge transport and reducing catalytic activation energy. In the disubstituted 4,4′-bipyridine derivatives, the redox gradient acts as the "electron transport framework" for catalytic activity, lowering the electron transfer energy barrier through a multi-step potential ladder; while the charge feedback of intermediates in the catalytic reaction acts as a "stabilizer" of the gradient, maintaining the integrity of the ladder structure. The disubstituents optimize this synergy by regulating the slope and potential distribution of the gradient, ultimately achieving a significant improvement in electrocatalytic performance. This synergistic interaction between the redox gradient and catalytic activity highlights the application potential of disubstituted 4,4′-bipyridine derivatives in energy-saving electrocatalysis.

[0034] (3) The bisubstituted 4,4′-bipyridine derivative of the present invention combines the redox activity of viologen and the structural tunability of propenyl groups, and is a high-efficiency, low-cost non-precious metal electrocatalytic oxygen evolution reaction catalyst, providing a new idea for the development of clean energy technology. Attached Figure Description

[0035] Figure 1 The image shows the 1H NMR spectrum of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine in Example 1 of this invention.

[0036] Figure 2 The HOMO and LOMO energy level distributions of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine in Example 1 of this invention are shown.

[0037] Figure 3 The resistance values ​​of the electrocatalytic material supported on the disubstituted 4,4′-bipyridine derivative and pure nickel foam in Example 1 of this invention are shown.

[0038] Figure 4 The Tafel slope of the electrocatalytic material supported on the disubstituted 4,4′-bipyridine derivative and pure nickel foam in Example 1 of this invention.

[0039] Figure 5 The above figures show the overpotential curves of the electrocatalytic materials of Example 1 and Comparative Example 1 of this invention.

[0040] Figure 6 This is an overpotential curve of the electrocatalytic material in Comparative Example 2 of the present invention.

[0041] Figure 7This is the overpotential curve of the electrocatalytic material in Comparative Example 3 of the present invention. Detailed Implementation

[0042] The present invention will now be described in detail with reference to the accompanying drawings and specific embodiments. These embodiments are based on the technical solution of the present invention and provide detailed implementation methods and specific operating procedures. However, the scope of protection of the present invention is not limited to the following embodiments.

[0043] Unless otherwise specified, the reagents, methods, instruments, and equipment used in this invention are conventional in the art. Unless otherwise specified, the reagents and materials used in the following examples are all commercially available.

[0044] Example 1:

[0045] This embodiment provides a bisubstituted 4,4′-bipyridine derivative and an electrocatalytic material containing this compound, the specific technical solution of which is as follows:

[0046] (1) Preparation of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine:

[0047] First, 3.5 g of 1-iodobutane and 3 g of 4,4′-bipyridine were mixed in 10 mL of acetonitrile solution and stirred at 60 °C for 24 h. The resulting reaction system was separated by filtration, and diethyl ether was added to the filtrate to precipitate the product. The precipitate, 1-butyl-4,4′-bipyridine, was dried to obtain an orange compound.

[0048] 1 g of the obtained product 1-butyl-4,4′-bipyridine was dissolved in 25 mL of acetonitrile, and 2 g of 3-chloropropene was added. The mixture was stirred at 80 °C for 48 h. A brown precipitate was formed by filtration, collected, washed with acetonitrile, and dried thoroughly to obtain the disubstituted 1-butyl-1′-(2-propenyl)-4,4′-bipyridine.

[0049] (2) Preparation of electrocatalytic materials supported on 1-butyl-1′-(2-propenyl)-4,4′-bipyridine:

[0050] Add 15 μL of naphthol to 500 μL of an ethanol-water solution (ethanol to water volume ratio 1:1), and sonicate until the solution is homogeneous and transparent to obtain the precursor solution. Add 10 mg of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine powder to the precursor solution and sonicate again until completely dissolved. 2 By adding the prepared precursor solution dropwise to nickel foam (about 30 mg) while heating and drying, an electrocatalytic material with electrocatalytic activity can be obtained.

[0051] The 1H NMR spectrum of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine obtained in this embodiment is as follows: Figure 1 As shown, this demonstrates the successful preparation of the compound.

[0052] The HOMO and LOMO energy level distributions of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine prepared in this embodiment are as follows: Figure 2 As shown in the figure, 1-Butyl-1′-(2-propenyl)-4,4′-bipyridine has a small energy level gap, facilitating electron transfer and making it suitable as a catalytic material. Density functional theory simulations show that the highest occupied molecular orbital (HOMO)-lowest occupied molecular orbital (LUMO) gap of 4,4′-bipyridine is 5.36 eV, with a deeper HOMO level of -7.42 eV. In contrast, the HOMO / LUMO levels of 1-Butyl-1′-(2-propenyl)-4,4′-bipyridine are -3.36 / -0.49 eV, with a band gap of 2.87 eV, indicating that the introduction of the allyl group effectively reduces the HOMO level and optical band gap.

[0053] Example 2:

[0054] This embodiment provides a bisubstituted 4,4′-bipyridine derivative and an electrocatalytic material containing this compound, the specific technical solution of which is as follows:

[0055] (1) Preparation of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine: prepared according to Example 1.

[0056] (2) Preparation of electrocatalytic materials supported on 1-butyl-1′-(2-propenyl)-4,4′-bipyridine:

[0057] 20 μL of naphthol was added to 500 μL of an ethanol-water solution (ethanol to water volume ratio of 2:1), and sonicated until the solution was homogeneous and transparent, yielding the precursor solution. 10 mg of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine powder was added to the precursor solution, and the solution was sonicated again until completely dissolved. (The solution was then dissolved in a 2×4 cm solution.) 2 By adding the prepared precursor solution dropwise to nickel foam (about 250 mg) while heating and drying, an electrocatalytic material with electrocatalytic activity can be obtained.

[0058] Comparative Example 1:

[0059] This embodiment provides a bisubstituted 4,4′-bipyridine derivative and an electrocatalytic material containing this compound, the specific technical solution of which is as follows:

[0060] (1) Preparation of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine: prepared according to Example 1.

[0061] (2) Preparation of electrocatalytic materials supported on 1-butyl-1′-(2-propenyl)-4,4′-bipyridine:

[0062] 10 μL of naphthol was added to 1000 μL of an ethanol-water solution (ethanol to water volume ratio 1:1), and sonicated until the solution was homogeneous and transparent, yielding the precursor solution. 5 mg of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine powder was added to the precursor solution, and the solution was sonicated again until completely dissolved. (The solution was then dissolved in a 2×4 cm solution.) 2 By adding a prepared precursor solution dropwise to nickel foam while heating and drying, an electrocatalytic material with electrocatalytic activity can be obtained.

[0063] Comparative Example 2:

[0064] This comparative example provides a monosubstituted 4,4′-bipyridine derivative and an electrocatalytic material containing this compound, the specific technical solution of which is as follows:

[0065] (1) Preparation of 1-butyl-1′-4,4′-bipyridine:

[0066] First, 3.5 g of 1-iodobutane and 3 g of 4,4′-bipyridine were mixed in 10 mL of acetonitrile solution and stirred at 60 °C for 24 h. The resulting reaction system was separated by filtration, and diethyl ether was added to the filtrate to precipitate the product. The precipitate, 1-butyl-4,4′-bipyridine, was dried to obtain an orange compound.

[0067] (2) Preparation of electrocatalytic materials supported on 1-butyl-4,4′-bipyridine:

[0068] Add 15 μL of naphthol to 500 μL of an ethanol-water solution (ethanol to water volume ratio 1:1), and sonicate until the solution is homogeneous and transparent to obtain the precursor solution. Add 10 mg of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine powder to the precursor solution and sonicate again until completely dissolved. 2 By adding a prepared precursor solution dropwise to nickel foam while heating and drying, an electrocatalytic material with electrocatalytic activity can be obtained.

[0069] Comparative Example 3:

[0070] This comparative example provides a monosubstituted 4,4′-bipyridine derivative and an electrocatalytic material containing this compound, the specific technical solution of which is as follows:

[0071] (1) Preparation of 1-(2-propenyl)-4,4′-bipyridine:

[0072] 1 g of 4,4′-bipyridine was dissolved in 25 mL of acetonitrile, and 2 g of 3-chloropropene was added. The mixture was stirred at 80 °C for 48 h. A brown precipitate was formed by filtration, collected, washed with acetonitrile, and dried thoroughly to obtain the disubstituted 1-(2-propenyl)-4,4′-bipyridine.

[0073] (2) Preparation of electrocatalytic materials supported on 1-(2-propenyl)-4,4′-bipyridine:

[0074] Add 15 μL of naphthol to 500 μL of an ethanol-water solution (ethanol to water volume ratio 1:1), and sonicate until the solution is homogeneous and transparent to obtain the precursor solution. Add 10 mg of 1-butyl-1′-(2-propenyl)-4,4′-bipyridine powder to the precursor solution and sonicate again until completely dissolved. 2 By adding a prepared precursor solution dropwise to nickel foam while heating and drying, an electrocatalytic material with electrocatalytic activity can be obtained.

[0075] The present invention characterizes the above-mentioned electrocatalytic materials by the following tests:

[0076] (1) Resistance and Tafel slope: Resistance reflects the "resistance" to charge transfer at the electrode-electrolyte interface, while Tafel slope reveals the relationship between reaction rate and energy input (overpotential). Together, they constitute a "two-dimensional evaluation system" for catalytic reaction kinetics—the smaller the resistance and the smaller the Tafel slope, the higher the electron transfer efficiency of the catalyst and the stronger its reaction initiation and acceleration capabilities.

[0077] Resistance testing procedure: In the three-electrode system, the working electrode is the substrate with the catalyst supported; the reference electrode is the Ag / AgCl electrode; the counter electrode is a platinum sheet; the electrolyte is a 1 mol / L KOH solution selected according to the reaction type, which needs to be deoxygenated in advance (by passing high-purity N2 for 30 minutes).

[0078] Resistance test parameter settings: Performed under the open-circuit voltage program of the CHI760e electrochemical workstation to ensure the electrode surface is in a stable state. Frequency range set to 10. 5 Hz (high frequency) to 10 -1 Hz (low frequency), covering impedance response related to charge transfer and diffusion; AC signal amplitude: 5-10mV (small amplitude to avoid disrupting the electrode surface equilibrium). Temperature: room temperature (25±2℃), requires constant temperature water bath control to avoid temperature fluctuations affecting impedance value.

[0079] The Tafel slope test procedure: In the three-electrode system, the working electrode is the substrate with the catalyst supported; the reference electrode is the Ag / AgCl electrode; the counter electrode is a platinum sheet; the electrolyte is a 1 mol / L KOH solution selected according to the reaction type, which needs to be deoxygenated in advance (by passing high-purity N2 for 30 minutes).

[0080] Tafel slope test parameter settings: Scanning method: linear scan, scanning from the open-circuit voltage towards the direction of the reaction. Scanning rate: 5-10mV / s (low-speed scanning reduces interference from capacitive current, ensuring that the current mainly comes from the Faraday reaction). Stirring: Turn on magnetic stirring (500-800rpm) to avoid bubbles generated by the reaction (such as O2, H2) adhering to the electrode surface and affecting current acquisition.

[0081] Data processing for the Tafel slope: Extract the current density (j) and corresponding voltage data from the polarization curve (LSV curve). Perform linear fitting in the dynamic control region; the slope of the fitted line is the Tafel slope.

[0082] (2) Overpotential testing process: In the three-electrode system, the working electrode is a nickel foam substrate loaded with the target catalyst. The reference electrode is Ag / AgCl, and the counter electrode is a platinum sheet. The electrolyte is 1 mol / L KOH (alkaline electrolyte), which needs to be deoxygenated with high-purity gas (O2 or H2) for 30 minutes in advance.

[0083] Overpotential test parameter settings: Linear scan, scanning from open circuit voltage (OCV) towards the reaction direction. Scan rate: 5-10 mV / s, covering the target current density range. Turn on magnetic stirring (500-800 rpm) to prevent bubbles (O2, H2) generated by the reaction from adhering to the electrode surface and affecting current stability. Room temperature (25±2℃), controlled by a constant temperature water bath to avoid potential drift caused by temperature fluctuations.

[0084] like Figure 3-4 As shown, the electrocatalytic material supported on a bisubstituted 4,4′-bipyridine derivative prepared in Example 1 was compared with bare nickel foam by electrochemical impedance spectroscopy (Nyquist plot) measurements. Figure 3 As shown, the semi-circular radius of the disubstituted 4,4′-bipyridine derivative is significantly smaller than that of nickel foam, indicating that it has lower charge transfer resistance and stronger conductivity. To further investigate the kinetics of the oxygen evolution reaction, Figure 4 The Tafel slope is given. The Tafel slope of the disubstituted 4,4′-bipyridine derivative is only 163 mA / dec, which is much lower than that of bare nickel foam (249 mA / dec), indicating that the disubstituted 4,4′-bipyridine derivative has superior electrocatalytic oxygen evolution reaction kinetics.

[0085] like Figure 5As shown in the overpotential curve, the electrocatalyst material supported on the disubstituted 4,4′-bipyridine derivative in Example 1 exhibits an overpotential of 10 mA·cm⁻¹. -2 The material exhibits a low overpotential of 228 mV at a given current density, which is beneficial for the oxygen evolution reaction, demonstrating that the prepared material possesses good electrocatalytic oxygen evolution performance. Figure 5 As shown, the electrocatalytic material with a low loading rate of the disubstituted 4,4′-bipyridine derivative in Comparative Example 1 exhibits performance at 10 mA·cm⁻¹. -2 The overpotential of 410 mV at the current density is much higher than that of the electrocatalytic material in Example 1. This indicates that the catalytic performance decreases as the loading rate of the disubstituted 4,4′-bipyridine derivative decreases.

[0086] like Figure 6 As shown, the monosubstituted 1-butyl-4,4′-bipyridine electrocatalyst material in Comparative Example 2 exhibits performance at 10 mA·cm⁻¹ -2 At a current density of 350 mV, the overpotential is significantly higher than that of the electrocatalytic material in Example 1. This indicates that the disubstituted 4,4′-bipyridine derivative exhibits better electrocatalytic performance than the allyl monosubstituted 4,4′-bipyridine derivative. Similarly, as... Figure 7 As shown, the monosubstituted 1-(2-propenyl)-4,4′-bipyr electrocatalyst in Comparative Example 3 exhibits performance at 10 mA·cm⁻¹ -2 The overpotential at the specified current density is 550 mV, which is much higher than that of the electrocatalytic material in Example 1. Therefore, the electrocatalytic performance of the disubstituted 4,4′-bipyridine derivative prepared in this invention is better than that of the allyl monosubstituted 4,4′-bipyridine derivative.

[0087] The above description of the embodiments is provided to enable those skilled in the art to understand and use the invention. It will be apparent to those skilled in the art that various modifications can be made to these embodiments, and the general principles described herein can be applied to other embodiments without inventive effort. Therefore, the present invention is not limited to the above embodiments, and any improvements and modifications made by those skilled in the art based on the disclosure of the present invention without departing from the scope of the invention should be within the protection scope of the present invention.

Claims

1. A disubstituted 4,4′-bipyridine derivative, characterized in that, It has the following general structural formula: In the formula, R1 is C 2-6 Alkyl group, R2 is C 3-6 The alkenyl group.

2. The disubstituted 4,4′-bipyridine derivative according to claim 1, characterized in that, The disubstituted 4,4′-bipyridine derivative has the following structural formula:

3. A method for preparing the disubstituted 4,4′-bipyridine derivative according to claim 1, characterized in that, The preparation method includes the following steps: S1: Haloalkanes and 4,4′-bipyridine are mixed in an organic solvent and reacted under heating conditions with stirring; the reaction system is separated into solid and liquid phases, and then an ether solvent is added to the filtrate to precipitate the intermediate compound; S2: The intermediate compound is reconstituted and then added to the haloalkene. The reaction is carried out under heating and stirring. The precipitate is collected and dried to obtain the 4,4′-bipyridine derivative. The general structural formulas of the haloalkanes and haloalkenes are X-R1 and X-R2, respectively, where X is any one of fluorine, chlorine, bromine, and iodine.

4. The method for preparing the disubstituted 4,4′-bipyridine derivative according to claim 3, characterized in that, In step S1, the molar ratio of 4,4′-bipyridine to haloalkanes is 1:(1 to 1.8).

5. The method for preparing the disubstituted 4,4′-bipyridine derivative according to claim 3, characterized in that, In step S2, the molar ratio of the intermediate compound to the haloalkene is 1:(1 to 2.2).

6. The method for preparing the disubstituted 4,4′-bipyridine derivative according to claim 3, characterized in that, In step S1, the heating temperature is 50-70℃, and the reaction time is 12-36h; In step S2, the heating temperature is 70-90℃, and the reaction time is 24-72h.

7. An electrocatalytic material, characterized in that, The material includes the disubstituted 4,4′-bipyridine derivative as described in claim 1; the electrocatalytic material is used for the electrocatalytic oxygen evolution reaction under alkaline conditions, and comprises nickel foam and the disubstituted 4,4′-bipyridine derivative supported on the nickel foam.

8. The electrocatalytic material according to claim 7, characterized in that, The mass ratio of the disubstituted 4,4′-bipyridine derivative to nickel foam is (1-2):6; 9. The electrocatalytic material according to claim 7, characterized in that, The electrocatalytic material was prepared by the following method: A precursor solution was prepared by adding a disubstituted 4,4′-bipyridine derivative to a naphthol solution until it was completely dissolved; the precursor solution was then dropped onto nickel foam and dried to obtain the electrocatalytic material.

10. The electrocatalytic material according to claim 9, characterized in that, The mass ratio of the disubstituted 4,4′-bipyridine derivative to naphthol is (5-10):1; The naphthol solution is an aqueous solution of naphthol in ethanol, with a volume ratio of water to ethanol of 1:(1-2).

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