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CN114479101B - Supramolecular gel composition - Google Patents

Supramolecular gel composition Download PDF

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CN114479101B
CN114479101B CN202210075022.9A CN202210075022A CN114479101B CN 114479101 B CN114479101 B CN 114479101B CN 202210075022 A CN202210075022 A CN 202210075022A CN 114479101 B CN114479101 B CN 114479101B
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CN114479101A (en
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杨海宽
刘颖
卢佳伸
曹敏仪
路嘉敏
王凯
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North University of China
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Abstract

The invention discloses a supermolecular gel composition which is prepared from 5,5' - (pentane-1, 5-diacyl bis (oxy)) bis (N) 1 ,N 3 -bis (6-butylamine pyridine-2-yl) isophthalamide as a first gel factor, barbituric acid modified polyoxometalate hybrid as a second gel factor, and dissolving the mixture in chloroform according to a molar ratio of 1: 0.9-1.1. The supermolecule gel composition has high thermal stability, good self-healing property and excellent mechanical property, and can be used as an adsorption material, a biological medicine material, a sensing and detecting material, an environmental response structure material and the like.

Description

Supramolecular gel composition
Technical Field
The invention belongs to the technical field of chemical synthesis and supermolecule science, relates to a supermolecule gel, and particularly relates to a supermolecule gel with high thermal stability, self-healing property and good mechanical property, and a preparation method of the gel.
Background
Supramolecular gels, one of the functional soft materials, have recently received much attention from scientists due to their excellent properties. The supramolecular gel generally refers to a soft material with an ordered structure, which is self-assembled by organic small molecule gel factors through a synergistic effect in an organic solvent. The organic small molecule gel factor forms three-dimensional network structures with different structures through the interaction of non-covalent bonds such as hydrogen bond force, pi-pi bond acting force, van der waals force and the like, the three-dimensional network structures can wrap and fix a large number of organic solvent molecules to form organic gel structures, and special functional molecular groups are introduced into the gel factor structures, so that the characteristics of the supermolecule gel are utilized, and the excellent performances in certain aspects, such as good thermal reversibility and response to the external environment, are generated, so that the organic small molecule gel factor has wide application in the aspects of chemical sensing, nano templates, dynamic functional materials and the like.
Although the supramolecular gel has many excellent characteristics, the supramolecular gel has good application prospects in many fields, the preparation of related gel factors has contingency, randomness and complexity, and the formed gel has certain limitations, so that the practical application and potential application range of the supramolecular gel are greatly limited.
The following are several key issues currently faced by supramolecular gels.
1. It is difficult to purposefully prepare the high-efficiency gelator which can be directly used.
The designed and prepared potential gelator can not necessarily form stable gel well in a certain solvent, so that great randomness and contingency exist in the design and preparation of the gelator.
2. The method for optimizing the performance of the gel factor is complex in steps and difficult in process operation.
The method for optimizing the gel performance reported at present is to introduce specific functional groups into the molecular structure of the gel factor with high-efficiency gel capability and modify the geometric configuration of the gel factor. However, the chemical modification increases the complexity and difficulty of the process for preparing the gel, and consumes manpower, material resources and financial resources.
3. The organogels prepared tend to exhibit poor gelling properties.
The reason is that the acting force for forming the supramolecular gel is non-covalent bond acting force with weaker intermolecular hydrogen bond, pi-pi accumulation acting force, van der waals force and the like, the gel structure cannot adapt to tiny change of external environment, and the performance is poorer.
For example, the gel often has poor thermal stability, the thermal motion of gel factors is easily accelerated by small rise of the environmental temperature, and the non-covalent force action among the gel factors is weakened, so that the gel structure is damaged, and the gel is macroscopically represented as the liquefaction phenomenon of the gel.
As another example, gels generally have no self-healing properties, since the non-covalent bonds connecting the gels are generally irreversible, and changes in the structural units of the gel due to changes in external conditions, the irreversible connection renders the gel incapable of self-healing, and macroscopically incapable of repairing the structure of the damaged site.
Also for example, gels have poor mechanical properties, are poorly defined due to their irreversible non-covalent bonds that are unable to form a re-establishment of reversible dynamic crosslinks in the gel network, have a low degree of bonding and crosslinking, macroscopically behave as poor viscoelasticity, etc.
Due to these performance leaks, practical applications of the gel are greatly limited.
The improvement of the thermal stability of the organogel greatly expands the application of the organogel as functional soft materials and the like; the improvement of the self-healing performance can not only prolong the service life of the organogel, but also greatly improve the use safety, and has great application potential in a plurality of fields such as sensing and detection, drug release, drivers, tissue engineering and the like; the improvement of mechanical properties relates to a great breakthrough in the fields of environmental response structural materials and the like. Therefore, the preparation of the supermolecular gel with excellent performance, which is simple and easy to operate, has profound practical significance.
Disclosure of Invention
The invention aims to provide a supermolecule gel composition with high thermal stability, high self-healing property and excellent mechanical property.
The supramolecular gel composition is a mixed system formed by dissolving a first gelator and a second gelator in chloroform according to the molar ratio of 1: 0.9-1.1.
Wherein the first gelator is a compound with the following structural formula, chemical formula C 57 H 64 N 12 O 10 Chemical name 5,5' - (pentane-1, 5-diacylbis (oxy)) bis (N) 1 ,N 3 Bis (6-butylamine pyridin-2-yl) isophthalamide.
Figure 190794DEST_PATH_IMAGE001
The second gelatorIs barbituric acid modified polyoxometalate with the structural formula of (C) 21 H 33 N 2 O 6 ) 2 [(OCH 2 ) 3 CNH] 2 (MnMo 6 O 18 )•[(C 4 H 9 ) 4 N] 3
Figure 522156DEST_PATH_IMAGE002
Wherein: POM is MnMo 6 O 18 TBA is (C) 4 H 9 ) 4 N。
Furthermore, the supramolecular gel composition is a mixed system which is formed by dissolving the first gelator and the second gelator in chloroform and has the concentration of 10-30 mg/mL.
The invention also provides a specific preparation method of the supramolecular gel composition, which is to add the first gelator and the second gelator into chloroform solvent according to the molar ratio of 1: 0.9-1.1, and after the first gelator and the second gelator are uniformly dissolved by ultrasonic combined heating treatment, the supramolecular gel composition is stood to form stable supramolecular gel.
Preferably, the standing time is not less than 3 hours.
More specifically, the first gelator of the present invention can be prepared by the following method.
1) And reacting 5- (benzyloxy) isophthalic acid with thionyl chloride to obtain 5- (benzyloxy) isophthaloyl dichloride.
2) Further reacting 5- (benzyloxy) isophthaloyl dichloride with N- (6-aminopyridin-2-yl) butanamide in a solution of triethylamine in chloroform to prepare 5- (benzyloxy) -N 1 ,N 3 -bis (6-butylaminopyridin-2-yl) isophthalamide.
3) And then 5- (benzyloxy) -N 1 ,N 3 Reaction of (6-butylaminopyridin-2-yl) isophthalamide in anhydrous methanol containing palladium on carbon and formic acid to give N 1 ,N 3 -bis (6-butylamine pyridin-2-yl) -5-hydroxyisophthalamide.
4) And finally, with N 1 ,N 3 Reacting (6-butylamine pyridine-2-yl) -5-hydroxyisophthalamide and 1, 5-dibromopentane in an acetone solution containing potassium carbonate and potassium iodide to prepare the target product 5,5' - (pentane-1, 5-diacyl bis (oxy)) bis (N) 1 ,N 3 -bis (6-butylamine pyridin-2-yl) isophthalamide.
Wherein, in the step 1), the mol ratio of the 5- (benzyloxy) isophthalic acid to the thionyl chloride is preferably 1: 5-10.
In the step 2), the mol ratio of the 5- (benzyloxy) isophthaloyl dichloride, the N- (6-aminopyridine-2-yl) butanamide and the triethylamine is preferably 1: 2.1-2.3.
In the step 3), 5- (benzyloxy) -N 1 ,N 3 The mol ratio of the (6-butylaminopyridin-2-yl) isophthalamide to the palladium on carbon and the formic acid is preferably 1: 4 to 4.3: 1.1 to 1.3.
In the step 4), N 1 ,N 3 The preferred molar ratio of the (6-butylamine pyridin-2-yl) -5-hydroxyisophthalamide to the 1, 5-dibromopentane to the potassium carbonate and the potassium iodide is 1: 0.3-0.5: 3-4: 1.3-1.5.
Further, the second gelator of the present invention is a barbituric acid-modified polyoxometalate hybrid disclosed in the applicant's CN 112570025A.
Compared with the common supermolecule gel in which the main intermolecular force is hydrogen bond force and van der waals force, the invention purposefully introduces polyoxometallate ion clusters into the second gel factor, reasonably utilizes the strong electrostatic interaction among the molecules, the cage-shaped rigid framework structure and the poor solubility of low-polarity solvents, greatly improves the thermal stability of the prepared gel through the combination of the first gel factor and the second gel factor, and forms the gel structure shown as the following.
Figure 413889DEST_PATH_IMAGE003
In the structure, the first gelator and the second gelator have strong six-fold hydrogen bond effect among molecules and belong to non-covalent bond force, and the non-covalent bond force enables the prepared supramolecular gel to have good self-healing capability through the reversible dynamic bonding effect of the hydrogen bond among the molecules.
In addition, the first gelator and the second gelator have enhanced hydrogen bonding effect, greatly enhance the crosslinking complexity of the three-dimensional supramolecular network structure of the gel, and further enhance the mechanical property of the gel.
The first gelator and the second gelator can not form gel independently, and can only form a stable structure as shown above when the first gelator and the second gelator exist simultaneously, and a solution system of the first gelator and the second gelator can form a stable supramolecular gel composition which has uniqueness, singleness and irreplaceability.
The present invention also has the interesting finding that the first gel factor and the second gel factor, when present alone, do not form a gel and must be used in combination.
Furthermore, when the second gelator is replaced by bis 4- (12-barbituric acid) -tetradecyloxy-4-oxosuccinate which does not contain polyoxometallate but has a completely identical molecular structure, gel formation still fails, and various properties cannot be mentioned.
Wherein, the compound bis 4- (12-barbituric acid) -tetradecyloxy-4-oxosuccinate has the following structural formula.
Figure 597746DEST_PATH_IMAGE004
Therefore, only when the first gelator and the second gelator exist simultaneously, the solution system can form the stable supramolecular gel material, and the formed supramolecular gel material has various excellent performances, so that the supramolecular gel material has uniqueness, singleness and irreplaceability.
The preparation method of the supramolecular gel composition is simple, the reaction condition is mild, the raw materials are easy to obtain, the prepared supramolecular gel composition has excellent thermal stability, the gel-sol phase transition temperature is far higher than the boiling point of the solvent, and the stability of the supramolecular gel composition in use in different environments is ensured. In addition, the supermolecule gel composition has good self-healing property, and is suitable for various functional materials needing high self-healing property. The supramolecular gel composition of the present invention also has superior mechanical properties and does not break when it is stretched.
Based on various excellent performances of the supramolecular gel composition, the supramolecular gel composition can be used as various functional soft materials such as an adsorption material, a biological medicine material, a sensing and detecting material, an environmental response structure material and the like, so as to meet various use requirements in different fields, and has wide application prospects.
Drawings
FIG. 1 shows intermediate product N for preparing first gelator 1 ,N 3 Nuclear magnetic resonance hydrogen spectrum of (6-butylamine pyridin-2-yl) -5-hydroxyisophthalamide.
FIG. 2 is a graph of the first gelator, i.e., 5' - (pentane-1, 5-diacylbis (oxy)) bis (N-N) 1 ,N 3 -bis (6-butylamine pyridin-2-yl) isophthalamide NMR spectrum.
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of a second gel factor, namely, a barbituric acid modified polyoxometalate hybrid.
Figure 4 is a graph comparing the supramolecular gel composition of the present invention with other products to form solutions.
Fig. 5 is a diagram of the self-healing process of the supramolecular gel composition of the invention.
Fig. 6 is a graph showing the mechanical properties of the supramolecular gel composition of the invention.
Detailed Description
The following describes in detail a specific embodiment of the present invention with reference to the drawings, examples and comparative examples. The following examples and comparative examples are only for more clearly illustrating the technical aspects of the present invention so that those skilled in the art can well understand and utilize the present invention, and do not limit the scope of the present invention.
The names and abbreviations of the experimental methods, production processes, instruments and equipment related to the examples and comparative examples of the present invention are all conventional names in the art, and are clearly and clearly understood in the related fields of use, and those skilled in the art can understand the conventional process steps and apply the corresponding equipment according to the names, and implement the process according to the conventional conditions or the conditions suggested by the manufacturers.
The various starting materials and reagents used in the examples and comparative examples of the present invention are not particularly limited in terms of their sources, and are all conventional products commercially available.
Example 1: a first gelator is prepared.
Adding 5g of 5- (benzyloxy) isophthalic acid into 200mL of thionyl chloride, heating to 45 ℃, reacting for 8h, cooling the reaction liquid to room temperature, and performing reduced pressure spin-drying to obtain 5- (benzyloxy) isophthaloyl dichloride.
Weighing 3g of 5- (benzyloxy) isophthaloyl dichloride, 3.5g of N- (6-aminopyridin-2-yl) butanamide and 2.1g of triethylamine, dissolving in 350mL of chloroform, reacting at 60 ℃ for 48 hours, cooling the reaction solution to room temperature, washing the reaction solution with distilled water, and performing vacuum spin-drying on the organic phase to obtain 5- (benzyloxy) -N 1 ,N 3 Bis (6-butylaminopyridin-2-yl) isophthalamide.
3g of 5- (benzyloxy) -N 1 ,N 3 Dissolving-bis (6-butylaminopyridin-2-yl) isophthalamide, 2.2g palladium carbon and 0.28g formic acid in 200mL absolute methanol, reacting at 40 ℃ for 72h, cooling the reaction solution to room temperature, washing the reaction solution with distilled water, and performing vacuum spin drying on the organic phase to obtain N 1 ,N 3 -bis (6-butylamine pyridin-2-yl) -5-hydroxyisophthalamide.
FIG. 1 shows the above preparation N 1 ,N 3 Nuclear magnetic resonance hydrogen spectrum of (6-butylamine pyridin-2-yl) -5-hydroxyisophthalamide. The solvent peaks are shown in the figure, all characteristic peaks of which give a clear assignment, and the spectrum does not contain any miscellaneous peaks, thus proving that the prepared compound has high purity.
1.5g of N are weighed out 1 ,N 3 Dissolving (6-butylamine pyridin-2-yl) -5-hydroxyisophthalamide, 0.3g 1, 5-dibromopentane, 1.4g potassium carbonate, and 0.7g potassium iodide in 200mL acetone, reacting at 56 deg.C for 70h, filtering the reaction solution, draining the filtrate, recrystallizing with dichloromethane, and drying under vacuum to give 5,5' - (pentane-1, 5-diacylbis (oxy))Bis (N) 1 ,N 3 Bis (6-butylamine pyridin-2-yl) isophthalamide, the first gelator.
FIG. 2 shows a NMR spectrum of the first gel factor. The solvent peaks are shown in the figure, all characteristic peaks of which give a clear assignment, and the spectrum does not contain any miscellaneous peaks, thus proving that the first gel factor prepared has higher purity.
Example 2: a second gelator is prepared.
5g of diethyl ethylmalonate, 7g of 11-bromo-1-undecanol and 1.3g of sodium hydride are weighed and added into 350mL of N, N-dimethylformamide, stirred and reacted at 60 ℃ for 20 hours, the reaction liquid is cooled to room temperature, the reaction liquid is washed with distilled water, and the organic phase is subjected to vacuum spin drying to obtain 11-diethyl ethylmalonate-1-undecanol.
Dissolving 6g of 11-ethyl diethyl malonate-1-undecanol, 1g of urea and 0.8g of sodium hydride in 250mL of N, N-dimethylformamide, stirring and reacting at 85 ℃ for 20h, cooling the reaction solution to room temperature, washing the reaction solution with distilled water, and carrying out reduced pressure spin drying on the organic phase to obtain 12-barbituric acid-tetradecanol.
Adding 3g of 12-barbituric acid-tetradecanol, 1.2g of succinic anhydride and 2g of triethylamine into 200mL of chloroform, stirring and reacting at 48 ℃ for 50 hours, carrying out reduced pressure spin-drying on the reaction liquid, recrystallizing with methanol, and carrying out vacuum drying to obtain 4- (12-barbituric acid) -tetradecyloxy-4-oxobutyric acid.
Weighing 2.5g 4- (12-barbituric acid) -tetradecyloxy-4-oxobutyric acid, 2g 2-ethoxy-1-ethoxycarbonyl-1, 2-dihydroquinoline, and 4g [ (C) 4 H 9 ) 4 N] 3 (MnMo 6 O 18 )[(OCH 2 ) 3 CNH 2 ] 2 Dissolving the polyoxometalate cluster in 400mL of acetonitrile, stirring at 55 ℃ for reaction for 70 hours, concentrating the reaction solution under reduced pressure, precipitating in dichloromethane, filtering and drying to obtain the barbituric acid modified polyoxometalate cluster hybrid, namely the second gel factor.
FIG. 3 shows a NMR spectrum of the second gelator. The solvent peaks are shown in the figure, all characteristic peaks of which give a clear assignment, and the spectrum does not contain any miscellaneous peaks, thus proving that the second gel factor prepared has higher purity.
Example 3.
Weighing 4.2mg of the first gelator and 10.8mg of the second gelator, adding the first gelator and the second gelator into a screw-mouth small bottle added with 1mL of chloroform, heating and carrying out ultrasonic treatment until the first gelator and the second gelator are completely dissolved, naturally cooling to room temperature, and standing for 3 hours to prepare the stable supramolecular gel.
Comparative example 1.
Supramolecular gels were prepared as in example 3 with 15mg of the first gelator and no second gelator added and were found to be incapable of forming gels.
Comparative example 2.
The supramolecular gel was prepared as in example 3 by weighing 15mg of the second gelator without adding the first gelator and was found to be incapable of forming a gel.
Comparative example 3.
8.9mg of the first gelator and 6.1mg of bis 4- (12-barbituric acid) -tetradecyloxy-4-oxosuccinate were weighed out, and supramolecular gel was prepared according to the method of example 3, and it was found that gel could not be formed.
Wherein bis 4- (12-barbituric acid) -tetradecyloxy-4-oxosuccinate having the following structural formula similar to that of the second gelator is used.
Figure 498706DEST_PATH_IMAGE004
Fig. 4 records a state diagram of the preparation of supramolecular gel-forming products in example 3 and comparative examples 1 to 3. Wherein, fig. 4a is a supramolecular gel formed by example 3, fig. 4b is a solution formed by comparative example 1 when the first gelator is used alone, fig. 4c is a solution formed by comparative example 2 when the second gelator is used alone, and fig. 4d is a solution formed by comparative example 3 when the first gelator and bis 4- (12-barbituric acid-based) -tetradecyloxy-4-oxosuccinate are used.
Therefore, only when the first gelator and the second gelator exist at the same time, the solution system can form a stable supramolecular gel composition, and the method has uniqueness, uniqueness and irreplaceability.
Example 4.
Weighing 5mg of first gelator and 13mg of second gelator, adding the first gelator and the second gelator into a screw-mouth vial added with 1mL of chloroform, heating and carrying out ultrasonic treatment until the first gelator and the second gelator are completely dissolved, naturally cooling to room temperature, and standing for 3h to prepare the stable supramolecular gel.
Vials containing the supramolecular gels prepared in example 3 and example 4, respectively, were placed upside down in a vacuum oven and heated at a heating rate of 12 ℃/h, and the gel-sol phase transition temperature of the gel was measured as it slides down to the bottom of the vial under the influence of gravity. The results show that the gel-sol phase transition temperatures of example 3 and example 4 are 93 ℃ and 97 ℃, respectively, both exceed 93 ℃, and are well above the solvent's own boiling point.
Example 5.
Weighing 7mg of first gelator and 18mg of second gelator, adding the first gelator and the 18mg of second gelator into a screw-mouth vial added with 1mL of chloroform, heating and carrying out ultrasonic treatment until the first gelator and the second gelator are completely dissolved, naturally cooling to room temperature, and standing for 3h to prepare the stable supramolecular gel.
After the prepared supramolecular gel is cut into two halves by a small knife, the two halves are put back to the original position and are simultaneously and quickly placed in a sealed bag, after the supramolecular gel composition is placed for 24 hours at room temperature without any stimulation, the self-healing process diagram of the supramolecular gel composition shown in the figure 5 is observed, and the two gel blocks cut before are adhered together to form an integral gel block, which shows that the gel has good self-healing capacity.
Example 6.
Weighing 8mg of first gelator and 20mg of second gelator, adding the first gelator and the second gelator into a screw-mouth small bottle added with 1mL of chloroform, heating and carrying out ultrasonic treatment until the first gelator and the second gelator are completely dissolved, naturally cooling to room temperature, and standing for 3h to prepare the stable supramolecular gel.
A gel strip with the length of 1cm is cut from the prepared supramolecular gel, the two ends of the gel strip are clamped by forceps, the gel strip is stretched with uniform force, the mechanical property of the gel strip is observed, the test result is shown in figure 6, and the gel strip is not broken when being stretched, which indicates that the gel composition has good mechanical property.
The above embodiments of the present invention are not intended to be exhaustive or to limit the invention to the precise form disclosed. Various changes, modifications, substitutions and alterations to these embodiments will be apparent to those skilled in the art without departing from the principles and spirit of this invention.

Claims (10)

1. A supramolecular gel composition is a mixed system formed by dissolving a first gelator and a second gelator in chloroform according to the molar ratio of 1: 0.9-1.1, wherein:
the first gelator is of formula C 57 H 64 N 12 O 10 Chemical name 5,5' - (Pentane-1, 5-Diacylbis (oxy)) bis (N) 1 ,N 3 -bis (6-butylamine pyridin-2-yl) isophthalamide represented by the following general structural formula:
Figure 658745DEST_PATH_IMAGE001
the second gel factor is barbituric acid modified polyoxometalate with the following structural formula (C) 21 H 33 N 2 O 6 ) 2 [(OCH 2 ) 3 CNH] 2 (MnMo 6 O 18 )•[(C 4 H 9 ) 4 N] 3
Figure 89726DEST_PATH_IMAGE002
Wherein: POM is MnMo 6 O 18 TBA is (C) 4 H 9 ) 4 N。
2. The supramolecular gel composition as claimed in claim 1, which is a mixed system of 10-30 mg/mL concentration formed by dissolving the first gelator and the second gelator in chloroform.
3. The supramolecular gel composition as claimed in claim 1, wherein said first gelator is prepared by the following method:
1) 5- (benzyloxy) isophthalic acid reacts with thionyl chloride to prepare 5- (benzyloxy) isophthaloyl dichloride;
2) Further reacting 5- (benzyloxy) isophthaloyl dichloride with N- (6-aminopyridin-2-yl) butanamide in a solution of triethylamine in chloroform to prepare 5- (benzyloxy) -N 1 ,N 3 -bis (6-butylaminopyridin-2-yl) isophthalamide;
3) And then 5- (benzyloxy) -N 1 ,N 3 Reaction of (6-butylaminopyridin-2-yl) isophthalamide in anhydrous methanol containing palladium on carbon and formic acid to give N 1 ,N 3 -bis (6-butyamine pyridin-2-yl) -5-hydroxyisophthalamide;
4) And finally, with N 1 ,N 3 Reacting (6-butylamine pyridine-2-yl) -5-hydroxy isophthalamide and 1, 5-dibromopentane in an acetone solution containing potassium carbonate and potassium iodide to prepare the target product 5,5' - (pentane-1, 5-diacyl bis (oxy)) bis (N) 1 ,N 3 -bis (6-butylamine pyridin-2-yl) isophthalamide.
4. The supramolecular gel composition as claimed in claim 3, wherein the molar ratio of 5- (benzyloxy) isophthalic acid to thionyl chloride in step 1) is 1: 5-10.
5. The supramolecular gel composition as claimed in claim 3, wherein the molar ratio of 5- (benzyloxy) isophthaloyl chloride, N- (6-aminopyridin-2-yl) butanamide and triethylamine in step 2) is 1: 2.1-2.3.
6. The supramolecular gel composition of claim 3, wherein 5- (benzyloxy) -N in step 3) 1 ,N 3 -bis (6-butylaminopyridin-2-yl) m-phenylenediThe mol ratio of formamide to palladium carbon to formic acid is 1: 4-4.3: 1.1-1.3.
7. The supramolecular gel composition of claim 3, wherein N in step 4) 1 ,N 3 The mol ratio of the (6-butylamine pyridine-2-yl) -5-hydroxy isophthalamide and the 1, 5-dibromopentane to the potassium carbonate and the potassium iodide is 1: 0.3-0.5: 3-4: 1.3-1.5.
8. The method for preparing the supramolecular gel composition as claimed in claim 1, wherein the first gelator and the second gelator are added into chloroform solvent according to the molar ratio of 1: 0.9-1.1, and after the uniform dissolution of the first gelator and the second gelator through ultrasonic combined heating treatment, the supramolecular gel composition is kept stand to form stable supramolecular gel.
9. The method for the preparation of supramolecular gel composition according to claim 8, wherein said resting time is not less than 3h.
10. Use of the supramolecular gel composition according to claim 1 as adsorption material, biomedical material, sensing and detection material, environmental responsive structural material.
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WO2013038153A1 (en) * 2011-09-14 2013-03-21 The University Court Of The University Of Aberdeen 18f-labelled barbiturate compounds for use as positron emission imaging agents
CN106750538A (en) * 2016-12-07 2017-05-31 中北大学 A kind of polyoxomolybdate polyethylene glycol hybrid and preparation method thereof
CN112570025A (en) * 2020-10-30 2021-03-30 中北大学 Barbituric acid modified polymetallic oxygen cluster hybrid and preparation method thereof

Patent Citations (3)

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WO2013038153A1 (en) * 2011-09-14 2013-03-21 The University Court Of The University Of Aberdeen 18f-labelled barbiturate compounds for use as positron emission imaging agents
CN106750538A (en) * 2016-12-07 2017-05-31 中北大学 A kind of polyoxomolybdate polyethylene glycol hybrid and preparation method thereof
CN112570025A (en) * 2020-10-30 2021-03-30 中北大学 Barbituric acid modified polymetallic oxygen cluster hybrid and preparation method thereof

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