CN115368636A - Waste cotton regenerated cellulose aerogel composite material loaded with fluorescent probe, preparation method thereof and application thereof in formaldehyde detection - Google Patents
Waste cotton regenerated cellulose aerogel composite material loaded with fluorescent probe, preparation method thereof and application thereof in formaldehyde detection Download PDFInfo
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Abstract
The invention discloses a fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material, a preparation method thereof and application thereof in formaldehyde detection, and the fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material for detecting formaldehydeThe probe aerogel composite material 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 fluorescence probe loaded aerogel composite material prepared by the invention has high sensitivity for detecting formaldehyde in air, obvious phenomenon, convenient identification, wide raw material source, large earth storage capacity, greenness, recoverability, simple preparation method, high yield and large-scale production.
Description
Technical Field
The invention belongs to the technical field of fluorescence detection, can realize the detection of formaldehyde in the environment, and particularly relates to a waste cotton regenerated cellulose aerogel composite material loaded with a fluorescence probe, a preparation method thereof and application thereof in formaldehyde detection.
Background
Formaldehyde is one of the gases harmful to human bodies in newly decorated rooms, and is mainly released from materials containing formaldehyde resins, such as: paint for walls, adhesives for wood products such as cellulose boards, plywood, particle board for doors, kitchen ware and furniture. For a long time, formaldehyde and carcinogens fall into one category. It is well known that small amounts of formaldehyde can cause irritation to the eyes, nose, and upper and lower respiratory tract. Prolonged exposure to formaldehyde can induce leukemia and lung inflammation, and can also contribute to exacerbation of asthma. Therefore, the normal value of formaldehyde in the room is limited to 0.08 mg/m according to the regulations 3 Within. Therefore, an effective and convenient method for detecting indoor formaldehyde is urgently needed.
Methods for detecting formaldehyde in air include electrochemical biosensors, gas chromatography, X-ray diffraction, and others. In recent years, fluorescent probes have been attracting much attention as excellent detection techniques because of their high selectivity and convenience of use, and are widely used for detection of various substances. Typically, the detection result of a fluorescent probe will vary depending on the probe concentration, excitation intensity and emission collection efficiency. In contrast, the ratiometric fluorescent probe has two fluorescent signals, and the interference of factors such as probe concentration, excitation intensity and emission collection efficiency on the probe can be minimized. At present, the disclosed detection fluorescent probes are fewer, and most of the fluorescent probes need to be assisted by other adsorptive carrier substances, so that the use is inconvenient.
Chitosan and cellulose are natural high molecular compounds which are low in price, renewable and rich in earth storage resources. The aerogel has the characteristics of a porous net structure, high specific surface area, high porosity, low density, high adsorbability and the like, so that the aerogel is applied to the aspects of environment, energy, buildings and the like. Therefore, the aerogel prepared by physically crosslinking chitosan and cellulose can be degraded after use, is environment-friendly and has the characteristics of the aerogel.
Therefore, the research and development of the material which is degradable, environment-friendly and can effectively avoid the interference of other factors for detecting the formaldehyde in the air is of great significance.
Disclosure of Invention
Aiming at the defects that a fluorescent probe for detecting formaldehyde in the air is inconvenient to use, low in sensitivity and incapable of being recycled, volatile organic compounds can affect the fluorescent probe in the prior art, the invention provides a waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe, a preparation method thereof and application thereof in formaldehyde detection. The cellulose source and the regenerated cellulose of the waste cotton textiles in the invention have the characteristics of environmental protection, contribution to reducing carbon emission and the like.
The invention is realized by the following technical scheme:
a waste cotton regenerated cellulose aerogel composite material loaded with a fluorescent probe is composed of a formaldehyde response type fluorescent probe, chitosan and cellulose;
the structural formula of the formaldehyde response type fluorescent probe is as follows:
。
further, the mass ratio of the formaldehyde response type fluorescent probe to the chitosan to the cellulose is 1:100:200-1000.
Furthermore, the cellulose is the cellulose of regenerated cotton fiber of waste cotton textiles.
In the invention, the preparation method of the loaded fluorescent probe aerogel composite material for detecting formaldehyde comprises the following steps:
(1) Dissolving a formaldehyde response type fluorescent probe into methanol to obtain a solution 1;
(2) Adding chitosan into an acetic acid solution, heating and stirring until the chitosan is dissolved, and adjusting the pH value to be neutral to obtain a solution 2;
(3) Placing cellulose in water and sodium periodate solution, heating and reacting in a dark place, adding ethylene glycol, continuing to react, 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 fluorescence probe-loaded aerogel composite material.
Further, the preparation method of the formaldehyde response type fluorescent probe comprises the following steps: placing allyl potassium trifluoroborate in an ammonia water methanol solution, stirring, adding the 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 the formaldehyde response type fluorescent probe, wherein the reaction equation of the formaldehyde response type fluorescent probe is as follows:
further, the molar ratio of the compound 1 to the potassium allyltrifluoroborate is 2:3; placing the allyl potassium trifluoroborate in an ammonia water methanol solution, stirring for 30 min at 0 ℃, heating to room temperature, adding the compound 1, and stirring for 8 h; the column chromatography purification method comprises the following steps: the solvent was removed by rotary distillation, and 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.
Further, the concentration of the ammonia water methanol solution is 7 mol/L.
Further, the mass ratio of the formaldehyde-responsive fluorescent probe in the step (1) to methanol is 1:791 of a glass fiber; the mass ratio of the chitosan to the acetic acid in the step (2) is 1:20, adjusting the pH with a 10wt% sodium hydroxide solution; the mass ratio of the cellulose, the sodium periodate, the glycol and the water in the step (3) is 1:1.391:1.29:70.
further, the concentration of acetic acid 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 invention, the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe is applied to detecting formaldehyde in air. The response principle of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe for detecting formaldehyde in the air is that allyl contained in the structure of the fluorescent probe is used as a reaction site with formaldehyde, and when the allyl and the formaldehyde are subjected to reaction and then undergo 2-aza-Cope rearrangement, the fluorescence is subjected to red shift, and the fluorescence intensity is obviously enhanced.
Advantageous effects
The aerogel composite material loaded with the fluorescent probe prepared by the invention has high sensitivity for detecting formaldehyde in air, obvious phenomenon, convenient identification, wide raw material source, large earth storage capacity, greenness, recoverability, simple preparation method, high yield and large-scale production. The cellulose raw material source and the waste cotton regenerated cellulose have the characteristics of environmental 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 synthesis route diagram of a waste cotton regenerated cellulose aerogel composite material loaded with a fluorescent probe;
FIG. 3 is a graph showing the change of fluorescence of a waste cotton regenerated cellulose aerogel composite material loaded with a fluorescence probe before and after formaldehyde is combined;
FIG. 4 is a graph showing fluorescence changes of a waste cotton regenerated cellulose aerogel composite material loaded with a fluorescent probe in formaldehyde gas overnight;
fig. 5 is a graph of 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 solutions of the present invention better understood, the following description is provided clearly and completely, and other similar embodiments obtained by those skilled in the art without creative efforts shall fall within the protection scope of the present application based on the embodiments in the present application.
Example 1:
(1) Dissolving 0.1 g allyl potassium trifluoroborate in 6 mL 7 mol/L ammonia methanol solution, stirring for 30 min at 0 ℃, raising the temperature to room temperature, adding 0.2 g compound 1, reacting 8 h, adding 50 mL saturated sodium bicarbonate solution after the reaction is finished, extracting for 4 times by dichloromethane, removing the solvent by rotary distillation of the extract, dissolving the solid in dichloromethane, and performing column chromatography by using a mixed solvent of dichloromethane and methanol with the volume ratio of 100 to obtain the formaldehyde response type fluorescent probe, wherein the mass spectrogram is shown in figure 1; 1 H NMR (400 MHz, CDCl 3 ) δ 7.65 (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 ) δ 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). For C 16 H 20 N 2 [M] + : 241.1699. Found: 241.1706；
(2) Dissolving the formaldehyde response type fluorescent probe 1 mg in the methanol solution of 2 ml to obtain 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 value to be neutral by using 10wt% sodium hydroxide solution to obtain solution 2;
(4) Shearing cellulose plates of regenerated cotton fibers of 5 g waste cotton textiles into small pieces, putting the small pieces into a beaker filled with 350 g deionized water and 6.45 g sodium periodate, heating 3 h away from light, adding 6.45 g into ethylene glycol, after the reaction is finished, washing with water, and removing supernatant to obtain a solution 3;
(5) Mixing 50 mu l of solution 1, 0.1 g solution 2 and 0.8 g solution 3 to obtain solution 4, and freeze-drying the solution 4 to obtain the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe.
The synthetic route is shown in the following figure 2:
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 value to be neutral by using 10wt% sodium hydroxide solution to obtain solution 2;
(2) Shearing cellulose plates of regenerated cotton fibers of 5 g waste cotton textiles into small pieces, putting the small pieces into a beaker filled with 350 g deionized water and 6.45 g sodium periodate, heating 3 h away from light, adding 6.45 g into ethylene glycol, after the reaction is finished, washing 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 waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe prepared in the embodiment 1 meets the fluorescent response of formaldehyde gas; firstly, detecting the fluorescence intensity of the waste cotton regenerated cellulose aerogel composite material loaded with a fluorescence probe before the waste cotton regenerated cellulose aerogel composite material is not combined with formaldehyde by using a fluorescence spectrometer; then, the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe is placed in a closed container containing formaldehyde gas, the aerogel loaded with the fluorescent probe after being combined with the formaldehyde gas is taken out, and the fluorescence intensity is detected on a fluorescence spectrometer, and as a result, as shown in fig. 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, and 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 by using a fluorescence spectrometer; then, after the aerogel composite was placed in a closed container containing formaldehyde gas overnight, the fluorescence intensity was measured again by the fluorescence spectrometer, and the results are shown in fig. 4. As can be seen from FIG. 4, the fluorescence intensity of the aerogel composite material without the loaded fluorescent probe is not changed before and after the aerogel composite material absorbs formaldehyde gas, which further illustrates that the fluorescence is enhanced by the reaction of the fluorescent probe and the formaldehyde gas, and FIG. 5 illustrates the change of the aerogel after absorbing formaldehyde in the range of 240-360 nm.
Claims (10)
1. A waste cotton regenerated cellulose aerogel composite material loaded with a 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:
。
2. the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe as claimed in claim 1, wherein the mass ratio of the formaldehyde-responsive fluorescent probe to the chitosan to the cellulose is 1:100:200-1000.
3. The waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe as claimed in claim 1, wherein the cellulose is waste cotton textile regenerated cellulose.
4. A method for preparing the fluorescent probe-loaded waste cotton regenerated cellulose aerogel composite material according to any one of claims 1~3, comprising the following steps:
(1) Dissolving a formaldehyde response type fluorescent probe into methanol to obtain a solution 1;
(2) Adding chitosan into an acetic acid solution, heating and stirring until the chitosan is dissolved, and adjusting the pH value to be neutral to obtain a solution 2;
(3) Placing cellulose in water and sodium periodate solution, heating and reacting in a dark place, adding ethylene glycol, continuing to react, 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 fluorescence probe-loaded aerogel composite material.
5. The method according to claim 4, wherein the formaldehyde-responsive fluorescent probe is prepared by: placing allyl potassium trifluoroborate in an ammonia water methanol solution, stirring, adding the 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 the formaldehyde response type fluorescent probe, wherein the reaction equation of the formaldehyde response type fluorescent probe is as follows:
6. the method according to claim 5, wherein the molar ratio of compound 1 to the potassium allyltrifluoroborate is 2:3; placing the allyl potassium trifluoroborate in an ammonia water methanol solution, stirring for 30 min at 0 ℃, heating to room temperature, adding the compound 1, and stirring for 8 h; the column chromatography purification method comprises the following steps: the solvent was removed by rotary distillation, and 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.
7. The method according to claim 4, wherein the concentration of the aqueous ammonia methanol solution is 7 mol/L.
8. The preparation method according to claim 3, wherein the mass ratio of the formaldehyde-responsive fluorescent probe in the step (1) to methanol is 1:791 of a glass fiber; the mass ratio of the chitosan to the acetic acid in the step (2) is 1:20, adjusting the pH with a 10wt% sodium hydroxide solution; the mass ratio of the cellulose, the sodium periodate, the glycol and the water in the step (3) is 1:1.391:1.29:70.
9. the method according to claim 3, wherein 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.
10. The application of the waste cotton regenerated cellulose aerogel composite material loaded with the fluorescent probe in the detection of formaldehyde in air according to claim 1 or 2.
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| CN110088187A (en) * | 2016-12-09 | 2019-08-02 | 新加坡国立大学 | Polysaccharide aeroge |
| CN108047060A (en) * | 2017-12-01 | 2018-05-18 | 河南省农业科学院农业质量标准与检测技术研究所 | A kind of pyrene derivatives fluorescent probe molecule of recognition detection formaldehyde and its preparation method and application |
| CN110117229A (en) * | 2018-02-05 | 2019-08-13 | 中国医学科学院药物研究所 | Fluorescent probe and the preparation method and application thereof |
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| 李战营: "纤维素基气凝胶的增强及吸附性能研究" * |
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