CN115015348B - Pillared arene and pillared arene-graphyne composite material with MA (MA) specificity recognition, preparation method and application thereof - Google Patents
Pillared arene and pillared arene-graphyne composite material with MA (MA) specificity recognition, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a pillared aromatic hydrocarbon with MA specificity recognition, a pillared aromatic hydrocarbon-graphdiyne composite material, a preparation method and application thereof, wherein the molecular formula of the pillared aromatic hydrocarbon with MA specificity recognition is C 55 O 30 H 40 Na 10 . According to the invention, the pillared arene with MA specific recognition is designed and synthesized, and the excellent host-guest recognition performance of the pillared arene and the characteristics of excellent conductivity, porosity, large specific surface area and the like of the graphite alkyne composite material are combined to prepare the pillared arene-graphite alkyne composite material with MA specific recognition and use the prepared composite material as an electrochemical sensor, so that the electrochemical analysis method which is simple, rapid, high in sensitivity, strong in specificity and applicable to detecting MA in a complex sample and does not need complex instruments and equipment is realized by using the sensor.
Description
Technical Field
The invention relates to a pillar aromatic hydrocarbon and pillar aromatic hydrocarbon-graphdiyne composite material, a preparation method and application thereof, in particular to a pillar aromatic hydrocarbon and pillar aromatic hydrocarbon-graphdiyne composite material with MA (MA) specificity identification, a preparation method and application thereof.
Background
Methamphetamine (MA), commonly known as Methamphetamine, was synthesized in 1919 in Japan from ephedrine for the treatment of respiratory diseases, 1938 Germany
The company starts to sell legally, and the world war II MA is used as an irritant drug, so that the substance is abused, and the substance is one of the most harmful drugs in the world at present.
Currently, the main methods for detecting MA are:
(1) Chromatography: thin layer chromatography (TCL), gas Chromatography (GC), high Performance Liquid Chromatography (HPLC). The TCL method is simple, convenient and quick to operate, does not need complex instruments and professional operators, and can be used for on-site determination of MA. However, the method is not easy to detect drugs with low content and similar chemical structure, and false positive often appears when the impurities in the drugs are not completely removed, and the result is unreliable. The GC and HPLC methods have the characteristics of good separation effect, high sensitivity and the like, but the method needs to pretreat the detected material, has long measurement time and high cost, and is not suitable for the on-site direct analysis of MA.
(2) Color-quality combination: compared with the chromatography, the gas chromatography-mass spectrometry (GC/MS) and the liquid chromatography-mass spectrometry (HPLC/MS) combine high separation capability of the chromatography with high identification capability of the mass spectrum, have good reproducibility, accuracy and sensitivity, and the detection of the MA and other poisons by the method becomes one of the internationally recognized standard methods at present. However, this method requires expensive equipment, specialized laboratories, and specialized chemical practitioners, and is not suitable as a method for on-site analysis of MA.
(3) And (3) spectrometry: the spectrum method has the advantages of small sample consumption, high analysis speed and the like, provides potential application prospects for on-site direct detection of MA with the appearance of low-cost portable spectrum instruments, but has higher requirements on the purity of samples. The biological detection material is very complex in composition and may contain a large amount of other interferents besides different kinds of drugs. There is therefore a major limitation to the use of spectroscopy in MA detection.
(4) Capillary electrophoresis method: the capillary electrophoresis method has the characteristics of high efficiency, short analysis time, trace amount, low price and the like, and is more and more concerned in drug detection and analysis, but the method is only suitable for analysis in a laboratory at present, so the method is not suitable for on-site detection of MA.
(5) Immunoassay method: compared with instrument analysis and detection, the immunoassay method is suitable for on-site rapid detection and analysis due to the characteristics of simplicity, convenience, high sensitivity, low detection cost and the like, and is widely applied to the field of rapid drug detection.
Although the methods have certain advantages and even some of the methods are well applied to actual detection, most of the methods need to pretreat a sample, remove interfering impurities and enrich trace components to be detected. Particularly, in the case of complex and large-scale detection of sample components, the method has the disadvantages of time consumption, complexity, expensive instrument, specialized operation and difficulty in miniaturization, and is not suitable for rapid detection on site.
Disclosure of Invention
The invention aims to overcome the defects and provide a pillared aromatic hydrocarbon and a pillared aromatic hydrocarbon-graphyne composite material with MA specific recognition, a preparation method and application thereof.
According to the method, the pillared aromatic hydrocarbon with MA specific recognition is designed and synthesized, and the excellent host-guest recognition performance of the pillared aromatic hydrocarbon and the characteristics of excellent conductivity, porosity, large specific surface area and the like of the graphdiyne composite material are combined to prepare the pillared aromatic hydrocarbon-graphdiyne composite material with MA specific recognition and use the prepared pillared aromatic hydrocarbon-graphdiyne composite material as an electrochemical sensor, so that the electrochemical analysis method which is simple, rapid, high in sensitivity, strong in specificity and suitable for detecting MA in a complex sample without complex instruments and equipment is realized by using the sensor.
The technical scheme adopted by the invention for realizing the aim is as follows:
a pillar arene with MA specific recognition has a molecular formula as follows: c 55 O 30 H 40 Na 10 The chemical structural formula is as follows:
in order to realize the specific recognition of MA molecules, the inventor modifies the column arene, designs and synthesizes multifunctional column arene with different terminal functional groups and different charges, researches the host-guest chemistry of MA and the column arene and multiple interaction between the MA and the column arene, and further screens out the functional column arene capable of recognizing MA with high selectivity, thereby obtaining the column arene with MA specific recognition.
A synthetic method of a pillar aromatic hydrocarbon with MA specific recognition comprises the following steps:
step 2, demethylating the methoxyl column [5] arene under the action of boron tribromide to obtain hydroxyl column [5] arene;
step 3, substituting phenolic hydroxyl groups through esterification reaction to prepare ester functionalized column [5] arene, and preparing carboxylated column [5] arene through ester hydrolysis;
and 4, neutralizing with acid and alkali to form salt to obtain the host molecule WP5.
The synthetic route is shown as the following formula:
the pillared aromatic hydrocarbon (WP 5) -Graphdine (GDY) composite material with MA specific recognition comprises the pillared aromatic hydrocarbon with MA specific recognition, the pillared aromatic hydrocarbon with MA specific recognition is obtained by introducing macrocyclic host supramolecules into the surface of the graphdine, and the pillared aromatic hydrocarbon is a 5 th generation supramolecular host macrocyclic compound after crown ether, cyclodextrin, calixarene and cucurbituril, has a unique electron-rich rigid cavity structure, is good in symmetry, is easy to modify at two ends of a molecule, and has strong host-guest recognition capability. Specifically, the composite material is as follows: WP5-GDY, the material has excellent conductivity and molecular recognition capability. Good electric conduction lays a foundation for constructing an electrochemical sensor, and excellent supermolecule recognition capability provides a precondition for selective recognition.
A preparation method of a pillared aromatic hydrocarbon-graphdine composite material with MA specific recognition comprises the following steps:
firstly, synthesizing a porous graphite alkyne composite material by adopting a one-pot method, firstly dissolving 1,3,5-triethyleneyne in dichloromethane, adding ultrapure water to form a layered solution, slowly adding palladium bis (triphenylphosphine) dichloride, cuprous iodide and 1,3,5-tribromobenzene into the mixed solution, and performing ultrasonic treatment; stirring the mixed solution at room temperature for reaction for 72 hours, and filtering, washing and vacuum drying the generated solid to obtain porous graphite alkyne;
and step two, dispersing the prepared GDY into a WP5 solution by using ultrasound, stirring overnight at room temperature, and centrifugally washing to obtain a WP5-GDY composite material, so as to control and assemble the surface of the MA-specific identified pillar aromatic hydrocarbons WP 5-GDY.
The application of the pillar aromatic hydrocarbon-graphite alkyne composite material with MA specific recognition in preparing the electrochemical sensor for realizing the quantitative detection of MA comprises the steps of modifying WP5-GDY composite material dispersion liquid on a cleaned bare electrode, and drying at room temperature to obtain the electrochemical sensor with the MA quantitative detection performance.
The mechanism of the pillared arene-graphdiyne composite material with MA specific recognition is as follows:
because the graphyne has the characteristic of sp and sp2 hybridization, the pillar arene and the graphyne have stronger non-covalent interaction to form a functional hybrid composite material, and the non-covalent interaction mainly comprises pi-pi action, hydrophobic action and hydrogen bond action. By taking the graphdiyne as a substrate and utilizing the unique host-guest recognition performance of a supramolecular host and the excellent conductivity of the graphdiyne through the non-covalent modification of macrocyclic supramolecular column arene, the sensitivity and the selectivity of the sensor are greatly improved, and the stability of a sensing system is enhanced. Due to the interaction between the structural features of the MA molecule and the structural features of WP5, the host-guest molecule recognition between MA and WP5 can be considered to occur through electrostatic interaction, pi-pi interaction and hydrophobic interaction, and the mechanism is shown in FIG. 2.
The invention has the beneficial effects that:
experiments show that the MA-WP 5 composite material has strong interaction force, and in addition, by analyzing the electrochemical behavior of MA with different concentrations on WP-GDY, the current signal intensity is increased along with the increase of the MA concentration and presents a linear relation along with the increase of the MA concentration, so that the pillared arene-graphdine composite material with MA specific recognition has a good application prospect in the preparation of electrochemical sensors for realizing the quantitative detection of MA.
Drawings
FIG. 1: the chemical structural formula of the pillar aromatic hydrocarbon WP5 with MA specific recognition is shown in the figure.
FIG. 2: the mechanism of the composite material WP5-GDY as an electrochemical sensor is shown schematically.
FIG. 3: nuclear magnetic hydrogen spectrum of WP5.
FIG. 4: infrared and thermal stability plots for WP 5-GDY.
FIG. 5: a result graph of the quantitative detection performance of the electrochemical sensor having the quantitative detection performance for MA.
Detailed Description
Example 1: synthesis of pillared arenes with MA specific recognition
The method specifically comprises the following steps:
step 2, demethylating the methoxyl column [5] arene under the action of boron tribromide to obtain hydroxyl column [5] arene;
step 3, substituting phenolic hydroxyl groups through esterification reaction to prepare ester functionalized column [5] arene, and preparing carboxylated column [5] arene through ester hydrolysis;
and 4, neutralizing with acid and alkali to form salt to obtain a host molecule WP5, wherein the molecular formula is as follows: c 55 O 30 H 40 Na 10 The structural formula is shown in figure 1.
When guest molecules MA of different volumes and equal concentrations are sequentially added to a solution of host molecules WP5 of constant concentration, the fluorescence intensity tends to decrease. With the addition of guest molecules, the fluorescence intensity becomes weaker and weaker. This change is due to the strong supramolecular interaction between MA and WP5. The positively charged MA and the negatively charged WP5 are adsorbed in the cavity, and the fluorescence intensity of the WP5 is reduced through charge transfer (the electrons of the host molecule are changed to promote the fluorescence to be reduced after the guest molecule is wrapped in the cavity of the host molecule). And further evaluating the binding force of MA and WP5 according to a method of solving the binding constant by using a double reciprocal method. The combination constant of the two is Ka =1.95 × 10 5 And reaches 5 orders of magnitude. This result further illustrates that there is a strong interaction between MA and WP5.
Characterization of WP 5:
as shown in FIG. 3, four peaks can be seen from the nuclear magnetic hydrogen spectrum of WP5, and the single peak at 6.64ppm of chemical shift is hydrogen on the benzene ring in WP5. Although there are 10 hydrogen atoms in common, WP5 is a symmetric macrocyclic molecule, so the chemical shifts of the hydrogens on the benzene ring are equivalent, and there is only one peak. The peak at a chemical shift of 4.7ppm is the peak for solvent heavy water. The singlet at 4.14 is the hydrogen of the methylene group in the side chain on WP5, with a total of 20 hydrogens. The last peak was at 3.79ppm and was assigned to a methylene group between two benzene rings, so there were 10 hydrogens. The highly symmetrical structure allows each hydrogen to be in the same chemical environment and no hydrogen is nearby, so that all are unimodal.
Example 2: preparation of pillared aromatic hydrocarbon-graphyne composite material with MA (MA) specificity recognition
The method specifically comprises the following steps:
firstly, synthesizing a porous graphite alkyne composite material by adopting a one-pot method, firstly dissolving 1,3,5-triethyleneyne in dichloromethane, adding ultrapure water to form a layered solution, slowly adding palladium bis (triphenylphosphine) dichloride, cuprous iodide and 1,3,5-tribromobenzene into the mixed solution, and performing ultrasonic treatment; stirring the mixed solution at room temperature for reaction for 72 hours, and filtering, washing and vacuum drying the generated solid to obtain porous graphite alkyne;
and step two, controlling and assembling the MA specific recognition column aromatic hydrocarbon (WP 5) to GDY surface, dispersing the prepared GDY into a WP5 solution by ultrasonic, stirring overnight at room temperature, and centrifugally washing to obtain the WP5-GDY composite material.
Characterization of WP 5-GDY:
as shown in FIG. 4, it can be seen from the infrared image of WP5 that it is at 1713cm -1 There is an absorption peak attributed to the carbonyl absorption peak at the carboxyl group, and this peak is also present in the infrared image of the composite WP 5-GDY. Furthermore, the IR spectrum of GDY can be as high as 2270cm -1 The peak is the peak of alkynyl, and is also present in the infrared image of the compound WP5-GDY, therefore, the above results prove that the two compounds are successful. Pure GDY has good thermal stability as seen in the thermal stability tests of WP5-GDY and GDY, while the stability of the composite is a little worse than GDY. The main reason is that there is an organic compound WP5, which decomposes at high temperature, again proving the successful recombination of WP5 and GDY.
As an application, the WP5-GDY composite can also be a WP5-GDY nanocomposite.
Example 3: preparation of electrochemical sensor with MA specific recognition
The method specifically comprises the steps of modifying the WP5-GDY composite material dispersion liquid onto a cleaned bare electrode, and drying at room temperature to obtain the electrochemical sensor with the MA quantitative detection performance.
Analyzing the electrochemical behavior of MA with different concentrations on WP-GDY, and increasing the oxidation peak at the corresponding recognition potential (the potential is the basis for qualitative recognition in practical application) along with the increase of the concentration of MA. The intensity of the current signal increases with increasing MA concentration and exhibits a linear relationship. The inventors analyzed the calibration between the concentration of MA and the current level and made a linear equation. Therefore, the inventor carries out electrochemical test on a sample to be tested through WP-GDY, a current peak exists at a corresponding qualitative identification potential to indicate that the sample contains MA, and the content of the MA can be obtained by substituting the measured current value into a linear equation.
As shown in FIG. 5, the inventors applied the electrochemical sensor to the detection of MA in actual biological samples and compared with the qualitative and quantitative results of LC-MS/MS. The method specifically comprises the following steps:
preparing 100 parts of actual biological samples (urine samples and blood samples) with the MA concentration ranges of 0.01ug/mL-0.5ug/mL and 0.5ug/mL-10ug/mL respectively, identifying and detecting the MA in the actual samples by using the constructed electrochemical sensor, and comparing with the qualitative and quantitative results of LC-MS/MS to verify and examine the methodological attributes such as specificity, sensitivity, linearity, detection range and the like of the electrochemical sensor for detecting the MA in the actual biological samples. The results were: the detection concentration ranged from 0.05. Mu.M to 30. Mu.M, with a detection limit of 0.03. Mu.M. The result is not much different from the result of LC-MS/MS measurement, which shows that the electrochemical method has feasibility for detecting MA.
Claims (3)
1. The pillared arene-grapyne composite material with MA specific recognition is characterized by comprising pillared arene with MA specific recognition, wherein the pillared arene is obtained by introducing large-ring main body supermolecules into the surface of grapyne GDY, has a unique electron-rich rigid cavity structure, is good in symmetry, is easy to modify at two molecular ends and has host-guest recognition capability, and the molecular formula of the pillared arene with MA specific recognition is as follows: c 55 O 30 H 40 Na 10 The chemical structural formula is as follows:
2. the preparation method of the pillar arene-graphdine composite material with the MA specific recognition function according to claim 1, wherein the MA is methamphetamine, and the method comprises the following steps:
firstly, synthesizing a porous graphite alkyne composite material by adopting a one-pot method, firstly dissolving 1,3,5-triethyleneyne in dichloromethane, adding ultrapure water to form a layered solution, slowly adding palladium bis (triphenylphosphine) dichloride, cuprous iodide and 1,3,5-tribromobenzene into the mixed solution, and performing ultrasonic treatment; stirring the mixed solution at room temperature for reaction for 72 hours, and filtering, washing and vacuum-drying the generated solid to obtain porous graphite alkyne GDY;
and step two, controlling and assembling the surface of the MA specific recognition column aromatic hydrocarbons WP5 to GDY, dispersing the prepared GDY into a WP5 solution through ultrasound, stirring overnight at room temperature, and performing centrifugal cleaning to obtain the WP5-GDY composite material.
3. The application of the pillar aromatic hydrocarbon-graphdiyne composite material with MA specific recognition in the preparation of the electrochemical sensor for realizing the quantitative detection of MA, wherein MA is methamphetamine, and the method is characterized by comprising the steps of modifying a dispersion liquid of the pillar aromatic hydrocarbon-graphdiyne composite material on a clean bare electrode, and drying at room temperature to obtain the electrochemical sensor with the MA quantitative detection performance, and the electrochemical sensor is used for realizing the quantitative detection of MA.
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