CN114539173A - Four-electron duplex hydroxy phenazine derivative and derivative, preparation method and application thereof - Google Patents
Four-electron duplex hydroxy phenazine derivative and derivative, preparation method and application thereof Download PDFInfo
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- CN114539173A CN114539173A CN202210152088.3A CN202210152088A CN114539173A CN 114539173 A CN114539173 A CN 114539173A CN 202210152088 A CN202210152088 A CN 202210152088A CN 114539173 A CN114539173 A CN 114539173A
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Abstract
The invention discloses a four-electron double-hydroxy phenazine and derivatives thereof, which have a structural general formula I
The compound consists of two phenazine molecules, which can accept four electrons. The four-electron duplex phenazine and the derivatives thereof can be used as a negative active material for an organic flow battery, and the energy density of the flow battery is greatly improved compared with that of a single phenazine molecule. The compound has larger molecular size, is beneficial to reducing the permeability between the anode and the cathode and prolonging the service life of the battery. Due to the electron-donating property of hydroxyl, the compound reduces the redox potential of the battery, and greatly widens the working voltage range of the flow battery. And the four phenolic hydroxyl groups are easily dissolved in an alkaline aqueous solution, so that the energy density of the flow battery is further improved. The assembled organic flow battery has wide application prospect in the fields of scale electricity storage of renewable energy and peak regulation of a power grid.
Description
Technical Field
The invention belongs to the field of electrochemical energy storage, and relates to a four-electron double-hydroxy phenazine and a derivative, a preparation method and application thereof.
Background
In recent years, renewable energy technologies such as solar energy and wind energy are rapidly developed, however, the power generation mode is greatly influenced by natural factors, has obvious randomness and volatility, and is prominent in phenomena such as wind abandonment and light abandonment at present. The energy storage technology is the key for changing random fluctuation energy into friendly energy, and the technical change of the energy storage technology has important significance for promoting the energy revolution. The energy storage industry is currently in an unprecedented key period based on coexistence with challenges, and as an important support technology for global energy reform, the energy storage industry becomes one of important strategies for energy sustainable development of various countries.
Among various electrochemical energy storage strategies, the flow battery is gradually the preferred of large-scale high-efficiency energy storage technology due to its advantages of high safety, long cycle life, environmental protection, high cost performance, quick response, flexible design and installation, and the like. Flow batteries are best suited for large-scale (megawatt/megawatt-hour) electrochemical energy storage (such as relatively independent energy and power control), high-current, high-power operation (fast response), high safety (not prone to combustion and explosion), and the like. The water system organic flow battery takes water-soluble organic redox active molecules as electrolyte, has high safety, low cost, easy performance regulation and control and environmental protection, and is a novel large-scale energy storage technology with great development prospect. In the field of water-based flow batteries, a series of molecules based on organic structural frameworks such as anthraquinone, viologen, ferrocene, nitrogen heteroaromatic rings, phenazines and the like have shown good performance and application prospect. However, most organic molecule active materials are in single electron and double electron transfer processes, and most organic molecules are small in size, so that the problem of cross contamination of electrolytes exists.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a four-electron-pair hydroxyphenyloxazine and a derivative thereof, wherein the compound can be used as a negative electrode material of an organic flow battery. The flow battery can accept four electrons, greatly improves the energy density of the flow battery, reduces the permeability between a positive electrode and a negative electrode, and prolongs the service life of the battery.
The second object of the present invention is to provide a method for preparing the above four-electron-pair hydroxyphenyloxazines and derivatives thereof.
The invention also aims to provide application of the four-electron double-hydroxy phenazine and derivatives thereof.
One of the purposes of the invention is realized by adopting the following technical scheme:
four-electron double-hydroxy phenazine and derivatives thereof with a structural general formula I
Wherein R is selected from H, CH2CH2CH2N+(CH3)3、CH2CH2CH2SO3Na。
The second purpose of the invention is realized by adopting the following technical scheme:
the preparation method of the four-electron double-hydroxy phenazine and the derivatives thereof comprises the following steps:
(1) adding benzidine and distilled water into a container, mixing and heating, and then adding 2, 5-dihydroxy p-benzoquinone into the mixture to obtain a mixture; the mixture is cooled to room temperature after reflux reaction, and then four-electron duplex hydroxyl phenazine is obtained after filtration, washing and drying;
(2) and (2) mixing and stirring the four-electron-duplex hydroxyphenyloxazine obtained in the step (1), organic strong base and organic solvent, then adding 3-bromopropyltrimethylammonium bromide or 1, 3-propane sultone into the mixture, carrying out reflux reaction, cooling to room temperature, filtering, washing and drying to obtain the four-electron-duplex hydroxyphenyloxazine derivative.
Further, the step (1) is that the adding molar ratio of the benzidine to the 2, 5-dihydroxy p-benzoquinone is 1: 3; in the step (2), the addition molar ratio of the four-electron double-linked hydroxyphenyloxazine to the 3-bromopropyltrimethylammonium bromide or the 1, 3-propane sultone is 1: 10.
Further, the organic strong base in the step (2) is selected from one of sodium methoxide and potassium methoxide, and the organic solvent is one of methanol and DMF.
The third purpose of the invention is realized by adopting the following technical scheme:
the four-electron duplex hydroxy phenazine or the derivative thereof can be used as a negative active material of an organic flow battery.
Further, the four-electron double-linked hydroxyphenyloxazine or the derivative thereof and the positive electrode active material can constitute an alkaline or neutral organic flow battery.
Further, the positive electrode material is selected from potassium iodide, potassium ferricyanide, tetramethylpiperidine oxide or hydroquinone derivative.
Further, the electrolyte in the alkaline organic flow battery is sodium hydroxide, lithium hydroxide, potassium hydroxide or sodium carbonate.
Further, the electrolyte in the neutral organic flow battery is sodium chloride, lithium chloride or ammonium chloride.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a four-electron double-hydroxy phenazine and a derivative thereof, wherein the compound consists of two phenazine molecules and can accept four electrons. The active material can be used as a negative electrode active material of an aqueous organic flow battery, and can greatly improve the energy density of the battery. So far, no four-electron system negative active material is reported. The invention also provides a preparation method of the compound, and the preparation process is simple and the required conditions are mild.
The invention also provides application of the compound in a negative active material of an organic flow battery. The molecular size of the compound is obviously increased relative to a single phenazine molecule, the permeability between a positive electrode and a negative electrode is reduced, and the service life of the battery is prolonged. The electron donating property of the hydroxyl in the four-electron double-hydroxy phenazine and the derivatives thereof reduces the redox potential of the battery and greatly widens the working voltage range of the flow battery. The contained phenolic hydroxyl groups are easily dissolved in an alkaline aqueous solution, and the energy density of the flow battery is further improved. The four-electron bi-hydroxy phenazine and the derivatives thereof are used as a negative electrode active material of a water system organic flow battery, and assembled with a positive electrode active material to form the organic flow battery, so that the four-electron bi-hydroxy phenazine and the derivatives thereof have wide application prospects in the fields of renewable energy scale electricity storage and power grid peak regulation.
Drawings
FIG. 1 is a cyclic voltammogram of a four-electron-duplex hydroxyphenyloxazine as a negative active material prepared in example 1 of the present invention;
FIG. 2 is a graph of the peak current versus the square root of the scanning rate for a four-electron-duplex hydroxyphenyloxazine as a negative active material, prepared in example 1 of the present invention;
fig. 3 is a battery window test chart of an H-type flow battery composed of four-electron duplex hydroxyphenyloxazine and potassium iodide, which is obtained in example 1 of the present invention;
FIG. 4 is a graph of 50 cycles of charging and discharging for an H-type flow battery composed of four-electron-duplex hydroxyphenyloxazine and potassium iodide, prepared in example 1 of the present invention;
fig. 5 is a graph of energy efficiency of an H-type flow battery composed of four-electron-duplex hydroxyphenyloxazine and potassium iodide obtained in example 1 of the present invention;
fig. 6 is a graph of coulombic efficiency and voltage efficiency of an H-type flow battery composed of four-electron-duplex hydroxyphenyloxazine and potassium iodide obtained in example 1 of the present invention.
Detailed Description
The present invention will be further described with reference to the accompanying drawings and the detailed description, and it should be noted that any combination of the embodiments or technical features described below can be used to form a new embodiment without conflict.
Example 1
A four-electron double-hydroxy phenazine compound is prepared by the following steps:
1.0g of benzidine and 75.0mL of distilled water were added to a 250mL round bottom flask, stirred for 10min and then heated to 70 ℃ to continue adding 1.37g of 2, 5-dihydroxy p-benzoquinone (the molar ratio of benzidine to 2, 5-dihydroxy p-benzoquinone is 1: 3). Reflux reaction for 1h, cooling to room temperature, separating out solid, suction filtering, washing twice with water, washing twice with ether, vacuum drying to obtain reddish brown product-tetraelectron double-hydroxy phenazine with yield of 80%.
MS(ESI),m/z:423.1[M+H]+.
Example 2
A four-electron double-hydroxy phenazine derivative is prepared by the following steps:
4.22g of the double-linked-hydroxy-phenazine prepared in example 1, 2.20g of sodium methoxide and 50mL of DMF are added into a 250mL round bottom flask, the mixture is stirred for 30min to obtain a mixture, 12.2g of 1, 3-propane sultone (the adding molar ratio of the four-electron double-linked-hydroxy-phenazine to the 1, 3-propane sultone is 1:10) is added into the mixture, the mixture is refluxed and reacted for 1h at the temperature of 150 ℃, the mixture is cooled to the room temperature, a solid is separated out, the solid is filtered, water and acetone are washed twice respectively, and the product of the four-electron double-linked-hydroxy-phenazine tetrasulfonate is obtained after vacuum drying, wherein the yield is 60%.
MS(ESI),m/z:906.1[M]-.
Experimental example 1
The electrochemical test results were as follows:
fig. 1 is a cyclic voltammetry graph of the tetraelectron-binodal hydroxyphenyloxazine prepared in example 1 of the present invention as a negative electrode active material, in which the electrolyte is an aqueous solution of sodium carbonate, the concentrations of the aqueous solution of sodium carbonate are 0.2mol/L, 0.3mol/L, 0.4mol/L, and 0.5mol/L, and the tetraelectron-binodal hydroxyphenyloxazine is added thereto and dissolved, respectively, so that the concentration of the tetraelectron-binodal hydroxyphenyloxazine is 0.01 mol/L. A three-electrode system is adopted, a glassy carbon electrode with the diameter of 3mm is adopted as a working electrode, a platinum electrode is adopted as an auxiliary electrode, a saturated silver chloride electrode (the potential of a standard vertebra electrode is 0.2V) is adopted as a reference electrode, and the sweep rate is 10 mV/s. As can be seen from the figure, the flow battery shows a pair of reversible redox peaks at different concentrations, and the reproducibility is good at different concentrations. The electrochemical reversibility of the four-electron duplex hydroxyphenyloxazine prepared in the embodiment 1 is good, and when silver/silver chloride is used as a reference electrode, the electron-donating property of the hydroxyl in the four-electron duplex hydroxyphenyloxazine reduces the redox potential of the battery (-0.867V vs. silver/silver chloride), and greatly widens the working voltage range of the flow battery.
FIG. 2 is a graph showing the relationship between the peak current and the square root of the scanning rate of a 0.5mol/L sodium carbonate solution of 0.01mol/L tetraelectron bishydroxyphenazine as a negative active material prepared in example 1 of the present invention, and the square root of the oxidation-reduction peak potential and the scanning rate (V)1/2) The slope of the linear fitting is in the same order of magnitude, and the four-electron duplex hydroxy phenazine is proved to have reversible electrochemical performance, and the diffusion coefficients of the oxidation reaction and the reduction reaction are approximately the same and are in the same order of magnitude.
The four-electron double-hydroxy phenazine obtained in the embodiment 1 of the invention is used as a negative active material, the number of the hydroxy groups is neutralized by alkali, the electrolyte is sodium carbonate, and the prepared sodium carbonate is 0.5mol/L aqueous solution. Dissolving the four-electron double-hydroxy phenazine in a sodium carbonate aqueous solution to prepare a solution with the concentration of the four-electron double-hydroxy phenazine of 0.01mol/L, and taking the solution as a negative electrode electrolyte; dissolving potassium iodide in a sodium carbonate solution to prepare a positive electrolyte with the same concentration; and respectively filling the positive electrolyte and the negative electrolyte in positive and negative H-shaped cells, and assembling the H-shaped flow battery by using a nafion membrane or a non-fluorine ion membrane as a diaphragm and using a graphite felt as a working electrode. The constant current 7mA was set for the charge and discharge test, and the test results are shown in fig. 3 to 6. The reversible chemical equation for the four-electron-pair hydroxyphenyloxazine obtained in example 1 of the present invention for the loss and gain of four electrons is shown below.
Fig. 3 is a battery window test chart of an H-type flow battery composed of four-electron duplex hydroxyphenyloxazine and potassium iodide prepared in example 1, where it is known that open-circuit voltages corresponding to the positive and negative electrodes are 1.325V, which is a better level of currently reported alkaline flow batteries. Fig. 4 is a graph of an H-type flow battery formed by four-electron-duplex hydroxyphenyloxazine and potassium iodide obtained in example 1 of the present invention, which shows that the flow battery is regularly charged and discharged, no side reaction occurs, and the battery has short discharge time and short charge time, wherein the average value of the charge time is 19.3s, and the average value of the discharge time is 14 s. Fig. 5 is an energy efficiency diagram of an H-type flow battery composed of four-electron-duplex hydroxyphenyloxazine and potassium iodide obtained in example 1 of the present invention, and it can be seen from the diagram that the flow battery obtained in the present invention has an energy efficiency of 93.3% and is stable and good in performance during cycling for 40 cycles. Fig. 6 is a graph of coulombic efficiency and voltage efficiency of an H-type flow battery composed of four-electron-duplex hydroxyphenyloxazine and potassium iodide obtained in example 1 of the present invention, and it can be seen from the graph that both the coulombic efficiency and the voltage efficiency are kept balanced and stable for 45 cycles, where the coulombic efficiency is 92% and the voltage efficiency is close to 100%.
In conclusion, the invention provides the four-electron double-hydroxy phenazine and the derivatives thereof, the compound consists of two phenazine molecules, can accept four electrons, and greatly improves the energy density of the flow battery compared with a single phenazine molecule. And the molecular size of the compound is obviously increased relative to a single phenazine molecule, so that the permeability between a positive electrode and a negative electrode is reduced, and the service life of the battery is prolonged. The electron-donating property of the hydroxyl in the four-electron double-hydroxy phenazine and the derivatives thereof reduces the redox potential of the battery and greatly widens the working voltage range of the flow battery. The contained phenolic hydroxyl groups are easily dissolved in an alkaline aqueous solution, and the energy density of the flow battery is further improved. The four-electron bi-hydroxy phenazine and the derivatives thereof are used as a negative electrode active material of a water system organic flow battery, and assembled with a positive electrode active material to form the organic flow battery, so that the four-electron bi-hydroxy phenazine and the derivatives thereof have wide application prospects in the fields of renewable energy scale electricity storage and power grid peak regulation.
The above embodiments are only preferred embodiments of the present invention, and the protection scope of the present invention is not limited thereby, and any insubstantial changes and substitutions made by those skilled in the art based on the present invention are within the protection scope of the present invention.
Claims (9)
1. The four-electron double-hydroxy phenazine and the derivatives thereof are characterized by having a structural general formula I
Wherein R is selected from H, CH2CH2CH2N+(CH3)3、CH2CH2CH2SO3Na。
2. The process for the preparation of four-electron-bis-hydroxyphenyloxazines and derivatives thereof as claimed in claim 1, comprising the following steps:
(1) adding benzidine and distilled water into a container, mixing and heating, and then adding 2, 5-dihydroxy p-benzoquinone into the mixture to obtain a mixture; the mixture is cooled to room temperature after reflux reaction, and then four-electron duplex hydroxyl phenazine is obtained after filtration, washing and drying;
(2) and (2) mixing and stirring the four-electron duplex hydroxyphenyloxazine obtained in the step (1), organic strong base and organic solvent, then adding 3-bromopropyltrimethylammonium bromide or 1, 3-propane sultone into the mixture, carrying out reflux reaction, cooling to room temperature, filtering, washing and drying to obtain the four-electron duplex hydroxyphenyloxazine derivative.
3. The method for preparing a four-electron-duplex hydroxyphenyloxazine and derivatives thereof as claimed in claim 2, wherein the molar ratio of the benzidine and the 2, 5-dihydroxy-p-benzoquinone added in step (1) is 1: 3; in the step (2), the addition molar ratio of the four-electron double-linked hydroxyphenyloxazine to the 3-bromopropyltrimethylammonium bromide or the 1, 3-propane sultone is 1: 10.
4. The method for preparing tetraelectron duplex hydroxyphenyloxazines and derivatives thereof as claimed in claim 2, wherein the organic strong base in step (2) is selected from one of sodium methoxide and potassium methoxide, and the organic solvent is selected from one of methanol and DMF.
5. The use of the tetraelectron-bis hydroxyphenyloxazines and derivatives thereof as claimed in claim 1, wherein the tetraelectron-bis hydroxyphenyloxazines or derivatives thereof are capable of being used as negative active materials in organic flow batteries.
6. The use of tetraelectron-duplex hydroxyphenyloxazines and derivatives thereof according to claim 5, wherein the tetraelectron-duplex hydroxyphenyloxazines or derivatives thereof and the positive electrode active material are capable of forming an alkaline or neutral organic flow battery.
7. The use of tetraelectronic twinhydroxy phenazine and its derivatives as claimed in claim 5, wherein the positive electrode material is selected from potassium iodide, potassium ferricyanide, tetramethylpiperidine oxide or hydroquinone derivatives.
8. The use of tetraelectronic duplex hydroxyphenyloxazines and derivatives thereof as claimed in claim 5, wherein the electrolyte in the alkaline organic flow battery is sodium hydroxide, lithium hydroxide, potassium hydroxide, or sodium carbonate.
9. The use of tetraelectronic duplex hydroxyphenyloxazines and derivatives thereof as claimed in claim 5, wherein the electrolyte in the neutral organic flow battery is sodium chloride, lithium chloride, or ammonium chloride.
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Cited By (1)
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