CN115368636B - Aerogel composite material loaded with fluorescent probes and preparation method and application thereof - Google Patents
Aerogel composite material loaded with fluorescent probes and preparation method and application thereof Download PDFInfo
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Abstract
The application discloses a fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material, a preparation method thereof and application thereof in formaldehyde detection, wherein the fluorescent probe-loaded aerogel composite material for detecting formaldehyde consists of a formaldehyde response type fluorescent probe, chitosan and cellulose; the structural formula of the formaldehyde response type fluorescent probe is as follows:the fluorescent probe loaded aerogel composite material prepared by the application has high sensitivity for detecting formaldehyde in air, obvious phenomenon, convenient identification, wide raw material source, large earth storage capacity, green and recoverable property, simple preparation method, high yield and large-scale production.
Description
Technical Field
The application belongs to the technical field of fluorescence detection, and can realize detection of formaldehyde in the environment, in particular relates to a waste cotton regenerated cellulose aerogel composite material loaded with a fluorescent probe, a preparation method thereof and application thereof in formaldehyde detection.
Background
Formaldehyde is one of the harmful gases in newly decorated rooms to the human body, mainly released from formaldehyde resin-containing materials such as: wall paint is used as adhesive in door, kitchen and furniture, cellulose board, plywood, shaving board and other wood products. Formaldehyde and toxic carcinogens have long been classified as a class. It is well known that small amounts of formaldehyde can cause irritation to the eyes, nose and upper and lower respiratory tracts. Prolonged exposure to formaldehyde induces leukemias and pulmonary inflammation, and also contributes to exacerbation of asthma. Therefore, the formaldehyde content is limited to 0.08 mg/m according to the normal value of formaldehyde in the relevant regulated room 3 Within the inner part. Therefore, an effective and convenient method for detecting formaldehyde in a room is highly desired.
Methods for detecting formaldehyde in air include electrochemical biosensors, gas chromatography, X-ray diffraction, and other methods. In recent years, fluorescent probes have been receiving high attention as an excellent detection technique because of their high selectivity and ease of use, and have been widely used for detection of various substances. In general, the detection result of a fluorescent probe is changed by the probe concentration, excitation intensity and emission collection efficiency. In contrast, the ratio-type fluorescent probe has two fluorescent signals, and the interference of factors such as probe concentration, excitation intensity, emission acquisition efficiency and the like on the probe can be reduced to the greatest extent. Currently, there are few fluorescent probes for detection that have been disclosed, and most require the use of other adsorptive carrier materials, which are inconvenient to use.
Chitosan and cellulose are natural high molecular compounds which are low in cost, renewable and rich in earth storage resources. Aerogel itself has the characteristics of porous network structure, high specific surface area, high porosity, low density, high adsorptivity, etc., and is applied to the aspects of environment, energy sources, buildings, etc. Therefore, chitosan and cellulose are selected to prepare aerogel through physical crosslinking, so that the aerogel is degradable after being used, and has the characteristics of aerogel while protecting environment.
Therefore, it is of great importance to develop a material which is degradable, environment-friendly and can effectively avoid interference of other factors with formaldehyde in the air.
Disclosure of Invention
Aiming at the defects that a fluorescent probe for detecting formaldehyde in air in the prior art is inconvenient to use, low in sensitivity, incapable of being recycled, and influenced by volatile organic compounds, the application provides a waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe, a preparation method thereof and application of the composite material in formaldehyde detection. The cellulose source and the regenerated cellulose of the waste cotton textiles have the characteristics of being green, environment-friendly, beneficial to reducing carbon emission and the like.
The application is realized by the following technical scheme:
a regenerated cellulose aerogel composite material of waste cotton loaded with fluorescent probes is composed of formaldehyde response type fluorescent probes, chitosan and cellulose;
the structural formula of the formaldehyde response type fluorescent probe is as follows:。
further, the mass ratio of the formaldehyde response fluorescent probe to the chitosan to the cellulose is 1:100:200-1000.
Further, the cellulose is the cellulose of regenerated cotton fibers of waste cotton textiles.
In the application, the preparation method of the formaldehyde-detecting supported fluorescent probe aerogel composite material comprises the following steps:
(1) Dissolving a formaldehyde response type fluorescent probe into methanol to obtain a solution 1;
(2) Adding chitosan into acetic acid solution, heating and stirring until the chitosan is dissolved, and regulating the pH value to be neutral to obtain solution 2;
(3) Placing cellulose into water and sodium periodate solution, adding glycol after light-shielding heating reaction, continuing the reaction, washing with water after the reaction is finished, and removing supernatant to obtain solution 3;
(4) And mixing the solution 1, the solution 2 and the solution 3 to obtain a solution 4, and freeze-drying the solution 4 to obtain the loaded fluorescent probe aerogel composite material.
Further, the preparation method of the formaldehyde response type fluorescent probe comprises the following steps: placing allyl potassium trifluoroborate into ammonia water and methanol solution, stirring, adding a compound 1, stirring for reaction, adding a saturated sodium bicarbonate solution after the reaction is finished, extracting with dichloromethane, and purifying by a chromatographic column to obtain a formaldehyde response type fluorescent probe, wherein the formaldehyde response type fluorescent probe reaction equation is as follows:
。
further, the molar ratio of the compound 1 to the allyl potassium trifluoroborate is 2:3, a step of; the allyl potassium trifluoroborate is placed in ammonia water and methanol solution, stirred for 30 min at 0 ℃, warmed to room temperature, added with compound 1 and stirred for 8 h; the column chromatography purification method comprises the following steps: the solvent was removed by rotary distillation, the solid was dissolved in dichloromethane and separated by column chromatography using a mixed solvent of dichloromethane and methanol in a volume ratio of 100:1.
Further, the concentration of the aqueous ammonia methanol solution was 7 mol/L.
Further, the mass ratio of the formaldehyde response fluorescent probe to the methanol in the step (1) is 1:791; the mass ratio of the chitosan to the acetic acid in the step (2) is 1:20, adjusting the pH by using 10wt% sodium hydroxide solution; the mass ratio of the cellulose, the sodium periodate, the ethylene glycol and the water in the step (3) is 1:1.391:1.29:70.
further, the acetic acid concentration in the step (2) is 2%, and the heating temperature is 30 ℃; the heating temperature in the step (4) is 30 ℃, and the reaction time is 3 h.
In the application, the application of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe in detecting formaldehyde in air is realized. The response principle of the waste cotton regenerated cellulose aerogel composite material of the fluorescent probe loaded with formaldehyde in the air is that allyl contained in the fluorescent probe structure is used as a reaction site with formaldehyde, when the allyl reacts with formaldehyde, after 2-aza-Cope rearrangement, fluorescence is subjected to red shift, and the fluorescence intensity is obviously enhanced.
Advantageous effects
The fluorescent probe loaded aerogel composite material prepared by the application has the advantages of high sensitivity for detecting formaldehyde in air, obvious phenomenon, convenient identification, wide raw material source, large earth storage capacity, green and recoverable property, simple preparation method, high yield and mass production. The cellulose raw material source and the waste cotton regenerated cellulose have the characteristics of green, environment protection, carbon emission reduction and environmental pollution reduction.
Drawings
FIG. 1 is a mass spectrum of a formaldehyde-responsive fluorescent probe;
FIG. 2 is a synthetic route diagram of a fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite;
FIG. 3 is a graph of the fluorescence change of the waste cotton regenerated cellulose aerogel composite material combined with formaldehyde before and after loading with fluorescent probes;
FIG. 4 is a graph showing the fluorescence change of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe in formaldehyde gas overnight;
fig. 5 is a graph showing the change of the absorption spectrum of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe in formaldehyde gas.
Detailed Description
In order to make the technical solution of the present application better understood, the following description of the technical solution of the present application will be made in a clear and complete manner, and other similar embodiments obtained by those skilled in the art without making any inventive effort on the basis of the embodiments of the present application shall fall within the scope of protection of the present application.
Example 1:
(1) 0.1. 0.1 g allyl potassium trifluoroborate is dissolved in 6 mL of 7 mol/L aqueous ammonia methanol solution,stirring at 0deg.C for 30 min, heating to room temperature, adding 0.2 g compound 1, reacting 8. 8 h, adding 50 ml saturated sodium bicarbonate solution after the reaction, extracting with dichloromethane for 4 times, rotary distilling the extractive solution to remove solvent, dissolving solid in dichloromethane, and separating by mixed solvent column chromatography of dichloromethane and methanol at volume ratio of 100:1 to obtain formaldehyde response fluorescent probe with mass spectrum shown in figure 1; 1 H NMR (400 MHz, CDCl 3 ) δ7.65 (dd,J= 18.3, 9.0 Hz, 3H), 7.36 (dd,J= 8.4, 1.5 Hz, 1H), 7.16 (dd,J= 9.0, 2.5 Hz, 1H), 6.91 (d,J= 2.2 Hz, 1H), 5.83 - 5.69 (m, 1H), 5.09 (dd,J= 25.0, 13.6 Hz, 2H), 4.10 (dd,J= 7.5, 5.9 Hz, 1H), 3.05 (d,J= 14.5 Hz, 6H), 2.61 - 2.42 (m, 2H), 2.11 (s, 2H). 13 C NMR (101 MHz, CDCl 3 ) Delta 148.73, 137.21, 134.87, 134.38, 128.70, 126.67, 125.10, 124.89, 117.98, 116.75, 106.47, 58.41, 55.55, 42.92, 40.95, 18.37.Hrms (ESI) calculated. For C 16 H 20 N 2 [M] + : 241.1699. Found: 241.1706；
(2) Dissolving the formaldehyde response fluorescent probe 1 mg in the step (1) in a methanol solution of 2 ml to obtain a solution 1;
(3) Adding 3 g chitosan into a beaker filled with 100 ml of 2% acetic acid solution, heating to 30 ℃, magnetically stirring until the chitosan is dissolved, and adjusting the pH to be neutral by using 10wt% sodium hydroxide solution to obtain solution 2;
(4) Cutting a cellulose plate of 5 g waste cotton textile regenerated cotton fibers into small blocks, placing the small blocks into a beaker filled with 350 g deionized water and 6.45 g sodium periodate, heating the small blocks in a dark place for 3 h, adding 6.45 g into ethylene glycol, after the reaction is finished, washing the small blocks with water, and removing supernatant to obtain a solution 3;
(5) 50 μl of solution 1, 0.1 g of solution 2 and 0.8 g of solution 3 are mixed to obtain solution 4, and the solution 4 is freeze-dried to obtain the waste cotton regenerated cellulose aerogel composite material loaded with fluorescent probes.
The synthetic route is shown in FIG. 2 below:
example 2
(1) Adding 3 g chitosan into a beaker filled with 100 ml of 2% acetic acid solution, heating to 30 ℃, magnetically stirring until the chitosan is dissolved, and adjusting the pH to be neutral by using 10wt% sodium hydroxide solution to obtain solution 2;
(2) Cutting a cellulose plate of 5 g waste cotton textile regenerated cotton fibers into small blocks, placing the small blocks into a beaker filled with 350 g deionized water and 6.45 g sodium periodate, heating the small blocks in a dark place for 3 h, adding 6.45 g into ethylene glycol, after the reaction is finished, washing the small blocks with water, and removing supernatant to obtain a solution 3;
(3) Mixing the solution 2 of 0.1 g and the solution 3 of 0.8 g to obtain a solution 4, and freeze-drying the solution 4 to obtain the waste cotton regenerated cellulose aerogel composite material.
Example 3
The fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material prepared in example 1 has fluorescent response to formaldehyde gas; firstly, detecting the fluorescence intensity of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe before the waste cotton regenerated cellulose aerogel composite material is combined with formaldehyde by using a fluorescence spectrometer; then, placing the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe in a closed container containing formaldehyde gas, taking out the aerogel loaded with the fluorescent probe after being combined with the formaldehyde gas, and detecting the fluorescence intensity on a fluorescence spectrometer, wherein the result is shown in figure 3, when the excitation wavelength is 360 nm, the emission wavelength of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe is 440 nm, the emission wavelength after being combined with the formaldehyde gas is 480 nm, the fluorescence is obviously red-shifted, the fluorescence intensity is obviously enhanced, and the color is changed from blue to yellow-green.
Example 4
Detecting the fluorescence intensity of the waste cotton regenerated cellulose aerogel composite material prepared in the embodiment 2 in a fluorescence spectrometer; then, after the aerogel composite was placed in a closed container containing formaldehyde gas overnight, the fluorescence intensity was again measured with a fluorescence spectrometer, and the result is shown in fig. 4. As can be seen from FIG. 4, the fluorescence intensity of the aerogel composite material without the fluorescent probe is unchanged before and after absorbing formaldehyde gas, further illustrating that the fluorescent probe reacts with the formaldehyde gas to enhance the fluorescence, and FIG. 5 illustrates the change of absorption of 240-360 nm after absorbing formaldehyde by the aerogel.
Claims (9)
1. The waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe is characterized by comprising a formaldehyde response type fluorescent probe, chitosan and cellulose;
the structural formula of the formaldehyde response type fluorescent probe is as follows:；
the mass ratio of the formaldehyde response type fluorescent probe to the chitosan to the cellulose is 1:100:200-1000;
the preparation method of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe comprises the following steps:
(1) Dissolving a formaldehyde response type fluorescent probe into methanol to obtain a solution 1;
(2) Adding chitosan into acetic acid solution, heating and stirring until the chitosan is dissolved, and regulating the pH value to be neutral to obtain solution 2;
(3) Placing cellulose into water and sodium periodate solution, adding glycol after light-shielding heating reaction, continuing the reaction, washing with water after the reaction is finished, and removing supernatant to obtain solution 3;
(4) And mixing the solution 1, the solution 2 and the solution 3 to obtain a solution 4, and freeze-drying the solution 4 to obtain the fluorescent probe loaded aerogel composite material.
2. The fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material of claim 1, wherein the cellulose is waste cotton textile regenerated cellulose.
3. A method for preparing the fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material according to any one of claims 1-2, which is characterized by comprising the following steps:
(1) Dissolving a formaldehyde response type fluorescent probe into methanol to obtain a solution 1;
(2) Adding chitosan into acetic acid solution, heating and stirring until the chitosan is dissolved, and regulating the pH value to be neutral to obtain solution 2;
(3) Placing cellulose into water and sodium periodate solution, adding glycol after light-shielding heating reaction, continuing the reaction, washing with water after the reaction is finished, and removing supernatant to obtain solution 3;
(4) And mixing the solution 1, the solution 2 and the solution 3 to obtain a solution 4, and freeze-drying the solution 4 to obtain the fluorescent probe loaded aerogel composite material.
4. The method of claim 3, wherein the method of preparing the formaldehyde-responsive fluorescent probe comprises: placing allyl potassium trifluoroborate into ammonia water and methanol solution, stirring, adding a compound 1, stirring for reaction, adding a saturated sodium bicarbonate solution after the reaction is finished, extracting with dichloromethane, and purifying by a chromatographic column to obtain a formaldehyde response type fluorescent probe, wherein the formaldehyde response type fluorescent probe reaction equation is as follows:
。
5. the preparation method according to claim 4, wherein the molar ratio of the compound 1 to the allyl potassium trifluoroborate is 2:3, a step of; the allyl potassium trifluoroborate is placed in ammonia water and methanol solution, stirred for 30 min at 0 ℃, warmed to room temperature, added with compound 1 and stirred for 8 h; the column chromatography purification method comprises the following steps: the solvent was removed by rotary distillation, the solid was dissolved in dichloromethane and separated by column chromatography using a mixed solvent of dichloromethane and methanol in a volume ratio of 100:1.
6. The method according to claim 4, wherein the concentration of the aqueous ammonia methanol solution is 7 mol/L.
7. The method according to claim 3, wherein the mass ratio of the formaldehyde-responsive fluorescent probe to methanol in the step (1) is 1:791; the mass ratio of the chitosan to the acetic acid in the step (2) is 1:20, adjusting the pH by using 10wt% sodium hydroxide solution; the mass ratio of the cellulose, the sodium periodate, the ethylene glycol and the water in the step (3) is 1:1.391:1.29:70.
8. a process according to claim 3, wherein the acetic acid concentration in step (2) is 2% and the heating temperature is 30 ℃.
9. Use of the fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material according to claim 1 or 2 for detecting formaldehyde in air.
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| Title |
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| Jun-Bin Li et al.A two-photon fluorescent probe for bio-imaging of formaldehyde in living cells and tissues.Analyst.2016,第141卷3395-3402. * |
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