CN113637111B - Synthesis of fluorescent hydrogel sensor based on ionic liquid and application of fluorescent hydrogel sensor in detection of p-nitroaniline - Google Patents
Synthesis of fluorescent hydrogel sensor based on ionic liquid and application of fluorescent hydrogel sensor in detection of p-nitroaniline Download PDFInfo
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- CN113637111B CN113637111B CN202110991839.6A CN202110991839A CN113637111B CN 113637111 B CN113637111 B CN 113637111B CN 202110991839 A CN202110991839 A CN 202110991839A CN 113637111 B CN113637111 B CN 113637111B
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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Abstract
The invention discloses synthesis of a fluorescent hydrogel sensor based on ionic liquid and application of the fluorescent hydrogel sensor in detection of paranitroaniline. The material can be used as a fluorescent sensor for rapidly detecting p-nitroaniline, has the advantages of high sensitivity, short detection time, good selectivity and the like, and can be applied to the detection of the p-nitroaniline in environmental domestic water samples.
Description
Technical Field
The invention belongs to the technical field of material chemistry, and relates to a synthetic method of a fluorescent hydrogel sensor based on ionic liquid; the invention also relates to application of the ionic liquid-based fluorescent hydrogel sensor synthesized by the synthesis method in detection of p-nitroaniline.
Background
P-nitroaniline (p-NA) is an important chemical intermediate, is widely used as a dye, a pesticide and a medical intermediate, and can be used for producing an antioxidant, a preservative and the like. In industrial production, p-NA is released into the environment in the form of industrial waste. Since p-NA has good solubility in water, it is easily permeated and accumulated in soil or groundwater. p-NA is highly toxic, mutagenic and carcinogenic. It is not only highly toxic to aquatic organisms, but also harmful to human health, and can be absorbed through skin and respiratory tract, and can cause diseases such as methemoglobinemia and hemolytic anemia. Therefore, the establishment of a method for rapidly, sensitively and selectively determining p-NA is of great significance. At present, the detection methods of p-NA mainly comprise spectrophotometry, surface enhanced Raman spectroscopy, electrochemical methods, fluorescence analysis methods, high performance liquid chromatography and the like. The fluorescence analysis method is simple in detection principle and convenient and fast to operate, and aromatic amine can be detected only through fluorescence enhancement or quenching. However, these methods all have some disadvantages, such as expensive instruments, long time consumption, complicated operation, low accuracy, poor stability, and being not suitable for rapid on-site detection.
The ionic liquid is a liquid ionic compound at room temperature or close to room temperature, and various ionic liquids can be synthesized by designing cations and anions. The organic fluorescent functional group is connected to the anion or cation structure of the alkenyl ionic liquid to prepare the alkenyl fluorescent ionic liquid, and then the polymer with the fluorescent ionic liquid structure is obtained through polymerization reaction. The ionic liquid structure in the polymer can improve the water solubility of the polymer, and is favorable for detecting target molecules in a water sample.
In recent years, among various solid-state sensing materials, flexible fluorescent hydrogel sensors have received increasing attention. This is because the hydrogel acts as a hydrophilic, swellable polymer network that allows the water soluble contaminants to diffuse efficiently into the hydrogel matrix. Furthermore, by appropriate molecular design, their chemical and physical properties can be fine-tuned to further enhance the binding affinity to the target molecule. Therefore, the flexible hydrogel chemical sensors can solve the problem of detection sensitivity limitation caused by the diffusion resistance and slow diffusion of water samples in the conventional hydrophobic and compact sensing membrane, so that high detection sensitivity is generated.
On the other hand, paper/textile based flexible fluorescent sensors are also receiving increasing attention due to their unique properties. The interwoven fibers of paper and textile can impart a layered porous structure to the prepared fluorescent sensor, which facilitates rapid and spontaneous capillary force driven diffusion of test samples in water. This capability may address some of the disadvantages of conventional rigid sensors, particularly sensitivity limitations due to hindered diffusion of contaminants in conventional dense thin film materials.
Disclosure of Invention
One of the purposes of the invention is to provide a synthesis method of the fluorescent hydrogel sensor based on the ionic liquid, the synthesis method is simple, and the product is prepared in one step.
The invention also aims to provide application of the fluorescent hydrogel sensor synthesized by the synthesis method in rapid and sensitive detection of p-nitroaniline.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a synthetic method of a fluorescent hydrogel sensor based on ionic liquid comprises the following specific steps:
1) adding 300-600 mg of hydroxyethyl methacrylate, 10-20 mg of 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride, 3.5-7 mg of N, N '-methylene bisacrylamide and 4-8 mg of azobisisobutyronitrile into 5-20 mL of an organic solvent, and taking the hydroxyethyl methacrylate, the 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride, the N, N' -methylene bisacrylamide and the azobisisobutyronitrile respectively; the mass ratio of the hydroxyethyl methacrylate to the 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride is 30: 1, and the molar amount of the N, N' -methylene bisacrylamide and the molar amount of the azobisisobutyronitrile are both 0.1-1% of the molar amount of the 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride monomer;
2) adding hydroxyethyl methacrylate, N' -methylene bisacrylamide, azobisisobutyronitrile and 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride into an organic solvent, carrying out ultrasonic treatment for 10min, pouring into a flask, adding a substrate material, vacuumizing and filling argon, carrying out three-time circular degassing, purging with argon, sealing the flask, and reacting in an oil bath at the temperature of 60-100 ℃ for 8-24H; and sequentially washing with ethanol, dimethyl sulfoxide and deionized water, and carrying out vacuum drying to synthesize the fluorescent hydrogel sensor.
The organic solvent adopts dimethyl sulfoxide or ethanol.
The base material is paper or textile.
According to the synthesis method, hydroxyethyl methacrylate, N' -methylene bisacrylamide, a fluorescent ionic liquid monomer and an initiator (azobisisobutyronitrile) are dissolved in dimethyl sulfoxide to prepare a mixed solution, the mixed solution is adsorbed on a substrate material, in-situ crosslinking polymerization is carried out under the heating condition, and the fluorescent hydrogel sensor is synthesized after washing and drying. The hydrogel sensor can be used as a fluorescence sensor for rapidly detecting p-nitroaniline, has the advantages of high sensitivity, short detection time, good selectivity and the like, and can be applied to the detection of the p-nitroaniline in environmental domestic water samples.
The fluorescent hydrogel sensor takes fluorescent ionic liquid as a functional monomer, and is polymerized with hydroxyethyl methacrylate and N, N' -methylene bisacrylamide serving as a cross-linking agent on a substrate material under the heating condition, so that a hydrogel network is wrapped on a fiber network of the substrate material, and the fluorescent hydrogel sensor capable of rapidly and sensitively detecting the paranitroaniline in a water sample is obtained.
The other technical scheme adopted by the invention is as follows: an application of the fluorescent hydrogel sensor synthesized by the synthesis method in detecting p-nitroaniline. The method specifically comprises the following steps: and dripping the p-nitroaniline solution with different concentrations onto the fluorescent hydrogel sensor, quenching the fluorescence of the sensor, and measuring the luminous intensity of the fluorescent hydrogel sensor to determine the content of the p-nitroaniline.
The invention synthesizes the fluorescent hydrogel sensor by taking the ionic liquid as the main raw material, and is applied to the detection of the paranitroaniline. The fluorescent hydrogel sensor has simple and convenient synthesis method, hydrophilic performance, can be used for detecting p-nitroaniline in a water sample, and has the advantages of easy operation, high sensitivity, short detection time, good selectivity and the like, and the detection limit is 36.23 nM.
Drawings
FIG. 1 is a microscopic electron micrograph of the fluorescent hydrogel sensor synthesized in example 1.
FIG. 2 is a partially enlarged microscopic electron micrograph of the fluorescent hydrogel sensor synthesized in example 1.
FIG. 3 is an infrared spectrum of the fluorescent hydrogel sensor synthesized in example 1.
FIG. 4 is a graph showing the response time of the fluorescent hydrogel sensor synthesized in example 1 to paranitroaniline.
FIG. 5 is a fluorescence spectrum of the fluorescent hydrogel sensor synthesized in example 1 in p-nitroaniline solutions of different concentrations.
Detailed Description
The invention is further described with reference to the following figures and detailed description.
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
Example 1
Weighing 300mg of hydroxyethyl methacrylate, 3.5mg of N, N' -methylenebisacrylamide, 4mg of azobisisobutyronitrile, 10 mg of 3- (anthracen-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride, adding into 10mL of dimethyl sulfoxide, performing ultrasonic treatment for 10min, adding into a flask, and adding blank paper; vacuumizing and filling argon, carrying out three-time circular degassing, purging with argon, sealing the flask, and placing the flask in an oil bath kettle at the temperature of 80 ℃ for reacting for 15 hours; and sequentially washing with ethanol, dimethyl sulfoxide and deionized water, and carrying out vacuum drying to synthesize the fluorescent hydrogel sensor.
1. Microscopic morphology of fluorescent hydrogel sensors.
Microscopic morphology: the microscopic morphology of the fluorescent hydrogel sensor synthesized in example 1 was observed by a scanning electron microscope, and as shown in fig. 1 and 2, the fiber network structure of the filter paper was wrapped with a hydrogel-like substance. Indicating that the fluorescent hydrogel had been successfully coated onto the filter paper fibers to form multiple cross-linked networks.
2. Infrared spectrogram of fluorescent hydrogel sensor
The infrared spectrum of the fluorescent hydrogel sensor synthesized in example 1 is shown in fig. 3. At 1161cm -1 And 1426cm -1 The bending vibration peak of the functional monomer imidazole group proves that the fluorescent hydrogel is successfully coated on the filter paper fiber.
The fluorescent hydrogel sensor synthesized in example 1 detects p-nitroaniline;
1) response time of fluorescent hydrogel sensor to paranitroaniline
The fluorescent hydrogel sensor synthesized in example 1 was added to a concentration of 10 -3 M in p-nitroaniline, and performing fluorescence measurement. As shown in fig. 4, the fluorescence intensity of the fluorescent hydrogel sensor rapidly dropped within 5 minutes, after which the curve substantially equilibrated. Indicating that the fluorescent hydrogel sensor can rapidly respond to paranitroaniline.
2) Fluorescence spectra of fluorescent hydrogel sensors in p-nitroaniline (p-NA) solutions of different concentrations
Eight portions of the fluorescent hydrogel sensor synthesized in example 1 were added with 0M p-NA in the first portion and 10 in the second portion -2 p-NA of M, third portion 10 -3 p-NA of M, fourth portion 10 -4 p-NA of M, fifth portion 10 -5 p-NA of M, sixth portion 10 -6 p-NA of M, seventh 10 -7 p-NA of M, 10 in the eighth portion -8 The change in fluorescence spectrum measured for p-NA of M is shown in FIG. 5. As can be seen in FIG. 5, the fluorescence intensity of the fluorescent hydrogel sensor continuously decreases as the concentration of p-NA increases. The fluorescent hydrogel sensor can effectively detect the paranitroaniline, and even trace paranitroaniline can be quickly detected.
Example 2
Weighing 600mg of hydroxyethyl methacrylate, 7mg of N, N' -methylenebisacrylamide, 8mg of azobisisobutyronitrile, and 20mg of 3- (anthracen-9-ylmethyl) -1-vinyl-1H-imidazol-3-ium chloride, adding into 20mL of dimethyl sulfoxide, performing ultrasonic treatment for 10min, adding into a flask, and adding a textile; vacuumizing and filling argon, carrying out three-time circular degassing, purging with argon, sealing the flask, and placing the flask in an oil bath kettle at the temperature of 60 ℃ for reaction for 24 hours; and sequentially washing with ethanol, dimethyl sulfoxide and deionized water, and carrying out vacuum drying to synthesize the fluorescent hydrogel sensor.
Example 3
Weighing 450mg of hydroxyethyl methacrylate, 5.25mg of N, N' -methylenebisacrylamide, 6mg of azobisisobutyronitrile and 15 mg of 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride, adding into 7.5mL of dimethyl sulfoxide, performing ultrasonic treatment for 10min, adding into a flask, and adding a textile; vacuumizing and filling argon, carrying out three-time circular degassing, purging with argon, sealing the flask, and placing the flask in an oil bath kettle at the temperature of 100 ℃ for reacting for 8 hours; and sequentially washing with ethanol, dimethyl sulfoxide and deionized water, and carrying out vacuum drying to synthesize the fluorescent hydrogel sensor.
Claims (5)
1. A synthetic method of a fluorescent hydrogel sensor is characterized by comprising the following steps: the synthesis method specifically comprises the following steps:
1) adding 300-600 mg of hydroxyethyl methacrylate, 10-20 mg of 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride, 3.5-7 mg of N, N '-methylene bisacrylamide and 4-8 mg of azobisisobutyronitrile into 5-20 mL of an organic solvent, and taking the hydroxyethyl methacrylate, the 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride, the N, N' -methylene bisacrylamide and the azobisisobutyronitrile respectively; the mass ratio of the hydroxyethyl methacrylate to the 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride is 30: 1, and the molar amount of the N, N' -methylene bisacrylamide and the molar amount of the azobisisobutyronitrile are both 0.1-1% of the molar amount of the 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride monomer;
2) adding hydroxyethyl methacrylate, N' -methylene bisacrylamide, azobisisobutyronitrile and 3- (anthracene-9-ylmethyl) -1-vinyl-1H-imidazole-3-onium chloride into an organic solvent, ultrasonically pouring into a container, adding a substrate material, vacuumizing and filling argon, circularly degassing, purging with argon, sealing the container, and reacting in an oil bath at the temperature of 60-100 ℃ for 8-24 hours; and washing, vacuum drying and synthesizing the fluorescent hydrogel sensor.
2. The method of claim 1, wherein the organic solvent is selected from the group consisting of dimethylsulfoxide and ethanol.
3. The method of claim 1, wherein the substrate material is paper or a textile.
4. The method for synthesizing a fluorescent hydrogel sensor according to claim 1, wherein in the step 2), after the reaction is completed, the reaction solution is sequentially washed with ethanol, dimethyl sulfoxide and deionized water.
5. The method for synthesizing the fluorescent hydrogel sensor according to claim 1, wherein the fluorescent hydrogel sensor is used for detecting p-nitroaniline.
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| US7497993B1 (en) * | 2004-09-07 | 2009-03-03 | The United States Of America As Represented By The United States Department Of Energy | Fluorescent temperature sensor |
| CN105524288A (en) * | 2015-12-16 | 2016-04-27 | 浙江大学 | Quantum dot-doped polyion liquid-polyacrylamide interpenetrating network hydrogel and preparation method thereof |
| CN108707209A (en) * | 2018-05-17 | 2018-10-26 | 辽宁大学 | The preparation method and its swellability of response polymeric ionic liquid hydrogel are tested |
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