Dynamic polyene amine compound as well as preparation method and application thereof

Abstract

The invention discloses a dynamic polyene amine compound as well as a preparation method and application thereof. The structural formula of the dynamic polyene amine compound is as shown in formula (I). The dynamic polyenamine compound is obtained by carrying out polymerization reaction on a binary amide activated alkynyl compound and a diamine compound in an organic solvent. The preparation method has the advantages of mild reaction conditions, no need of catalyst, simple and easily available raw materials, high atom utilization rate, high polymer yield, high molecular weight and excellent stereoselectivity. The dynamic polyene amine compound prepared by the invention has the properties of good processability, film-forming property, high thermal stability, non-traditional luminescence and the like, and the dynamic enamine bond contained in the dynamic polyene amine compound prepared by the invention can realize accurate degradation and structural replacement of a polymer under mild conditions.

Description

Technical Field

[0001] The invention belongs to the technical field of polymer chemistry and materials science, and specifically relates to a dynamic polyenamine compound and a preparation method and application thereof. Background Art

[0002] Dynamic bonds (including dynamic covalent bonds and supramolecular interactions) are a type of chemical bonds that can be reversibly broken and reorganized under certain conditions. Therefore, polymers carrying dynamic bonds exhibit unique stimulus-responsive properties that traditional polymers do not have. The introduction of dynamic covalent bonds endows polymers with good dynamic properties, such as stimulus responsiveness, processability, degradability, and self-healing properties.

[0003] Alkynes are one of the readily available or easily synthesized chemical raw materials. Using alkynes to construct functional polymers has important academic and technical significance and has attracted widespread attention from scientists. Click polymerization has the characteristics of high efficiency, high selectivity, atom economy, simple product separation, and mild reaction conditions. A series of click polymerizations based on activated alkynes have been developed. This type of click polymerization reaction has the advantages of mild conditions, fast reaction rate, high yield, and atom economy. It meets the definition of click chemistry and is a new type of click reaction. It has become a powerful tool for preparing functional polymers. In recent years, Tang Benzhong's research group and others have developed a series of highly efficient spontaneous click polymerization reactions of activated alkynes and amine monomers. For example, 100% all-E-configuration polyester enamines were prepared with high yield and high molecular weight by using the spontaneous polymerization reaction of ester alkynes and amine monomers at room temperature (J.Am.Chem.Soc., 2017, 139, 5437-5443.;Macromolecules 2019, 52, 4526-4533.;Macromolecules 2020, 53, 2516-2525.;). Since the reactivity of amide-activated alkyne monomers is weak and side reactions such as alkyne self-polymerization easily occur under alkaline conditions, there are currently few studies on click polymerization reactions involving amide-activated alkynes. Therefore, it is of great significance to prepare dynamic polyenamine compounds by non-catalyzed click polymerization of alkynes and amines under mild conditions. Summary of the invention

[0004] In view of the shortcomings of the prior art, the object of the present invention is to provide a method for preparing a dynamic polyenamine compound, which is based on the click reaction of alkyne-amine and has simple reaction, high efficiency and easy operation.

[0005] Another object of the present invention is to provide a polyenamine compound obtained by the above method, wherein the polyenamine compound has good processing performance, excellent degradability and non-traditional luminescent properties.

[0006] The purpose of the present invention is achieved through the following technical solutions:

[0007] A dynamic polyeneamine compound, the structural formula is as follows:

[0008]

[0009] Wherein, n is an integer from 2 to 200, R 1 , R 2 Each is independently an organic group, R 3 Each is independently a hydrogen atom or an organic group.

[0010] Preferably, R 1 , R 2 Each is independently selected from any one of the following chemical structural formulas 1 to 31; R 3 Each is independently selected from a hydrogen atom or any one of the following chemical formulas 32 to 35;

[0011]

[0012]

[0013] wherein m, h, and k are each independently an integer of 1 to 100; X is each independently selected from -NH-, -PH-, -O-, -S-, or -SiH2-; and * represents a substitution position.

[0014] The preparation method of the above-mentioned dynamic polyenamine compound comprises the following steps:

[0015] The diamide activated alkynyl compound and the diamine compound are polymerized in an organic solvent to obtain a dynamic polyenamine compound;

[0016] The structural formula of the diamide activated alkynyl compound is shown in formula (II):

[0017]

[0018] The structural formula of the diamine compound is shown in formula (III);

[0019]

[0020] R 1 , R 2 Each is independently an organic group, R 3 Each is independently a hydrogen atom or an organic group.

[0021] The preparation method can be carried out in a variety of organic solvents. Preferably, the organic solvent is one or more of tetrahydrofuran, dichloromethane, chloroform, toluene, methanol, acetonitrile, 1,4-dioxane, dimethyl sulfoxide and N,N-dimethylformamide. As a further preference, the organic solvent is acetonitrile or dimethyl sulfoxide. In this case, the obtained polyenamine compound has good solubility, high yield and molecular weight, and is convenient for the next step of application.

[0022] Preferably, the polymerization reaction temperature is 20-100°C; more preferably, the polymerization reaction temperature is 50-70°C, more preferably 60°C.

[0023] Preferably, the polymerization reaction is carried out in the absence of a catalyst;

[0024] Preferably, the polymerization reaction is carried out under atmospheric atmosphere.

[0025] Preferably, the polymerization reaction time is 0.25 to 36 hours, more preferably 6 to 24 hours.

[0026] Preferably, the molar ratio of the diamide activated alkynyl compound to the diamine compound is 1:(0.7-1.3), and the concentration of the diamide activated alkynyl compound in the organic solvent is 0.1-5 mol / L. As further preferred, the molar ratio of the diamide activated alkynyl compound to the diamine compound is 1:1, and the concentration of the diamide activated alkynyl compound in the organic solvent is 0.7-1.2 mol / L.

[0027] Preferably, after the polymerization reaction is completed, the product is dissolved in an organic solvent, then added to ether or acetone for precipitation, the precipitate is collected, and dried to constant weight to obtain a dynamic polyenamine compound;

[0028] Further preferably, after the polymerization reaction is completed, the reaction solution is dissolved in methanol for dilution, and then added into acetone as a precipitant for precipitation, and the precipitate is collected and dried to constant weight to obtain a dynamic polyenamine compound.

[0029] The above-mentioned dynamic polyenamine compounds are used in polymer degradation or structural replacement. The polymer is degraded or the structure is replaced dynamically through the enamine bond.

[0030] The above-mentioned dynamic polyenamine compounds are used in the preparation of biological imaging agents or degradable materials.

[0031] The above-mentioned dynamic polyamine compounds are used in self-assembly or preparation of nanoparticles, such as self-assembly loaded fluorescent materials or pharmaceutically active materials.

[0032] The polyenamine compound prepared by the present invention has good thermal stability and excellent processability. The polyenamine compound obtained by the present invention contains enamine dynamic bonds and can be degraded. This property also provides certain possibilities for the compound to be used as a drug carrier in the biological field, and it is also very promising in the development of environmentally friendly chemistry such as degradable materials. The main chain of the dynamic polyenamine compound obtained by the present invention has more heteroatoms such as oxygen and nitrogen, resulting in the polymer having non-traditional luminescence phenomenon. This property is also very promising in the fields of ion detection, biological imaging, etc.

[0033] Compared with the prior art, the present invention has the following advantages:

[0034] 1. The preparation method of the present invention realizes the preparation of dynamic polyenamine by non-catalyzed polymerization of amide-activated acetylene monomers and diamine monomers under relatively mild conditions. As far as we know, this polymerization reaction has not been reported before, and provides a new path for the preparation of dynamic polyenamine. Therefore, it is innovative and extremely important.

[0035] 2. The raw materials for the preparation method of the present invention are easily available and can be purchased directly or prepared through simple reactions; the polymerization conditions are mild, the process is simple, the polymerization efficiency is high, and a polymer with a high molecular weight can be obtained with a high yield in a short reaction time.

[0036] 3. The preparation method of the present invention has excellent regioselectivity and stereoselectivity, and no by-products are generated during the polymerization process, which complies with atom economy.

[0037] 4. The preparation method of the present invention does not require any catalyst and can be carried out under appropriate heating conditions, thereby avoiding the cytotoxicity caused by catalyst residues and the impact on the photoelectric properties of the material.

[0038] 5. The dynamic polyenamine compound prepared by the present invention has good thermal stability and non-traditional luminescent properties.

[0039] 6. The dynamic polyenamine compound prepared by the present invention has good imaging function for cells.

[0040] 7. The dynamic polyeneamine compound prepared by the present invention can react with amine monomers under acidic conditions to undergo precise polymer degradation and structural replacement.

[0041] 8. The dynamic polyenamine compound prepared by the present invention can self-assemble into wheat grain-shaped nanoparticles in a poor solvent. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 This is a comparison chart of the nuclear magnetic resonance hydrogen spectra of the dynamic polyenamine compound prepared in Example 1 of the present invention and its corresponding monomer in deuterated DMSO.

[0043] Figure 2 This is a comparison chart of the carbon NMR spectra of the dynamic polyenamine compound prepared in Example 1 of the present invention and its corresponding monomer in deuterated DMSO.

[0044] Figure 3 This is a thermogravimetric curve of the dynamic polyenamine compound prepared in Example 1 of the present invention.

[0045] Figure 4 The dynamic polyenamine compound prepared in Example 1 of the present invention is (1*10 - 2 mol / L) fluorescence emission spectrum.

[0046] Figure 5 The cytotoxicity test of Example 1 of the present invention in normal human cells L929 and mouse cancer cells 4T1 respectively.

[0047] Figure 6 This is a cell imaging diagram of Example 1 of the present invention in HELA cells.

[0048] Figure 7 1 is the GPC curve of Example 1 of the present invention before and after dynamic degradation in the presence of diethylamine and KHSO4.

[0049] Figure 8 This is the SEM image of the self-assembly of polymer P1. DETAILED DESCRIPTION

[0050] The present invention is further described in detail below in conjunction with specific embodiments and drawings, but the implementation and protection of the present invention are not limited thereto. For process parameters not particularly noted, conventional techniques may be used.

[0051] Example 1

[0052] A dynamic polyeneamine compound, the structural formula of which is shown in P1:

[0053]

[0054] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as follows:

[0055]

[0056] Among them, the synthesis method of monomer M1 can be synthesized according to the synthesis method of the applicant in the published document (Nat. Commun. 11, 3250 (2020).); M2 is N N'-diethylethylenediamine, which can be purchased on the market, and in this example it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased on the market, and in this example it is purchased from Anage Reagent Company.

[0057] The preparation steps of the dynamic polyenamine compound are as follows:

[0058] 89 mg (0.5 mmol) of monomer M1 was added to a 10 ml polymerization tube, and 0.5 mL of acetonitrile was injected with a syringe. After the monomer was completely dissolved, 58 mg (0.5 mmol) of monomer M2 was added with a micro-injector, and the reaction was carried out at 60°C for 24 hours. After the reaction was completed, 2 ml of methanol was added to dissolve, and the obtained polymer solution was added dropwise to acetone stirred at 500 rpm, and then allowed to stand, filtered, and dried to obtain a dynamic polyenamine compound P1.

[0059] According to the determination and analysis, the yield of the final product, the dynamic polyenamine compound P1, is 91%, the weight average molecular weight is 13100, and the molecular weight distribution is 1.24.

[0060] The NMR spectra of the dynamic polyenamine compound and its corresponding monomer are shown in Figure 1 , Figure 2 From the figure, it can be determined that the polymer is a dynamic polyenamine compound. The chemical shifts of 7.35ppm and 4.56ppm correspond to the characteristic peaks of trans hydrogen atoms on the vinyl group of the dynamic polyenamine compound, and no characteristic peaks of cis hydrogen atoms on the vinyl group are found, indicating that the polymerization method has excellent spatial selectivity.

[0061] Figure 3 is the thermogravimetric curve of P1. Figure 3 From the thermogravimetric curve, it can be seen that the temperature corresponding to 5% weight loss of polymer P1 is 247°C, indicating that the main chain of polymer P1 has good thermal stability.

[0062] from Figure 4 From the fluorescence emission spectrum (excitation wavelength is 400nm), it can be seen that the fluorescence emission peak of polymer P1 is 482nm.

[0063] The polymer P1 is easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, and N,N-dimethylformamide at room temperature, indicating excellent processability.

[0064] Figure 5 Cytotoxicity test of polymer P1. The survival rates of normal human cells L929 and mouse cancer cells 4T1 in polymer P1 are both over 80%, indicating that polymer P1 has low cytotoxicity.

[0065] Figure 6 This is a laser confocal microscopy photo of HELA cells after the polymer was stained. The polymer can be well engulfed by HELA cells and stain the cells.

[0066] Figure 7 Figure 2 is the GPC curve of polymer P1 before and after degradation. After adding diethylamine and KHSO4, the molecular weight of polymer P1 decreased due to the dynamic replacement of enamine bonds, indicating that the precise degradation of the polymer was successfully achieved.

[0067] Figure 8 This is a SEM image of the self-assembly of polymer P1. Through the rapid sedimentation method, it was found that polymer P1 self-assembled into wheat grain-shaped nanoparticles, indicating that the amide and enamine structures contained in the polymer can form a large number of hydrogen bonds, making the polymer have self-assembly behavior.

[0068] Example 2

[0069] A dynamic polyeneamine compound, the structural formula of which is shown in P2:

[0070]

[0071] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as follows:

[0072]

[0073] The synthesis method of monomer M1 is the same as that of Example 1; monomer M3 is N N'-dimethylethylenediamine, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company.

[0074] The preparation steps of the dynamic polyenamine compound are as follows:

[0075] 89 mg (0.5 mmol) of monomer M1 was added to a 10 ml polymerization tube, and 0.5 mL of acetonitrile was injected with a syringe. After the monomer was completely dissolved, 44 mg (0.5 mmol) of monomer M3 was added with a microinjector, and the reaction was carried out at 60°C for 24 hours. After the reaction was completed, 2 ml of methanol was added to dissolve, and the obtained polymer solution was added dropwise to acetone stirred at 500 rpm, and then allowed to stand, filtered, and dried to obtain a dynamic polyenamine compound P2.

[0076] After analysis, the yield of the final product, dynamic polyenamine compound P2, was 82%, the weight average molecular weight was 9300, and the molecular weight distribution was 1.18. The polymer P2 was easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0077] Example 3

[0078] A dynamic polyeneamine compound, the structural formula of which is shown in P3:

[0079]

[0080] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as shown in Formula (III):

[0081]

[0082] Among them, the synthesis method of monomer M1 is the same as that of Example 1; monomer M4 is N,N'-diethyl-1,6-diaminohexane, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company.

[0083] The preparation steps of the dynamic polyenamine compound are as follows:

[0084] 89 mg (0.5 mmol) of monomer M1 was added to a 10 ml polymerization tube, and 0.5 mL of acetonitrile was injected with a syringe. After the monomer was completely dissolved, 72.1 mg (0.5 mmol) of monomer M4 was added with a microinjector, and the reaction was carried out at 60°C for 24 hours. After the reaction was completed, 2 ml of methanol was added to dissolve, and the obtained polymer solution was added dropwise to acetone stirred at 500 rpm, and then allowed to stand, filtered, and dried to obtain a dynamic polyenamine compound P3.

[0085] After analysis, the yield of the final product, dynamic polyenamine compound P3, was 87%, the weight average molecular weight was 11300, and the molecular weight distribution was 1.33. The polymer P3 was easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0086] Example 4

[0087] A dynamic polyeneamine compound, the structural formula of which is shown in P4:

[0088]

[0089] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as shown in Formula (IV):

[0090]

[0091] Among them, the synthesis method of monomer M1 is the same as that of Example 1; monomer M5 is N,N'-dibenzyl-1,3-propylenediamine, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company.

[0092] The preparation steps of the dynamic polyenamine compound are as follows:

[0093] 89 mg (0.5 mmol) of monomer M1 was added to a 10 ml polymerization tube, and 0.5 mL of acetonitrile was injected with a syringe. After the monomer was completely dissolved, 127.2 mg (0.5 mmol) of monomer M4 was added with a microinjector, and the reaction was carried out at 60°C for 24 hours. After the reaction was completed, 2 ml of methanol was added to dissolve, and the obtained polymer solution was added dropwise to acetone stirred at 500 rpm, and then allowed to stand, filtered, and dried to obtain a dynamic polyenamine compound P4.

[0094] After analysis, the yield of the final product, dynamic polyenamine compound P4, was 78%, the weight average molecular weight was 10100, and the molecular weight distribution was 1.18. The polymer P4 was easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0095] Example 5

[0096] A dynamic polyeneamine compound, the structural formula of which is shown in P5:

[0097]

[0098] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as shown in Formula (V):

[0099]

[0100] Among them, the synthesis method of monomer M1 is the same as that of Example 1; monomer M6 is 1,3-di(4-piperidinyl)propane, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company.

[0101] The preparation steps of the dynamic polyenamine compound are as follows:

[0102] 89 mg (0.5 mmol) of monomer M1 and 105.2 mg (0.5 mmol) of monomer M6 were added to a 10 ml polymerization tube, and 0.5 ml of acetonitrile was injected with a syringe, and the mixture was reacted at 60°C for 24 hours. After the reaction, 2 ml of methanol was added to dissolve the mixture, and the obtained polymer solution was added dropwise to acetone stirred at 500 rpm, and then allowed to stand, filtered, and dried to obtain a dynamic polyenamine compound P5.

[0103] After analysis, the yield of the final product, dynamic polyenamine compound P5, was 93%, the weight average molecular weight was 14100, and the molecular weight distribution was 1.28. The polymer P5 was easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0104] Example 6

[0105] A dynamic polyeneamine compound, the structural formula of which is shown in P6:

[0106]

[0107] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as shown in Formula (VI):

[0108]

[0109] The synthesis method of monomer M7 is the same as that of Example 1; monomer M2 is N N'-diethylethylenediamine, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company.

[0110] The preparation steps of the dynamic polyenamine compound are as follows:

[0111] Add 95 mg (0.5 mmol) of monomer M7 to a 10 ml polymerization tube, inject 0.5 mL of acetonitrile with a syringe, and after the monomer is completely dissolved, add 58 mg (0.5 mmol) of monomer M2 with a microinjector, and react at 60°C for 24 hours. After the reaction is completed, add 2 ml of methanol to dissolve, and drop the obtained polymer solution into acetone stirred at 500 rpm, then let it stand, filter, and dry to obtain a dynamic polyenamine compound P6.

[0112] After analysis, the yield of the final product, dynamic polyenamine compound P6, was 96%, the weight average molecular weight was 14500, and the molecular weight distribution was 1.27. The polymer P6 was easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0113] Example 7

[0114] A dynamic polyeneamine compound, the structural formula of which is shown in P7:

[0115]

[0116] The dynamic polyenamine compound is prepared by amide-activated alkyne monomers and amine monomers through alkyne-amine click polymerization, and the reaction equation is as shown in Formula (VII):

[0117]

[0118] The synthesis method of monomer M8 is the same as that of Example 1; monomer M2 is N N'-diethylethylenediamine, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company; the solvent is ultra-dry acetonitrile, which can be purchased from the market, and in this example, it is purchased from Anage Reagent Company.

[0119] The preparation steps of the dynamic polyenamine compound are as follows:

[0120] 103 mg (0.5 mmol) of monomer M8 was added to a 10 ml polymerization tube, and 0.5 mL of acetonitrile was injected with a syringe. After the monomer was completely dissolved, 58 mg (0.5 mmol) of monomer M2 was added with a microinjector, and the reaction was carried out at 60°C for 24 hours. After the reaction was completed, 2 ml of methanol was added to dissolve, and the obtained polymer solution was added dropwise to acetone stirred at 500 rpm, and then allowed to stand, filtered, and dried to obtain a dynamic polyenamine compound P6.

[0121] After analysis, the yield of the final product polyenamine compound P7 is 93%, the weight average molecular weight is 12500, and the molecular weight distribution is 1.18. The polymer P7 is easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0122] Example 8

[0123] This embodiment provides a method for preparing polymer P1, which is different from embodiment 1 in that the solvent used is methanol, the amount of monomer M1 added is 133 mg (0.75 mmol), the amount of monomer M2 added is 87 mg (0.75 mmol), and the reaction time is 3 h. Other conditions are the same as embodiment 1.

[0124] According to the analysis, the yield of the dynamic polyenamine compound P1 is 83%, the weight average molecular weight is 12500, and the molecular weight distribution is 1.25. The polymer P1 is easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0125] Example 9

[0126] This example provides a method for preparing a polymer P1, which is different from Example 1 in that the solvent used is DMSO and the reaction temperature is 80° C. Other conditions are the same as in Example 1.

[0127] According to the analysis, the yield of the dynamic polyenamine compound P1 is 85%, the weight average molecular weight is 10500, and the molecular weight distribution is 1.25. The polymer P1 is easily soluble in common organic solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide, etc. at room temperature, indicating excellent processability.

[0128] The above embodiments are only preferred implementation modes of the present invention and are only used to explain the present invention rather than to limit the present invention. Any changes, substitutions, modifications, etc. made by those skilled in the art without departing from the spirit of the present invention should fall within the scope of protection of the present invention.

Claims

1. A dynamic polyeneamine compound, characterized in that: The structural formula is as follows: Wherein, n is an integer from 2 to 200, R 1 , R 2 Each is independently an organic group, R 3 Each is independently a hydrogen atom or an organic group.

2. The dynamic polyenamine compound according to claim 1, characterized in that: R 1 , R 2 Each is independently selected from any one of the following chemical structural formulas 1 to 31; R 3 Each is independently selected from a hydrogen atom or any one of the following chemical formulas 32 to 35; wherein m, h, and k are each independently an integer of 1 to 100; X is each independently selected from -NH-, -PH-, -O-, -S-, or -SiH2-; and * represents a substitution position.

3. The method for preparing the dynamic polyenamine compound according to any one of claims 1 to 2, characterized in that: The following steps are involved: The diamide activated alkynyl compound and the diamine compound are polymerized in an organic solvent to obtain a dynamic polyenamine compound; The structural formula of the diamide activated alkynyl compound is shown in formula (II): The structural formula of the diamine compound is shown in formula (III); R 1 , R 2 Each is independently an organic group, R 3 Each is independently a hydrogen atom or an organic group.

4. The method for preparing the dynamic polyenamine compound according to claim 3, characterized in that: The organic solvent is one or more of tetrahydrofuran, dichloromethane, chloroform, toluene, methanol, acetonitrile, 1,4-dioxane, dimethyl sulfoxide and N,N-dimethylformamide.

5. The method for preparing the dynamic polyenamine compound according to claim 3, characterized in that: The polymerization reaction temperature is 20-100° C.; the polymerization reaction is carried out without a catalyst; and the polymerization reaction is carried out in an atmospheric atmosphere.

6. The method for preparing the dynamic polyenamine compound according to claim 3, characterized in that: The polymerization reaction time is 0.25 to 36 hours.

7. The method for preparing the dynamic polyenamine compound according to claim 3, characterized in that: The molar ratio of the diamide activated alkynyl compound to the diamine compound is 1:(0.7-1.3), and the concentration of the diamide activated alkynyl compound in the organic solvent is 0.1-5 mol / L.

8. Use of the dynamic polyenamine compound according to any one of claims 1 to 2 in polymer degradation or structural replacement.

9. Use of the dynamic polyenamine compound according to any one of claims 1 to 2 in the preparation of biological imaging agents or degradable materials.

10. Use of the dynamic polyenamine compound according to any one of claims 1 to 2 in self-assembly or preparation of nanoparticles.

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