CN114539140B - Preparation method of AIE nano-particles and visual detection ammonia gas decal - Google Patents

Preparation method of AIE nano-particles and visual detection ammonia gas decal Download PDF

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CN114539140B
CN114539140B CN202210060697.6A CN202210060697A CN114539140B CN 114539140 B CN114539140 B CN 114539140B CN 202210060697 A CN202210060697 A CN 202210060697A CN 114539140 B CN114539140 B CN 114539140B
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sticker
aie
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ammonia
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CN114539140A (en
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姜慧娥
陈立娟
刘新华
李尼浩
赵素秋
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Shaanxi University of Science and Technology
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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
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    • G01N21/64—Fluorescence; Phosphorescence
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Abstract

The invention discloses an AIE nanoparticle, which is prepared by firstly reacting 2, 6-diformyl-4-methylphenol and isoniazid according to a certain mass ratio under specific conditions, then self-assembling the product in a mixed solution of DMF and water to form the fluorescent nanoparticle, and preparing the fluorescent nanoparticle with aggregation-induced emission (AIE) property at low cost, wherein the fluorescent intensity of the nanoparticle is gradually enhanced along with the increase of water content. Then, the conventionally used sticker is immersed in the fluorescent nanoparticle solution to prepare the visible real-time ammonia monitoring sticker, and the material can quantitatively detect NH 3 The method has the advantages of simple preparation method, high sensitivity to ammonia gas detection, convenience and quickness, good selectivity, real-time detection, short response time, high accuracy and the like, and can be widely applied to real-time monitoring such as food preservation, environmental safety and the like.

Description

Preparation method of AIE nano-particles and visual detection ammonia gas decal
Technical Field
The invention belongs to the technical field of biomass functional materials for gas detection, relates to AIE nano-particles, and also relates to a method for preparing a visual detection ammonia gas sticker by using the nano-particles.
Background
Ammonia (NH) 3 ) Is an organic volatile gas which is used as a signal of vertebrate thyroid hormone regulation process to influence the development of organisms and central nervous systems, and ammonia is widely applied to fields such as chemical fertilizers, explosives, refrigerants, medicines, synthetic fibers, dyes and the like as a chemical intermediate to be widely applied to textiles and foodIndustrial processes for the production of products, polymers, explosives, fertilizers, detergents and pharmaceuticals. At the same time, ammonia is a great potential hazard to humans. For example, exposure of the human body to ammonia gas environment is prone to stimulate permanent adverse damage to respiratory tract mucous membranes, even inhalation of low concentration ammonia can poison the human body, and life safety can be threatened when serious; ammonia can cause overgrowth of aquatic plants and further harm the environment; ammonia in the atmosphere seriously affects PM2.5 and acid rain, so that air pollution is increasingly serious, and the sustainable development of society is restricted to be countless in annual fire, explosion and poisoning events caused by ammonia leakage. Therefore, detection and measurement of ammonia concentration has attracted considerable attention in many fields. The detection of ammonia has wide application in the industries of pharmacy, agrochemistry, food and the like, and the ammonia sensor is widely applied to the industries of automobiles, environment monitoring, chemical industry and the like. Therefore, the method is convenient, quick and highly selective for detecting the ammonia gas, and has great significance in the aspects of chemical engineering, environmental science, medicine and the like.
Current detection of NH 3 Common methods include gas chromatography and high performance liquid chromatography, however, these methods have some disadvantages such as expensive equipment, slow detection speed, etc. The fluorescence analysis method has the advantages of high sensitivity, convenience, high speed, good selectivity, real-time detection, short response time, high accuracy and the like, and has great application potential in the field of gas analysis.
Aggregation-induced emission (AIE) molecules are often used to prepare fluorescent materials because of their good solid state light emitting effect. Paper is used as biomass material, has the characteristics of wide sources, low price, environmental friendliness and the like, and is widely applied.
Disclosure of Invention
The invention aims to provide an AIE nanoparticle, which is prepared by combining 2, 6-diformyl-4-methylphenol with isoniazid and self-assembling the nano particles in a solution.
The invention aims to provide a preparation method of AIE nano-particles.
It is another object of the present invention to provide a method for preparing a visual inspection ammonia decal using the above nanoparticles.
The first technical scheme adopted by the invention is that the AIE nano-particles are synthesized by the following steps:
the second technical scheme adopted by the invention is that the preparation method of the AIE nano-particles comprises the following specific preparation steps:
step 1, adding 2, 6-diformyl-4-methylphenol, isoniazid and 40-60mL of methanol into a round bottom flask, stirring to dissolve, and refluxing for 5-10 hours at 70 ℃;
step 2, mixing dichloromethane and methanol in a volume ratio of 20:1 to form a mixed solvent as a developing agent, monitoring the reaction progress degree, stopping the reaction in the step 1 until two raw material points disappear, cooling to room temperature, and carrying out suction filtration to obtain a pale yellow powder product; dissolving the pale yellow powder product into a mixed solution of DMF and water to prepare the nano-particles with the concentration of 3mM-10mM, and self-assembling at the temperature of 20-35 ℃.
The fluorescent nanoparticles exhibit AIE properties in a DMF and water mixed solution having a water content of 0% -10%.
The third technical scheme adopted by the invention is that the method for preparing the visual real-time ammonia monitoring sticker by using the AIE nano-particles specifically comprises the following steps:
and (3) immersing the sticker in a fluorescent nanoparticle solution with AIE properties for 2-10 hours, taking out the sticker, and airing at the temperature of 25-35 ℃ to obtain the sticker for visual real-time monitoring of ammonia gas.
Using NH 3 After fumigation, the fluorescence color of the sticker is changed from yellow to orange under a 365nm ultraviolet lamp, and the sticker can be recognized by naked eyes.
NH 3 When the concentration is in the range of 0.5-20ppm, the visualized real-time monitoring of the ammonia gas can be carried out on NH 3 And (5) carrying out quantitative detection.
The beneficial effects of the invention are as follows:
1. the invention provides a preparation method of AIE nano particles, and the prepared fluorescent nano particles avoid the phenomenon that fluorescence is weakened or even quenched when fluorescent molecules are in an aggregation state, and have good solid state light-emitting effect. In addition, the preparation method of the fluorescent nanoparticle with AIE property provided by the invention has the advantages of simple and feasible operation process and high yield.
2. The invention also provides a preparation method of the decal for visually monitoring ammonia in real time. The biomass functional material is prepared by a one-step simple impregnation method. The functional material can quantitatively detect NH through fluorescence spectrum 3 The method has the advantages of simple preparation method, high sensitivity to ammonia gas detection, convenience and quickness, good selectivity, real-time detection, short response time, high accuracy and the like.
Drawings
FIG. 1 is a Scanning Electron Microscope (SEM) image of AIE nanoparticles of the present invention in DMF;
FIG. 2 shows AIE nanoparticles of the invention in DMF-H 2 SEM images in O (9:1, v:v) mixed solution;
FIG. 3 shows AIE nanoparticles of the invention in DMF and H 2 O fluorescence spectrograms in solvents with different proportions;
FIG. 4 is a graph of fluorescence lifetime of AIE nanoparticles of the present invention in DMF;
FIG. 5 is a graph of fluorescence lifetime of AIE nanoparticles of the present invention in the solid state;
FIG. 6 is a graph showing the comparison of fluorescence intensity of a decal for visually monitoring ammonia gas in real time and the material fumigated with different organic amine gases according to the present invention;
FIG. 7 is a graph showing the visual detection of NH at different concentrations of ammonia decal according to the present invention 3 Fluorescence spectrum after fumigation;
FIG. 8 is a photograph of a decal of the present invention visually inspected for ammonia decals under 365nm ultraviolet light;
FIG. 9 is the use of NH 3 The invention visually detects the photo of the ammonia decal after fumigation under the irradiation of 365nm ultraviolet lamp;
FIG. 10 is NH 3 When the concentration is in the range of 0.5-20ppm, the fluorescence intensity and NH of the ammonia decal at 580nm are visually detected 3 Non-linear fit of concentration plots.
Detailed Description
The invention will be described in detail below with reference to the drawings and the detailed description.
The synthesis route of the AIE nanoparticle is as follows:
the preparation method of the fluorescent nanoparticle comprises the following specific steps:
step 1, adding 2, 6-diformyl-4-methylphenol, isoniazid and 40-100mL of methanol into a round bottom flask, stirring to dissolve, and refluxing for 5-10 hours; setting the temperature to 70 ℃ in the step 1;
step 2, mixing dichloromethane and methanol in a volume ratio of 20:1 to form a mixed solvent as a developing agent, monitoring the reaction progress degree, stopping the reaction in the step 1 until two raw material points disappear, cooling to room temperature, and carrying out suction filtration to obtain a pale yellow powder product; dissolving the pale yellow powder product into a mixed solution of DMF and water to prepare the nano-particles with the concentration of 3mM-10mM, and self-assembling at the temperature of 20-35 ℃.
DMF-H with water content of 0% -10% 2 In the O mixed solution, the fluorescent nanoparticles exhibit AIE properties.
The preparation method of the visual detection ammonia gas sticker comprises the following specific steps:
and (3) immersing the conventionally used sticker in the fluorescent nanoparticle solution containing the fluorescent nanoparticle in the step (1) in the technical scheme (1) for 2-10 hours, taking out the sticker, and airing at the temperature of 25-35 ℃ to obtain the visible real-time ammonia monitoring sticker.
Example 1
Synthesis of AIE nanoparticles:
step 1, adding 2, 6-diformyl-4-methylphenol, isoniazid and 40-60mL of methanol into a round bottom flask, stirring to dissolve, and refluxing for 5-10 hours at 70 ℃;
step 2, mixing dichloromethane and methanol in a volume ratio of 20:1 to form a mixed solvent as a developing agent, monitoring the reaction progress degree, stopping the reaction in the step 1 until two raw material points disappear, cooling to room temperature, and carrying out suction filtration to obtain a pale yellow powder product; dissolving the pale yellow powder product into a mixed solution of DMF and water to prepare the nano-particles with the concentration of 3mM-10mM, and self-assembling at the temperature of 20-35 ℃.
Example 2
The pale yellow powder product prepared in example 1 was subjected to nuclear magnetic characterization:
1 H NMR(600MHz,DMSO-d 6 )δ12.38(s,2H),12.22(s,1H),8.81(d,J＝5.3Hz,4H),8.74(s,2H),7.90–7.81(m,4H),7.61(s,2H),2.34(s,3H). 13 C NMR(151MHz,DMSO):δ161.93,155.38,150.87,150.16,147.73,140.44,131.31,128.91,122.00,120.20,20.36.
example 3
Fluorescent nanoparticles in DMF and DMF-H 2 Microcosmic morphology in O (9:1, v:v) mixed solution:
fluorescent nanoparticles were shown as dispersed single particles in pure DMF as shown in fig. 1; in DMF-H 2 In the O (9:1, V:V) mixed solution, the fluorescent nanoparticles were represented in a cluster form as shown in FIG. 2, thereby proving that H was added to DMF solution 2 After O, the fluorescent nanoparticles begin to aggregate.
Example 4
Effect of different water content on fluorescent nanoparticle fluorescence properties:
DMF-H at different water contents 2 In the O mixed solution, 358nm is taken as excitation wavelength, and in the pure DMF solution, the fluorescent nano particles have maximum emission peak at 580nm, and the fluorescence intensity is weaker; when the water content was increased from 0% to 10%, the fluorescence intensity of the fluorescent nanoparticle was gradually increased as the water content in DMF was increased, as shown in fig. 3, thereby illustrating that the fluorescent nanoparticle exhibited AIE characteristics.
Example 5
Quantum yield and fluorescence lifetime of fluorescent nanoparticles in DMF and in solid state:
the quantum yield of the fluorescent nanoparticle in DMF was 0.872, and the fluorescence lifetime was 0.86ns, as shown in fig. 4; the quantum yield of the solid state fluorescent nanoparticle was 13.4% and the fluorescence lifetime was 1.94ns, as shown in fig. 5. From this, it can be demonstrated that the fluorescent nanoparticle has good solid state light emitting properties.
Example 6
Visualized real-time ammonia gas monitoring sticker pair NH 3 Is detected by fluorescence spectrum selectivity;
using p-phenylenediamine (PPDA), 2-nitroaniline (2-NA), 3-nitroaniline (3-NA), triethylamine (TEA), diethylamine (DEA), NH at a mass concentration of 25wt% 2 NH 2 (N 2 H 4 ) Ethylenediamine (EDA) and ammonia (NH) 3 ) The fluorescence intensity contrast chart of the separately fumigated prepared decal is shown in fig. 6: PPDA, 2-NA, 3-NA, TEA, DEA, N 2 H 4 The fluorescence intensity of the decal after EDA fumigation is not obviously changed, and the fluorescence of the decal after ammonia fumigation is obviously enhanced. The results show that the decal can be used for NH in a plurality of organic amine gases 3 High-selectivity identification is performed.
Example 7
Visualized real-time ammonia gas monitoring sticker pair NH 3 Is used for quantitative detection of (a):
NH was used at a concentration of 0ppm, 0.5ppm, 1ppm, 2ppm, 3ppm, 4ppm, 5ppm, 10ppm, 15ppm, 20ppm 3 The decals were fumigated separately and the fluorescence spectrum changes were detected as shown in FIG. 7, along with NH 3 The fluorescence intensity of the sticker is gradually enhanced due to the increase of the concentration; under the irradiation of 365nm ultraviolet lamp, naked eyes can directly observe, as shown in FIG. 8, the sticker presents yellow color; by NH 3 After fumigation, the decal turned orange in color as shown in fig. 9. When NH 3 When the concentration is in the range of 0.5-20ppm, the fluorescence intensity and NH of the sticker 3 The concentration shows good nonlinear relation (R 2 =0.993), as shown in fig. 10, it is demonstrated that the sticker of the present invention can quantitatively detect NH well 3 。

Claims (3)

1. The method for preparing the visual real-time ammonia monitoring sticker by using the fluorescent nano-particles with AIE properties is characterized by comprising the following steps of:
the method specifically comprises the following steps:
immersing the sticker in a fluorescent nanoparticle solution with AIE properties for 2-10 hours, taking out the sticker, and airing at the temperature of 25-35 ℃ to obtain the sticker for visual real-time monitoring of ammonia gas;
fluorescent nanoparticles with AIE properties were synthesized as follows:
in a mixed solution of DMF with water having a water content of 0% -10%, the fluorescent nanoparticles exhibit AIE properties;
the preparation method of the fluorescent nanoparticle with AIE property comprises the following specific preparation steps:
step 1, adding 2, 6-diformyl-4-methylphenol, isoniazid and 40-60mL of methanol into a round bottom flask, stirring to dissolve, and refluxing for 5-10 hours at 70 ℃;
step 2, mixing dichloromethane and methanol in a volume ratio of 20:1 to form a mixed solvent as a developing agent, monitoring the reaction progress degree, stopping the reaction in the step 1 until two raw material points disappear, cooling to room temperature, and carrying out suction filtration to obtain a pale yellow powder product; dissolving the pale yellow powder product into a mixed solution of DMF and water to prepare the nano-particles with the concentration of 3mM-10mM, and self-assembling at the temperature of 20-35 ℃.
2. The detection method for the sticker prepared by the method for preparing the sticker for visually monitoring ammonia in real time by using the fluorescent nanoparticle with AIE property as claimed in claim 1 is characterized in that: using NH 3 After fumigation, the fluorescence color of the sticker is changed from yellow to orange under a 365nm ultraviolet lamp, and the sticker can be recognized by naked eyes.
3. The fluorescent nanoparticle of claim 1 having AIE properties for visualizationThe detection method of the sticker prepared by the method for monitoring ammonia in real time is characterized by comprising the following steps of: NH (NH) 3 When the concentration is in the range of 0.5-20ppm, the visualized real-time ammonia gas monitoring sticker can be used for NH 3 And (5) carrying out quantitative detection.
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CN108191760A (en) * 2018-02-05 2018-06-22 陕西科技大学 For detecting fluorescence probe of Cu (II) and its preparation method and application
CN110003095A (en) * 2019-03-14 2019-07-12 陕西科技大学 Cd with AIE property2+Fluorescence probe and its preparation method and application

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CN108191760A (en) * 2018-02-05 2018-06-22 陕西科技大学 For detecting fluorescence probe of Cu (II) and its preparation method and application
CN110003095A (en) * 2019-03-14 2019-07-12 陕西科技大学 Cd with AIE property2+Fluorescence probe and its preparation method and application

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