Fullerene C60 pyrroline derivative and preparation method thereof

Abstract

The invention discloses a fullerene C60 pyrroline derivative and a preparation method thereof, and belongs to the field of fullerene derivative synthesis. The preparation method comprises the following specific preparation steps: taking fullerene C60, a TBAOH methanol solution, benzophenone imine or benzophenone oxime and I2 as raw materials, taking o-dichlorobenzene or methylbenzene as a solvent, reacting under the protection of inert gas, and carrying out reduced pressure distillation, separation and purification to obtain the target fullerene C60 pyrroline derivative. The preparation method has the advantages of simple synthesis process, environmental friendliness, mild reaction conditions, good chemical selectivity and the like.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic synthesis and particularly relates to a fullerene C 60 Pyrroline derivatives and methods for their preparation. Background Art

[0002] Since the discovery of fullerene in 1985, its unique physical and chemical properties have attracted the deep attention of scientific researchers. Functionalization of the carbon skeleton of fullerene by introducing various functional groups has become an important research hotspot in the field of fullerenes. Fullerene functionalization can give fullerenes more properties to meet the needs of specific fields. Fullerene derivatives have excellent electron transport properties and are often used as electron acceptors in organic solar cells. In perovskite solar cells, fullerene derivatives can not only serve as electron transport layers, but also as additives or interface modification layers of the perovskite layer, which helps to improve the photoelectric conversion efficiency and stability of the battery.

[0003] Fullerene C 60 Pyrroline derivatives are a special class of organic compounds whose structure consists of fullerene C 60 The molecule is formed by chemical bonding with the pyrroline ring. Pyrroline is a five-membered heterocyclic ring containing a nitrogen atom, and the pyrroline ring is found in many biologically active molecules. Fullerene pyrroline derivatives may have biological activity. The pyrroline structure can provide reaction sites, allowing fullerene pyrroline derivatives to interact with specific biological molecules, showing anticancer and antiviral activities, showing important research value.

[0004] In the study, it was found that at present, the fullerene C 60 The reaction synthesis process of pyrroline derivatives has the following problems: using heavy metal salts as catalysts will cause environmental pollution; there are many types of reaction substrates, and the catalysts are expensive, resulting in high economic costs; the reaction conditions are relatively harsh and require precise control of the conditions to prevent the occurrence of side reactions and the increase of by-products.

[0005] Therefore, the present invention designs a new method that is environmentally friendly, has high reaction selectivity and mild reaction conditions, which will be of great significance for the future realization of structural diversification and functionalization of fullerene C 60 The synthesis of pyrroline derivatives is of great significance for developing new synthetic strategies for fullerene derivatives. Summary of the invention

[0006] The purpose of the present invention is to provide a fullerene C 60Pyrroline derivatives and preparation methods thereof. The method is simple to operate, has mild reaction conditions and high selectivity, and on the one hand, reduces the reaction temperature, reduces the types of reaction substrates, does not use expensive catalysts, and reduces the reaction cost; on the other hand, it avoids heavy metal pollution, making the reaction more green and environmentally friendly.

[0007] In order to achieve the above object, the first aspect of the present invention provides a fullerene C 60 Pyrroline derivatives, the fullerene C 60 The structural formula of the pyrroline derivative is shown in Formula I, wherein R is selected from H and one of the groups shown in Formula II.

[0008]

[0009] The fullerene C provided by the present invention 60 Pyrroline derivatives are a special class of organic compounds with novel structures. 60 Fullerene molecules are formed by chemical bonding with pyrroline rings. Pyrroline is a five-membered heterocyclic ring containing a nitrogen atom. Pyrroline rings are found in many biologically active molecules. Fullerene pyrroline derivatives may have biological activities such as antioxidant and anti-tumor activities, showing important research value and huge application potential.

[0010] A second aspect of the present invention provides a fullerene C 60 The preparation method of pyrroline derivatives comprises the following preparation steps:

[0011] Step 1: Add fullerene C to the round-bottom flask under inert gas protection. 60 , an organic solvent, benzophenone imine or benzophenone oxime and TBAOH methanol solution, stirring and reacting at a certain temperature for 1 to 2 hours;

[0012] Step 2: Add I2 to the mixed solution obtained in step 1, react for 0.5 to 1 hour, stop the reaction, and naturally cool to room temperature to obtain a reaction solution;

[0013] Step 3: Take the reaction solution of step 2, use a vacuum rotary evaporator to remove the solvent under reduced pressure, wash with methanol to obtain a crude product, and vacuum dry for 6 to 12 hours;

[0014] Step 4: Separate and purify the crude product obtained in step 3 by high performance liquid chromatography to obtain the target fullerene C 60 Pyrroline derivatives.

[0015] In the technical solution of the present invention, when the reaction reagent is benzophenone imine, the chemical reaction that occurs is as shown in Formula III; when the reaction reagent is benzophenone oxime, the chemical reaction that occurs is as shown in Formula IV.

[0016]

[0017] In the technical solution of the present invention, step 1: under the protection of inert gas, add fullerene C into a round-bottom flask. 60 , organic solvent, benzophenone imine or benzophenone oxime and TBAOH methanol solution, stir and react at a certain temperature for 1 to 2 hours. The choice of TBAOH methanol solution can improve the selectivity of the reaction. The choice of organic solvent is to ensure that fullerene C 60 The solubility of is conducive to the reaction, while avoiding reaction with fullerene itself, and the use of inert gas is to isolate the air and prevent the reaction system from being disturbed by oxygen and moisture in the air, so as to ensure the smooth progress of the reaction; Step 2: Add I2 to the mixed solution obtained in step 1, react for 0.5 to 1 hour, stop the reaction, and naturally cool to room temperature to obtain a reaction solution. In this step, the addition of I2 is to promote the fullerene C 60 Step 3: Take the reaction solution of step 2, use a rotary evaporator to remove the solvent under reduced pressure, wash with methanol to obtain a crude product, and vacuum dry for 6 to 12 hours. The purpose of this step is to remove unreacted reagents and impurities, improve the purity of the product, help simplify the subsequent separation steps, save time and resources; Step 4: Separate and purify the crude product obtained in step 3 by high performance liquid chromatography to obtain the target fullerene C 60 Pyrroline derivatives. High performance liquid chromatography can provide a high-purity separation effect to ensure the purity of fullerene derivatives. In summary, the preparation method has the characteristics of simple experimental operation and high selectivity.

[0018] Preferably, the fullerene C 60 , tetrabutylammonium hydroxide (TBAOH), benzophenone imine or benzophenone oxime and I2 in a molar ratio of 1:2-10:10-20:2-5.

[0019] In the technical solution of the present invention, the fullerene C 60 The molar ratio of tetrabutylammonium hydroxide (TBAOH), benzophenone imine or benzophenone oxime and I2 added is 1:2-10:10-20:2-5. Within this range, each substance can fully react to ensure the optimal yield and prevent the waste of drugs. If the ratio of the reactants is lower than this value, it may lead to incomplete reaction; on the contrary, if the ratio exceeds this value, it may cause excessive consumption of drugs.

[0020] Preferably, when the benzophenone oxime is used as a raw material to prepare the derivative, a trace amount of CO2 needs to be introduced.

[0021] In the technical scheme of the present invention, when preparing the derivative using benzophenone oxime as the raw material in step 1, a trace amount of CO2 needs to be introduced to regulate the progress of the reaction and improve the selectivity of the reaction. If an excessive amount is added, the by-products will increase and the yield will decrease.

[0022] Preferably, the inert gas is Ar or N2, preferably Ar.

[0023] In the technical solution of the present invention, the inert gas in step one is Ar or N2. Both inert gases can effectively isolate the air, protect the reaction system, and provide conditions for the stable and efficient reaction.

[0024] Preferably, the organic solvent is o-dichlorobenzene or toluene, preferably o-dichlorobenzene.

[0025] In the technical solution of the present invention, the organic solvent in step 1 is toluene or o-dichlorobenzene, both of which are used as solvents for the reaction, and are effective for the fullerene C 60 It has higher solubility, better chemical stability and thermal stability, and is helpful for the reaction to proceed.

[0026] Preferably, the concentration of the TBAOH methanol solution is 1.0 mol / L.

[0027] Preferably, the reaction temperature is 25-80°C.

[0028] In the technical solution of the present invention, the reaction temperature is 25 to 80°C, which is firstly beneficial to the target fullerene C 60 The production of pyrroline derivatives also ensures the stable progress of the reaction, which is safe, easy to control and simple to operate.

[0029] Preferably, the fullerene C 60 The concentration in organic solvents is 1.0-2.5 mg / mL.

[0030] In the technical solution of the present invention, the fullerene C 60 The concentration in organic solvent is 1.0~2.5mg / mL. Within this range, fullerene C 60 It can be well dissolved in the solvent, reducing the amount of raw materials used while not exceeding its solubility limit, avoiding incomplete dissolution and uneven reaction caused by excessively high concentration, and is conducive to the continuous progress of the reaction.

[0031] Preferably, the high performance liquid chromatography method uses a pyrenylpropyl bonded silica gel chromatography column (Buckyprep) as a separation column and toluene as a mobile phase to separate the fullerene C 60 Separation and purification of pyrroline derivatives.

[0032] In the technical solution of the present invention, the purification method adopted is high performance liquid chromatography (HPLC), specifically: using Buckyprep as a separation column and toluene as a mobile phase, dissolving the crude fullerene derivative product in toluene, and separating and purifying it by a high performance liquid chromatograph to obtain a pure product. This method can achieve a good purification effect.

[0033] Compared with the prior art, the technical solution of the present invention has the following beneficial effects:

[0034] (1) The present invention successfully synthesized a novel fullerene C 60 Pyrroline derivatives have enriched the types of fullerene derivatives. These derivatives can be used in optoelectronic devices, solar cells, organic light-emitting diodes (OLEDs), biomedicine and other fields, and have broad application prospects.

[0035] (2) The present invention synthesizes the fullerene C 60 The preparation method of pyrroline derivatives has the advantages of being environmentally friendly, simple to operate, having few by-products, and having mild reaction conditions. It overcomes the problems of using heavy metal salts as catalysts in previous technologies, which may cause environmental pollution, produce a large number of by-products, and have a wide variety of reaction substrates, and realizes a simpler and more efficient synthesis process. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 Fullerene C 60 Schematic diagram of the molecular structure of pyrroline derivative 1

[0037] Figure 2 Fullerene C 60 Schematic diagram of the molecular structure of pyrroline derivative 2

[0038] Figure 3 Fullerene C in Examples 1, 2, 3, and 4 60 Pyrroline derivatives 1 1 H NMR spectrum

[0039] Figure 4 Fullerene C in Examples 1, 2, 3, and 4 60 Pyrroline derivatives 1 1 C NMR spectrum

[0040] Figure 5 Fullerene C in Examples 5, 6, 7, and 8 60 Pyrroline derivatives 2 1 H NMR spectrum

[0041] Figure 6 Fullerene C in Examples 5, 6, 7, and 8 60 Pyrroline derivatives 2 1 C NMR spectrum

[0042] Figure 7 Fullerene C in Examples 1, 2, 3, and 4 60 UV-visible absorption spectrum of pyrroline derivative 1

[0043] Figure 8 Fullerene C in Examples 5, 6, 7, and 8 60 UV-visible absorption spectrum of pyrroline derivative 2 DETAILED DESCRIPTION

[0044] Unless otherwise specified, the instruments, drugs, reagents, etc. used in the following examples can be purchased from commercial channels, and the methods of use of the relevant instruments, drugs, reagents, etc. shall be carried out in accordance with the relevant operating instructions.

[0045] The present invention will be further described below through examples, with the purpose of allowing researchers in the field to understand the present invention in more detail. However, the present invention is not limited to the following examples, and relevant technical personnel should understand this.

[0046] In particular, in all the following examples, the addition of N times the molar equivalent of a drug means that the amount of the drug to be added is the amount of fullerene C added in this example. 60 N times the amount of substance.

[0047] Example 1

[0048] The specific steps are:

[0049] Under Ar protection, o-dichlorobenzene (30 mL) was first added to the round-bottom flask, followed by 10 times the molar equivalent of benzophenone imine (116 μL) and 6 times the molar equivalent of TBAOH methanol solution (416 μL). The mixture was heated in an oil bath at 60 °C. After reacting for 0.5 h, fullerene C was added to the round-bottom flask. 60 (50 mg), and then react for 1 hour; then add 2 times the molar equivalent of I2 (35 mg) to the mixed solution obtained by the reaction, react for 0.5 hour, stop the reaction, and naturally cool to room temperature to obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to reduce pressure and distill, the solvent is decompressed and rotated out in the rotary evaporator, rinsed with methanol, and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 1, yield 36%.

[0050] Example 2

[0051] The specific steps are:

[0052] Under N2 protection, toluene (40 mL) was first added to the round-bottom flask, followed by 20 times the molar equivalent of benzophenone imine (233 μL) and 10 times the molar equivalent of TBAOH methanol solution (694 μL). The mixture was heated in an oil bath at 70°C. After reacting for 1 hour, fullerene C was added to the round-bottom flask. 60 (50 mg), and then react for 0.5 hours; then add 5 times the molar equivalent of I2 (88 mg) to the mixed solution obtained by the reaction, react for 1 hour, stop the reaction, and naturally cool to room temperature to obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to reduce pressure and distill, the solvent is decompressed and rotated out in the rotary evaporator, rinsed with methanol, and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 1, yield 39%.

[0053] Example 3

[0054] The specific steps are:

[0055] Under Ar protection, toluene (40 mL) was first added to the round-bottom flask, followed by 15 times the molar equivalent of benzophenone oxime (205 mg) and 8 times the molar equivalent of TBAOH methanol solution (555 μL) were added to the reaction round-bottom flask, and the solid was completely dissolved by ultrasonication, and then a trace amount of CO2 was introduced, and the mixture was heated in an oil bath at 60°C. After reacting for 1 hour, fullerene C was added to the round-bottom flask. 60 (50 mg), and then react for 0.5 hours; then add 3 times the molar equivalent of I2 (53 mg) to the mixed solution obtained by the reaction, react for 0.5 hours, stop the reaction, and naturally cool to room temperature to obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to reduce pressure and distill, the solvent is decompressed and rotated out in the rotary evaporator, rinsed with methanol, and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 1, yield 37%.

[0056] Example 4

[0057] The specific steps are:

[0058] Under N2 protection, o-dichlorobenzene (30 mL) was first added to the round-bottom flask, followed by 10 times the molar equivalent of benzophenone oxime (137 mg) and 3 times the molar equivalent of TBAOH methanol solution (208 μL) were added to the reaction round-bottom flask, and the solid was completely dissolved by ultrasonication, and then a trace amount of CO2 was introduced, and the mixture was heated in an 80°C oil bath. After reacting for 0.5 hours, fullerene C was added to the round-bottom flask. 60 (50 mg), and then react for 1 hour; then add 5 times the molar equivalent of I2 (88 mg) to the mixed solution obtained by the reaction, react for 0.5 hour, stop the reaction, and naturally cool to room temperature to obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to distill under reduced pressure, the solvent is decompressed in the rotary evaporator, and it is washed with methanol and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 1, yield 38%.

[0059] Example 5

[0060] The specific steps are:

[0061] Under Ar protection and room temperature (25°C), toluene (40 mL) was first added to the round-bottom flask, followed by 15 times the molar equivalent of benzophenone imine (175 μL) and 4 times the molar equivalent of TBAOH methanol solution (278 μL). After reacting for 1 hour, fullerene C was added to the round-bottom flask. 60 (50 mg), and then react for 1 hour; then add 3 times the molar equivalent of I2 (53 mg) to the mixed solution obtained by the reaction, react for 0.5 hour, stop the reaction, and obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to reduce pressure and distill, the solvent is decompressed and spun out in the rotary evaporator, rinsed with methanol, and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and a Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 2, yield 42%.

[0062] Example 6

[0063] The specific steps are:

[0064] Under N2 protection, o-dichlorobenzene (30 mL) was first added to the round-bottom flask, followed by 10 times the molar equivalent of benzophenone imine (116 μL) and 2 times the molar equivalent of TBAOH methanol solution (139 μL). The mixture was heated to 50°C and reacted for 1 hour. Fullerene C was then added to the round-bottom flask. 60(50 mg), and then react for 1 hour; then add 5 times the molar equivalent of I2 (88 mg) to the mixed solution obtained by the reaction, react for 1 hour, stop the reaction, and naturally cool to room temperature to obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to reduce pressure and distill, the solvent is decompressed and rotated out in the rotary evaporator, rinsed with methanol, and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 2, yield 37%.

[0065] Example 7

[0066] The specific steps are:

[0067] Under Ar protection and room temperature (25°C), toluene (40 mL) was first added to the round-bottom flask, followed by 20 times the molar equivalent of benzophenone oxime (274 mg) and 10 times the molar equivalent of TBAOH methanol solution (694 μL) were added to the reaction round-bottom flask, and the solid was completely dissolved by ultrasonication, and then a trace amount of CO2 was introduced. After reacting for 1 hour, fullerene C was added to the round-bottom flask. 60 (50 mg), and then react for 1 hour; then add 5 times the molar equivalent of I2 (88 mg) to the mixed solution obtained by the reaction, react for 0.5 hour, stop the reaction, and obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to distill under reduced pressure, the solvent is decompressed in the rotary evaporator, and it is washed with methanol and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and a Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 2, yield 39%.

[0068] Example 8

[0069] The specific steps are:

[0070] Under the protection of N2, toluene (40 mL) was first added to the round-bottom flask, and the oxygen in the solvent was removed by stirring. Then, 10 times the molar equivalent of benzophenone oxime (137 mg) and 4 times the molar equivalent of TBAOH methanol solution (278 μL) were added to the reaction round-bottom flask. The solid was completely dissolved by ultrasonication, and a trace amount of CO2 was introduced. The mixed solution was heated to 40°C. After reacting for 1 hour, fullerene C was added to the round-bottom flask. 60(50 mg), and then react for 1 hour; then add 2 times the molar equivalent of I2 (35 mg) to the mixed solution obtained by the reaction, react for 0.5 hour, stop the reaction, and naturally cool to room temperature to obtain the final reaction solution; take the reaction solution obtained in the previous step, use a vacuum rotary evaporator to reduce pressure and distill, the solvent is decompressed and rotated out in the rotary evaporator, rinsed with methanol, and filtered to obtain a crude reaction product; then use high performance liquid chromatography (HPLC) with toluene as the mobile phase and Buckyprep separation column to separate and purify the crude product to obtain the target fullerene C 60 Pyrroline derivative 2, yield 38%.

[0071] Fullerene C 60 The NMR and UV-visible absorption spectrum test data of pyrroline derivative 1 are as follows: 1 H NMR (600MHz, CS2 / CDCl3) δ8.03(d,J=7.8Hz,2H),7.80(d,J=7.4Hz,2H),7.58(t,J=7.5Hz,1H),7.45(dt,J=20.3,7.6Hz,4H),7.35(t,J=7.3Hz,1H). like Figure 3 . 13 C NMR(150MHz,CS2 / CDCl3)(all 2C unless indicated)δ172.60(1C,C=N),166.06(1C,C=N),154.13,150.25,147.09(1C),146.93(1C),146.59,146.26,146.21,145.82(3 C),145.78,145.52,145.42,145.29,145.22,145.08,144.77,144.19(3C),143.02,142.67,142.64,142.44,142.21(1C),142. 14,142.06,141.93,141.72,141.59,141.09(1C),140.42,138.95,136.11,134.67(1C,Ph),132.41(1C,Ph),130.05(4C,Ph),1 29.38(Ph),128.98(Ph),128.37(4C,Ph),128.28(Ph),127.93(4C,Ph),127.62(4C,Ph),94.07(1C),83.00(1C),82.54(1C,CN). like Figure 4 . UV-vis (Toluene): λ max / nm:432,466,699. Figure 7 .

[0072] Fullerene C 60 The NMR and UV-visible absorption spectrum test data of pyrroline derivative 2 are as follows: 1 H NMR (600MHz, CS2 / CDCl3) δ8.92 (s, 1H), 8.05 (d, J = 7.9Hz, 4H), 7.45 (t, J = 7.8Hz, 4H), 7.34 (t, J = 7.4Hz, 2H). like Figure 5 . 13 C NMR(150MHz,CS2 / CDCl3)(all 2C unless indicated)δ159.23(1C,C=N),153.47,148.82,146.90(1C),146.73(1C),146.15,145.86,145.69,1 45.67(4C),145.64,145.25(4C),145.18,145.11,144.90,144.69,144.05,143.95,142.89,142.54,1 42.47,142.20,141.90,141.86,141.80,141.73,141.51,141.48,140.49,138.94,136.77(1C,Ph),1 34.46(1C,Ph),129.42(4C,Ph),128.08(4C,Ph),127.82(Ph),96.99(1C),84.84(1C),81.24(1C,CN). like Figure 6 . UV-vis (Toluene): λ max / nm:432,464,702. Figure 8 .

[0073] All the above-mentioned embodiments are only preferred embodiments of the present invention, and are not exhaustive of the feasible implementations of the present invention. The requirements stated in the claims of this patent are within the scope of protection, and only minor non-creative changes are made to the experimental steps and processes involved in this patent, which are considered to be within the scope of protection of this patent.

Claims

1. A fullerene C 60 A pyrroline derivative, characterized in that The fullerene C 60 The structural formula of the pyrroline derivative is shown in Formula I, wherein R is selected from H and one of the groups shown in Formula II.

2. A fullerene C according to claim 1 60 A method for preparing a pyrroline derivative, characterized in that: The method comprises the following preparation steps: Step 1: Add fullerene C to the round-bottom flask under inert gas protection. 60 , an organic solvent, benzophenone imine or benzophenone oxime and TBAOH methanol solution, stirring and reacting at a certain temperature for 1 to 2 hours; Step 2: Add I2 to the mixed solution obtained in step 1, react for 0.5 to 1 hour, stop the reaction, and naturally cool to room temperature to obtain a reaction solution; Step 3: Take the reaction solution of step 2, use a vacuum rotary evaporator to remove the solvent under reduced pressure, wash with methanol to obtain a crude product, and vacuum dry for 6 to 12 hours; Step 4: Separate and purify the crude product obtained in step 3 by high performance liquid chromatography to obtain the target fullerene C 60 Pyrroline derivatives.

3. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: The fullerene C 60 , tetrabutylammonium hydroxide (TBAOH), benzophenone imine or benzophenone oxime and I2 in a molar ratio of 1:2-10:10-20:2-5.

4. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: When the benzophenone oxime is used as a raw material to prepare the derivative, a small amount of CO2 needs to be introduced.

5. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: The inert gas is Ar or N2.

6. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: The organic solvent is o-dichlorobenzene or toluene.

7. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: The concentration of the TBAOH methanol solution is 1.0 mol / L.

8. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: The reaction temperature is 25-80°C.

9. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: The fullerene C 60 The concentration in organic solvents is 1.0-2.5 mg / mL.

10. The fullerene C according to claim 2 60 A method for preparing a pyrroline derivative, characterized in that: Also includes: The high performance liquid chromatography method uses a pyrenepropyl bonded silica gel chromatography column (Buckyprep) as a separation column and toluene as a mobile phase to analyze the fullerene C 60 Separation and purification of pyrroline derivatives.

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