Soxhdrocarbon dendritic macromolecular compound as well as preparation method and application thereof

Abstract

The invention relates to the technical field of macromolecular materials, and particularly discloses a Soxhlet dendritic macromolecular compound and a preparation method and application thereof.The preparation method comprises the steps that under inert atmosphere protection, a compound A, a compound B and potassium carbonate are subjected to a nucleophilic substitution reaction in N, N-dimethylformamide, a protecting group is removed after the reaction is finished, and a compound C is obtained; under the protection of inert atmosphere, adding the compound C, the compound D and potassium carbonate into N, N-dimethylformamide, carrying out nucleophilic substitution reaction to obtain a single alkynyl intermediate compound, and carrying out coupling reaction on the single alkynyl intermediate compound and bis (triethyl phosphine) platinum iodide to obtain a compound E; according to the method, 1, 3, 5-triacetylene benzene is taken as a core and is subjected to a coupling reaction with a compound E to obtain a first-generation isohydrocarbon dendritic macromolecular compound G1, and then second-generation isohydrocarbon dendritic macromolecular compounds G2 and G3 are prepared through repeated and alternately iterative deprotection-coupling reaction. The synthesis process is simple, the yield is high, and the high-algebraic isohydrocarbon dendritic macromolecular compound can be successfully prepared.

Description

Technical Field

[0001] The invention belongs to the technical field of macromolecular materials, and relates to a catenane dendritic macromolecular compound, and in particular to a catenane dendritic macromolecular compound and a preparation method and application thereof. Background Art

[0002] Classical mechanically interlocked molecules (MIMs) such as catenanes, rotaxanes, and molecular trefoil knots have attracted much attention due to their unique topological structures and controllable dynamic properties. These molecular structures have shown broad application potential in many emerging fields such as artificial molecular machines, luminescent materials, molecular recognition, and catalysis. In recent years, through sophisticated molecular design and precise integration of functions, MIMs have achieved remarkable research results in many scientific research fields (Angew. Chem. Int. Ed. 2017, 56, 11094; Nature 2022, 612, 78; J. Am. Chem. Soc. 2023, 145, 26791). In addition, relying on the aesthetic value of the structure and the synergistic amplification effect, more and more high-order mechanically interlocked macromolecules have been successfully constructed, which not only provides high-quality model compounds for studying structure-performance relationships, but also serves as a potential platform for the development of smart materials.

[0003] Among the many types of complex structures, dendrimers, with their precise three-dimensional nanomolecular structure, have shown broad application potential as a nanotechnology platform in the medical field, and are particularly suitable for use as carriers of drugs and other functional objects. On the one hand, its internal cavity structure enables efficient functional object encapsulation; on the other hand, its rich surface functional groups give it excellent object loading capacity. It is worth noting that current research focuses on introducing multifunctional rotaxanes as primitives into the dendrimer skeleton, and has shown excellent performance in photocatalysis, circularly polarized luminescence, and drug encapsulation (Nat. Commun. 2018, 9, 497; Acc. Chem. Res. 2021, 54, 4091).

[0004] Compared with rotaxanes, the dynamic properties of catenane bring richer conformational expressions, making them more advantageous in the application of drug carriers. However, catenane-based dendrimers, especially dendrimers in which each branch is composed of catenane units, are still relatively scarce due to the high challenges of the synthesis process. The existing technology only reports the dynamic covalent assembly of catenane trimers [2], which are the first generation of catenane dendrimers, through the metal ion template strategy. However, its yield is less than 30%, and it is impossible to prepare higher-generation dendrimers. Summary of the invention

[0005] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide a catenane dendrimer compound and a preparation method and application thereof. The synthesis process of the present invention is simple and has a high yield, and a high-generation catenane dendrimer compound can be successfully prepared.

[0006] The technical solution of the present invention is achieved in this way:

[0007] A method for preparing a catenane dendrimer compound comprises the following steps:

[0008] S1: Under the protection of an inert atmosphere, compound A, compound B and potassium carbonate undergo a nucleophilic substitution reaction in N,N-dimethylformamide, and after the reaction, the protecting group is removed to obtain compound C; wherein the structural formulas of compound A, compound B and compound C are as follows:

[0009]

[0010] S2: Under the protection of an inert atmosphere, compound C, compound D and potassium carbonate are added to N,N-dimethylformamide for a nucleophilic substitution reaction to obtain a monoacetyl intermediate compound, which is then coupled with ditriethylphosphine platinum iodide to obtain compound E; wherein the structural formulas of compound D and compound E are as follows:

[0011]

[0012] S3: 1,3,5-triethynylbenzene is used as the core, and a coupling reaction is performed with compound E to obtain the first-generation catenane dendrimer compound G1, and then the second-generation catenane dendrimer compound G2 and the third-generation catenane dendrimer compound G3 are obtained by repeated alternating deprotection-coupling reactions; the structural formulas of compounds G1, G2 and G3 are as follows:

[0013]

[0014]

[0015]

[0016] Furthermore, in step S1, the molar ratio of compound A to compound B is 2 to 10:1, preferably 5:1.

[0017] Furthermore, in step S2, the molar ratio of compound C to compound D is 1:1 to 3, preferably 1:2.

[0018] Furthermore, in step S3, when synthesizing compound G1, the molar ratio of 1,3,5-triethynylbenzene to compound E is 1:1-7, preferably 1:3; when synthesizing compound G2, the molar ratio of G1 after deprotection to compound E is 1:1-9, preferably 1:7; when synthesizing compound G3, the molar ratio of G2 after deprotection to compound E is 1:10-30, preferably 1:14.

[0019] Furthermore, in step S1 and step S2, the nucleophilic substitution reaction temperature is 35 to 70° C., preferably 70° C.; and the reaction time is 2 to 16 h, preferably 12 h.

[0020] Furthermore, in step S2, the coupling reaction temperature is 20-30° C., and the reaction time is 2-16 h, preferably 12 h.

[0021] Furthermore, in step S3, the temperature of the deprotection reaction and the coupling reaction is 20-30° C., the deprotection reaction time is 1-16 h, preferably 12 h, and the coupling reaction time is 1-10 h, preferably 6 h.

[0022] Furthermore, compound A is synthesized by the following method: after repeatedly evacuating and passing nitrogen through the reactor, chloroform and triethylamine are injected into the reactor; then 3-chlorosulfonylbenzoyl chloride and triethylene glycol di-p-benzylamine ether are dissolved in chloroform respectively to obtain 3-chlorosulfonylbenzoyl chloride-chloroform solution and triethylene glycol di-p-benzylamine ether-chloroform solution, and then the two chloroform solutions are simultaneously added to the reactor at a rate of 10 mL / h through a syringe pump, and then stirred overnight; after the reaction is completed, compound A is obtained by washing, distillation and purification.

[0023] The application of the catenane dendrimer compound described above for reversible encapsulation of small molecule drugs.

[0024] Compared with the prior art, the present invention has the following beneficial effects:

[0025] 1. The synthesis process of the present invention is simple and efficient, and no small molecules and oligomers are produced as byproducts. The target catenane dendrimer compound is the only product, which reduces the subsequent complex purification steps, not only improves the synthesis efficiency, but also effectively reduces the synthesis cost. At the same time, the present application successfully obtains high-generation, monodisperse catenane dendrimer compounds, solves the synthesis problem of high-generation dendrimer compounds, and provides the possibility for industrial production.

[0026] 2. The catenane dendrimer compound prepared by the present invention contains a large number of crown ether-like moieties, which endow the molecule with good biocompatibility. Therefore, the catenane dendrimer compound can be used as a biomedical material, especially in terms of drug transport carriers, and has broad application prospects. Compared with traditional drug transport carriers, catenane dendrimer compounds can achieve reversible encapsulation and release of drug molecules, and as the number of catenane dendrimers increases, the number of complexing guests is also significantly amplified, thereby improving the efficiency and loading capacity of drug transport. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 -Structural formula of compound G1.

[0028] Figure 2 -Structural formula of compound G2.

[0029] Figure 3 -Structural formula of compound G3.

[0030] Figure 4 - High resolution mass spectrum of compound E in Example 1.

[0031] Figure 5 - High resolution mass spectrum of compound G1 in Example 1.

[0032] Figure 6 -H NMR spectra of compounds E, G1, G2 and G3 in Example 1.

[0033] Figure 7 -NMR phosphorus spectra of compounds E, G1, G2 and G3 in Example 1.

[0034] Figure 8 -H NMR spectrum of compound G1 in Example 1 on dopamine salt (DA).

[0035] Fig. 9 -H NMR spectrum of dopamine salt (DA) coated with compound G2 in Example 1.

[0036] Fig.10 -H NMR spectrum of dopamine salt (DA) coated by compound G3 in Example 1. DETAILED DESCRIPTION

[0037] The present invention is further described in detail below in conjunction with the accompanying drawings and specific embodiments.

[0038] Example 1

[0039] (1) Synthesis of Compound A ([2]catenane precursor)

[0040] The structural formula of compound A is: The synthesis method is as follows: vacuuming and nitrogen-filling a three-necked round-bottom flask three times repeatedly, and then injecting 160 mL of chloroform and 0.7 mL of triethylamine into the three-necked round-bottom flask; then dissolving the compound 3-chlorosulfonylbenzoyl chloride (239 mg, 1 mmol) and the compound triethylene glycol di-p-benzylamine ether (360 mg, 1 mmol) in 40 mL of chloroform to obtain a 3-chlorosulfonylbenzoyl chloride-chloroform solution and a triethylene glycol di-p-benzylamine ether-chloroform solution, and then adding the chloroform solutions of the above two compounds into the system at a speed of 10 mL / h simultaneously through a syringe pump, and stirring at room temperature overnight after the addition is completed. After the reaction, the system was washed with 1M dilute hydrochloric acid (50 ml), 1M potassium hydroxide solution (50 mL), and saturated brine (50 mL) in sequence, and the solvent was distilled off under reduced pressure. The crude product was purified by flash column chromatography (eluent: dichloromethane:acetone = 10:1 to 5:1, v / v) to obtain a white powder compound A with a yield of 20%.

[0041] (2) Synthesis of Compound C

[0042] Compound A (250 mg, 0.255 mmol) and potassium carbonate (7 mg, 0.051 mmol) were added to 50 mL of N, N-dimethylformamide under a nitrogen atmosphere, and the system was stirred at room temperature for 30 min, followed by the addition of compound B (18.2 mg, 0.051 mmol), and the system was heated to 70 ° C and stirred for 12 hours. After the reaction was completed, 50 mL of dichloromethane was added to the system, and then poured into 100 mL of ice water. The water layer was extracted with dichloromethane (5 × 50 mL), the combined organic layer was washed with water (5 × 50 mL) and dried over anhydrous magnesium sulfate, and finally the magnesium sulfate was removed by filtration and the filtrate was concentrated under vacuum. The crude product was purified by rapid column chromatography (eluent: ethyl acetate: n-hexane = 1:3, v / v) to obtain a white glassy solid compound with a yield of 87%. Then the compound (400 mg, 0.287 mmol) was dissolved in 80 mL of tetrahydrofuran solution, and a tetrahydrofuran solution (10 mL) of tetrabutylammonium fluoride (374 mg, 1.4 mmol) was slowly added under ice bath conditions, and then the system was removed from the ice bath, slowly returned to room temperature and stirred for one hour. After the reaction was completed, 5 mL of deionized water was added to the system to quench the reaction, and then the water layer was extracted with dichloromethane (5×50 mL), and the combined organic layer was washed with water (5×50 mL) and dried over anhydrous magnesium sulfate. Finally, the magnesium sulfate was removed by filtration and the filtrate was concentrated under vacuum conditions. The crude product was purified by rapid column chromatography (eluent: ethyl acetate: n-hexane = 1:2, v / v) to obtain a white glassy solid compound C with a yield of 98%.

[0043] The reaction route is:

[0044]

[0045] (3) Synthesis of Compound E

[0046] Compound C (21 mg, 0.018 mmol) and potassium carbonate (5 mg, 0.036 mmol) were added to 10 mL of N, N-dimethylformamide under a nitrogen atmosphere, and the system was stirred at room temperature for 30 min, followed by the addition of compound D (19 mg, 0.036 mmol), and the system was heated to 70 ° C and stirred for 2 days. After the reaction was completed, 50 mL of dichloromethane solution was added to the system, and then poured into 100 mL of ice water. The water layer was extracted with dichloromethane (5×50 mL), the combined organic layer was washed with water (5×50 mL) and dried over anhydrous magnesium sulfate, and finally the magnesium sulfate was removed by filtration and the filtrate was concentrated under vacuum. The crude product was purified by rapid column chromatography (eluent: dichloromethane: acetone = 10:1, v / v) to obtain a white glassy solid compound with a yield of 86%. Then the compound (25 mg, 0.015 mmol) and ditriethylphosphine platinum iodide (42 mg, 0.062 mmol) were weighed in a 10 mL flask, the air in the flask was replaced with nitrogen three times, and then chloroform (4 mL) and diisopropylamine (2 mL) were injected. Subsequently, cuprous iodide (0.5 mg) was added under a nitrogen atmosphere, and stirred at room temperature for 6 hours. After the reaction was completed, the solvent was dried and purified by rapid column chromatography (eluent: dichloromethane: acetone = 5:1, v / v) to obtain a light yellow glassy solid compound E with a yield of 90%.

[0047] The reaction route is as follows:

[0048]

[0049] (4) Synthesis of catenane dendrimer compounds G1, G2 and G3

[0050] (4.1) 1,3,5-triethynylbenzene (20 mg, 0.133 mmol) and [2] catenane monomer (compound E) (1.0 g, 0.400 mmol) were placed in a branched bottle, and the nitrogen atmosphere was replaced three times before adding a mixed solution of deoxygenated dichloromethane and diethylamine. Subsequently, a catalytic amount of cuprous iodide (1 mg) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature overnight. After the reaction was completed, the solvent was dried in vacuo, and the first-generation catenane dendrimer compound G1 was obtained by separation by preparative gel permeation chromatography. The structural formula of compound G1 is shown in FIG. Figure 1 shown.

[0051] Then the first generation catenane dendrimer compound containing triisopropylsilyl protecting group was dissolved in tetrahydrofuran, and tetrabutylammonium fluoride (120 mg, 0.46 mmol) in tetrahydrofuran was slowly added under ice bath condition, and then the system was removed from ice bath, slowly returned to room temperature and stirred for one hour. After the reaction was completed, 5 mL of deionized water was added to the system to quench the reaction, and then the water layer was extracted with dichloromethane (5×50 mL), and the combined organic layers were successively used with water (5×50 mL), and the solvent was spin-dried. The crude product was separated by preparative gel permeation chromatography to obtain the first generation catenane dendrimer compound without protecting group, and the yield was 92%.

[0052] (4.2) The first-generation catenane dendrimer compound (190 mg, 0.035 mmol) obtained without protecting groups and the catenane monomer (compound E) (510 mg, 0.245 mmol) were weighed in a branched bottle of suitable size, and the mixed solution of deoxygenated dichloromethane and diethylamine was added after replacing nitrogen three times. Subsequently, a catalytic amount of cuprous iodide (1 mg) was added under nitrogen atmosphere, and the mixture was stirred at room temperature overnight. After the reaction was completed, the solvent was dried in vacuo, and the second-generation catenane dendrimer compound G2 was obtained by separation by preparative gel permeation chromatography. The structural formula of compound G2 is shown as follows: Figure 2 shown.

[0053] Then the second-generation catenane dendrimer compound was dissolved in tetrahydrofuran, and a tetrahydrofuran solution of tetrabutylammonium fluoride (120 mg, 0.46 mmol) was slowly added under ice bath conditions, and then the system was removed from the ice bath, slowly restored to room temperature and stirred for one hour. After the reaction was completed, 5 mL of deionized water was added to the system to quench the reaction, and then the water layer was extracted with dichloromethane (5×50 mL), and the combined organic layers were successively used with water (5×50 mL), and the solvent was dried by spin drying. The crude product was separated by preparative gel permeation chromatography to obtain the second-generation catenane dendrimer compound without the protecting group, and the yield was 75%.

[0054] (4.3) The obtained second-generation catenane dendrimer compound (100 mg, 0.0063 mmol) without protecting groups and catenane monomer (compound E) (181 mg, 0.088 mmol) were weighed in a branched bottle of suitable size, and the mixed solution of deoxygenated dichloromethane and diethylamine was added after replacing nitrogen three times. Subsequently, a catalytic amount of cuprous iodide (1 mg) was added under nitrogen atmosphere, and the mixture was stirred at room temperature overnight. After the reaction was completed, the solvent was vacuum dried and separated by preparative gel permeation chromatography to obtain the third-generation catenane dendrimer compound G3 with a yield of 67%. The structural formula of compound G3 is as follows: Figure 3 shown.

[0055] 1. The high-resolution mass spectra of compound E and compound G1 prepared in this example are shown in Figure 4 and Figure 5 As shown, the hydrogen nuclear magnetic resonance spectra and phosphorus nuclear magnetic resonance spectra of compounds E, G1, G2 and G3 prepared in this example are respectively as shown in Figure 6 and Figure 7 It can be seen from the figure that compound E, compound G1, compound G2 and compound G3 were successfully prepared.

[0056] 2. Deuterated dichloromethane was used as a medium for solution-phase drug encapsulation. First, compound G1 (20 mg), compound G2 (30 mg) and compound G3 (40 mg) were dissolved in 500 μL of dichloromethane, respectively. Then, different equivalents of dopamine salt (3 equivalents of dopamine 11 mg in G1; 9 equivalents of dopamine 17 mg in G2; 21 equivalents of dopamine 23 mg in G3) were gradually added to the solutions of compound G1, compound G2 and compound G3. The H NMR spectra of compound G1, G2 and G3 encapsulating dopamine salt (DA) were as follows: Figure 8 , Fig. 9 and Fig.10 As shown in the figure, it can be seen that the H NMR spectrum shows obvious host-guest interaction, successfully realizing the encapsulation of small molecule drugs by catenane dendrimer macromolecular compounds, and as the catenane dendrimers are subsequently deprotonated by in situ addition of an organic base (DBU), decomplexation is achieved, thereby achieving the purpose of reversible encapsulation and release of the drug.

[0057] Example 2

[0058] This embodiment is the same as Embodiment 1, except that, when synthesizing compound C, compound A in this embodiment is (120 mg, 0.123 mmol); when synthesizing compound E, compound D in this embodiment is (10 mg, 0.018 mmol); when synthesizing compound G1, compound E in this embodiment is (2.0 g, 0.88 mmol); when synthesizing compound G2, compound E in this embodiment is (1.02 g, 0.46 mmol); when synthesizing compound G3, compound E in this embodiment is (400 mg, 0.18 mmol).

[0059] In this example, the yield of compound C is 52%, the yield of compound E is 85%, and the yields of compounds G1, G2 and G3 are 53%, 50% and 43% respectively.

[0060] Example 3

[0061] This embodiment is the same as Embodiment 1, except that, when synthesizing Compound C, Compound B in this embodiment is (10 mg, 0.028 mmol); when synthesizing Compound E, Compound D in this embodiment is (30 mg, 0.054 mmol); when synthesizing Compound G1, Compound E in this embodiment is (0.66 g, 0.266 mmol); when synthesizing Compound G2, Compound E in this embodiment is (0.68 g, 0.315 mmol); when synthesizing Compound G3, Compound E in this embodiment is (281 mg, 0.126 mmol).

[0062] In this example, the yield of compound C is 43%, the yield of compound E is 57%, and the yields of compounds G1, G2 and G3 are 70%, 54% and 65% respectively.

[0063] Comparative Example 1

[0064] This comparative example is the same as Example 1, except that, when synthesizing compound C, compound A in this example is (50 mg, 0.051 mmol); when synthesizing compound E, compound D in this example is (5 mg, 0.009 mmol); when synthesizing compound G1, compound E in this example is (150 mg, 0.117 mmol); when synthesizing compound G2, compound E in this example is (150 mg, 0.069 mmol); when synthesizing compound G3, compound E in this example is (80 mg, 0.036 mmol).

[0065] In this comparative example, the yield of compound C is 20%, the yield of compound E is 37%, and the yields of compounds G1, G2 and G3 are 15%, 26% and 13% respectively. In addition, the product system is more complicated, which increases the difficulty of separation.

[0066] Comparative Example 2

[0067] This comparative example is the same as Example 1, except that, when synthesizing compound C, compound B in this example is (30 mg, 0.084 mmol); when synthesizing compound E, compound D in this example is (10 mg, 0.018 mmol); when synthesizing compound G1, cuprous iodide in this example is (2 mg, 0.010 mmol); when synthesizing compound G2, cuprous iodide in this example is (3 mg, 0.015 mmol); when synthesizing compound G3, cuprous iodide in this example is (3 mg, 0.015 mmol).

[0068] In this comparative example, the yield of compound C is 10%, the yield of compound E is 17%, and the yield of compound G1 is 2%, respectively, and no G2 and G3 products can be obtained. It can be seen that in the coupling reaction catalyzed by cuprous iodide in the present invention, the amount of cuprous iodide is the best when it is a catalytic amount (2%), and excessive cuprous iodide will seriously affect the occurrence of the reaction.

[0069] Finally, it should be noted that the above embodiments of the present invention are only examples for illustrating the present invention, and are not intended to limit the implementation methods of the present invention. For those skilled in the art, other different forms of changes and modifications can be made based on the above description. It is impossible to list all implementation methods here. Any obvious changes or modifications derived from the technical solution of the present invention are still within the scope of protection of the present invention.

Claims

1. A method for preparing a catenane dendrimer compound, characterized in that: The specific steps include: S1: Under the protection of an inert atmosphere, compound A, compound B and potassium carbonate undergo a nucleophilic substitution reaction in N,N-dimethylformamide, and after the reaction, the protecting group is removed to obtain compound C; wherein the structural formulas of compound A, compound B and compound C are as follows: S2: Under the protection of an inert atmosphere, compound C, compound D and potassium carbonate are added to N,N-dimethylformamide for a nucleophilic substitution reaction to obtain a monoacetyl intermediate compound, which is then coupled with ditriethylphosphine platinum iodide to obtain compound E; wherein the structural formulas of compound D and compound E are as follows: S3: 1,3,5-triethynylbenzene is used as the core, and a coupling reaction is performed with compound E to obtain the first-generation catenane dendrimer compound G1, and then the second-generation catenane dendrimer compound G2 and the third-generation catenane dendrimer compound G3 are obtained by repeated alternating deprotection-coupling reactions; the structural formulas of compounds G1, G2 and G3 are as follows:

2. The method for preparing a catenane dendrimer compound according to claim 1, characterized in that: In step S1, the molar ratio of compound A to compound B is 2 to 10:1, preferably 5:

1.

3. The method for preparing a catenane dendrimer compound according to claim 1, characterized in that: In step S2, the molar ratio of compound C to compound D is 1:1 to 3, preferably 1:

2.

4. The method for preparing a catenane dendrimer compound according to claim 1, characterized in that: In step S3, when synthesizing compound G1, the molar ratio of 1,3,5-triethynylbenzene to compound E is 1:1-7, preferably 1:3; when synthesizing compound G2, the molar ratio of G1 after deprotection to compound E is 1:1-9, preferably 1:7; when synthesizing compound G3, the molar ratio of G2 after deprotection to compound E is 1:10-30, preferably 1:

14.

5. The method for preparing a catenane dendrimer compound according to claim 1 or 2, characterized in that: In step S1 and step S2, the nucleophilic substitution reaction temperature is 35-70° C., preferably 70° C.; the reaction time is 2-16 h, preferably 12 h.

6. The method for preparing a catenane dendrimer compound according to claim 1, characterized in that: In step S2, the coupling reaction temperature is 20-30° C., and the reaction time is 2-16 h, preferably 12 h.

7. The method for preparing a catenane dendrimer compound according to claim 1, characterized in that: In step S3, the temperature of the deprotection reaction and the coupling reaction is 20-30° C., the deprotection reaction time is 1-16 h, preferably 12 h, and the coupling reaction time is 1-10 h, preferably 6 h.

8. The method for preparing a catenane dendrimer compound according to claim 1, characterized in that: Compound A is synthesized by the following method: after repeatedly evacuating and passing nitrogen through the reactor, chloroform and triethylamine are injected into the reactor; then 3-chlorosulfonylbenzoyl chloride and triethylene glycol di-p-benzylamine ether are dissolved in chloroform respectively to obtain 3-chlorosulfonylbenzoyl chloride-chloroform solution and triethylene glycol di-p-benzylamine ether-chloroform solution, and then the two chloroform solutions are simultaneously added into the reactor at a speed of 10 mL / h through a syringe pump, and then stirred overnight; after the reaction is completed, the compound A is obtained by washing, distillation and purification.

9. A catenane dendrimer compound, characterized in that: The first-generation catenane dendrimer compound G1, the second-generation catenane dendrimer compound G2 and the third-generation catenane dendrimer compound G3 are prepared by the method for preparing a catenane dendrimer compound according to any one of claims 1 to 8.

10. Use of a catenane dendrimer compound as claimed in any one of claim 9 for reversible encapsulation of small molecule drugs.

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