CN110836882B - Adopts N-P-4-HN @ UiO-66-NH2Method for determining HCHO content of composite material - Google Patents

Adopts N-P-4-HN @ UiO-66-NH2Method for determining HCHO content of composite material Download PDF

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CN110836882B
CN110836882B CN201911153318.2A CN201911153318A CN110836882B CN 110836882 B CN110836882 B CN 110836882B CN 201911153318 A CN201911153318 A CN 201911153318A CN 110836882 B CN110836882 B CN 110836882B
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CN110836882A (en
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夏莲
王秀丽
王昊
田晓霞
程圆圆
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Qufu Normal University
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Abstract

The invention belongs to the field of metal-organic framework sensors, and particularly relates to a sensor adopting N-P-4-HN @ UiO-66-NH2Method for determining HCHO content of composite material. The method comprises the following steps: 1) preparing an N-P-4-HN material; 2) preparation of N-P-4-HN @ UiO-66-NH2A composite material; 3) drawing a working curve; 4) and (6) detecting. The principle adopted by the invention is as follows: when N-P-4-HN is connected with HCHO, HCHO prohibits the intramolecular energy transfer of N-P-4-HN, thereby enhancing the fluorescence of N-P-4-HN at 553nm, weakening the fluorescence at 430nm, UiO-66-NH, by the internal rate effect2The adsorption of N-P-4-HN makes the fluorescence change more obvious, and the measurement is carried out through the change of the fluorescence spectrum. The determination method has the characteristics of high selectivity and high sensitivity.

Description

Adopts N-P-4-HN @ UiO-66-NH2Method for determining HCHO content of composite material
Technical Field
The invention belongs to the field of metal-organic framework sensors, and particularly relates to a sensor adopting N-P-4-HN @ UiO-66-NH2Method for measuring HCHO content of composite material.
Background
An organic Metal framework (MOFs) is a crystalline porous novel functional material with a periodic network framework formed by connecting transition Metal ions or ion clusters and organic ligands containing oxygen elements or nitrogen elements through self-assembly. The MOFs serving as a novel functional material has the advantages of ultrahigh porosity, lower density, overlarge specific surface area, functional adjustability, a special topological structure and the like, and is widely applied to the aspects of selective gas adsorption/separation, catalytic reaction, optics, magnetics and the like. MOFs present great development potential and attractive development prospects in modern materials science. However, the applications of MOFs materials in the field of analytical chemical sensing are far behind other fields.
At present, N-P-4-HN @ UiO-66-NH is not found to be adopted at home and abroad2A method for determining HCHO content of the composite material is reported.
Disclosure of Invention
The invention aims to provide a high-selectivity and high-sensitivity N-P-4-HN @ UiO-66-NH2Method for determining HCHO content of composite material.
The invention adopts N-P-4-HN @ UiO-66-NH2The method for determining the HCHO content of the composite material comprises the following steps:
1) preparation of N-P-4-HN Material
Dissolving 4-bromo-1, 8-naphthalic anhydride in ethanol, adding alanine for reflux reaction, cooling, adding water for recrystallization, dissolving a recrystallization product in ethanol, adding hydrazine hydrate for reflux reaction, and evaporating to dryness to obtain an N-P-4-HN material;
2) preparation of N-P-4-HN @ UiO-66-NH2Composite material
Mixing N-P-4-HN material and UiO-66-NH2Dissolving the material in ethanol, stirring, standing, centrifuging, washing with deionized water to obtain N-P-4-HN @ UiO-66-NH2A composite material;
3) drawing a working curve
Adding N-P-4-HN @ UiO-66-NH2The composite material is dispersed into aqueous solution to prepare dispersion liquid with the concentration of 2mg/mL, and 100 mu L N-P-4-HN @ UiO-66-NH is removed2The dispersion was added to a centrifuge tube containing 800. mu.L of deionized water and 100. mu.L of deionized water was added from 0mol/L to 5X 10-5Oscillating the HCHO standard solution with the concentration of mol/L to uniformly mix the HCHO standard solution, testing the fluorescence emission spectrum of the HCHO standard solution under the excitation of 362nm by using a fluorescence spectrometer after 10min, and drawing a working curve according to the relation between the fluorescence intensity and the HCHO concentration;
4) detection of
Replacing HCHO standard solution with the sample to be tested, adding by a standard addition method, oscillating to uniformly mix, testing the fluorescence emission spectrum of the sample under the excitation of 362nm by using a fluorescence spectrometer after 10min, and substituting the fluorescence intensity into a working curve to obtain the HCHO concentration in the sample to be tested;
wherein, the sample to be detected is 1% white spirit.
Wherein:
UiO-66-NH in step 2)2The preparation method of the composite material comprises the following steps:
adding zirconium tetrachloride, 2-amino terephthalic acid and benzoic acid into a container, adding N, N-dimethylformamide and hydrochloric acid, performing ultrasonic treatment, heating for reaction, cooling and centrifuging after the reaction is finished to obtain a crude product, washing with DMF (dimethyl formamide) and ethanol respectively, and drying to obtain the product.
In step 2), N-P-4-HN material and UiO-66-NH2The mass ratio of the materials is 2: 1.
the N-P-4-HN @ UiO-66-NH2The linear range of the HCHO content of the composite material is 1-3 mu mol/L, and the correlation coefficient is 0.99332.
The N-P-4-HN @ UiO-66-NH2The lower limit of detection of the composite material for determining the content of HCHO is 0.173 mu mol/L.
The N-P-4-HN @ UiO-66-NH2The detection temperature for detecting the HCHO content of the composite material is 10-30 ℃.
Preferably, the invention adopts N-P-4-HN @ UiO-66-NH2The method for determining the HCHO content of the composite material comprises the following specific steps:
1) preparation of UiO-66-NH2Material
0.0932g of zirconium tetrachloride, 0.0664g of 2-aminoterephthalic acid and 0.73g of benzoic acid were weighed accurately into a 20mL screw-cap glass vial, dissolved in 14.0mL of N, N-Dimethylformamide (DMF) and 72. mu.L of concentrated hydrochloric acid and sonicated for 15 min. The glass bottle is heated and reacted for 24 hours under the condition of oil bath at the temperature of 120 ℃, and magnetic stirring is continuously carried out. After the reaction is finished, cooling to room temperature, centrifuging to obtain yellow crystals, and repeatedly washing with DMF and ethanol for 3 times respectively. The resulting crystals were dried at 60 ℃.
2) Preparation of N-P-4-HN Material
Dissolving 4-bromo-1, 8-naphthalic anhydride (5mmol) in 30mL of ethanol, adding alanine (10mmol), refluxing at 90 ℃ for 4 hours, cooling to room temperature, adding to 1000mL of water, recrystallizing, dissolving the product in 90mL of ethanol, adding hydrazine hydrate (20mmol), refluxing at 90 ℃ for 6 hours, and rotary evaporating the product to dryness to obtain the product N-propyl-4-hydrazone-naphthalimide (namely N-P-4-HN).
3) Preparation of N-P-4-HN @ UiO-66-NH2Composite material
10mg of N-P-4-HN and 5mg of UiO-66-NH2Dissolving the material in 10mL ethanol, magnetically stirring for 2h, standing, centrifuging, washing with deionized water to obtain N-P-4-HN @ UiO-66-NH2A composite material.
4) Drawing a working curve
Adding N-P-4-HN @ UiO-66-NH2The composite material is dispersed in an aqueous solution to prepare a dispersion liquid with the concentration of 2 mg/mL. 100 mu L N-P-4-HN @ UiO-66-NH was removed2The dispersion was added to a centrifuge tube containing 800. mu.L of deionized water and 100. mu.L of the dispersion was added from 0mol/L to 5X 10-5And oscillating the HCHO standard solution with the concentration of mol/L to fully and uniformly mix the HCHO standard solution, testing the fluorescence emission spectrum of the HCHO standard solution under the excitation of 362nm by using a fluorescence spectrometer after 10min, and drawing a working curve according to the relation between the fluorescence intensity and the HCHO concentration.
5) Detection of
Replacing HCHO standard solution with the sample to be tested, adding by a standard addition method, oscillating to uniformly mix, testing the fluorescence emission spectrum of the sample under the excitation of 362nm by using a fluorescence spectrometer after 10min, and substituting the fluorescence intensity into a working curve to obtain the HCHO concentration in the sample to be tested;
wherein, the sample to be detected is 1% white spirit.
N-P-4-HN @ UiO-66-NH prepared by the invention2The application principle of the composite material for determining the content of HCHO is as follows: when N-P-4-HN is connected with HCHO, HCHO prohibits the intramolecular energy transfer of N-P-4-HN, thereby enhancing the fluorescence of N-P-4-HN at 553nm, weakening the fluorescence at 430nm, UiO-66-NH, by the internal rate effect2The adsorption of N-P-4-HN makes the fluorescence change more obvious, and the measurement is carried out through the change of the fluorescence spectrum.
Compared with the prior art, the invention has the following beneficial effects:
1) the preparation process is simple and is carried out at room temperature without using highly toxic reagents.
2)UiO-66-NH2The highly uniform nanoscale cavity and the large specific surface area not only play an important role in the specific recognition of the target, but also promote the enrichment of the target in the pores, thereby achieving a lower detection limit and higher sensitivity.
3) The response is quick, and the detection can be carried out after 10 min.
4) The method adopts N-P-4-HN @ UiO-66-NH2The method for determining the HCHO content of the composite material has the characteristics of high selectivity and high sensitivity.
Drawings
FIG. 1 is a schematic representation of the present invention N-P-4-HN @ UiO-66-NH2Transmission electron micrographs of the composite;
FIG. 2 shows UiO-66-NH according to the invention2And N-P-4-HN @ UiO-66-NH2XRD diffractogram of the composite;
FIG. 3 shows UiO-66-NH according to the invention2And N-P-4-HN @ UiO-66-NH2N of composite material2Adsorption-desorption graph;
FIG. 4 shows N-P-4-HN @ UiO-66-NH corresponding to 50. mu. mol/L HCHO in example 1 of the present invention2Composite materials were prepared with N-P-4-HN: UiO-66-NH2Ratio plot of fluorescence intensity at 553m to 466.4nm for ratio change;
FIG. 5 shows N-P-4-HN @ UiO-66-NH corresponding to 50. mu. mol/L HCHO in example 1 of the present invention2The ratio of the fluorescence intensity of the composite material with the change of temperature at 553m to 466.4nm is shown;
FIG. 6 is N-P-4-HN @ UiO-66-NH caused by HCHO at various concentrations in example 1 of the present invention2A composite material fluorescence spectrum change diagram (A) and a linear relation diagram (B) in the range of 0-5 mu mol/L;
FIG. 7 is a selectivity control of the composite material prepared in example 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
The UiO-66-NH2The preparation process of the material is as follows:
0.0932g of zirconium tetrachloride, 0.0664g of 2-aminoterephthalic acid and 0.73g of benzoic acid were weighed accurately into a 20mL screw-cap glass vial, dissolved in 14.0mL of N, N-Dimethylformamide (DMF) and 72. mu.L of concentrated hydrochloric acid (HCl) and sonicated for 15 min. The glass bottle is heated and reacted for 24 hours under the condition of oil bath at the temperature of 120 ℃, and magnetic stirring is continuously carried out. After the reaction is finished, cooling to room temperature, centrifuging to obtain yellow crystals, and repeatedly washing with DMF and ethanol for 3 times respectively. The resulting crystals were dried at 60 ℃.
The preparation process of the N-P-4-HN material is as follows:
dissolving 4-bromo-1, 8-naphthalic anhydride (5mmol) in 30mL of ethanol, adding alanine (10mmol), refluxing at 90 ℃ for 4 hours, cooling to room temperature, adding to 1000mL of water, recrystallizing, dissolving the product in 90mL of ethanol, adding hydrazine hydrate (20mmol), refluxing at 90 ℃ for 6 hours, and rotary evaporating the product to dryness to obtain the product N-propyl-4-hydrazone-naphthalimide (namely N-P-4-HN).
The N-P-4-HN @ UiO-66-NH2The preparation process of the composite material is as follows:
10mg of N-P-4-HN and 5mg of UiO-66-NH2Dissolving in 10mL ethanol, magnetically stirring for 2h, standing, centrifuging, and washing with deionized water.
The process of drawing the working curve is as follows:
adding N-P-4-HN @ UiO-66-NH2The composite material is dispersed in an aqueous solution to prepare a dispersion liquid with the concentration of 2 mg/mL. 100 mu L N-P-4-HN @ UiO-66-NH was removed2The dispersion was added to a centrifuge tube containing 800. mu.L of deionized water and 100. mu.L of the dispersion was added from 0mol/L to 5X 10-5HCHO standard solution with mol/L concentration is shaken to be mixed evenlyAnd after 10min, testing the fluorescence emission spectrum of the sample by using a fluorescence spectrometer under the excitation of 362nm, and drawing a working curve according to the relation between the fluorescence intensity and the HCHO concentration.
The detection process is as follows:
replacing HCHO standard solution with the sample to be tested, adding by a standard addition method, oscillating to uniformly mix, testing the fluorescence emission spectrum of the sample under the excitation of 362nm by using a fluorescence spectrometer after 10min, and substituting the fluorescence intensity into a working curve to obtain the HCHO concentration in the sample to be tested;
wherein, the sample to be detected is 1% white spirit.
FIG. 4 shows N-P-4-HN @ UiO-66-NH corresponding to 50. mu. mol/L HCHO in example 1 of the present invention2Composite materials were prepared with N-P-4-HN: UiO-66-NH2Ratio-varying fluorescence intensity ratio plot at 553nm and 466.4 nm; when the ratio is between 0.5 and 2, N-P-4-HN @ UiO-66-NH2The fluorescence of the + HCHO solution gradually increased at the ratio of 553nm to 466.4nm intensity. Furthermore, the fluorescence ratio values were approximately the same in the range of 2 to 5. Therefore, we chose 2 as the best ratio value to detect HCHO. N-P-4-HN attenuated at 430nm, N-P-4-HN @ UiO-66-NH2Decrease at 466.4nm due to UiO-66-NH2There is emission at 466.4nm, the emissions overlap.
FIG. 5 shows N-P-4-HN @ UiO-66-NH corresponding to 50. mu. mol/L HCHO in example 1 of the present invention2The ratio of 553nm to 466.4nm of the fluorescence intensity of the composite material with the change of temperature is shown; when the temperature is between 0 and 10 ℃, N-P-4-HN @ UiO-66-NH2The fluorescence of the + HCHO solution gradually increases at an intensity ratio of 553nm to 466.4nm, hardly changes at a temperature of 10 to 30 ℃, and gradually decreases at a temperature of 30 to 60 ℃. Therefore, we chose 10-30 ℃ as the optimal temperature for detection of HCHO.
FIG. 6A is a graph of the concentration of HCHO induced N-P-4-HN @ UiO-66-NH at various concentrations under optimal reaction conditions for example 1 of the present invention2The fluorescence intensity change curve of the composite material shows that N-P-4-HN @ UiO-66-NH increases with the HCHO concentration2The fluorescence intensity of the composite material is gradually enhanced at 553nm, gradually reduced at 466.4nm, and the ratio of the fluorescence intensity at 553nm to that at 466.4nm is gradually increasedHigh.
FIG. 6B shows HCHO concentration between 1 and 3. mu. mol L-1Within the scope, the embodiments of the invention exhibit good linear range for detecting HCHO. Linear result Y0.19791X +0.07384, R2The lowest detection limit was 0.173. mu. mol L, 0.99332-1。
FIG. 7 is a selectivity control of an example of the present invention, and in order to demonstrate the selectivity of the composite material of the present invention for HCHO, a control group was designed to measure the change in fluorescence intensity of the composite material in the presence of interfering substances. The result shows that the fluorescence intensity of the composite material can be changed only in the presence of the object to be detected, and other various interference substances basically do not influence the change of the fluorescence intensity.
Example 2
N-P-4-HN @ UiO-66-NH prepared in example 1 was used2The composite material is successfully applied to the detection of HCHO in 10% white spirit by a standard addition method.
The method comprises the following specific steps;
1) commercially available white spirit was prepared by adding three different concentrations (1, 2 and 3 μmolL)-1) The recovery experiment was performed on HCHO of (1). In the test solution, the white spirit was finally diluted 10-fold.
2) Otherwise as in example 1.
As can be seen from table 1, the recovery was in the range of 97.2-102.7% with a relative standard deviation (n-3) of less than 5%, indicating that the accuracy and precision of the composite in detecting HCHO in 1% white spirit samples was high.
TABLE 1 recovery test results
White spirit sample Scalar quantity (μ M) Detected quantity (μ M) Recovery (%, n ═ 3) Relative standard deviation RSD (%, n ═ 3)
Sample 1 1.00 1.05 105.00 1.89
Sample 2 2.00 2.04 102.22 2.70
Sample 3 3.00 3.25 93.32 7.52

Claims (3)

1. Adopts N-P-4-HN @ UiO-66-NH2The method for measuring the HCHO content of the composite material is characterized by comprising the following steps: the method comprises the following steps:
1) preparation of N-P-4-HN Material
Dissolving 4-bromo-1, 8-naphthalic anhydride in ethanol, adding alanine for reflux reaction, cooling, adding water for recrystallization, dissolving a recrystallized product in ethanol, adding hydrazine hydrate for reflux reaction, and evaporating to dryness to obtain a product, namely N-propyl-4-hydrazone-naphthalimide which is an N-P-4-HN material;
2) preparation of N-P-4-HN @ UiO-66-NH2Composite material
Mixing N-P-4-HN material and UiO-66-NH2Material solutionDissolving in ethanol, stirring, standing, centrifuging, washing with deionized water to obtain N-P-4-HN @ UiO-66-NH2A composite material;
3) drawing a working curve
Adding N-P-4-HN @ UiO-66-NH2The composite material is dispersed into aqueous solution to prepare dispersion liquid with the concentration of 2mg/mL, and 100 mu LN-P-4-HN @ UiO-66-NH is removed2The dispersion was added to a centrifuge tube containing 800. mu.L of deionized water and 100. mu.L of the dispersion was added from 0mol/L to 5X 10-5Oscillating the HCHO standard solution with the concentration of mol/L to uniformly mix the HCHO standard solution, testing the fluorescence emission spectrum of the HCHO standard solution under the excitation of 362nm by using a fluorescence spectrometer after 10min, and drawing a working curve according to the relation between the fluorescence intensity and the HCHO concentration;
4) detection of
Replacing HCHO standard solution with the sample to be tested, adding by a standard addition method, oscillating to uniformly mix, testing the fluorescence emission spectrum of the sample under the excitation of 362nm by using a fluorescence spectrometer after 10min, and substituting the fluorescence intensity into a working curve to obtain the HCHO concentration in the sample to be tested;
wherein the sample to be detected is 1% white spirit;
in step 2), N-P-4-HN material is reacted with UiO-66-NH2The mass ratio of the materials is 2: 1;
the N-P-4-HN @ UiO-66-NH2The linear range of the HCHO content measured by the composite material is 1-3 mu mol/L, and the correlation coefficient is 0.99332;
the N-P-4-HN @ UiO-66-NH2The lower limit of detection of the composite material for determining the content of HCHO is 0.173 mu mol/L.
2. The method of claim 1 using N-P-4-HN @ UiO-66-NH2The method for measuring the HCHO content of the composite material is characterized by comprising the following steps: UiO-66-NH in step 2)2The preparation method of the composite material comprises the following steps:
adding zirconium tetrachloride, 2-amino terephthalic acid and benzoic acid into a container, adding N, N-dimethylformamide and hydrochloric acid, performing ultrasonic treatment, heating for reaction, cooling and centrifuging after the reaction is finished to obtain a crude product, washing the crude product with DMF (dimethyl formamide) and ethanol respectively, and drying to obtain the product.
3. The method of claim 1 using N-P-4-HN @ UiO-66-NH2The method for measuring the HCHO content of the composite material is characterized by comprising the following steps: the N-P-4-HN @ UiO-66-NH2The detection temperature for detecting the HCHO content of the composite material is 10-30 ℃.
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