CN108732218A - A kind of electrochemical sensor measuring 2,4,6- trichlorophenol, 2,4,6,-Ts and its preparation and application - Google Patents
A kind of electrochemical sensor measuring 2,4,6- trichlorophenol, 2,4,6,-Ts and its preparation and application Download PDFInfo
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Abstract
The invention belongs to a kind of molecular engram detection fields, and in particular to electrochemical sensor and its preparation and application of the one kind based on molecular imprinting technology 2,4,6- trichlorophenol, 2,4,6,-Ts of measurement.The present invention is directed to existing 2, in the electrochemical analysis techniques of 4,6- trichlorophenol, 2,4,6,-Ts, and 2,4,6- trichlorophenol, 2,4,6,-Ts have similar oxidation potential with its analogue, cause the specific recognition to object not good enough.Electrochemical sensor prepared by the present invention is to can be used for 2,4,6- trichlorophenol, 2,4,6,-T of Selective recognition based on molecular imprinting technology.Electrode modified material uses carbon quantum dot-polymer composite film, of low cost, environmentally protective；Sensor is prepared simply, and reaction condition is mild, and process is easy to control, has preferable sensitivity and stronger anti-interference to template molecule.It can be used for the quantitative analysis of 2,4,6- trichlorophenol, 2,4,6,-Ts.
Description
Technical field
The invention belongs to molecular engram detection fields, and in particular to one kind measuring 2,4,6- trichlorines based on molecular imprinting technology
The electrochemical sensor of phenol and its preparation and application.
Background technology
With the modernization of development and the industrial or agricultural of global economy, the pollutant kind being discharged into environment and quantity and day
All to increase, this greatly will influence and endanger human health and entire ecological environment.In all kinds of environmental contaminants, with chlorophenols object
Matter is that the persistence organic pollutant of representative is more typical poisonous and harmful substance in environment, with " teratogenesis, carcinogenic, cause is prominent
Become " three cause effects.The use of a large amount of chlorophenols has had resulted in the pollution of ecological environment.At the same time, chlorophenol is by drinking
The various route of exposure such as water, soil and food have an adverse effect to health, are directly detrimental to health.2,4,6- trichlorines
Phenol (2,4,6-TCP) has very strong bactericidal properties, is commonly used for timber and the preservative of industrial textile；Meanwhile it can be with
As production agricultural chemical insecticide or the raw material of industry of disinfectant pentachlorophenol (PCP).U.S. environment protection mechanism by 2,4,
The chlorophenols such as 6-TCP are included in the pollution list of 129 kinds of priority acccess controls.Substance of this kind is also included in by China《National Hazard product
Register》.Therefore, efficient, accurate, quick, the highly sensitive monitoring to 2,4,6-TCP becomes the important of food and environment safety check
Task, can be prevent and remedy pollution, environmental science management and planning, scientific basis is provided.
Currently, for 2,4,6-TCP measurement common immunoassays method, chromatography and its joint technology and electrochemical analysis
Technology etc..The above method can sensitively monitor the content of 2,4,6-TCP.But immunoassay, chromatography and its joint technology etc.
The limitations such as that there are sample pre-treatments is relatively complicated for method, and cost of determination is higher.Electrochemical analysis techniques are easy to operate because having,
Quickly in real time, the advantages of being easy to miniaturization is more paid close attention to by scientific researcher.Because 2,4,6-TCP and its analogue have
There is similar oxidation potential, 2,4,6-TCP content is detected using electrochemical analysis techniques, the selectivity of method needs further
Improve.
Molecular imprinting technology, which may be considered that, has special binding site, the binding site and template molecule shape,
Size and functional group etc. are similar to unanimously.Typically, molecularly imprinted polymer (Molecularly imprinted
Polymer, MIPs) it is a kind of synthetic material, can be by solvent appropriate, function monomer, crosslinking agent and template molecule
It is copolymerized and is prepared.Template molecule can be object itself or be similar to target substance.Then removed from polymer architecture
Part or all of template molecule is removed, the particular space that can carry out perfect matching with target molecule is obtained.It is with others identification
System is compared, and molecularly imprinted polymer has many good characteristics, such as at low cost, easily prepared, physical stability height etc..Therefore,
Applications of the MIPs in many fields becomes more and more attractive, especially in Solid Phase Extraction, chromatographic isolation and sensing
Alternatively property adsorbent is widely used in device technology.By molecular imprinting technology is distinctive highly selective and electrochemical analysis techniques
Combine, can prepare has the molecular imprinting electrochemical sensor that specific recognition responds to target molecule.Currently, based on dividing
The report that sub- engram technology prepares the electrochemical sensor for detecting 2,4,6-TCP contents is less.
2,4,6-TCP content is quantitative determined based on the electrochemical sensor of molecular imprinting technology by preparing a kind of,
This sensor has many advantages, such as that sensitive, at low cost, selectivity is good, and reaction condition is mild, can be carried for 2,4,6-TCP content analysis
For theoretical and technical support.
Invention content
The present invention is intended to provide a kind of electrochemical method based on molecular imprinting technology measurement 2,4,6-TCP, with carbon quantum
The laminated film of point-polymer composition is sensitizer, to improve the electric conductivity and electron transfer rate of electrode.With 2,4,6-
TCP is template molecule, and o-phenylenediamine or pyrroles are function monomer, and be made by electrochemical polymerization technology has spy to 2,4,6-TCP
The solid phase electrochemical sensing electrode of opposite sex identification response.The electrode has preferable stability, highly sensitive and highly selective
The advantages that.
In the present invention in the preparation method of the electrochemical sensor based on molecular imprinting technology, sensor electrochemistry is influenced
Can factor include mainly：The ratio of the formation of molecularly imprinted polymer, template molecule and function monomer and prepared sensing
Selective response etc. of the device to target molecule.By being optimized to conditions above, can build selective to 2,4,6-TCP
The molecular imprinting electrochemical sensor of response.
The present invention uses biological material to prepare green carbon quantum dot solution first, with the carbon amounts being scattered in certain solvent
Son point and the mixed solution drop coating of polymer (such as chitosan) solution composition are placed in the bare glassy carbon electrode polished under infrared lamp
Drying, is prepared into film.Then modified electrode is placed in 2,4,6-TCP, o-phenylenediamine or pyrroles's (molar ratio 0.1:1~10:
1) mixed solution, with 0.05M phosphate buffers adjusting pH value of solution for 5~9, after mixing, in 0-1.0V potential ranges,
Cyclic voltammetry scan 20 is carried out with the sweep speed of 50mV/s to enclose.Wait for after natural drying, by the electrode of above-mentioned preparation with 0.1%~
The NaOH solution of 5% (m/V) is eluent, and cyclic voltammetry scan is carried out in 0-1.5V potential ranges with same sweep speed
6 circles, eluted template molecule, you can 2,4,6-TCP molecular imprinting electrochemical sensors are made.For the ease of comparison, except being not added with mould
Outside plate molecule 2,4,6-TCP, non-trace electrode is prepared with same preparation method.
In the method, by using the potassium ferricyanide as probe, indirect determination 2,4, the content of 6-TCP.In order to evaluate
Whether the formation of molecularly imprinted polymer and imprinting effect, modified with bare glassy carbon electrode, carbon quantum dot-chitosan laminated film
The trace of trace electrode and absorption 2,4,6-TCP after electrode, the trace electrode of non-eluted template molecule, eluted template molecule
Cycle voltammetry behavior of the electrode in the potassium ferricyanide confirms (see attached drawing 1).In order to prepare the electrochemical sensing of superior performance
Device, to the ratio of template molecule-function monomer (o-phenylenediamine) carried out investigate optimization, the results show when template molecule with
The ratio of function monomer (o-phenylenediamine) is 1:When 6, the performance of prepared electrochemical sensor is more excellent (see attached drawing 2).
Electrochemical sensor prepared by the present invention is to be used for Selective recognition 2,4,6-TCP based on molecular imprinting technology
Electrochemical sensor, have preferable sensitivity (see attached drawing 3) and stronger anti-interference (see attached drawing 4).It can be used for ring
The detection of 2,4,6-TCP in the fields such as border water sample, textile, cosmetics or food.
The application has following advantage：
The present invention is directed to existing 2, in 4,6-TCP electrochemical analysis techniques, 2,4,6-TCP to be had with its analogue
There is similar oxidation potential, causes the specific recognition to object not good enough.Electrochemical sensor prepared by the present invention is different
In other 2,4,6-TCP sensing analytical methods, first, the present invention is a kind of electrochemical sensor, with carbon quantum dot-polymer
Laminated film is sensing matrix decorative material, greatly improves the electric conductivity of sensing matrix, of low cost, environmentally protective；Second,
The present invention is to can be used for Selective recognition 2,4,6-TCP based on molecular imprinting technology, makes the sensor to object 2,4,6-
TCP has stronger specific recognition capability, improves its anti-interference ability；Third, the preparation process of sensor is in room temperature, water phase
Middle progress.It prepares and is not necessarily to special protection, simple for process, process is easy to control；Fourth, sensor has preferable sensitivity (see attached
Fig. 3) and stronger anti-interference (see attached drawing 4), can be used for 2 in the fields such as environmental water sample, textile, cosmetics or food,
The analysis application of 4,6- trichlorophenol, 2,4,6,-Ts.
Description of the drawings
Fig. 1：Cyclic voltammogram of the different functional electrodes in potassium ferricyanide solution.(a) bare glassy carbon electrode, (b) carbon amounts
Sub- point-chitosan laminated film modified electrode, (c) the trace electrode of non-eluted template molecule, (d) print after eluted template molecule
Apodized electrode (e) adsorbs the trace electrode of 2,4,6-TCP.
Fig. 2：Influence of the ratio of template molecule and function monomer (o-phenylenediamine) to performance of electrochemical sensors.
Fig. 3：The difference that the current strength of electrochemical sensor prepared by the present invention changes with object 2,4,6-TCP concentration
Pulse voltammetry (DPV) response diagram.It is followed successively by curve a to f from top to bottom, curve a-f corresponds to 2,4,6-TCP concentration difference respectively
It is 0.8,1,2,8,10,40 μM.
Fig. 4：The anti-interference test of prepared electrochemical sensor.
Specific implementation mode
The technical solution further illustrated the present invention with reference to specific embodiment, these embodiments should not be understood as
It is the limitation to technical solution.
Biological material prepares carbon quantum dot in accordance with the following steps：The biological material is absorbent cotton, the green
The preparation method of carbon quantum dot is to be crushed biological material, is scattered in distilled water, it is stainless to be placed on polytetrafluoroethyllining lining
It is closed in steel reaction kettle.Hydro-thermal reaction 12h is carried out in 180 DEG C.After the completion of reaction, its cooled to room temperature is waited for.Gained is produced
Object carry out ultrasonic disperse, filtering, centrifugation, removal precipitation after, dialyse to gained supernatant, after freeze-drying to get
Carbon quantum dot；Carbon quantum dot is scattered in solvent up to carbon quantum dot solution；
The solvent of the dispersion carbon quantum dot is distilled water.
Embodiment 1
The preparation of sensor：
Volumetric concentration 4% is taken to be scattered in the carbon quantum dot solution in distilled water and 1% chitosan acetic acid solution of mass concentration
Mixed solution totally 5 μ L (volume ratios 3:1), drop coating is placed under infrared lamp and dries in the bare glassy carbon electrode surface polished.Afterwards
It is placed in the mixed solution (molar ratio 1 of 1mM 2,4,6-TCP ethanol-water solutions, 1mM o-phenylenediamine ethanol-water solutions:1), with
It is 5 that 0.05M phosphate buffers, which adjust pH value of solution, within the scope of 0-1.0V, carries out cyclic voltammetric with the sweep speed of 50mV/s and sweeps
Retouch 20 circles, electrochemical polymerization film forming.Film to be polymerized at room temperature after natural drying, by the electrode of above-mentioned preparation in 0-1.5V current potential models
In enclosing, cyclic voltammetry scan 6 is carried out in the NaOH solution of 1% (m/V) with same sweep speed and is enclosed, eluted template molecule,
It waits for after natural drying to get trace electrode.
Embodiment 2
The preparation of sensor：
Volumetric concentration 4% is taken to be scattered in the carbon quantum dot solution in distilled water and 1% chitosan acetic acid solution of mass concentration
Mixed solution totally 9 μ L (volume ratios 3:1), drop coating is placed under infrared lamp and dries in the bare glassy carbon electrode surface polished.Afterwards
It is placed in the mixed solution (molar ratio 1 of 1mM 2,4,6-TCP ethanol-water solutions, 6mM o-phenylenediamine ethanol-water solutions:6), with
It is 7 that 0.05M phosphate buffers, which adjust pH value of solution, within the scope of 0-1.0V, carries out cyclic voltammetric with the sweep speed of 50mV/s and sweeps
Retouch 20 circles, electrochemical polymerization film forming.Film to be polymerized at room temperature after natural drying, by the electrode 0-1.5V current potential models of above-mentioned preparation
In enclosing, cyclic voltammetry scan 6 is carried out in the NaOH solution of 1% (m/V) with same sweep speed and is enclosed, eluted template molecule,
It waits for after natural drying to get trace electrode.
Embodiment 3
The preparation of sensor：
Volumetric concentration 4% is taken to be scattered in the carbon quantum dot solution in distilled water and 1% chitosan acetic acid solution of mass concentration
Mixed solution totally 9 μ L (volume ratios 3:1), drop coating is placed under infrared lamp and dries in the bare glassy carbon electrode surface polished.Afterwards
It is placed in the mixed solution (molar ratio 1 of 1mM 2,4,6-TCP ethanol solutions, 6mM epolamine solution:6), with 0.05M phosphoric acid
It is 7 that buffer solution, which adjusts pH value of solution, and within the scope of 0-1.0V, the item that cyclic voltammetry scan 20 encloses is carried out with the sweep speed of 50mV/s
Electrochemical polymerization forms a film under part.Film to be polymerized at room temperature after natural drying, by the electrode 0-1.5V potential ranges of above-mentioned preparation
It is interior, using the NaOH solution of same sweep speed 1% (m/V) as elution template molecule, wait for after natural drying to get print
Apodized electrode.
Embodiment 4
The preparation of sensor：
Take that volumetric concentration 4% is scattered in the carbon quantum dot solution in distilled water and mass concentration 0.5%Nafion ethyl alcohol is molten
Liquid mixed solution totally 8 μ L (volume ratios 2:1), drop coating is placed under infrared lamp and dries in the bare glassy carbon electrode surface polished.Afterwards
It is placed in the mixed solution (molar ratio 1 of 1mM 2,4,6-TCP ethanol solutions, 3mM o-phenylenediamine ethanol solutions:3), with 0.05M
It is 7 that phosphate buffer, which adjusts solution ph, and within the scope of 0-1.0V, cyclic voltammetry scan 20 is carried out with the sweep speed of 50mV/s
Electrochemical polymerization forms a film under conditions of circle.Film to be polymerized at room temperature after natural drying, by the electrode 0-1.5V electricity of above-mentioned preparation
Position range in, using same sweep speed 1% (m/V) NaOH solution as elution template molecule, wait for naturally dry
Afterwards to get trace electrode.
Embodiment 5
The preparation of sensor：
Take that volumetric concentration 4% is scattered in the carbon quantum dot solution in distilled water and 0.5% polyvinyl alcohol of mass concentration is water-soluble
Liquid mixed solution totally 10 μ L (volume ratios 1:1), drop coating is placed under infrared lamp and dries in the bare glassy carbon electrode surface polished.
It is placed on the mixed solution (molar ratio 1 of 1mM 2,4,6-TCP ethanol solutions, 9mM o-phenylenediamine ethanol solutions:9), with
It is 7 that 0.05M phosphate buffers, which adjust pH value of solution, within the scope of 0-1.0V, carries out cyclic voltammetric with the sweep speed of 50mV/s and sweeps
Electrochemical polymerization forms a film under conditions of retouching 20 circles.Film to be polymerized at room temperature after natural drying, by the electrode 0- of above-mentioned preparation
In 1.5V potential ranges, using same sweep speed 1% (m/V) NaOH solution as elution template molecule, wait for from
To get trace electrode after so drying.
Embodiment 6
The detection of 2,4,6- trichlorophenol, 2,4,6,-T standard solution
Using trace electrode made from embodiment 2 as working electrode, Ag/AgCl electrodes are reference electrode, and platinum filament is auxiliary electricity
Pole.In 5mM K3[Fe(CN)6] in solution (KCl containing 0.1M is as supporting electrolyte), add the 2 of various concentration, 4,6-TCP marks
Quasi- solution detects electrochemical response signal by detection means of DPV.The experimental results showed that under conditions of 7 pH, 2,4,6-
Logarithm (in 0.8~40 μM of concentration range) in a linear relationship between the logarithm of peak current signal, detection limit of TCP concentration
For 0.24 μM (S/N=3) (see attached drawing 3).
Embodiment 7
The detection of 2,4,6- trichlorophenol, 2,4,6,-Ts in environmental water sample
Using trace electrode made from embodiment 2 as working electrode, Ag/AgCl electrodes are reference electrode, and platinum filament is auxiliary electricity
Pole.Electrochemical response signal is detected by detection means of DPV.The 2,4,6-TCP in tap water is carried out using standard addition method
Quantitative analysis, recovery of standard addition is in 97.60%~102.6% range.
Technical scheme of the present invention is not limited to examples detailed above, and the other embodiments obtained according to the technique and scheme of the present invention are equal
It should fall into the claim of the present invention.
Claims (8)
1. a kind of preparation method for the electrochemical sensor measuring 2,4,6- trichlorophenol, 2,4,6,-Ts, it is characterised in that：It comprises the steps of,
1) biological material is used to prepare green carbon quantum dot solution；
2) carbon quantum dot being scattered in solvent and polymer solution be sufficiently mixed preparing mixed solution；
3) by the mixed solution drop coating in step 2) in the bare glassy carbon electrode polished；
4) bare glassy carbon electrode after drop coating in step 3) is placed under infrared lamp and is dried；
5) it is template molecule and then electrode prepared by step 4) to be placed in 2,4,6-TCP, with one in o-phenylenediamine or pyrroles
In kind or the mixed solution that two kinds are function monomer, wherein a concentration of 0.5~10mM of template molecule, the concentration of function monomer
For 1~9mM；Template molecule is 0.1 according to molar ratio with function monomer:1~10:1 ratio is mixed, and is adjusted with buffer solution
PH value of solution is 5~9, and cyclic voltammetry scan is carried out in 0-1.0V potential ranges with the sweep speed of 50mV/s after mixing,
Electrochemical polymerization forms a film；
6) by step 5) prepare electrode using aqueous slkali as eluent, with same sweep speed in 0-1.5V potential ranges into
Row cyclic voltammetry scan, eluted template molecule, you can 2,4,6-TCP molecular imprinting electrochemical sensors are made.
2. preparation method as described in claim 1, it is characterised in that：
Biological material described in step 1) is one or more of absorbent cotton, bagasse or peanut shell, described green
The preparation method of color carbon quantum dot is to be crushed above-mentioned biological material, is scattered in distilled water, is placed in polytetrafluoroethylene (PTFE)
It serves as a contrast in stainless steel cauldron, it is closed；Carry out hydro-thermal reaction；After the completion of reaction, its cooled to room temperature is waited for；By products therefrom into
Row ultrasonic disperse, filtering, centrifugation dialyse to gained supernatant, after removal precipitates to get carbon amounts after freeze-drying
Sub- point；Carbon quantum dot is scattered in solvent up to carbon quantum dot solution；
The solvent of the dispersion carbon quantum dot is one or both of distilled water, ethyl alcohol.
3. preparation method as described in claim 1, it is characterised in that：
Polymer solution described in step 2) is chitosan solution, Nafion solution or poly-vinyl alcohol solution；
The volumetric concentration of the carbon quantum dot solution is 3%~6%, and the mass concentration of polymer solution is 0.5%~1%；Carbon
The volume ratio of quantum dot solution and polymer solution is 0.5:1~6:1；
The solvent of the solution is one or more of distilled water, ethyl alcohol or acetic acid.
4. preparation method as described in claim 1, it is characterised in that：
Mixed solution described in step 3) drips Tu in the bare glassy carbon electrode polished as follows：It is drawn with microsyringe
5~10 μ L are through the uniform mixed solution of ultrasonic disperse, and drop coating is on the GC130 to have polished, diameter 3mm bare glassy carbon electrodes.
5. preparation method as described in claim 1, it is characterised in that：
The solvent of the step 5) mixed solution is one or both of ethyl alcohol, distilled water；
The template molecule is 1 according to molar ratio with function monomer:6 ratio is mixed.
6. preparation method as described in claim 1, it is characterised in that：
Aqueous slkali described in step 6) is NaOH eluents, a concentration of 0.1%~5% (m/V).
7. a kind of using the electrochemical sensing for measuring 2,4,6- trichlorophenol, 2,4,6,-Ts made from any preparation method in claim 1~6
Device.
8. the electrochemical sensor described in a kind of claim 7 is in determination of the environment water sample, textile, cosmetics or field of food
The application of the content of 2,4,6- trichlorophenol, 2,4,6,-Ts.
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| CN109828013A (en) * | 2019-03-11 | 2019-05-31 | 哈尔滨理工大学 | Electrochemical cathode synthesize a kind of metal-organic framework materials and its in Electrochemical Detection water 2,4,6- trichlorophenol, 2,4,6,-T application |
| CN109828013B (en) * | 2019-03-11 | 2021-04-09 | 哈尔滨理工大学 | Metal organic framework material synthesized by electrochemical cathode and application of metal organic framework material in electrochemical detection of 2,4, 6-trichlorophenol in water |
| CN112326753A (en) * | 2020-09-30 | 2021-02-05 | 天津科技大学 | Preparation method and application of triclosan molecularly imprinted membrane electrochemical sensor |
| CN112326753B (en) * | 2020-09-30 | 2023-06-23 | 天津科技大学 | Preparation method and application of triclosan molecular imprinting membrane electrochemical sensor |
| CN113311042A (en) * | 2021-06-02 | 2021-08-27 | 江苏理工学院 | Bisphenol A molecularly imprinted electrochemical sensor and preparation method and application thereof |
| CN113311042B (en) * | 2021-06-02 | 2023-04-25 | 江苏理工学院 | Bisphenol A molecularly imprinted electrochemical sensor and preparation method and application thereof |
| CN114839245A (en) * | 2022-05-06 | 2022-08-02 | 南京师范大学 | Carbon quantum dot modified electrode for detecting cyhalothrin and preparation method and application method thereof |
| CN114839245B (en) * | 2022-05-06 | 2024-04-19 | 南京师范大学 | Carbon quantum dot modified electrode for detecting cyhalothrin and preparation method and application method thereof |
| CN115060777A (en) * | 2022-07-08 | 2022-09-16 | 江苏理工学院 | Ratiometric electrochemical aptamer sensor for simultaneously detecting malathion and omethoate, preparation method and application |
| CN115060777B (en) * | 2022-07-08 | 2023-06-23 | 江苏理工学院 | Rate electrochemical aptamer sensor for simultaneously detecting malathion and omethoate, and preparation method and application thereof |
| CN115201309A (en) * | 2022-08-13 | 2022-10-18 | 昆明理工大学 | Preparation method and application of hydroxyl radical electrochemical sensor |
| CN115201309B (en) * | 2022-08-13 | 2024-01-05 | 昆明理工大学 | Preparation method and application of hydroxyl radical electrochemical sensor |
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