Polypropylamine compound as well as preparation method and application thereof
The preparation of polypropynylamine compounds via KA² coupling reaction solves the problem of converting small-molecule propynylamine into the polymer backbone, achieving efficient synthesis and high refractive properties of the polymer, and has broad application potential.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SOUTH CHINA UNIV OF TECH
- Filing Date
- 2026-04-02
- Publication Date
- 2026-05-15
AI Technical Summary
Existing technologies struggle to extend the conversion potential of small-molecule propargylamine to the polymer backbone, and the polymerization reaction suffers from low reaction efficiency and unpurifiable byproducts.
Aromatic diyne compounds, aliphatic diketone compounds, and cyclic secondary amine compounds were polymerized in the presence of cuprous bromide catalyst using the KA² coupling reaction, and then post-processed to obtain polypropyne amine compounds.
The novel polymer structure and efficient main chain reconstruction were achieved. The polymerization conditions were mild, the process was simple, the polymerization efficiency was high, the group tolerance was strong, and the polymer had high molecular weight and high refractive properties.
Smart Images
Figure CN122037110A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the fields of polymer chemistry and materials science, and in particular to a polypropynylamine compound, its preparation method, and its application. Background Technology
[0002] Polypropyne, as a uniquely structured polymer platform, possesses a high refractive index and unique luminescent properties due to the synergistic effect of aromatic rings, carbon-carbon triple bonds, and heteroatoms in its main chain. More importantly, it offers exceptional modifiability and functional tunability derived from the alkynyl and amine groups. Currently, small-molecule propyne chemistry has demonstrated rich transformation potential, such as carboxylation and cyclization, asymmetric functionalization, and the construction of nitrogen-containing heterocycles. However, extending this potential to polymer main chain reconstruction faces significant challenges; to date, only A-based... 3 The only reported case of coupling-synthesized polypropyne containing -NH- bonds being converted into polythiazolidinyl imines is that the remodeling type is limited by the precursor structure. More importantly, the polymer system places higher demands on the reaction, requiring extremely high specificity to avoid unpurifiable byproducts and to overcome the reaction efficiency problems that may exist with large molecular chains.
[0003] The KA² coupling reaction is a direct dehydration condensation reaction of a ketone, alkyne, and amine in the presence of a catalyst to generate a secondary propargylamine. This reaction was first reported in 2010, but its application has primarily focused on small molecule synthesis. This is because the reactivity of ketones is much lower than that of acetylene. 3 The aldehydes used in coupling reactions, therefore, the three-component coupling reactions of ketones are still largely underdeveloped, and their polymerization reactions have not yet been reported. Developing a KA-based... 2 The polymerization method of coupling reaction, which can synthesize a class of polypropyne that can meet other reconstruction conditions, has important scientific significance and application value. Summary of the Invention
[0004] The purpose of this invention is to provide a polypropynylamine compound, its preparation method, and its application, in order to solve the above-mentioned technical problems.
[0005] To achieve the above-mentioned objectives, the present invention provides the following technical solution: This invention provides a polypropynylamine compound having the following general structural formula: ; Where n is an integer between 2 and 400, R 1 For substituted aromatic groups, R 2 R 3 R 4 It is an independent alkyl group.
[0006] Furthermore, the polypropynylamine compound is selected from one of the following structural formulas: , , , , , , , , .
[0007] This invention also provides a method for preparing polypropynylamine compounds, comprising the following steps: Aromatic diyne compounds, aliphatic diketone compounds, and cyclic secondary amine compounds were polymerized in toluene in the presence of cuprous bromide catalyst. After the reaction was completed, the polypropyne amine compounds were obtained through post-treatment.
[0008] Furthermore, the aromatic diyne compound is selected from any of the following structural formulas: .
[0009] Furthermore, the aliphatic diketone compound is selected from any of the following structural formulas: ; The cyclic diamine compound is selected from any of the following structural formulas: .
[0010] Furthermore, the molar ratio of the aromatic diyne, aliphatic diketone, and cyclic secondary amine compounds is 1:1:2~3; The concentration of the aromatic diyne compound in toluene is 0.25~3.0 mol / L.
[0011] Furthermore, the amount of the cuprous bromide catalyst used is 4-20% of the total mass of the reactants.
[0012] Furthermore, the polymerization reaction is carried out under stirring conditions, with a stirring speed of 200~500 rpm; the polymerization temperature is 60~120℃, and the time is 0.2~9h.
[0013] Furthermore, the post-processing steps are as follows: after the reaction is completed, the reaction solution is cooled, diluted with 1 to 4 times the volume of the reaction solution with toluene, and then the diluted solution is dropped into a settling agent for sedimentation. The precipitate is collected and dried at 40 to 60°C to constant weight. The settling agent is methanol or a mixed solution of methanol and saturated saline solution.
[0014] This invention also provides the application of polypropynylamine compounds in refractive or luminescent materials.
[0015] The beneficial effects of this invention are: (1) The preparation method of the present invention has readily available raw materials that can be directly purchased commercially and are inexpensive; the polymerization conditions are mild, the process is simple, and the polymerization efficiency is high.
[0016] (2) The preparation method of the present invention is the first polymerization reaction, which has not been reported before. The synthesized polymer has a novel structure and can be used for main chain reconstruction to prepare polymers with new structures.
[0017] (3) The preparation method of the present invention has strong group tolerance and can introduce a variety of functional groups into the monomer.
[0018] (4) The polypropyne compounds of the present invention have high molecular weight, good thermal stability and high refractive properties, and are expected to be used as refractive materials or as luminescent materials. Attached Figure Description
[0019] Figure 1 The images show the 1H NMR spectra of the polypropynylamine compound and its corresponding monomer prepared in Example 1 of this invention in deuterated chloroform, where A is the 1H NMR spectrum of 1,4-diethynylbenzene in deuterated chloroform; B is the 1H NMR spectrum of tetrahydropyrrole in deuterated chloroform; C is the 1H NMR spectrum of the model small molecule of propynylamine compound in deuterated chloroform; and D is the 1H NMR spectrum of polypropynylamine in deuterated chloroform.
[0020] Figure 2 The images show the carbon NMR spectra of the polypropynylamine compound and its corresponding monomer prepared in Example 1 of this invention in deuterated chloroform, where A is the carbon NMR spectrum of 1,4-diethynylbenzene in deuterated chloroform; B is the carbon NMR spectrum of 4,4'-dicyclohexanone in deuterated chloroform; C is the carbon NMR spectrum of the model small molecule of propynylamine compound in deuterated chloroform; and D is the carbon NMR spectrum of polypropynylamine in deuterated chloroform.
[0021] Figure 3 The images show the infrared absorption spectra of polypropynylamine and propynylamine-like compound model small molecules prepared in Example 1 of this invention, where A is the infrared absorption spectrum of the propynylamine-like compound model small molecules and B is the infrared absorption spectrum of polypropynylamine prepared in Example 1.
[0022] Figure 4 The thermogravimetric curve of polypropynylamine prepared in Example 1 of this invention is shown.
[0023] Figure 5 The refractive index diagrams are for the polypropyne compounds P1-P2, P4, P6 and P8-P9 prepared in Examples 1-2, 4, 6 and 8-9.
[0024] Figure 6 The images show the UV-Vis absorption and fluorescence emission spectra of toluene solutions of polypropynylamine compounds and propynylamine-type model small molecules prepared in Example 1 of this invention. A represents the UV-Vis absorption spectrum of toluene solutions of polypropynylamine P1 and its model compounds prepared in Example 1; B represents the fluorescence emission spectrum of toluene solutions of polypropynylamine P1 and its model compounds prepared in Example 1, where M refers to the model compound of polypropynylamine prepared in Example 1. Detailed Implementation
[0025] This invention provides a polypropynylamine compound having the following general structural formula: ; Where n is an integer between 2 and 400, R 1 For substituted aromatic groups, R 2 R 3 R 4 It is an independent alkyl group.
[0026] In this invention, n is preferably an integer between 50 and 300.
[0027] In this invention, the polypropynylamine compound is preferably selected from one of the following structural formulas: , , , , , , , , .
[0028] This invention also provides a method for preparing polypropynylamine compounds, comprising the following steps: Aromatic diyne compounds, aliphatic diketone compounds, and cyclic secondary amine compounds were polymerized in toluene in the presence of cuprous bromide catalyst. After the reaction was completed, the polypropyne amine compounds were obtained through post-treatment.
[0029] In this invention, the aromatic diyne compound is selected from any of the following structural formulas: .
[0030] In this invention, the aliphatic diketone compound is selected from any of the following structural formulas: ; The cyclic diamine compound is selected from any of the following structural formulas: .
[0031] In this invention, the molar ratio of the aromatic diyne, aliphatic diketone, and cyclic secondary amine compounds is 1:1:2~3, preferably 1:1:2.2~2.8, and more preferably 1:1:2.4~2.6; The concentration of the aromatic diyne compound in toluene is 0.25~3.0 mol / L, preferably 0.5~2.5 mol / L, and more preferably 1~2 mol / L.
[0032] In this invention, the amount of the cuprous bromide catalyst is 4-20% of the total mass of the reactants, preferably 4-15%, and more preferably 4-10%.
[0033] In this invention, the polymerization reaction is carried out under stirring conditions, with a stirring speed of 200~500 rpm, preferably 300~400 rpm; a polymerization temperature of 60~120℃, preferably 80~110℃; and a time of 0.2~9h, preferably 1~8h, and more preferably 2~6h.
[0034] In this invention, the post-processing steps are as follows: after the reaction is completed, the reaction solution is cooled and diluted with 1 to 4 times the volume of the reaction solution, preferably 1 to 2 times the volume; then the diluted solution is dropped into a settling agent for sedimentation, the precipitate is collected and dried at 40 to 60°C to constant weight, preferably 50 to 55°C; the settling agent is methanol or a mixed solution of methanol and saturated saline solution.
[0035] This invention also provides the application of polypropynylamine compounds in refractive or luminescent materials.
[0036] The technical solutions provided by the present invention will be described in detail below with reference to the embodiments, but they should not be construed as limiting the scope of protection of the present invention.
[0037] Example 1
[0038] A polypropyne compound, the structural formula of which is shown in P1. .
[0039] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (I):
[0040] Of these, monomer M1 is 4-phenylethynyl ether. M2 is 4-4'-dicyclohexanone, purchased from Bitmain. M3 is tetrahydropyrrole, purchased from Aladdin.
[0041] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 109 mg (0.5 mmol) of monomer M1, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 73 mg (1.0 mmol) of monomer M3 was added. 2 mL of toluene was injected into the tube, and the mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P1.
[0042] Analysis showed that the yield of polypropynylamine P1 was 93%, the weight-average molecular weight was 15,100, and the molecular weight distribution was 1.46.
[0043] The 1H NMR spectra of polypropyne compound P1, its corresponding monomer, and model small molecules of propyne compounds are as follows: Figure 1 Carbon NMR spectrum, such as Figure 2 Infrared absorption spectrum such as Figure 3 .
[0044] Proton NMR spectrum (400 MHz, CDCl3) δ (TMS, ppm): 7.39 (s, 4H), 6.91 (s, 4H), 2.78 (d, J = 64.6 Hz, 8H), 2.14 (s, 2H), 1.98 (s, 2H), 1.79 (d, J = 22.5Hz, 8H), 1.67-1.40 (m, 12H), 1.18 (s, 2H).
[0045] Carbon NMR spectrum (100 MHz, CDCl3) δ (TMS, ppm): 151.43, 133.46, 118.79,91.84, 89.50, 86.06, 83.47, 60.11, 57.60, 47.51, 46.90, 41.44, 41.09, 37.99,36.49, 36.22, 30.32, 29.97, 27.43, 27.10, 24.64, 24.48, 24.09, 23.59.
[0046] The thermogravimetric curve of polypropyne compound P1 is as follows: Figure 4 The thermal decomposition temperature with a 5% weight loss is 180℃.
[0047] Figure 6The UV-Vis absorption and fluorescence emission spectra of toluene solutions of the obtained P1 and its model compounds are shown. In toluene solution, the maximum UV absorbance of polypropynylamine compound P1 is at 269 nm, while that of its model compound is at 279 nm. At an excitation wavelength of 300 nm, the emission peak of polypropynylamine compound P1 is at 365 nm, while that of its model compound is at 363 nm.
[0048] Example 2
[0049] A polypropyne-based compound, the structural formula of which is shown on P2:
[0050] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (II):
[0051] Of these, monomer M4 is 1,4-diaethynylbenzene, purchased from Energie. M2 is 4,4'-dicyclohexanone, purchased from Bidet. M3 is tetrahydropyrrole, purchased from Aladdin.
[0052] The preparation steps of the polypropynylamine compound are as follows: In a 10 mL polymerization tube, 63 mg (0.5 mmol) of monomer M4, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 73 mg (1.0 mmol) of monomer M3 was added. 2 mL of toluene was injected into the tube, and the mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P2.
[0053] Analysis showed that the yield of polypropynylamine compound P2 was 92%, the weight-average molecular weight was 8400, and the molecular weight distribution was 1.51.
[0054] Example 3
[0055] A polypropyne compound, the structural formula of which is shown on page 3:
[0056] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (III):
[0057] Of these, monomer M5 is 1,3-diethynylbenzene, purchased from Energie. M2 is 4,4'-dicyclohexanone, purchased from Bidet. M3 is tetrahydropyrrole, purchased from Aladdin.
[0058] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 63 mg (0.5 mmol) of monomer M5, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 73 mg (1.0 mmol) of monomer M3 was added, and 2 mL of toluene was injected into the tube. The mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P3.
[0059] Analysis showed that the yield of polypropynylamine P3 was 90%, the weight-average molecular weight was 8100, and the molecular weight distribution was 1.42.
[0060] Example 4
[0061] A polypropyne compound, the structural formula of which is shown on page 4:
[0062] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (iv):
[0063] Of these, monomer M6 is 4,4'-diethynylbiphenyl, purchased from Energie. M2 is 4,4'-dicyclohexanone, purchased from Bidex. M3 is tetrahydropyrrole, purchased from Aladdin.
[0064] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 101 mg (0.5 mmol) of monomer M6, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 73 mg (1.0 mmol) of monomer M3 was added. 2 mL of toluene was injected into the tube, and the mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P4.
[0065] Analysis showed that the yield of polypropynylamine P4 was 93%, the weight-average molecular weight was 11,200, and the molecular weight distribution was 1.48.
[0066] Example 5
[0067] A polypropyne compound, the structural formula of which is shown on page 5:
[0068] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (V):
[0069] Of these, monomer M6 is 4,4'-diethynylbiphenyl, purchased from Energie. M7 is decane-2,9-dione, purchased from Bitmain. M3 is tetrahydropyrrole, purchased from Aladdin.
[0070] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 101 mg (0.5 mmol) of monomer M6, 85 mg (0.5 mmol) of monomer M7 and 12 mg (0.08 mmol) of cuprous bromide were added sequentially, followed by 73 mg (1.0 mmol) of monomer M3. 2 mL of toluene was injected into the tube, and the mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P5.
[0071] Analysis showed that the yield of polypropynylamine P5 was 98%, the weight-average molecular weight was 8300, and the molecular weight distribution was 1.69.
[0072] Example 6
[0073] A polypropyne compound, the structural formula of which is shown on page 6:
[0074] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, and the reaction equation is shown in equation (VI):
[0075] Of these, monomer M8 is tetraphenylethylene, M2 is 4-4'-dicyclohexanone, purchased from Bitmain. M3 is tetrahydropyrrole, purchased from Aladdin.
[0076] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 190 mg (0.5 mmol) of monomer M6, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 73 mg (1.0 mmol) of monomer M3 was added. 2 mL of toluene was injected into the tube, and the mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P6.
[0077] Analysis showed that the yield of polypropynylamine P6 was 84%, the weight-average molecular weight was 9500, and the molecular weight distribution was 1.41.
[0078] Example 7
[0079] A polypropyne compound, the structural formula of which is shown on page 7:
[0080] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (VII):
[0081] Of these, monomer M9 is 1,6-bis(4-ethynylphenoxy)hexane. M2 is 4-4'-dicyclohexanone, purchased from Bitmain. M3 is tetrahydropyrrole, purchased from Aladdin.
[0082] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 159 mg (0.5 mmol) of monomer M9, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 73 mg (1.0 mmol) of monomer M3 was added. 2 mL of toluene was injected into the tube, and the mixture was heated to 100 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P7.
[0083] Analysis showed that the yield of polypropynylamine P7 was 93%, the weight-average molecular weight was 12,700, and the molecular weight distribution was 1.57.
[0084] Example 8
[0085] A polypropyne compound, the structural formula of which is shown on page 8:
[0086] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (viii):
[0087] Of these, monomer M6 is 4,4'-diethynylbiphenyl, purchased from Energie. M2 is 4,4'-dicyclohexanone, purchased from Bitmain. M10 is piperidine, purchased from Aladdin.
[0088] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 101 mg (0.5 mmol) of monomer M6, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 85 mg (1.0 mmol) of monomer M10 was added. 2 mL of toluene was injected into the tube, and the mixture was heated to 110 °C and stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P8.
[0089] Analysis showed that the yield of polypropynylamine P8 was 79%, the weight-average molecular weight was 10,900, and the molecular weight distribution was 2.10.
[0090] Example 9
[0091] A polypropyne compound, the structural formula of which is shown on page 9:
[0092] The polypropynylamine is prepared by direct reaction of alkyne, ketone and amine, as shown in formula (IX):
[0093] Of these, monomer M8 is tetraphenylethylene. M2 is 4,4'-dicyclohexanone, purchased from Bitmain. M10 is piperidine, purchased from Aladdin.
[0094] The preparation steps of the polypropynylamine are as follows: In a 10 mL polymerization tube, 190 mg (0.5 mmol) of monomer M8, 97 mg (0.5 mmol) of monomer M2, and 12 mg (0.08 mmol) of cuprous bromide were added sequentially. Then, 85 mg (1.0 mmol) of monomer M10 was added. 2 mL of toluene was injected into the tube, and the temperature was raised to 110 °C. The mixture was stirred at 360 rpm for 3 hours while maintaining the temperature. After the reaction was completed, the mother liquor was dissolved in 2 mL of toluene and then added dropwise to methanol. The mixture was allowed to stand, filtered, and dried at 55 °C to constant weight to obtain polypropynylamine P9.
[0095] Analysis showed that the yield of polypropynylamine P9 was 60%, the weight-average molecular weight was 9300, and the molecular weight distribution was 1.60.
[0096] As can be seen from the above embodiments, the present invention provides a method for preparing polypropynylamine compounds. The raw materials for this preparation method are readily available, the polymerization conditions are mild, the process is simple, the polymerization efficiency is high, and the functional groups are highly tolerant, allowing for the introduction of various functional groups into the monomer.
[0097] The refractive indices of polypropyne compounds P1-P2, P4, P6, and P8-P9 prepared in Examples 1-2, 4, 6, and 8-9 are as follows: Figure 5 The polypropyne-based compound has a high refractive index, indicating that this type of polymer has potential applications in the field of optics.
[0098] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.
Claims
1. A polypropynylamine compound, characterized in that, The polypropynylamine compounds have the following general structural formula: ； Where n is an integer between 2 and 400, R 1 For substituted aromatic groups, R 2 R 3 R 4 It is an independent alkyl group.
2. The polypropynylamine compound according to claim 1, characterized in that, The polypropynylamine compound is selected from one of the following structural formulas: 、 、 、 、 、 、 、 、 。 3. The method for preparing the polypropynylamine compound according to claim 1 or 2, characterized in that, Includes the following steps: Aromatic diyne compounds, aliphatic diketone compounds, and cyclic secondary amine compounds were polymerized in toluene in the presence of cuprous bromide catalyst. After the reaction was completed, the polypropyne amine compounds were obtained through post-treatment.
4. The preparation method according to claim 3, characterized in that, The aromatic diyne compounds are selected from any of the following structural formulas: 。 5. The preparation method according to claim 3, characterized in that, The aliphatic diketone compound is selected from any of the following structural formulas: ； The cyclic diamine compound is selected from any of the following structural formulas: 。 6. The preparation method according to any one of claims 3 to 5, characterized in that, The molar ratio of the aromatic diyne, aliphatic diketone, and cyclic secondary amine compounds is 1:1:2~3; The concentration of the aromatic diyne compound in toluene is 0.25~3.0 mol / L.
7. The preparation method according to claim 6, characterized in that, The amount of cuprous bromide catalyst used is 4-20% of the total mass of the reactants.
8. The preparation method according to claim 3 or 7, characterized in that, The polymerization reaction is carried out under stirring conditions, with a stirring speed of 200~500 rpm; the polymerization temperature is 60~120℃, and the time is 0.2~9h.
9. The preparation method according to claim 3, characterized in that, The post-processing steps are as follows: after the reaction is completed, the reaction solution is cooled, diluted with 1 to 4 times the volume of the reaction solution with toluene, and then the diluted solution is dropped into a settling agent for sedimentation. The precipitate is collected and dried at 40 to 60°C to constant weight. The settling agent is methanol or a mixed solution of methanol and saturated saline solution.
10. The use of the polypropynylamine compound of claim 1 or 2 in refractive or luminescent materials.