CN107907522A - A kind of perfluorochemical molecular engram fluorescence probe and its application method and application - Google Patents
A kind of perfluorochemical molecular engram fluorescence probe and its application method and application Download PDFInfo
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Abstract
The present invention provides a kind of perfluorochemical molecular engram fluorescence probe and its application.The fluorescence probe is prepared by following steps：Chitosan is swollen with weak acid solution, the mixing of perfluorochemical template molecule is added, epoxychloropropane is then added and amino carbon quantum dot carries out 4~12h of cross-linking reaction, finally with elution template molecule, elution time is 4~12h, up to perfluorochemical molecular engram fluorescence probe；The mass ratio of wherein chitosan and perfluorochemical template molecule is 300~800 ︰ 1~5；The mass ratio of chitosan, amino carbon quantum dot and epoxychloropropane is 300~800 ︰, 0.05~0.2 ︰ 0.12~0.35.Fluorescence probe of the present invention combines the enrichment of sample and detection together, detect more convenient, the content of perfluorochemical is directly can obtain after fluorescence probe capture perfluorochemical by detecting its fluorescence intensity so that the detection to perfluorochemical is more quick and easy；And the sensitivity of detection and specific selectivity higher, anti-tampering property are stronger.
Description
Technical field
The invention belongs to analytical chemistry field, more particularly, to a kind of perfluorochemical molecular engram fluorescence probe and
Its application method and application.
Background technology
Perfluorochemical（PFCs）It is a kind of polluter being prevalent in environment, while PFCs is difficult to degrade, from
And cause it persistently to exist in the environment and be enriched with by the transmission of biological chain by living organism, the existing many countries in the whole world and ground
Area is reported in environment and a variety of biological samples, including detecting PFCs in the matrix such as human blood, serum.Due to the life of PFCs
Thing is enriched with and its potential bio-toxicity, this kind of compound have been to be concerned by more and more people.Wherein perfluorooctane sulfonate
(PFOS) and perfluoro caprylic acid (PFOA) is the two kinds of perfluorochemicals for being most often detected and discussing, and both compounds are a variety of
The final converted products of PFCs in the environment.At present, the analysis detection to perfluorochemical mainly uses chromatograph-mass spectrometer,
This method needs sample-pretreating method, the reagent consumptions such as cumbersome Solid Phase Extraction big and time-consuming.Therefore, establish a kind of fast
Analysis detection of fast, sensitive and high selectivity the method to PFCs in the biological samples such as blood, urine is of great significance.
Carbon quantum dot is a kind of nano material with high fluorescence property occurred after semiconductor-quantum-point.Semiconductor amount
Son point cadmium selenide, cadmium telluride etc. limit its use due to containing heavy metal ion.And the synthetic method letter of carbon quantum dot
Single, good water solubility, small toxicity, it is using more and more extensive.Molecular imprinting technology refers to prepare to a certain specific target molecule
（Template molecule, microsphere）With molecular recognition performance（Specific selectivity）Molecularly imprinted polymer technology.Molecule is known
Do not refer to that there is space structure, size and chemical functional group and the host molecule of guest molecule complementation can identify and with reference to object
Molecule.Have the characteristics that compatibility and the higher, strong interference immunity of selectivity and stability are good, preparation is simple, service life is long.Cause
This, molecular imprinting technology is widely used in analytical chemistry field such as chromatographic isolation, Solid Phase Extraction, solid phase microextraction field.
In recent years, also there is research work that fluorescent material quantum dot is incorporated into molecular imprinting technology, prepare with spy
The molecular engram fluorescent material of opposite sex identification.But at present using perfluorochemical as template molecule molecular engram fluorescence probe also not
Have been reported that.It would therefore be highly desirable to provide a kind of perfluorochemical molecular engram fluorescence probe so that the detection of perfluorochemical is cleverer
It is quick, more accurate.
The content of the invention
It is an object of the invention to provide a kind of perfluorochemical molecular engram fluorescence probe.Fluorescence probe of the present invention
It is to be combined to obtain with carbon quantum dot by the perfluorochemical molecularly imprinted polymer of chitosan and perfluorochemical preparation.It is described glimmering
Light probe combines the enrichment of sample and detection together, and detection is more convenient；It is and lower, special to the detection limit of perfluorochemical
Selective higher, anti-tampering property are stronger, so that the detection to perfluorochemical is more accurate and sensitive.
Another object of the present invention is to provide the application method of the perfluorochemical molecular engram fluorescence probe.
It is still another object of the present invention to provide the perfluorochemical molecular engram fluorescence probe in detection perfluor chemical combination
Application in thing.
The above-mentioned purpose of the present invention is achieved by following scheme：
A kind of perfluorochemical molecular engram fluorescence probe, is prepared by following steps：Chitosan is swollen with weak acid solution, then is added
Enter the mixing of perfluorochemical template molecule, then add epoxychloropropane and amino carbon quantum dot carries out 4~12h of cross-linking reaction,
Elution template molecule is finally used, elution time is 4~12h, up to perfluorochemical molecular engram fluorescence probe；
The mass ratio of wherein chitosan and perfluorochemical template molecule is 160~300 ︰ 1；Chitosan, amino carbon quantum dot and
The mass ratio of epoxychloropropane is 4000~8000 ︰, 1 ︰ 1770~2365.
The fluorescence probe of the present invention is while possessing molecule distinguishability, or signal detector, by traditional sample
Enrichment and detection combine together, i.e., directly can obtain entirely by detecting its fluorescence intensity after fluorescence probe capture perfluorochemical
The content of fluorine compounds so that the analysis detection to perfluorochemical is more convenient, more rapidly.
If chitosan is too low with the mass ratio of perfluorochemical template molecule, template molecule may largely be present in shell and gather
Glycan molecule internal gutter, template molecule are difficult to elute completely, the final accuracy for influencing testing result；If the dosage of carbon quantum dot
Excessively, then quantum dot fluorescence is too strong, can cover the reaction signal of target product, causes fluoroscopic examination result inaccurate.If crosslinking
For agent epoxychloropropane using very few, then molecular engram is unsuccessful, can not capture target molecule well；If crosslinking agent used
The more or reaction time is long, then chitosan is modified to rigid structure completely, can not carry out molecular fluorescence detection sample introduction.
The present invention is using chitosan as function monomer, by the dosage and cross-linking reaction time that control crosslinking agent so that shell gathers
Cross-linking reaction occurs for sugar, by the modified control of chitosan in moderate scope so that the fluorescence probe microballoon of preparation is in saturating
Bright shape, and there is excellent swelling behavior under slightly acidic condition, so as to not interfere with fluorescence detection, reduce because fluorescence is visited
The error that the color of pin itself may be brought.
Common fluorescence probe is easy to the phenomenon for fluorescent quenching occur, Jin Erwu under the conditions of having existing for chaff interferent
Method obtains accurate testing result.And existing non-targeted molecule itself is more in biological sample, to the interference of fluorescence probe
It is larger, common fluorescence probe in the biological sample in use, the possibility for fluorescent quenching occur is very big so that limit its
Application in biology sample detection.Using chitosan molecule as function monomer in the present invention, it specifically binds with template molecule, together
When carbon quantum dot be in inside chitosan molecule, carbon quantum dot and perfluorochemical intermolecular distance are smaller in detection process,
The phenomenon of stable Fluorescence Increasing can occur, and be not easy Fluorescence-quenching occur.Therefore, fluorescence probe of the present invention
With preferable interference free performance, it is not easy Fluorescence-quenching occurred by the presence of other materials when detecting biological sample.
During with eluted template molecule in eluent, if elution time is too short, template molecule does not elute completely, leads
Cause the testing result in detection process inaccurate；But if elution time is too long, the carbon amounts in rapid wear carbon loss quantum dot fluorescence probe
It is sub-, cause the change unobvious of fluorescence intensity, detection sensitivity reduces.
Preferably, the mass ratio of the chitosan and perfluorochemical template molecule is 200~280 ︰ 1~2.
Preferably, the mass ratio of chitosan, amino carbon quantum dot and epoxychloropropane for 4000~8000 ︰, 1 ︰ 1770~
2365。
Preferably, the cross-linking reaction time is 12h, elution time 8h.Cross-linking reaction time from add epoxy chloropropionate
Alkane and amino carbon quantum dot start to calculate.
Preferably, perfluorochemical template molecule is PFOS or PFOA.
Preferably, weak acid solution used in chitosan swelling is acetum.The volume fraction of acetum used for 1~
3%。
Preferably, the eluent is the alkaline solution of organic solvent；It is highly preferred that the elution is acetone and hydroxide
The mixed liquor of sodium, its volume ratio are 1 ︰ 1~3.
Preferably, carbon quantum dot is prepared using following methods：By citric acid and ethylenediamine after mixing, by solution
It is transferred to reaction in hydrothermal reaction kettle and obtains amino-carbon quantum dot solution；Again by the solution through it is excessive, freeze-drying after to obtain the final product
Carbon quantum dot solid.
Preferably, the mass ratio of citric acid and ethylenediamine is 3~4 ︰ 0.9~2.7.
Preferably, hydrothermal temperature is 160~200 DEG C；Reaction time is 4~6h.
Preferably, bag filter interception is 300~600D.
The application method of fluorescence probe provided by the invention is：It is 3~4 that sample to be tested weak acid solution is adjusted pH,
The fluorescence probe is added under the conditions of 30 DEG C~50 DEG C and reacts 20~90min, fluorescence probe is filtered to isolate and carries out fluorescence inspection
Survey.
Sample is adjusted to faintly acid, on the one hand, be because perfluorochemical is more stable under mildly acidic conditions, solvent borne
More preferably；On the other hand, be because the fluorescence probe swelling behavior under mildly acidic conditions of the present invention is more preferable, can be in faintly acid
Under the conditions of be uniformly scattered in sample, can quickly and completely capture the perfluorochemical in sample so that testing result is more
To be accurate.
Preferably, pH of the sample after weak acid is adjusted is 3~4；It is highly preferred that pH of the sample after weak acid is adjusted is 4.
Preferably, the reaction temperature is 40 DEG C；Reaction time is 30min.
The present invention also protects the application of fluorescence probe perfluorochemical content in biological sample is detected at the same time.
Preferably, the application of fluorescence probe PFOS or PFOA in biological sample is detected.
Compared with prior art, it is of the invention to have the following advantages and beneficial effect：
The fluorescence probe of the present invention is while possessing molecule distinguishability, or signal detector, by traditional example enrichment
Combine together with detection, i.e., directly can obtain perfluorinate by detecting its fluorescence intensity after fluorescence probe capture perfluorochemical
The content of compound so that the detection to perfluorochemical is more quick and easy.
Meanwhile detection sensitivity and specific selectivity higher, anti-tampering property of the fluorescence probe of the present invention to perfluorochemical
It is stronger, so that testing result is more accurate.
Brief description of the drawings
Fig. 1 is the transmission electron microscope picture of carbon quantum dot used in embodiment 1.
Fig. 2 is that the fluorescence probe prepared in embodiment 1~3 detects the standard curve of perfluorochemical.
Specific embodiment
Present disclosure is further illustrated with reference to specific embodiment, but should not be construed as limiting the invention.
Without departing from the spirit and substance of the case in the present invention, the simple modifications or substitutions made to the method for the present invention, step or condition,
Belong to the scope of the present invention；Unless otherwise specified, technological means used in embodiment is well known to those skilled in the art
Conventional means.
The preparation of perfluorochemical molecular engram carbon quantum dot fluorescence probe of the present invention, wherein using PFOS as template point
It is prepared by son.
Embodiment 1
（1）3.0g citric acids are weighed, add 33mL deionized waters, magnetic agitation 5min makes solid all dissolve.Add 1.0mL second
Diamines（Carried out in fume hood）, 10 min of magnetic agitation.Hydrothermal reaction kettle is transferred the solution into, tightens and is put into baking oven 160
4h is reacted at DEG C.The bag filter dialysis 48h that interception is 300D, during which constantly changes water.Dialyzate is freezed dry with glass culture dish
It is dry to obtain the thick carbon quantum dot solid of brown color.
（2）1% acetic acid is added to be swollen in 0.3g chitosans；Add template molecule PFOS 1mg.3h is stirred at room temperature；
The aqueous solution that 1mL contains 50 μ g carbon quantum dots is added, 100 μ L epoxychloropropane are crosslinked at 40 DEG C of constant temperature again after stirring evenly
4h.After take weight in wet base 20g chitosan molecule trace fluorescent materials, be 1 using acetone and 0.5M sodium hydroxides volume ratio:1 mixing
Solution 30mL, is stirred at room temperature elution 4h.
Step（2）In, the mass ratio of chitosan and perfluorochemical template molecule is 300 ︰ 1；Chitosan, amino carbon quantum
The mass ratio of point and epoxychloropropane is 6000 ︰, 1 ︰ 2362.
Embodiment 2
（1）The preparation process of carbon quantum dot is with embodiment 1, and difference is that citric acid used is 3.5 g, and ethylenediamine is
2.0mL, reaction temperature are reaction time 5h at 170 DEG C.The interception of bag filter is 400D.
（2）2% acetic acid is added to be swollen in 0.5g chitosans；Add 3 mg of template molecule PFOS.Stir at room temperature
3h；The aqueous solution that 1mL contains 100 μ g carbon quantum dots is added, 200 μ L epoxychloropropane are handed at 40 DEG C of constant temperature again after stirring evenly
Join 8h.After take weight in wet base 20g chitosan molecule trace fluorescent materials, be 1 using acetone and 0.5M sodium hydroxides volume ratio:2 it is mixed
Close solution 45mL, the room temperature elution 8h under conditions of stirring.
Step（2）In, the mass ratio of chitosan and perfluorochemical template molecule is 166.67 ︰ 1；Chitosan, amino-carbon
The mass ratio of quantum dot and epoxychloropropane is 5000 ︰, 1 ︰ 2362.
Embodiment 3
（1）The preparation process of carbon quantum dot is with embodiment 1, and difference is that citric acid used is 4.0 g, ethylenediamine 1.5
ML, reaction temperature are reaction time 6h at 180 DEG C.The interception of bag filter is 500D.
（2）Add 3% acetic acid to be swollen in 0.8g chitosans, add template molecule PFOS 5mg, stir 3h at room temperature；
The aqueous solution that 1mL contains 200 μ g carbon quantum dots is added, 300 μ L epoxychloropropane are crosslinked at 40 DEG C of constant temperature again after stirring evenly
12h.After take weight in wet base 20g chitosan molecule trace fluorescent materials, be 1 using acetone and 0.5M sodium hydroxides volume ratio:3 mixing
Solution 60mL, the room temperature elution 12h under conditions of stirring.
Step（2）In, the mass ratio of chitosan and perfluorochemical template molecule is 160 ︰ 1；Chitosan, amino carbon quantum
The mass ratio of point and epoxychloropropane is 4000 ︰, 1 ︰ 1771.
Embodiment 4
With embodiment 1, difference is step for all raw material types, dosage and method（2）In, chitosan and perfluorochemical
The mass ratio of template molecule is 240 ︰ 1；The mass ratio of chitosan, amino carbon quantum dot and epoxychloropropane is 4000 ︰, 1 ︰ 1800.
Embodiment 5
With embodiment 1, difference is step for all raw material types, dosage and method（2）In, chitosan and perfluorochemical
The mass ratio of template molecule is 260 ︰ 1；The mass ratio of chitosan, amino carbon quantum dot and epoxychloropropane is 5000 ︰, 1 ︰ 2000.
Embodiment 6
With embodiment 1, difference is step for all raw material types, dosage and method（2）In, chitosan and perfluorochemical
The mass ratio of template molecule is 280 ︰ 1；The mass ratio of chitosan, amino carbon quantum dot and epoxychloropropane is 6000 ︰, 1 ︰ 2200.
Comparative example 1
This comparative example use raw material type, dosage and preparation process with embodiment 1, difference be using etc. quality fine jade
Lipolysaccharide replaces chitosan.
Comparative example 2
This comparative example use raw material type, dosage and preparation process with embodiment 1, difference be using etc. quality penta
Dialdehyde replaces epoxychloropropane.
Comparative example 3
For raw material type, dosage and the preparation process that this comparative example uses with embodiment 1, difference is chitosan, carbon quantum
The mass ratio of point and epoxychloropropane is 4000 ~ 8000:1:3000.
Comparative example 4
For raw material type, dosage and the preparation process that this comparative example uses with embodiment 1, difference is chitosan and template point
The mass ratio of sub- PFOS is 100:1.
Comparative example 5
For raw material type, dosage and the preparation process that this comparative example uses with embodiment 1, difference is that cross-linking reaction time is
16h。
Comparative example 6
For raw material type, dosage and the preparation process that this comparative example uses with embodiment 1, difference is that elution time is 2h.
Performance test：Test sensitivity, specific selectivity and the anti-interference of fluorescence probe.
（1）Test the sensitivity of fluorescence probe
Make fluorescence response standard curve of the fluorescence probe to PFOS of the preparation of embodiment 1~6.
PFOS is configured to the standard solution that concentration is 1~1000 pg/L with the HAc that volume fraction is 2%.In 40 DEG C of bars
Under part, 10mL standard solution and 1g fluorescence probe hybrid reaction 30min are taken, fluorescence probe is glimmering after detection capture perfluorochemical
Luminous intensity, observation fluorescence intensity is with PFOS concentration situations of change.According to Stern-Volmer equations F0/ F=1+Ksv [C], with dense
Degree [C] is abscissa, relative intensity of fluorescence F0/ F is ordinate, and the result obtained according to detection draws fluorescence response curve.
Obtained standard curve is as shown in Figure 2.By being calculated using fluorescence probe of the present invention and its detection
The detection of method is limited to 5.1pg/L, it follows that the detection limit of fluorescence probe of the present invention has sensitive well the bottom of compared with
Degree.
（2）Test the specific selectivity of fluorescence probe
Fluorescence probe prepared by embodiment 1~6 and comparative example 1~6 detects the PFOS samples of concentration known, and PFOS is removed in sample
Outside, other any materials are not added with, this time testing result is denoted as detects for the first time.After detection, perfluor is added in the sample
Octanoic acid（PFOA）, neopelex（SDBS）, lauryl sodium sulfate, dodecyl sodium sulfate and perfluor -1- fourth sulphurs
Acid, then be detected using same method, this time detection is denoted as second of detection.Pass through testing result twice and concentration known
Comparison, and the difference value between testing result verifies the specific selection performance of fluorescence probe twice, and testing result is shown in
Table 1.
Fluorescence probe detection PFOS results (pg/L) prepared by 1 embodiment 1~6 of table and comparative example 1~6
| Sequence number | Perfluorochemical molecular concentration/pg/L in sample | First time detectable concentration/pg/L | Second of detectable concentration/pg/L | Third time detectable concentration/pg/L | 4th detectable concentration/pg/L | 5th detectable concentration/pg/L |
| Embodiment 1 | 22 | 21 | 22 | 22 | 21 | 22 |
| Embodiment 2 | 22 | 22 | 20 | 21 | 21 | 21 |
| Embodiment 3 | 22 | 22 | 22 | 21 | 21 | 21 |
| Embodiment 4 | 22 | 22 | 22 | 20 | 21 | 22 |
| Embodiment 5 | 22 | 20 | 20 | 21 | 20 | 20 |
| Embodiment 6 | 22 | 21 | 20 | 20 | 20 | 21 |
| Comparative example 1 | 22 | 0 | 0 | 0 | 0 | 0 |
| Comparative example 2 | 22 | 10 | 5 | 7 | 9 | 5 |
| Comparative example 3 | 22 | 0 | 0 | 0 | 0 | 0 |
| Comparative example 4 | 22 | 16 | 14 | 12 | 10 | 11 |
| Comparative example 5 | 22 | 0 | 0 | 0 | 0 | 0 |
| Comparative example 6 | 22 | 11 | 8 | 9 | 7 | 7 |
As can be known from Table 1, the actual content of PFOS is very in 2 results detected of fluorescence probe for preparing of the present invention and sample
Close, maximum difference also only has 2pg/L, and the result of five detections also only has 2 pg/L, table almost without difference, maximum difference
The fluorescence probe that the bright present invention is prepared can be fine to the specific selectivity of PFOS, in the similar compound of various structures at the same time
In the presence of, can specific recognition PFOS, improve the accuracy of testing result.But fluorescence probe inspection prepared by comparative example 1,3 and 5
Do not detect the presence of PFOS in sample, and in the result and sample that comparative example 2,4 and 6 detects PFOS actual content difference compared with
Greatly, the difference and between repeated detection result is also larger, and testing result is extremely inaccurate, and repeatability is bad.
（3）Test the anti-interference of fluorescence probe
Using human blood as sample, a certain amount of PFOS is added into sample, is prepared using embodiment 1~6 and comparative example 1~7
Fluorescence probe detects the sample.The change in fluorescence situation of fluorescence probe is observed in detection process, it is sudden according to whether fluorescence occurs
Phenomenon go out to distinguish the interference free performance of fluorescence probe.
Fluorescence probe situation prepared by 2 embodiment 1~6 of table and comparative example 1~6
| Sequence number | Detect for the first time | Second of detection | Third time detects |
| Embodiment 1 | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon |
| Embodiment 2 | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon |
| Embodiment 3 | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon |
| Embodiment 4 | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon |
| Embodiment 5 | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon |
| Embodiment 6 | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon | Do not occur fluorescent quenching or weaken phenomenon |
| Comparative example 1 | Unstressed configuration | Unstressed configuration | Unstressed configuration |
| Comparative example 2 | Fluorescence first strengthens, rear to weaken | Fluorescence first strengthens, rear to weaken | Fluorescence first strengthens, rear to weaken |
| Comparative example 3 | Unstressed configuration | Unstressed configuration | Unstressed configuration |
| Comparative example 4 | Fluorescence first strengthens, rear quenching | Fluorescence first strengthens, rear quenching | Fluorescence first strengthens, rear quenching |
| Comparative example 5 | Unstressed configuration | Unstressed configuration | Unstressed configuration |
| Comparative example 6 | Fluorescence Increasing, it is rear to weaken | Fluorescence first strengthens to be quenched afterwards | Fluorescence first strengthens to be quenched afterwards |
As can be known from Table 2, the fluorescence probe that prepared by the present invention does not occur fluorescent quenching or decrease in detection process three times
Phenomenon occurs, it was demonstrated that fluorescence probe prepared by the present invention has preferable antijamming capability, is less prone to fluorescent weakening or quenching
Phenomenon, can ensure the accuracy of testing result.And there is a degree of fluorescence in detection process in comparative example 2,4 and 6
Decrease or Quenching, ultimately result in testing result inaccuracy.
Claims (10)
1. a kind of perfluorochemical molecular engram fluorescence probe, it is characterised in that prepared by following steps：By chitosan weak acid
Solution is swollen, and is added the mixing of perfluorochemical template molecule, is then added epoxychloropropane and amino carbon quantum dot is handed over
Connection 4~12h of reaction, finally with elution template molecule, elution time is 4~12h, up to perfluorochemical molecular engram
Fluorescence probe；
Wherein, the mass ratio of chitosan and perfluorochemical template molecule is 160~300 ︰ 1；Chitosan, amino carbon quantum dot and
The mass ratio of epoxychloropropane is 4000~8000 ︰, 1 ︰ 1770~2365.
2. fluorescence probe according to claim 1, it is characterised in that the matter of the chitosan and perfluorochemical template molecule
It is 200~280 ︰ 1~2 to measure ratio.
3. fluorescence probe according to claim 1, it is characterised in that chitosan, amino carbon quantum dot and epoxychloropropane
Mass ratio is：4000~8000 ︰, 1 ︰ 1770~2365.
4. fluorescence probe according to claim 1, it is characterised in that cross-linking reaction time 12h；Elution time is 8h.
5. fluorescence probe according to claim 1, it is characterised in that perfluorochemical template molecule is PFOS or PFOA.
6. fluorescence probe according to claim 1, it is characterised in that weak acid solution used in the chitosan swelling is molten for acetic acid
Liquid.
7. fluorescence probe according to claim 1, it is characterised in that the eluent is the alkaline solution of organic solvent.
8. the application method of any fluorescence probe of claim 1~7, it is characterised in that including following process：It will treat test sample
It is 3~4 that product weak acid solution, which adjusts pH, and the fluorescence probe is added under the conditions of 30 DEG C~50 DEG C and reacts 20~90min, filtering
Isolate fluorescence probe and carry out fluoroscopic examination.
9. the application method of fluorescence probe according to claim 9, it is characterised in that pH of the sample after weak acid is adjusted is 4；
Reaction temperature is 40 DEG C；Reaction time is 30min.
10. the application of any fluorescence probe of claim 1~7 perfluorochemical content in biological sample is detected.
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| CN116144360A (en) * | 2023-01-08 | 2023-05-23 | 北方工业大学 | Preparation method of rare earth up-conversion fluorescent probe |
| WO2023123136A1 (en) * | 2021-12-29 | 2023-07-06 | 北京建工环境修复股份有限公司 | Fluorescent conjugated polymer quantum dot probe, preparation method therefor and application thereof |
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| CN101298039A (en) * | 2008-01-18 | 2008-11-05 | 清华大学 | Preparation of chitosan molecular imprinting adsorbing agent |
| WO2011053803A2 (en) * | 2009-10-30 | 2011-05-05 | The Ohio State University | Multi-functional biodegradable particles for selectable targeting, imaging, and therapeutic delivery and use thereof for treating ocular disorders |
| CN104327271A (en) * | 2014-09-29 | 2015-02-04 | 西南大学 | Molecularly imprinted polymer based on core-shell quantum dot and application thereof |
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| CN101298039A (en) * | 2008-01-18 | 2008-11-05 | 清华大学 | Preparation of chitosan molecular imprinting adsorbing agent |
| WO2011053803A2 (en) * | 2009-10-30 | 2011-05-05 | The Ohio State University | Multi-functional biodegradable particles for selectable targeting, imaging, and therapeutic delivery and use thereof for treating ocular disorders |
| CN104327271A (en) * | 2014-09-29 | 2015-02-04 | 西南大学 | Molecularly imprinted polymer based on core-shell quantum dot and application thereof |
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| CN109135736A (en) * | 2018-08-16 | 2019-01-04 | 南昌航空大学 | A kind of nitrogen-doped carbon quantum dot and the preparation method and application thereof |
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