CN110483933B - Supermolecule assembly film material prepared by using pyridine heterocyclic azobenzene - Google Patents

Supermolecule assembly film material prepared by using pyridine heterocyclic azobenzene Download PDF

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CN110483933B
CN110483933B CN201910800253.XA CN201910800253A CN110483933B CN 110483933 B CN110483933 B CN 110483933B CN 201910800253 A CN201910800253 A CN 201910800253A CN 110483933 B CN110483933 B CN 110483933B
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李双雯
崔永生
林松
李鑫
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North China Institute of Aerospace Engineering
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Abstract

The invention discloses a method for preparing a supermolecule assembly film material by using pyridine heterocyclic azobenzene. The film material has excellent ultraviolet responsiveness and stability. The system is expected to promote the application of the intelligent response material in a complex environment, and provides an idea for the subsequent construction of a multi-response complex.

Description

Supermolecule assembly film material prepared by using pyridine heterocyclic azobenzene
Technical Field
The invention relates to a supermolecular assembly film material prepared by pyridine heterocyclic azobenzene.
Background
When the material generates microcracks or breaks, the temperature of the material is increased, so that the hydrogen bonds are rearranged, and self-repairing is realized. Leibler et al use hydrogen bond donors and flexible units to assemble to form supramolecular polymer networks, and a large number of hydrogen bonds in elastomers improve the mechanical strength of the materials and impart the function of self-repair to the elastomers. The system adopts the interaction of dimer and trimer fatty acid and a hydrogen bond donor, so that the glass transition temperature of the polymer is reduced to 28 ℃. Meanwhile, a large number of net structures in the system effectively prevent the polymer from crystallizing, after the elastomer is cut off by a knife, the two surfaces are mutually contacted, the hydrogen bonds of the contact surfaces are rearranged, and finally the fracture surfaces are completely repaired.
Great et al prepared azobenzene/polymer composites at different charge ratios by an electrostatic assembly method to prepare a stimulus responsive film. The film can be obviously deformed under the ultraviolet irradiation, can continue to curl after the ultraviolet irradiation is stopped, and can finally return to the initial flat state.
However, the response performance of the materials is still poor, the sensitivity is not high, and the self-supporting property of the self-assembled film is not good. The invention prepares an azobenzene monomer, which is compounded with a polymer through supermolecular acting force to prepare a photoresponse material with good self-supporting performance.
Disclosure of Invention
In view of the above problems, the present invention provides a method for preparing a supramolecular assembly thin film material by using pyridine heterocyclic azobenzene. The invention utilizes the supermolecule assembly based on multiple hydrogen bond action to prepare the optically-driven spiral system with good stability and quick response, and widens the application of the supermolecule assembly based on multiple hydrogen bond in the optically-driven device.
The technical scheme of the invention comprises the following steps:
S1preparing pyridine heterocyclic azobenzene AZO, comprising the steps of:
S1-1weighing 25 mmol of 5-amino isophthalic acid, dissolving the 5-amino isophthalic acid in 60mL of 0.1 mol/L hydrochloric acid solution, placing the solution in an ice water bath (the temperature is 0 ℃), slowly dripping 25mL of 0.1 mol/L sodium nitrite solution into the 5-amino isophthalic acid hydrochloric acid solution, and stirring the solution at the temperature of 2 ℃ for 3 hours to obtain a diazonium salt solution;
S1-2dissolving 25 mmol of 2, 6-dicarboxylpyridine in 60mL of 0.1 mol/L hydrochloric acid solution, and stirring at 2 ℃ until the 2mmol of 2, 6-dicarboxylpyridine is completely dissolved;
S1-3will step S1-1The prepared diazonium salt solution is slowly dripped into the step S under magnetic stirring1-2Reacting the solution prepared in the step (1) for 4 hours at the temperature of 2 ℃; adjusting the solution to be neutral (Ph = 7) by using saturated sodium carbonate and deionized water, carrying out suction filtration on the product, washing a filter cake by using the deionized water, drying the washed filter cake for 24 hours at 40 ℃ in vacuum to obtain a crude product, finally recrystallizing the crude product by using an ethanol/water mixed solution, and carrying out separation and purification by using silica gel column chromatography to obtain pyridine heterocyclic azobenzene AZO, wherein the molecular structure of the pyridine heterocyclic azobenzene AZO is as follows:
Figure 17433DEST_PATH_IMAGE001
；
S2dissolving pyridine heterocyclic azobenzene and sodium hydroxide in deionized water according to the molar ratio of 1:1-5 to prepare a solution I; simultaneously adding polydimethyl diDissolving the allyl ammonium chloride in deionized water to prepare a polydimethyldiallyl ammonium chloride aqueous solution with the concentration of 0.1-1 g/mL;
S3will step S2Dropwise adding the prepared aqueous solution of the polydimethyl diallyl ammonium chloride into the aqueous solution of the pyridine heterocyclic azobenzene while stirring, wherein the mass ratio of the pyridine heterocyclic azobenzene to the polydimethyl diallyl ammonium chloride is 1:2-22, and fully stirring for 20-48h to obtain an assembly solution;
S4will step S3The assembly solution in the step (1) is dialyzed for a plurality of times, NaCl in a reaction system is fully removed, and the dialyzed solution is concentrated by rotary evaporation;
S5preparing the concentrated assembly solution into a self-assembly aqueous solution with the concentration of 1-5mg/mL, then adding ethanol, wherein the volume ratio of the ethanol to the assembly aqueous solution is 1:2, fully and uniformly mixing, then dropwise adding the self-assembly aqueous solution into a polytetrafluoroethylene mold rinsed by the ethanol, firstly placing the mold at 25 ℃ for 5-20h to slowly volatilize the solvent, then placing the mold into a vacuum oven for drying, and taking out the film from the mold after completely drying to prepare the supramolecular assembly film material.
Preferably, step S4The temperature of the medium rotary evaporation is 80 ℃.
Preferably, step S5The temperature of vacuum drying is 40 ℃.
Compared with the prior art, the invention has the following beneficial effects: the invention utilizes pyridine heterocyclic AZO benzene AZO with four carboxyl groups and poly dimethyl diallyl ammonium chloride PDAC to prepare the AZO/PDAC assembly film material in an electrostatic self-assembly mode. The film material has excellent ultraviolet responsiveness and stability. The system is expected to promote the application of the intelligent response material in a complex environment, and provides an idea for the subsequent construction of a multi-response complex.
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In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without inventive exercise.
FIG. 1 is a SEM image of a pyridine heterocyclic azobenzene supramolecular assembly film material prepared in example 1 of the invention;
FIG. 2 is an SEM image of the pyridine heterocyclic azobenzene supramolecular assembly film material prepared in comparative example 1;
FIG. 3 is an SEM image of the pyridine heterocyclic azobenzene supramolecular assembly film material prepared in comparative example 2;
FIG. 4 is a UV-VIS curve of the pyridine heterocyclic azobenzene supramolecular assembly film material prepared in example 1 under the irradiation of ultraviolet light;
FIG. 5 is a UV-VIS curve of the pyridine heterocyclic azobenzene supramolecular assembly film material prepared in example 1 of the invention recovering in the dark.
FIG. 6 is a photograph showing the driving and recovery of the pyridine heterocyclic azobenzene supramolecular assembly thin-film material prepared in example 1 of the present invention under the irradiation of ultraviolet light;
FIG. 7 is a picture of the UV response of the film material prepared in comparative example 2.
Detailed Description
The invention is further illustrated by the following examples and figures.
Example 1
S1The preparation method of the pyridine heterocyclic azobenzene AZO comprises the following specific steps:
S1-1weighing 25 mmol of 5-amino isophthalic acid, dissolving the 5-amino isophthalic acid in 60mL of 0.1 mol/L hydrochloric acid solution, placing the solution in an ice water bath (the temperature is 0 ℃), slowly dripping 25mL of 0.1 mol/L sodium nitrite solution into the 5-amino isophthalic acid hydrochloric acid solution, and stirring the solution at the temperature of 2 ℃ for 3 hours to obtain a diazonium salt solution;
S1-2dissolving 25 mmol of 2, 6-dicarboxylpyridine in 60mL of 0.1 mol/L hydrochloric acid solution, and stirring at 2 ℃ until the 2mmol of 2, 6-dicarboxylpyridine is completely dissolved;
S1-3will step S1-1Prepared diazonium salt solution in magnetic fieldSlowly dropwise adding into the step S under the stirring of force1-2Reacting the solution prepared in the step (1) for 4 hours at the temperature of 2 ℃; adjusting the solution to be neutral (pH = 7) by using saturated sodium carbonate and deionized water, carrying out suction filtration on the product, washing a filter cake by using the deionized water, drying the washed filter cake for 24 hours at 40 ℃ in vacuum to obtain a crude product, finally recrystallizing the crude product by using an ethanol/water mixed solution, and carrying out separation and purification by using a silica gel column chromatography to obtain purified pyridine heterocyclic azobenzene AZO;
S2dissolving 1mmol of AZO and 4 mmol of NaOH in 50 mL of deionized water to prepare AZO aqueous solution; dissolving polydimethyl diallyl ammonium chloride in deionized water to prepare a polydimethyl diallyl ammonium chloride aqueous solution with the concentration of 0.26 g/mL;
S3dropwise adding the prepared aqueous solution of the poly-dimethyl-diallyl ammonium chloride into the aqueous solution of AZO while stirring, wherein the mass ratio of the pyridine heterocyclic azobenzene to the poly-dimethyl-diallyl ammonium chloride is 1:10.2, and fully stirring for 24 hours to obtain an assembly solution;
S4removing NaCl in the assembly solution by a multi-dialysis method, and carrying out rotary evaporation and concentration on the dialyzed solution at the temperature of 80 ℃ to obtain a concentrated solution;
S5preparing a concentrated AZO/PDAC solution into a 3 mg/mL aqueous solution, taking 5mL of the solution, adding 0.25 mL of ethanol, mixing uniformly, dropwise adding the solution into a polytetrafluoroethylene mold rinsed with ethanol, slowly volatilizing the solvent at 25 ℃, basically drying, putting the solution into a vacuum oven, drying for 24 hours at 40 ℃, removing the residual solvent in the film, and taking the film out of the mold after complete drying to obtain the supramolecular assembly film material, wherein (a) in figure 1 is an AZO/PDAC film surface microstructure, and (b) is an AZO/PDAC film section microstructure. As can be seen from FIG. 1, the surface of the prepared AZO/PDAC film is continuous, flat and smooth, and no aggregates appear. Meanwhile, the film is cut to have a thickness of about 1.3 μm as measured from the cross section of the film, and then can be used for a multi-stimulus response test. Irradiating the supramolecular assembly film material prepared in the example 1 under ultraviolet light, and obtaining UV-VIS kojiThe line is shown in fig. 4, and the UV-VIS curve of the supramolecular assembly thin film material after UV irradiation is restored in the dark is shown in fig. 5. As can be seen from FIGS. 4 and 5, the UV-VIS absorption spectrum demonstrates that the AZO/PDAC film has stable and recyclable photoisomerization performance and can be stably recycled under the irradiation of ultraviolet light (UV-365 nm) and in a dark environment.
The supramolecular assembly film material prepared in example 1 was more visually observed in figure 6 when irradiated with uv light and allowed to recover in the dark.
Example 2
S1Preparation of pyridine heterocyclic azobenzene AZO, procedure as in example 1;
S2dissolving 1mmol of AZO and 5 mmol of NaOH in 50 mL of deionized water to prepare AZO aqueous solution; dissolving polydimethyl diallyl ammonium chloride in deionized water to prepare a polydimethyl diallyl ammonium chloride aqueous solution with the concentration of 0.5 g/mL;
S3dropwise adding the prepared aqueous solution of the poly dimethyl diallyl ammonium chloride into the aqueous solution of AZO while stirring, wherein the mass ratio of the pyridine heterocyclic azobenzene to the poly dimethyl diallyl ammonium chloride is 1:21.3, and fully stirring for 20 hours to fully complete electrostatic self-assembly of AZO and PDAC to obtain an assembly solution;
S4removing NaCl in the assembly solution by a multi-dialysis method, and carrying out rotary evaporation and concentration on the dialyzed solution at the temperature of 80 ℃ to obtain a concentrated solution;
S5preparing the concentrated AZO/PDAC solution into a 5mg/mL aqueous solution, taking 5mL solution, adding 0.25 mL ethanol, mixing uniformly, dropwise adding into a polytetrafluoroethylene mold rinsed by ethanol, slowly volatilizing the solvent at 25 ℃, basically drying, putting into a vacuum oven, drying at 40 ℃ for 24h, removing residual solvent in the film, completely drying, and taking out the film from the mold to obtain the supramolecular assembly film material.
Example 3
S1Preparation of pyridine heterocyclic azobenzene AZO, procedure as in example 1;
S2dissolving 10mmol of AZO and 50 mmol of NaOH in 100 mL of deionized water to prepare AZO aqueous solution; dissolving polydimethyl diallyl ammonium chloride in deionized water to prepare a polydimethyl diallyl ammonium chloride aqueous solution with the concentration of 1 g/mL;
S3dropwise adding the prepared aqueous solution of the poly dimethyl diallyl ammonium chloride into the aqueous solution of AZO while stirring, wherein the mass ratio of the pyridine heterocyclic azobenzene to the poly dimethyl diallyl ammonium chloride is 1:4.2, and fully stirring for 48 hours to fully complete electrostatic self-assembly of AZO and PDAC to obtain an assembly solution;
S4removing NaCl in the assembly solution by a multi-dialysis method, and carrying out rotary evaporation and concentration on the dialyzed solution at the temperature of 80 ℃ to obtain a concentrated solution;
S5preparing the concentrated AZO/PDAC solution into 1 mg/mL aqueous solution, taking 5mL solution, adding 0.25 mL ethanol, mixing uniformly, dropwise adding into a polytetrafluoroethylene mold rinsed by ethanol, slowly volatilizing the solvent at 25 ℃, basically drying, putting into a vacuum oven, drying at 40 ℃ for 24h, removing residual solvent in the film, completely drying, and taking out the film from the mold to obtain the supramolecular assembly film material.
Example 4
S1Preparation of pyridine heterocyclic azobenzene AZO, procedure as in example 1;
S2dissolving 2mmol of AZO and 4 mmol of NaOH in 20 mL of deionized water to prepare AZO aqueous solution; dissolving polydimethyl diallyl ammonium chloride in deionized water to prepare a polydimethyl diallyl ammonium chloride aqueous solution with the concentration of 0.35 g/mL;
S3dropwise adding the prepared aqueous solution of the poly dimethyl diallyl ammonium chloride into the aqueous solution of AZO while stirring, wherein the mass ratio of the pyridine heterocyclic azobenzene to the poly dimethyl diallyl ammonium chloride is 1:2.7, and fully stirring for 30 hours to fully complete electrostatic self-assembly of AZO and PDAC to obtain an assembly solution;
S4removal of the assembly solution by means of multiple dialysisCarrying out rotary evaporation and concentration on the dialyzed solution at the temperature of 80 ℃ to obtain concentrated solution;
S5preparing the concentrated AZO/PDAC solution into 2.5 mg/mL aqueous solution, taking 5mL solution, adding 0.25 mL ethanol, mixing uniformly, dropwise adding into a polytetrafluoroethylene mold rinsed by ethanol, slowly volatilizing the solvent at 25 ℃, basically drying, putting into a vacuum oven, drying at 40 ℃ for 24h, removing residual solvent in the film, and taking out the film from the mold after complete drying to obtain the supramolecular assembly film material.
Comparative example 1
According to the preparation method of example 1, step S was changed3The mass ratio of the pyridine heterocyclic azobenzene AZO to the poly dimethyl diallyl ammonium chloride is 1:1, and the rest processes are unchanged, so that the supramolecular assembly film material is prepared, and the SEM of the supramolecular assembly film material is shown in figure 2. When the mass ratio of AZO to PDAC is 1:1, the addition amount of PDAC is reduced, the azobenzene proportion is increased, and obvious aggregates appear on the surface of the film, because azobenzene molecules are excessive, and are separated out from the interior of the film in the film forming process and are gathered on the surface. Due to the fact that the azobenzene molecular absorption coefficient is large, when azobenzene aggregates exist on the surface of the film, incident light can be absorbed by the azobenzene on the surface, and the photoresponse performance of the AZO/PDAC film can be affected.
Comparative example 2
According to the preparation method of example 1, step S was changed3The mass ratio of the pyridine heterocyclic azobenzene AZO to the poly dimethyl diallyl ammonium chloride is 1:25, and the rest processes are unchanged, so that the supramolecular assembly film material is prepared, and the SEM of the supramolecular assembly film material is shown in figure 3. In the process of supermolecule assembly of azobenzene and PDAC, the azobenzene addition amount is small, the polymer content is high, the surface of the film is continuous, smooth and flat, and azobenzene aggregates do not appear. However, as can be seen from fig. 7, the film material prepared in comparative example 2 has no obvious capability of responding to ultraviolet rays, when the mass ratio of AZO to PDAC is 1:25, the addition amount of azobenzene is too low, the ultraviolet light responsiveness of the film is obviously reduced, and the film does not show obvious ultraviolet light driving performance under ultraviolet light irradiation.
The principles and embodiments of the present invention have been described herein using specific examples, which are provided only to help understand the method and the core concept of the present invention; meanwhile, for a person skilled in the art, according to the idea of the present invention, the specific embodiments and the application range may be changed. In view of the above, the present disclosure should not be construed as limiting the invention.

Claims (1)

1. A method for preparing a supramolecular assembly film material by using pyridine heterocyclic azobenzene is characterized by comprising the following steps:
S1preparing pyridine heterocyclic azobenzene AZO, comprising the steps of:
S1-1weighing 25 mmol of 5-amino isophthalic acid, dissolving the 5-amino isophthalic acid in 60mL of 0.1 mol/L hydrochloric acid solution, placing the solution in an ice water bath, slowly dripping 25mL of 0.1 mol/L sodium nitrite solution into the 5-amino isophthalic acid salt solution, and stirring the solution at the temperature of 2 ℃ for 3 hours to obtain a diazonium salt solution;
S1-2dissolving 25 mmol of 2, 6-dicarboxylpyridine in 60mL of 0.1 mol/L hydrochloric acid solution, and stirring at 2 ℃ until the 2mmol of 2, 6-dicarboxylpyridine is completely dissolved;
S1-3will step S1-1The prepared diazonium salt solution is slowly dripped into the step S under magnetic stirring1-2Reacting the solution prepared in the step (1) for 4 hours at the temperature of 2 ℃; adjusting the solution to be neutral by using saturated sodium carbonate and deionized water, carrying out suction filtration on the product, washing a filter cake by using the deionized water, drying the washed filter cake for 24 hours at 40 ℃ in vacuum to obtain a crude product, finally recrystallizing the crude product by using an ethanol/water mixed solution, and carrying out separation and purification by using a silica gel column chromatography to obtain pyridine heterocyclic azobenzene AZO;
S2will step S1Dissolving prepared pyridine heterocyclic azobenzene and sodium hydroxide in deionized water according to the molar ratio of 1:1-5 to prepare pyridine heterocyclic azobenzene aqueous solution; simultaneously dissolving the poly-dimethyl diallyl ammonium chloride in deionized water to prepare a poly-dimethyl diallyl ammonium chloride water solution with the concentration of 0.1-1 g/mL;
S3will step S2Dropwise adding the prepared aqueous solution of poly dimethyl diallyl ammonium chloride into the aqueous solution of pyridine heterocyclic azobenzene while stirring, wherein the mass ratio of the pyridine heterocyclic azobenzene to the poly dimethyl diallyl ammonium chloride is 1:2-22, and fully stirring for 20-48h to obtain an assembly solution;
S4will step S3The assembly solution in the step (1) is dialyzed for a plurality of times, NaCl in a reaction system is fully removed, and the dialyzed solution is concentrated by rotary evaporation at the temperature of 80 ℃;
S5preparing the concentrated assembly solution into a self-assembly aqueous solution with the concentration of 1-5mg/mL, then adding ethanol, wherein the volume ratio of the ethanol to the assembly aqueous solution is 1:2, fully and uniformly mixing, then dropwise adding the self-assembly aqueous solution into a polytetrafluoroethylene mold rinsed by the ethanol, firstly placing the mold at 25 ℃ for 5-20h to slowly volatilize the solvent, then placing the mold into a vacuum oven for drying, taking out the film from the mold after completely drying, and preparing the supramolecular assembly film material, wherein the drying temperature is 40 ℃.
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