CN113621081B - Dialdehyde cellulose-based Schiff base fluorescent probe for detecting Al3+, and preparation method and application thereof - Google Patents
Dialdehyde cellulose-based Schiff base fluorescent probe for detecting Al3+, and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a method for detecting Al3+The dialdehyde cellulose base Schiff base fluorescent probe and the preparation method and the application thereof. The method takes dialdehyde cellulose as a raw material, and the dialdehyde cellulose is condensed with sebacoyl hydrazine to prepare dialdehyde cellulose-sebacoyl hydrazine mono Schiff base; and further condensing the dialdehyde cellulose-sebacoyl dihydrazide mono-Schiff base with 2-hydroxy-1-naphthaldehyde to prepare the dialdehyde cellulose-sebacoyl dihydrazide-2-hydroxy-1-naphthaldehyde bis-Schiff base. Adding Al into DMF suspension of dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base under 365nm ultraviolet irradiation3+Then, the fluorescence color of the solution changes from colorless to blue, for Al3+The detection limit of (2) reaches 6.06 multiplied by 10‑7M as detected Al3+The fluorescent probe for ions has good application prospect.
Description
Technical Field
The invention belongs to the technical field of fluorescence detection, and relates to a method for detecting Al3+The dialdehyde cellulose base Schiff base fluorescent probe and the preparation method and the application thereof.
Background
Cellulose is a natural polymer which is widely distributed and contains most cellulose in nature. Each glucose ring of the cellulose contains 3 hydroxyl groups, and the 3 hydroxyl groups can be subjected to oxidation, etherification, crosslinking, esterification and other reactions, so that the functional modification and application of the cellulose are realized, and the cellulose is endowed with new performance. Periodate is capable of oxidizing hydroxyl groups at positions ortho to the C2 and C3 on cellulose to aldehyde groups, thereby yielding dialdehyde cellulose. 2-hydroxy-1-naphthaldehyde is one of the most widely used fluorophores, is often used for synthesizing excellent precursors of different fluorescence chemical sensors, is grafted to dialdehyde cellulose macromolecules to obtain the dialdehyde cellulose-based fluorescent material, not only has the excellent performance of the dialdehyde cellulose macromolecules, but also can overcome the limitations of small molecular fluorescent compounds: such as fluorescence quenching due to easy aggregation; difficult to reuse; fluorescent small molecules are difficult to process and mold, and cannot be used for manufacturing devices and the like. Meanwhile, the fluorescent group is connected with the polymer skeleton by a stable chemical bond, so that the problem that the fluorescent micromolecules are easy to lose in the material prepared by physically mixing the fluorescent micromolecules with the polymer can be effectively avoided. Therefore, the development of various dialdehyde cellulose-based functional materials has very important significance and has wide application prospects in the fields of biological imaging, detection sensing, information anti-counterfeiting and the like.
Aluminum is the third most abundant element in the earth's crust next to oxygen and silicon, the most abundant metallic element. Because of its advantages of small density, good ductility and strong corrosion resistance, it is widely used in many fields such as food and medicine packaging, kitchen ware, aerospace, etc. Although the use of aluminum brings great convenience to our lives, excessive use of aluminum not only causes harm to the ecological environment, but also aluminum ions are inevitably concentrated in the human body through water and food. When the human body contacts or takes excessive Al for a long time3+In time, functional disorder of human organs can be caused, and particularly, aluminum ions have strong affinity with human brain tissues and are easy to accumulate in the brain tissues, so that the central nervous system of a human is seriously injured, and then nervous system diseases are caused. Excessive concentration of aluminum in the body can cause bone decalcification, easily cause bone atrophy, lethargy, anemia, anorexia, ovarian atrophy and the like, can inhibit phosphorus absorption of intestinal tracts, interfere normal metabolism of calcium and phosphorus in the body, can cause degeneration of cranial nerves, memory deterioration, and influence on intelligence and character, even presents senile dementia. At present, the method，Al3+The detection methods mainly comprise an electrochemical method, a chemical titration method, a spectrophotometry and the like, and the technologies have the defects of complicated operation, low practicability, low sensitivity and the like due to more limitation factors. Fluorescence detection technique for detecting Al3+Has the advantages of convenient operation, high sensitivity and the like.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a method for detecting Al3+The DMF suspension of the dialdehyde cellulose base Schiff base fluorescent probe does not emit fluorescence under the irradiation of 365nm ultraviolet light, but Al is added3+The back solution can emit blue fluorescence, and can be used for Al3+Detection of (3). The invention also provides a preparation method of the dialdehyde cellulose base Schiff base fluorescent probe. The invention also aims to solve another technical problem of providing an application of the dialdehyde cellulose-based Schiff base fluorescent probe.
In order to solve the technical problems, the invention adopts the technical scheme that:
for detecting Al3+The dialdehyde cellulose base Schiff base fluorescent probe is dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde Schiff base, and the structural formula is as follows:
the preparation method of the dialdehyde cellulose base Schiff base fluorescent probe comprises the following steps:
(1) dispersing dialdehyde cellulose in ethylene glycol monomethyl ether by using the dialdehyde cellulose as a raw material, adding sebacoyl hydrazine to perform condensation reaction with the dialdehyde cellulose to prepare dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base;
(2) dispersing dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base in ethanol, adding 2-hydroxy-1-naphthaldehyde, and further condensing with dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base to obtain dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base.
The preparation steps of the dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base in the step (1) are as follows:
1) adding 1.0 g of dialdehyde cellulose, 40-60 mL of ethylene glycol monomethyl ether and 1.8-2.5 g of sebacoyl hydrazine into a 100 mL three-neck flask equipped with a stirrer, a thermometer and a reflux condenser, then dripping 3-5 drops of acetic acid into the flask, and stirring and refluxing for 24 hours at 125 ℃;
2) and (3) carrying out suction filtration on the reaction liquid, washing with hot ethylene glycol monomethyl ether and distilled water, and then carrying out vacuum drying at 45 ℃ for 24-36 h to obtain the dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base.
The preparation steps of the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base in the step (2) are as follows:
1) adding 0.5 g of dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base, 40-60 mL of ethanol and 0.8-1.2 g of 2-hydroxy-1-naphthaldehyde into a 100 mL three-neck flask equipped with a stirrer, a thermometer and a reflux condenser, then dripping 3-5 drops of acetic acid into the flask, and stirring and carrying out reflux reaction at 80 ℃ for 24 hours;
2) and (3) carrying out suction filtration on the reaction liquid, fully washing with ethanol, and carrying out vacuum drying at 45 ℃ for 24-36 h to obtain the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base.
The dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is used for detecting Al3+The use of (1).
The application is that under 365nm ultraviolet irradiation, DMF suspension of dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base does not emit fluorescence, and Al is added3+After that, the fluorescence color of the solution changed from colorless to blue.
The dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is used as a fluorescent probe for detecting Al3+The use of (1).
The invention takes dialdehyde cellulose as raw material, firstly, the dialdehyde cellulose and sebacoyl hydrazine are subjected to condensation reaction to prepare dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base, and then the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is further condensed with 2-hydroxy-1-naphthaldehyde. Dialdehyde cellulose-sebacoyl hydrazine-2-DMF suspension of hydroxy-1-naphthaldehyde bis-Schiff base does not emit fluorescence under 365nm ultraviolet irradiation, and Al is added3+Then, the fluorescence color of the solution is gradually changed into blue, which can be used for detecting Al3+Using a fluorescent probe.
Has the advantages that: compared with the prior art, the invention has the following advantages: cellulose is used as a natural polymer which is most widely distributed and contained in nature, and has wide sources and low price. The cellulose-based fluorescent probe obtained by grafting the 2-hydroxy-1-naphthaldehyde onto the cellulose macromolecules not only has excellent performance of the cellulose macromolecules, but also overcomes a plurality of limitations of small molecular fluorescent compounds. The prepared dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base fluorescent probe has the characteristics of good luminous performance, stable structure and the like, and Al is added into DMF suspension of the probe under the irradiation of 365nm ultraviolet light3+Then, the fluorescence color of the solution is gradually changed from colorless to blue, for Al3+Up to a detection limit of 6.06X 10-7M as detection Al3+The fluorescent probe for ions has good application prospect.
Drawings
FIG. 1 is a chart showing (a) the IR spectrum of dialdehyde cellulose, (b) the IR spectrum of dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base, and (c) the IR spectrum of dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base;
FIG. 2 is a fluorescence spectrum of dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base;
FIG. 3 shows dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base added with Al in DMF3+Front and back fluorescence spectra;
FIG. 4 is a fluorescence spectrum of dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base added with different metal ions in DMF;
FIG. 5 shows that dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is added with Al with different concentrations in DMF3+Fluorescence spectrum of (2).
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, specific embodiments thereof are described in detail below with reference to examples of the specification.
Example 1
The synthesis reaction formula of the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is as follows:
1.0 g of dialdehyde cellulose, 50 mL of ethylene glycol monomethyl ether and 1.84 g of sebacoyl hydrazine are added into a 100 mL three-neck flask provided with a stirrer, a thermometer and a reflux condenser, then 3-5 drops of acetic acid are dropped into the flask, and the mixture is stirred and refluxed for 24 hours at 125 ℃. And (3) carrying out suction filtration on the reaction liquid, washing the reaction liquid with hot ethylene glycol monomethyl ether and distilled water, and then carrying out vacuum drying for 24 hours at the temperature of 45 ℃ to obtain the dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base. Adding 0.5 g of dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base and 0.82 g of 2-hydroxy-1-naphthaldehyde into 50 mL of ethanol, dripping 3-5 drops of acetic acid, stirring and refluxing at 80 ℃ for reaction for 24 hours, carrying out suction filtration on the reaction liquid, fully washing the reaction liquid with ethanol, and carrying out vacuum drying at 45 ℃ for 24 hours to obtain the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base.
The structure of dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is analyzed by FT-IR. FIG. 4 is an infrared spectrum of dialdehyde cellulose, dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base and dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base respectively. As can be seen from the figure, the infrared spectra of the dialdehyde cellulose, the dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base and the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base appear at 3400cm-1The left and right strong peaks are stretching vibration of O-H, 2931 cm-1And C-H stretching vibration is achieved through position saturation. The infrared spectrum of the dialdehyde cellulose is at 1725 cm-1The C = O telescopic vibration of carbonyl group in aldehyde group appears, 881 cm-1Is the vibration absorption peak of the hemiacetal. Dialdehyde cellulose-sebacoyl hydrazine at 1725 cm-1The characteristic peak disappears and is at 1675cm-1A new absorption peak appears at the position of the crystal,this peak is attributed to C = N stretching vibration, 1325 cm-1C-N stretching vibration is adopted, and the reaction between the aldehyde group of the dialdehyde cellulose and the amino group of the sebacoyl hydrazine is shown. The infrared spectrogram of the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is 1675cm in comparison with the dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base-1C = N stretching vibration also occurred, but the intensity of the peak was weakened due to further consumption of the amino group on the sebacoyl dihydrazide. The results show that the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base is successfully prepared.
Example 2
The prepared dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-schiff base is pressed into tablets, and the fluorescence emission spectrum of the solid is measured, as shown in figure 2. The results show that the maximum emission wavelength of solid fluorescence is at 425 nm.
Dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base was added to DMF to prepare a DMF suspension with a concentration of 8.0 mg/mL, and fluorescence emission spectra in DMF was measured, as shown in FIG. 3. The results show that in the DMF system, Al is not added3+When Al is added, the fluorescence intensity is weak3+Then, the fluorescence intensity was sharply increased, and the maximum emission wavelength was 450 nm (excitation wavelength was 355 nm, excitation slit broad band was 15 nm, and emission slit broad band was 5.0 nm).
Adding dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base into DMF to prepare DMF suspension with the concentration of 8.0 mg/mL, wherein 1 part is used as a blank sample, and Al is added into other parts respectively3+、Cu2+、La3+、Cd2+、Cr3+、Co2+、Mn2+、Ni2+、Fe2+、Na+、K+、Fe3+、Ca2+、Zn2+、Pb2+、Ag+、Sn2+、Bi3+、Mg2+、Hg2+The fluorescence emission spectrum of the solution was measured, and the results are shown in FIG. 3. As can be seen from FIG. 4, Al is added3+Then, the maximum emission wavelength of the solution was 450 nm, and the fluorescence intensity of the solution was significantly enhanced. While other analytes are addedThe change in fluorescence intensity of the solution was small. This shows that dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base pairs with Al3+Has good selectivity.
Adding dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base into DMF to prepare DMF suspension with the concentration of 8.0 mg/mL, and measuring that Al with different concentrations is added3+Fluorescence emission spectra after ionization. As shown in fig. 5. The results show that with Al3+The concentration is gradually increased, and the fluorescence signal intensity of the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base at 450 nm is gradually increased, which indicates that the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base can be used for detecting Al in the solution3+Concentration of, to Al3+The detection limit of (2) reaches 6.06 multiplied by 10-7 M。
Claims (7)
1. For detecting Al3+The dialdehyde cellulose base Schiff base fluorescent probe is characterized in that the structural formula is as follows:
2. the method for preparing the dialdehyde cellulose-based Schiff base fluorescent probe as set forth in claim 1, which is characterized by comprising the following steps:
(1) dispersing dialdehyde cellulose in ethylene glycol monomethyl ether by using the dialdehyde cellulose as a raw material, adding sebacoyl hydrazine to perform condensation reaction with the dialdehyde cellulose to prepare dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base;
(2) dispersing dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base in ethanol, adding 2-hydroxy-1-naphthaldehyde, and further condensing with dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base to obtain dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base.
3. The method for preparing dialdehyde cellulose-based Schiff base fluorescent probe according to claim 2, wherein the preparation of dialdehyde cellulose-sebacoyl dihydrazide mono-Schiff base in step (1) comprises the following steps:
1) adding 1.0 g of dialdehyde cellulose, 40-60 mL of ethylene glycol monomethyl ether and 1.8-2.5 g of sebacoyl hydrazine into a 100 mL three-neck flask equipped with a stirrer, a thermometer and a reflux condenser, then dripping 3-5 drops of acetic acid into the flask, and stirring and refluxing for 24 hours at 125 ℃;
2) and (3) carrying out suction filtration on the reaction liquid, washing with hot ethylene glycol monomethyl ether and distilled water, and then carrying out vacuum drying at 45 ℃ for 24-36 h to obtain the dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base.
4. The method for preparing the dialdehyde cellulose-based Schiff base fluorescent probe as claimed in claim 2, wherein the preparation steps of the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde Schiff base in the step (2) are as follows:
1) adding 0.5 g of dialdehyde cellulose-sebacoyl hydrazine mono-Schiff base, 40-60 mL of ethanol and 0.8-1.2 g of 2-hydroxy-1-naphthaldehyde into a 100 mL three-neck flask equipped with a stirrer, a thermometer and a reflux condenser, then dripping 3-5 drops of acetic acid into the flask, and stirring and carrying out reflux reaction at 80 ℃ for 24 hours;
2) and (3) carrying out suction filtration on the reaction liquid, fully washing with ethanol, and carrying out vacuum drying at 45 ℃ for 24-36 h to obtain the dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base.
5. The dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base of claim 1 for detecting Al3+The use of (1).
6. The use according to claim 5, wherein the DMF suspension of dialdehyde cellulose-sebacoyl dihydrazide-2-hydroxy-1-naphthaldehyde bis-Schiff base does not fluoresce under 365nm ultraviolet light irradiation, and Al is added3+After that, the fluorescence color of the solution changed from colorless to blue.
7. The dialdehyde cellulose-sebacoyl hydrazine-2-hydroxy-1-naphthaldehyde bis-Schiff base as the fluorescent probe in the detection of Al3+The use of (1).
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