CN105092564A - ZnTCPP/TOAB light-emitting electrode, preparing method and application of electrode to light-emitting imaging platform - Google Patents
ZnTCPP/TOAB light-emitting electrode, preparing method and application of electrode to light-emitting imaging platform Download PDFInfo
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Abstract
The invention discloses a ZnTCPP/TOAB light-emitting electrode, a preparing method and application of the electrode to a light-emitting imaging platform. The surface of the light-emitting electrode is decorated with ZnTCPP and TOAB, wherein the mole ratio of ZnTCPP to TOAB is 10:0.2-1. In the preparing process of the electrode, at first, a printing electrode is washed and blown dry, then a TOAB methylbenzene solution is prepared, ZnTCPP is dissolved into the TOAB methylbenzene solution, the mixture is ultrasonically oscillated and mixed to obtain a mixed solution of ZnTCPP and TOAB, and finally the mixed solution drips on the printing electrode to coat the printing electrode, so that the ZnTCPP/TOAB light-emitting electrode is obtained. On the basis of the electrode, a light-emitting imager carrying a CCD camera and an electrochemical workstation are introduced, the light-emitting imaging platform can be constructed, and life entity metabolite detection is achieved. The detecting platform is sensitive in signal, the metabolite is visible to the naked eyes, detection lower limit is small, a new thought is provided for light-emitting imaging and detecting of the life entity metabolite, and analysis application of electrochemistry and electroluminescence technologies is expanded.
Description
Technical field
The invention belongs to electrogenerated chemiluminescence field, be specifically related to a kind of ZnTCPP/TOAB lighting electrode, preparation method and the application in luminescence imaging platform thereof.
Background technology
Electrogenerated chemiluminescence (electrochemiluminescence, ECL) with high sensitivity and low background famous, as a kind of powerful analysis means, be applied to food hygiene medical industry at present.The luminescence efficiency of luminophor is depended in the sensitivity of ECL in essence.Wherein, cathodic electroluminescence body is occupied an leading position with semiconductor nanocrystal, but such material is generally containing toxic ingredient, and ECL intensity is not high and rely on exogenous strong oxidizer as coreagent enhanced sensitivity, greatly more the widely using of restriction ECL technology.Therefore efficient negative electrode ECL luminophor is found and the ECL detection method utilizing its development simple and easy, stable, very necessary.
Inspire by conventional anodes ECL luminophor and bipyridyl ruthenium electronic structure of molecule, there is relatively low HOMO and lumo energy, there is the organic zinc complex of metal-ligand charge transmission can become negative electrode ECL alternative luminophor through theory speculates, and existing research confirms its representative complex four-carboxyl phenyl zinc protoporphyrin (Zn (II) meso-Tetra (4-carboxyphenyl) Porphine, ZnTCPP) splendid luminescent properties is had, and stable.Porphyrin, as common electrogenerated chemiluminescence material, can realize strong luminous, but because organic phase is as the limitation of the system of inspection, cannot be applied to the inspection of life entity in organic phase.
Summary of the invention
Strong luminescence cannot be realized and the limitation being applied to the detection of life entity metabolic product in aqueous phase system to overcome prior art mesoporphyrin, the present invention with four-carboxyl phenyl zinc protoporphyrin (ZnTCPP) for shiner, by four octyl group ammonium bromide (Tetraoctylammoniumbromide, TOAB) stability of ZnTCPP at electrode surface is strengthened, provide a kind of ZnTCPP/TOAB lighting electrode and preparation method thereof, and realize the Visual retrieval of life entity metabolic product by imaging mode.
For achieving the above object, the invention provides a kind of ZnTCPP/TOAB lighting electrode, described electrode face finish has ZnTCPP and TOAB, and wherein, the mol ratio of ZnTCPP and TOAB is 10:0.2 ~ 1.
Mol ratio more preferably 10:0.4 ~ 0.8 of described ZnTCPP and TOAB.
Further, present invention also offers a kind of preparation method of ZnTCPP/TOAB lighting electrode, concrete steps are as follows: cleaning of first printing electrode dries up, then TOAB toluene solution is prepared, and ZnTCPP is dissolved in TOAB toluene solution, sonic oscillation mixes, and obtains the mixed solution of ZnTCPP and TOAB, finally mixed solution is dripped on being coated onto and printing electrode, obtain ZnTCPP/TOAB lighting electrode.
In addition, the present invention also provides a kind of life entity metabolic product detection platform based on ECL imaging, especially relate to a kind of detection platform of the emiocytosis hydrogen peroxide based on ECL imaging, described detection platform comprises ZnTCPP/TOAB lighting electrode, luminescence imaging instrument and electrochemical workstation.
Further, the present invention also provides a kind of detection method of the life entity metabolic product detection platform based on the imaging of ZnTCPP/TOAB lighting electrode, in particular to a kind of detection method of the hydrogen peroxide detection platform based on the imaging of ZnTCPP/TOAB lighting electrode, concrete grammar is as follows: first mixed with HEPES damping fluid equal-volume by the liquid to be measured containing life entity metabolic product, dripping is coated onto on ZnTCPP/TOAB lighting electrode, then chemiluminescence imaging instrument is placed in, the fluid dynamics constant potential module of coupling electrochemical workstation, CCD imaging, finally calculate hot spot gray scale summation, namely the concentration of life entity metabolic product in liquid to be measured is obtained by gray scale-concentration conversion formula.
Described life entity metabolic product is the material that can be used as ZnTCPP electrogenerated chemiluminescence co-reactant produced in life entity metabolic process.
Electronegative and the structure end of ZnTCPP in the present invention is with four carboxyls, in organic phase, solubleness is low, and TOAB positively charged and have amphipathic, pass through electrostatic interaction, the hydrophilic radical of TOAB is combined with the carboxyl of ZnTCPP, and hydrophobic grouping is exposed to organic phase thus the dispersiveness that ZnTCPP has been had in organic phase.In the process of this external modified electrode, because the film forming that TOAB is good, ZnTCPP is firmly fixed on electrode surface, avoids the carboxyl of ZnTCPP and the contact of water and be dissolved in the water, enhance the stability of ZnTCPP at electrode surface, ensure that result reappearance.
Compared with prior art, the present invention has following remarkable advantage: (1) successfully achieves the strong luminescence of derivatives of porphyrin in aqueous phase system, provides possibility for derivatives of porphyrin is applied in body to detect; (2) from cyclic voltammetry common in prior art electroanalysis field, that electrogenerated chemiluminescence method detects biosome metabolic product is different, the present invention by imaging realize detecting visual, can realize quantitatively detecting to life entity metabolic product; (3) electrode production process is simple and quick, only ZnTCPP and TOAB need be mixed in proportion, drips to be applied to and prints electrode; (4) material and testing process safety non-toxic, ZnTCPP and TOAB is safety nuisance free material, and testing process does not relate to other noxious materials; (5) signal is sensitive, Monitoring lower-cut is low, and Monitoring lower-cut can reach 1nM.
Accompanying drawing explanation
Fig. 1 is the structure schematic diagram of the life entity metabolic product detection platform based on ECL imaging of the present invention.
Fig. 2 is the ECL intensity map of the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 1 ~ 5 prepares.
Fig. 3 is that the ZnTCPP/TOAB lighting electrode SEM that embodiment 7 prepares schemes.
Fig. 4 is the ultraviolet spectrum phenogram of the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 2 prepares.
Fig. 5 is the fluorescence spectrum phenogram of the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 2 prepares.
Fig. 6 is the ECL signal stabilization testing result figure of the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 2 prepares.
Fig. 7 is the ECL spectrum of the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 2 prepares under different condition in embodiment 11, wherein, a is under saturated condition of nitrogen gas, the HEPES dissolving 320 μMs of hydrogen peroxide detects liquid, b is that the HEPES of dissolved air under natural conditions detects liquid, and c is that the HEPES under saturated nitrogen detects liquid.
Fig. 8 is the ECL spectrum of the electrode being co-reactant with hydrogen peroxide in embodiment 12, and wherein, a is the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 2 prepares, and b drips the electrode scribbling TOAB solution.
Fig. 9 is the formed hot spot figure of the linear relationship chart of concentration of hydrogen peroxide and hot spot gray-scale value in embodiment 13 and the hydrogen peroxide HEPES solution of variable concentrations gradient, wherein, a figure is the linear relationship chart of concentration of hydrogen peroxide and hot spot gray-scale value, and b is the formed hot spot figure of the hydrogen peroxide HEPES solution of variable concentrations gradient.
Figure 10 is the hot spot image that embodiment 14 detects concentration of hydrogen peroxide in sample.
Embodiment
Below in conjunction with the drawings and specific embodiments, the present invention is described in further detail.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
Embodiment 1 ~ 5 is take glass-carbon electrode as basal electrode, preparation ZnTCPP/TOAB electrogenerated chemiluminescence electrode, and detecting with ZnTCPP/TOAB is the ECL intensity of electroluminescent material.
Embodiment 1
The preparation of electrogenerated chemiluminescence electrode and ECL intensity detection
Step 1, by respectively ethanol, the water cleaning of diameter 5mm glass-carbon electrode, high-purity N
2dry up;
The TOAB toluene solution of step 2, preparation 10mM, then ZnTCPP is dissolved in TOAB toluene solution, sonic oscillation mixes, and obtain the mixed solution of ZnTCPP and TOAB, wherein the concentration of ZnTCPP is 0.2mM;
Step 3, get the above-mentioned mixed solution of 10 μ L and drip on the glass-carbon electrode that is coated in and processed, obtain ZnTCPP/TOAB electrogenerated chemiluminescence electrode.
Step 4, electrogenerated chemiluminescence electrode is placed in HEPES and detects liquid, detect ECL intensity by electrogenerated chemiluminescence instrument, as shown in Figure 2, standardized ECL intensity is 0.7 to result.
Embodiment 2
Embodiment 2 is 0.4mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 1, and other are identical with embodiment 1.As shown in Figure 2, standardized ECL intensity is 0.9 to result.
Embodiment 3
Embodiment 3 is 0.6mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 1, and other are identical with embodiment 1.As shown in Figure 2, standardized ECL intensity is 0.55 to result.
Embodiment 4
Embodiment 4 is 0.8mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 1, and other are identical with embodiment 1.As shown in Figure 2, standardized ECL intensity is 0.5 to result.
Embodiment 5
Embodiment 5 is 1mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 1, and other are identical with embodiment 1.As shown in Figure 2, standardized ECL intensity is 0.3 to result.
Fig. 2 is the ECL intensity map of the electrogenerated chemiluminescence electrode that embodiment 1 ~ 5 prepares, and concentration is that the electrode that the ZnTCPP of 0.2mM ~ 1mM prepares all has good ECL intensity.The ECL intensity comparing the electrode that variable concentrations ZnTCPP prepares is known, and when ZnTCPP concentration is 4mM, ECL intensity is the highest.
Embodiment 6 ~ 10 is to print electrode as basal electrode, and preparation can be used for the ZnTCPP/TOAB lighting electrode of luminescence imaging.
Embodiment 6
The preparation of lighting electrode
Step 1, diameter 3mm printed electrode respectively with ethanol, water cleaning, high-purity N
2dry up;
The TOAB toluene solution of step 2, preparation 10mM, then ZnTCPP is dissolved in TOAB toluene solution, sonic oscillation mixes, and obtain the mixed solution of ZnTCPP and TOAB, wherein the concentration of ZnTCPP is 0.2mM;
Step 3, get the above-mentioned mixed solution of 10 μ L drip be coated in processed print electrode on, obtain ZnTCPP/TOAB lighting electrode.
Embodiment 7
Embodiment 7 is 0.4mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 6, and other are identical with embodiment 6.
Embodiment 8
Embodiment 8 is 0.6mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 6, and other are identical with embodiment 6.
Embodiment 9
Embodiment 9 is 0.8mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 6, and other are identical with embodiment 6.
Embodiment 10
Embodiment 10 is 1mM with the unique concentration unlike ZnTCPP in step 2 of embodiment 6, and other are identical with embodiment 6.
Characterize
1, SEM characterizes
ZnTCPP/TOAB lighting electrode embodiment 7 prepared carries out SEM sign, and result as shown in Figure 3.Can find out that from SEM figure TOAB has good film forming, ZnTCPP/TOAB master-objective membrane structure is even and fine and close, ensure that the reappearance of experimental result.
2, Spectroscopic Characterization
(1) ultraviolet characterizes
The mixed solution DMF of ZnTCPP and TOAB embodiment 2 prepared dilutes 100 times, then the uv absorption of the mixed solution of ZnTCPP and TOAB, the DMF solution of the ZnTCPP of same concentrations and the DMF solution of TOAB after DMF dilution is measured, obtain the ultraviolet spectrogram of each solution, result as shown in Figure 4.In Fig. 4, a is the mixed solution of ZnTCPP and the TOAB after DMF dilution, and b is the DMF solution of ZnTCPP, and c is the DMF solution of TOAB.
(2) Fluorescent Characterization
The mixed solution DMF of ZnTCPP and TOAB embodiment 2 prepared dilutes 100 times, then the fluorescent emission of the DMF solution of the mixed solution of ZnTCPP and TOAB, the DMF solution of the ZnTCPP of same concentrations, the DMF solution of TCPP and the TOAB after DMF dilution is measured, obtain the fluorescence spectrum figure of each solution, result as shown in Figure 5.In Fig. 5, a is the mixed solution of ZnTCPP and the TOAB after DMF dilution, and b is the DMF solution of ZnTCPP, and c is the DMF solution of TCPP, and d is the DMF solution of TOAB.As can be seen from Fig. 4 and Fig. 5, the DMF solution of TOAB does not have uv absorption, uv absorption and the fluorescence emission peak of the mixed solution of ZnTCPP and TOAB and the DMF solution of ZnTCPP all do not offset, rational explanation is that ZnTCPP and TOAB does not directly form chemical combination key, but it is electronegative after the ionization of the carboxyl of ZnTCPP, the ammonium radical ion positively charged of TOAB, the combination both being realized by electrostatic interaction.
3, lighting electrode exports the detection of ECL signal stabilization
As working electrode after electrogenerated chemiluminescence pole drying embodiment 2 prepared, take Ag/AgCl as contrast electrode, platinum electrode is to electrode, and adjustment current potential is-1.8 ~-0.5V, and sweep velocity is 200mVS
-1, scanning 10 ~ 20 circle, detect and export ECL signal stabilization, result as shown in Figure 6.As can be seen from the figure, ZnTCPP/TOAB lighting electrode stable luminescence and intensity is considerable.
Embodiment 11
Utilize the fluid dynamics constant potential module of electrochemical workstation, i.e. ampere i ~ t Curve Technique, regulate current potential to be-1.7V, record the electrogenerated chemiluminescence spectrum of the ZnTCPP/TOAB electrogenerated chemiluminescence electrode that embodiment 2 under different condition prepares under power on condition, result as shown in Figure 7.Wherein, in Fig. 7, a is under saturated condition of nitrogen gas, and the HEPES dissolving 320 μMs of hydrogen peroxide detects liquid, and b is that the HEPES of dissolved air under natural conditions detects liquid, and c is that the HEPES under saturated nitrogen detects liquid.As can be seen from Figure 7, hydrogen peroxide is the co-reactant of ZnTCPP.
Embodiment 12
Utilize the fluid dynamics constant potential module of electrochemical workstation, i.e. ampere i ~ t Curve Technique, current potential is regulated to be-1.7V, 10mLHEPES (pH=7.4) electrolytic solution and 1mL10M hydrogen peroxide are added electrolytic tank and is placed in luminoscope, record electrogenerated chemiluminescence electrode that embodiment 2 prepares under power on condition and simple drip the electrogenerated chemiluminescence spectrum scribbling the electrode of TOAB solution, result as shown in Figure 8.Wherein, in Fig. 8, a is the electrogenerated chemiluminescence electrode that embodiment 2 prepares, b drips the electrode scribbling TOAB solution, as seen from the figure, the ECL spectral intensity taking hydrogen peroxide as the electrogenerated chemiluminescence electrode of co-reactant is high, reach the intensity that can be caught by CCD, for the quantitative hydrogen peroxide of follow-up imaging provides condition.
Embodiment 13
The foundation of peroxide standard curve
First get that 20 μ L concentration of hydrogen peroxide gradients are 1nM, 10nM, 100nM, 1 μM, 10 μMs, 100 μMs, hydrogen peroxide HEPES (pH=7.4) solution of 1mM drips the lighting electrode surface being applied to embodiment 7 and preparing, then lighting electrode is placed in chemiluminescence imaging instrument, the fluid dynamics constant potential module of coupling electrochemical workstation, i.e. ampere i ~ t Curve Technique, current potential is regulated to be-1.7V, time shutter is 1min, CCD imaging, utilize ImageJ software to calculate the gray-scale value summation of hot spot under different concentration of hydrogen peroxide, result as shown in Figure 9.Wherein, in Fig. 9, a figure is the linear relationship chart of concentration of hydrogen peroxide and hot spot gray-scale value, and linear fit formula is y=1381.9lg (c)+32952, R
2=0.9761, b figure is the formed hot spot figure of the hydrogen peroxide HEPES solution of variable concentrations gradient.
Embodiment 14
Sample detection
Met-Leu-Phe (N-formylmethionyl-leucyl-phenylalanine, fMLP) can irritation cell secretion hydrogen peroxide.First mouse macrophage 8h is cultivated with the DMEM cell culture fluid that concentration is 1 μM, then gained cell culture fluid is mixed with HEPES damping fluid equal-volume, getting 20 μ L mixing drops is coated onto on the lighting electrode that embodiment 7 prepares, chemiluminescence imaging instrument is placed in subsequently by dripping the lighting electrode scribbling sample solution, the fluid dynamics constant potential module of coupling electrochemical workstation, i.e. ampere i ~ t Curve Technique, current potential is regulated to be-1.7V, time shutter is 1min, CCD imaging, result as shown in Figure 10.ImageJ software is utilized to calculate hot spot gray scale summation, the gray values that known sample detection obtains is 30835.33, substitute in the linear fit formula of concentration of hydrogen peroxide and hot spot gray-scale value, under known fMLP spread effect, the concentration of hydrogen peroxide of emiocytosis is 0.0294 μM.
Only as the explanation of the life entity metabolic product detection platform of the present invention's structure in above-described embodiment, be not limited in hydrogen peroxide.
Claims (9)
1. a ZnTCPP/TOAB lighting electrode, is characterized in that, described electrode face finish has ZnTCPP and TOAB, and wherein, the mol ratio of ZnTCPP and TOAB is 10:0.2 ~ 1.
2. ZnTCPP/TOAB lighting electrode as claimed in claim 1, it is characterized in that, the mol ratio of described ZnTCPP and TOAB is 10:0.4 ~ 0.8.
3. the preparation method of a ZnTCPP/TOAB lighting electrode, it is characterized in that, concrete steps are as follows: cleaning of first printing electrode dries up, then TOAB toluene solution is prepared, and ZnTCPP is dissolved in TOAB toluene solution, sonic oscillation mixes, and obtains the mixed solution of ZnTCPP and TOAB, finally mixed solution is dripped on being coated onto and printing electrode, after drying, namely obtain ZnTCPP/TOAB lighting electrode.
4. the preparation method of ZnTCPP/TOAB lighting electrode as claimed in claim 3, it is characterized in that, in the mixed solution of described ZnTCPP and TOAB, the concentration of TOAB is the concentration of 10mM, ZnTCPP is 0.2mM ~ 1mM.
5. the preparation method of ZnTCPP/TOAB lighting electrode as claimed in claim 3, it is characterized in that, in the mixed solution of described ZnTCPP and TOAB, the concentration of ZnTCPP is 0.4mM ~ 0.8mM.
6. the life entity metabolic product detection platform based on the imaging of ZnTCPP/TOAB lighting electrode, it is characterized in that, described detection platform comprises ZnTCPP/TOAB lighting electrode, luminescence imaging instrument and electrochemical workstation, and described life entity metabolic product is the material that can be used as ZnTCPP electrogenerated chemiluminescence co-reactant produced in life entity metabolic process.
7., as claimed in claim 6 based on the life entity metabolic product detection platform of ZnTCPP/TOAB lighting electrode imaging, it is characterized in that, described life entity metabolic product is hydrogen peroxide.
8. the detection method based on the life entity metabolic product detection platform of ZnTCPP/TOAB lighting electrode imaging, it is characterized in that, concrete steps are as follows: first mixed with HEPES damping fluid equal-volume by the liquid to be measured containing life entity metabolic product, dripping is coated onto on ZnTCPP/TOAB lighting electrode, then chemiluminescence imaging instrument is placed in, the fluid dynamics constant potential module of coupling electrochemical workstation, CCD imaging, finally calculate hot spot gray scale summation, namely obtained the concentration of life entity metabolic product in liquid to be measured by gray scale-concentration conversion formula.
9., as claimed in claim 8 based on the detection method of the life entity metabolic product detection platform of ZnTCPP/TOAB lighting electrode imaging, it is characterized in that, described life entity metabolic product is hydrogen peroxide.
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| CN108152210A (en) * | 2017-11-24 | 2018-06-12 | 东南大学 | A kind of special Electrochemiluminescdetection detection cell of screen printing electrode |
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| CN113087715A (en) * | 2021-03-15 | 2021-07-09 | 南京理工大学 | Method for preparing porphyrin self-assembly nano structure by microemulsion method |
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