CN112391047A - Temperature stimulation responsive perylene diimide supramolecular fluorescent gel, preparation method and application - Google Patents
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Abstract
The invention discloses a temperature stimulation responsive perylene diimide supramolecular fluorescent gel, a preparation method and application thereof. Compared with the existing fluorescent material, the perylene diimide supramolecular fluorescent gel obtained by the invention has the advantages of narrow temperature stimulation response performance, good reversible cycle response performance, low input cost, simple synthetic route and the like, is suitable for amplified synthesis and practical production application, and has huge application prospects in the technical fields of medical equipment, quality safety, scientific anti-counterfeiting, environmental science and the like.
Description
Technical Field
The invention belongs to the field of chemical material preparation and temperature sensing materials, and relates to preparation and application of temperature stimulus responsive perylene diimide supramolecular fluorescent gel, in particular to temperature stimulus responsive perylene diimide supramolecular fluorescent gel, and a preparation method and application thereof.
Background
Since Friedlander synthesized perylene diimide compounds for the first time in 1913, perylene diimide compounds are molecules with large pi-pi electron conjugate structures and rigid planes, and are widely applied to the organic dye and paint industries due to excellent dyeing performance and photo-thermal stability. Meanwhile, because the light emitting areas of the compounds are positioned in a visible light area and have the characteristics of extremely high fluorescence quantum efficiency (close to 100%) and the like, the synthesis, performance research and application of the compounds become hot spots in the research field, and especially the research in a plurality of fields such as organic field effect transistors, solar cells, electroluminescent diodes, biology and the like is more concerned. In recent years, research on perylene diimides has begun to relate to the field of molecular aggregates, and research on their self-assembling supramolecular aggregates has become a recent hotspot. When the concentration of the PDI solution is increased, pi-pi stacking is easily formed between aromatic nuclei, and the solution can self-assemble to form aggregates which are mainly divided into H-aggregation and J-aggregation. The aggregate formation has great influence on the light emitting property of PDI, and a series of materials with different light emitting properties can be obtained by adjusting the self-assembly behavior of PDI. Therefore, the perylene diimide supramolecular polymer is designed and synthesized, and the multifunctional supramolecular fluorescent self-assembly material with special laser responsiveness is expected to be obtained.
Due to the dynamic reversible characteristic of non-covalent bond interaction in the supermolecule assembly, the supermolecule assembly is endowed with very special properties, such as cyclability, stimulus responsiveness, self-repairability and the like. However, the non-covalent bond property of supramolecules is still required to be explored by researchers for designing and synthesizing temperature stimulus responsive fluorescent materials. The application generates perylene diimide supermolecule UPy-TEGPDI-UPy by click chemical reaction of 2-ureido-4 [1H ] -pyrimidone sulfydryl derivative UPy-SH capable of forming quadruple hydrogen bonds and perylene diimide compound DAC-TEGPDI, the solubility of the perylene diimide supermolecule with amphiphilic groups in water is increased, self-assembly of the perylene diimide supermolecule into fluorescent nanoparticles in a mixed solution of N, N-dimethylformamide and water is facilitated, gel prepared based on the nanoparticles and PEG has high-sensitivity stimulus response performance to temperature, and temperature change between 20 ℃ and 45 ℃ can be detected through change of fluorescence. The temperature stimulation responsive supramolecular fluorescent nanomaterial has a good application prospect in the fields of biomedicine, intelligent sensing materials and the like.
The present invention has been made in view of this situation.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the temperature stimulation responsive perylene diimide supramolecular fluorescent gel and the preparation method and application thereof.
In order to solve the technical problems, the invention adopts the technical scheme that:
the temperature stimulation responsive perylene diimide supramolecular fluorescent gel is formed by self-assembling polyethylene glycol and perylene diimide supramolecules in a certain proportion in a mixed solvent of N, N-dimethylformamide and water, wherein the structural formula of the perylene diimide supramolecules is as follows:
a preparation method of temperature stimulus responsive perylene diimide supramolecular fluorescent gel comprises the following steps:
(1) sequentially adding 3,4,9, 10-tetracarboxylic anhydride and 1-amino-3, 6, 9-trioxa-11-undecanol serving as raw materials into N, N-dimethylformamide, heating and refluxing for 20 hours, concentrating after reaction, precipitating in petroleum ether, dissolving by using chloroform, filtering, concentrating, and drying in vacuum to obtain a dark red solid, thereby obtaining N, N' -bis (2- (2- (2-hydroxyethoxy) ethyl) perylene diimide TEGPDI with two hydroxyl groups at two ends. TEGPDI and acryloyl chloride are added into dry dichloromethane at 0 ℃, triethylamine acid-binding agent is added, reaction is carried out for 12 hours at room temperature, after the reaction is finished, the obtained mixture is concentrated, and then column purification is carried out by using a mixed solvent of dichloromethane and anhydrous methanol as an eluent, so as to obtain a deep red solid, namely the perylene diimide compound DAC-TEGPDI esterified at two ends.
(2) Respectively adding products DAC-TEGPDI and 1- (6- (heptane-3-yl) -4-oxyl-1, 4-dihydropyrimidine-2-yl) -3- (2-thioethyl) urea UPy-SH into dichloromethane, adding triethylamine catalyst, reacting at room temperature, and after the reaction is finished, using a mixed solvent of dichloromethane and anhydrous methanol as an eluent to pass through a column for purification to obtain red solid, namely the perylene diimide supermolecule UPy-TEGPDI-UPy.
(3) And (3) self-assembling UPy-TEGPDI-UPy in a solution with the volume ratio of N, N-dimethylformamide DMF to water being 1: 0-1: 9 to form the temperature stimulus responsive perylene diimide supramolecular fluorescent nanoparticles.
(4) Adding UPy-TEGPDI-UPy with the molar ratio of 1: 1.1-1.8 and polyethylene glycol PEG with the molecular weight of 10000 into DMF and water in a volume ratio of 1: 1-1.5 of the solution to form the temperature stimulation responsive perylene diimide supramolecular fluorescent gel.
The perylene diimide supramolecular UPy-TEGPDI-UPy prepared by the preparation method has the following specific reaction process:
the temperature stimulation responsive perylene diimide supramolecular fluorescent gel prepared by the preparation method is applied to temperature sensing.
After the technical scheme is adopted, compared with the prior art, the invention has the following beneficial effects.
The invention takes UPy-TEGPDI-UPy as the ratio of DMF to water by volume as 1: 0-1: 9, the perylene diimide supermolecule fluorescent nanoparticles are formed by self-assembly in the solution, the fluorescence of the solution is changed from yellow green to red, the fluorescence at 542nm is quenched, and the fluorescence at 645nm is gradually enhanced.
UPy-TEGPDI-UPy the volume ratio of DMF to water was 1: self-assembling in the solution of 1-1.5 to form perylene diimide supramolecular fluorescent nanoparticles which show red fluorescence. The solution was heated from 20 ℃ to 80 ℃ and the fluorescence changed from red to yellow-green. The fluorescence intensity gradually decreased at 645nm and increased at 542 nm.
Adding a certain amount of polyethylene glycol PEG with the molecular weight of 10000 and UPy-TEGPDI-UPy into DMF and water in a volume ratio of 1: 1-1.5, heating to 45 ℃ to form a solution, and cooling to 20 ℃ to form perylene diimide supramolecular fluorescent gel, wherein the fluorescence of the perylene diimide supramolecular fluorescent gel changes from light red to yellow green along with the increase of the temperature. The fluorescence intensity at 542nm is gradually enhanced, the fluorescence is slowly enhanced within the range of 20-37 ℃, and the fluorescence can generate a sudden increase phenomenon at 37-39 ℃.
The invention provides a preparation method and application of temperature stimulus responsive perylene diimide supramolecular fluorescent gel, and the perylene diimide supramolecular fluorescent gel has high-sensitivity reversible temperature stimulus responsive fluorescence change and is expected to be widely applied in the fields of biological medicines, intelligent materials and the like.
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the invention and together with the description serve to explain the invention without limiting the invention to its proper form. It is obvious that the drawings in the following description are only some embodiments, and that for a person skilled in the art, other drawings can be derived from them without inventive effort. In the drawings:
FIG. 1 is a UPy-TEGPDI-UPy mass spectrum prepared.
FIG. 2 is an ultraviolet-visible absorption spectrum of a perylene diimide supramolecular fluorescent nanoparticle solution.
FIG. 3 is a fluorescence emission spectrum of the perylene diimide supramolecular fluorescent nanoparticle solution.
FIG. 4 is a schematic diagram of the particle size of the perylene diimide supramolecular fluorescent nanoparticles.
FIG. 5 is a schematic diagram of the change of the fluorescence of the perylene diimide supramolecular fluorescent nanoparticle solution with the temperature.
FIG. 6 is a graph showing the change of fluorescence emission spectra of perylene diimide supramolecular fluorescent gel with temperature.
FIG. 7 is a broken line diagram showing the change of fluorescence emission intensity of the perylene diimide supramolecular fluorescent gel at 542nm with temperature.
FIG. 8 is a schematic diagram of reversible change of fluorescence at 542nm of perylene diimide supramolecular fluorescent gel under temperature stimulation.
FIG. 9 is a diagram of the perylene diimide supramolecular fluorescent gel as a function of temperature.
It should be noted that the drawings and the description are not intended to limit the scope of the inventive concept in any way, but to illustrate it by a person skilled in the art with reference to specific embodiments.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and the following embodiments are used for illustrating the present invention and are not intended to limit the scope of the present invention.
Example 1: preparation of perylene diimide supermolecule UPy-TEGPDI-UPy
The method comprises the following specific steps:
(1) 3,4,9, 10-tetracarboxylic anhydride (0.8g, 2.04mmol) and 1-amino-3, 6, 9-trioxa-11-undecanol (1.0g, 5.17mmol) were added to a 25mL two-neck round-bottom flask in this order, 10mLN, N-dimethylformamide was added, heating and refluxing were carried out for 20 hours, concentration was carried out after reaction, precipitation was carried out in petroleum ether, dissolution with chloroform, filtration, concentration and vacuum drying were carried out to obtain a deep red solid, and the perylene imide compound TEGPDI (1.4g, 92% yield) having hydroxyl groups at both ends was obtained.
(2) A1000 mL single neck round bottom flask was prepared, and the compound TEGPDI (742mg, 1mmol) was dissolved in 500mL of anhydrous dichloromethane, placed at 0 ℃ and then acryloyl chloride (226.275mg, 2.5mmol) and triethylamine (500. mu.L, 3.60mmol) were added in that order, and after the addition was complete, the reaction was stirred at room temperature for 24 hours. After completion of the reaction, the resulting mixture was concentrated and purified by column chromatography using dichloromethane and anhydrous methanol (v: v ═ 50:1) as eluent, and dried in vacuo to give DAC-TEGPDI (286mg, 34% yield) as a dark red solid.
(3) The product DAC-TEGPDI (286mg, 0.34mmol) and the mercapto derivative UPy-SH (316mg, 1mmol) of 2-ureido-4 [1H ] -pyrimidinone were added to 20ml of dichloromethane, and triethylamine (100 μ L, 0.71mmol) was further added, respectively, to carry out a reaction at room temperature, and after completion of the reaction, the resulting mixture was concentrated and then purified by column chromatography using dichloromethane and anhydrous methanol (v: v ═ 100:1) as eluents to give UPy-TEGPDI-UPy (102mg, yield 20%) as a red solid.
Example 2: preparation of perylene diimide supermolecule fluorescent nano particle
UPy-TEGPDI-UPy prepared in example 1 was prepared as a 1mM DMF solution, 150. mu.L was added to the sample bottle, and 1.35mL of DMF was added. Then 1.5mL of pure water is slowly added to prepare the UPy-TEGPDI-UPy fluorescent nanoparticles, and the fluorescence color of the solution is red.
Example 3: ultraviolet-visible absorption spectrum and fluorescence spectrum test of perylene diimide supramolecular fluorescent nanoparticles
The solution of example 2 was tested for uv-vis absorption spectra of DMF solutions of the same concentration as UPy-TEGPDI-UPy and it can be seen from figure 2 that the absorption of the nanoparticles is significantly blue-shifted and significant pi-pi stacking occurs. When the fluorescence emission spectrum is measured, as can be seen from fig. 3, the fluorescence intensity of the nanoparticles at 542nm is obviously reduced, the fluorescence at 645nm and red is obviously enhanced, and the fluorescence colors of the solution are respectively yellow green and red.
Example 4: and (3) testing the particle size of the perylene diimide supramolecular fluorescent nanoparticles.
The sample of example 2 was subjected to a particle size test using 1mL of the solution, and as can be seen from fig. 4, the average particle size of the perylene diimide supramolecular fluorescent nanoparticles was 231.6 nm.
Example 5: and (3) testing the change of the temperature on the fluorescence responsiveness of the perylene diimide supermolecule fluorescent nanoparticle solution.
3ml of the same solution as in example 2 was prepared, and the fluorescence emission spectra thereof at 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃ and 70 ℃ were measured, and as can be seen from FIG. 5, the fluorescence intensity at 645nm slightly decreased with the temperature increase, while the fluorescence at 542nm increased significantly, and the fluorescence color of the solution changed from red to yellow-green.
Example 5: preparation of perylene diimide supramolecular fluorescent gel
0.7g of PEG-10000 was added to the same solution as in example 2, heated to 45 ℃ to fully dissolve it, and cooled to 20 ℃ to form perylene diimide supramolecular fluorescent gel.
Example 6: testing the Effect of temperature on fluorescence of gels
When the change of the fluorescence with the temperature is measured, the fluorescence intensity is gradually enhanced at 542 as can be seen from fig. 6, the fluorescence at 542nm within the range of 20-37 ℃ is slowly enhanced as can be seen from fig. 7, the gel is changed from a solid state to a liquid state at 37-39 ℃, the fluorescence at 542nm generates a sudden increase phenomenon, and the fluorescence color is changed from light red to yellow green at 20-39 ℃. As can be seen from FIG. 8, this gel has a very good reversible cycling temperature stimulus responsiveness. Fig. 9 shows a real graph of fluorescence of the bracelet prepared using the gel as a function of temperature.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (5)
1. The temperature stimulation responsive perylene diimide supramolecular fluorescence gel is characterized by being formed by self-assembling polyethylene glycol and perylene diimide supramolecules in a certain proportion in a mixed solvent of N, N-dimethylformamide and water, wherein the perylene diimide supramolecules simultaneously have hydrophilic and hydrophobic groups, and the structural formula of the perylene diimide supramolecules is as follows:
2. a preparation method of temperature stimulus responsive perylene diimide supramolecular fluorescent gel is characterized by comprising the following steps:
(1) heating and refluxing 3,4,9, 10-tetracarboxylic anhydride and 1-amino-3, 6, 9-trioxa-11-undecanol serving as raw materials in N, N-dimethylformamide, separating and purifying to obtain N, N' -bis (2- (2- (2-hydroxyethoxy) ethyl) perylene diimide TEGPDI with two hydroxyl ends, carrying out esterification reaction on the TEGPDI and acryloyl chloride in dry dichloromethane and under the condition of triethylamine acid-binding agent, and separating and purifying to obtain a perylene diimide compound DAC-TEGPDI with two esterified ends;
(2) performing click chemical reaction on the product DAC-TEGPDI and 1- (6- (heptane-3-yl) -4-oxyl-1, 4-dihydropyrimidine-2-yl) -3- (2-thioethyl) urea UPy-SH in dichloromethane under the condition of triethylamine catalyst, and separating and purifying to obtain perylene diimide supermolecule UPy-TEGPDI-UPy;
(3) self-assembling UPy-TEGPDI-UPy in a solution with the volume ratio of N, N-dimethylformamide DMF to water being 1: 0-1: 9 to form temperature stimulus responsive perylene diimide supramolecular fluorescent nanoparticles;
(4) adding a certain amount of UPy-TEGPDI-UPy and polyethylene glycol PEG with the molecular weight of 10000 into DMF and water in a volume ratio of 1: 1-1.5 of the solution to form the temperature stimulation responsive perylene diimide supramolecular fluorescent gel.
3. The preparation method of the temperature stimulus-responsive perylene diimide supramolecular fluorescent nanoparticle gel as claimed in claim 2, wherein the molar ratio of the perylene diimide compound, 1- (6- (heptane-3-yl) -4-oxo-1, 4-dihydropyrimidin-2-yl) -3- (2-thioethyl) urea and triethylamine in the step (2) is 1: 1-4: 2-5.
4. The preparation method of the temperature stimulus-responsive perylene diimide supramolecular fluorescent nanoparticle gel as claimed in claim 2, wherein the molar ratio of the perylene diimide supramolecular UPy-TEGPDI-UPy and polyethylene glycol PEG used in the step (4) is 1: 1.1-1.8.
5. Use of the temperature stimulus-responsive perylene diimide supramolecular fluorescent gel according to claim 1 or prepared by the method according to any one of claims 2 to 4 in temperature sensing.
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| CN113072696A (en) * | 2021-04-28 | 2021-07-06 | 河南农业大学 | Preparation method of linear-annular reversible topological structure polymer |
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