CN108794475A - A kind of sensing fluorescent carbon point of alcohol, preparation method and applications - Google Patents
A kind of sensing fluorescent carbon point of alcohol, preparation method and applications Download PDFInfo
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- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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Abstract
The present invention provides a kind of sensing fluorescent carbon point of alcohol, preparation method and applications, and chemical structural formula is as follows：Preparation method is with N- methyl-1s, 2- phenylenediamine dihydrochlorides are raw material, absolute ethyl alcohol is solvent, carbon dots are synthesized in 180-200 DEG C of reaction 12h of autoclave of polytetrafluoroethylliner liner, are purified to crude product with silica gel column chromatography, using ethyl acetate as eluant, eluent, except solvent and after being further dried, the carbon dots of purifying are finally obtained through vacuum.It is of the invention can quickly, efficiently, specific recognition ethyl alcohol, this fluorescent carbon point can be used for detecting the alcohol content in different white wine.
Description
Technical field
The present invention relates to fluorescent nano material preparation fields, and in particular to a kind of sensing fluorescent carbon point of alcohol, preparation side
Method and its application.
Background technology
Alcohol（Ethyl alcohol）It is the required medicines of medical institutions and first-aid kit for domestic use, is one of most common external preparation.Alcohol
The component part of disinfectant and cosmetics is acted not only as, while being also the important component of mankind's beverage wine.Data
It shows, in the major traffic accidents that China occurred in recent years, nearly one third is caused by driving when intoxicated.For people
Safety, alcohol leakage detection, monitoring and the monitoring to driving when intoxicated all be highly important.Therefore, it is badly in need of exploitation
Quickly, efficiently, the carbon dots of specific recognition alcohol.The carbon dots that the present invention synthesizes can be used to the measurement of alcohol.
At the end of the 20th century, nanotechnology initially enters the sight of people, over time, is mutually handed between different subjects
Fork, fusion, infiltration, nanotechnology also begin to constantly incorporate modern science and technology.Pass through people going deep into nanotechnology
Solution, the properties such as the unique optics of nano material, electromagnetism, thermodynamics cause the interest of many scientists.Even to this day, respectively
Kind nano material achieves multinomial application in fields such as chemistry, physics, pharmacy, life science, medicine.Carbon quantum dot, letter
Claim carbon dots, be a kind of zero dimension fluorescence carbon nanomaterial developed rapidly in recent years, because its optical property is excellent, toxicity is low,
Good biocompatibility and have huge Scientific Research Potential in ambits such as molecular biology, Pharmaceutical Analysis, cell biologies.Carbon
The structure proximate of point is ball-type, and for grain size generally in 10 nm or so, molecular weight is generally also only thousands of, usually by carbon, hydrogen, oxygen, nitrogen
These four basic elements are constituted.Carbon dots provided by the invention have quick, efficient, specific recognition alcohol content performance.
Invention content
The present invention proposes a kind of sensing fluorescent carbon point of alcohol, preparation method and applications, with N- methyl-1s, 2- benzene two
The reaction of amine dihydrochloride generates the carbon dots with nitrogen positive charge, has very strong response to alcohol；Simultaneously because its carbon dots is with very
Strong positive charge and lipophilicity can rapidly enter cell and be detected.
Realize the technical scheme is that：A kind of fluorescent carbon point of sensing alcohol, structural formula are as follows：
。
Described is the preparation method of yellow fluorescence carbon dots, and steps are as follows：With N- methyl-1s, 2- phenylenediamine dihydrochlorides are
Raw material, absolute ethyl alcohol are solvent, synthesize carbon dots in 180-200 DEG C of 12 h of reaction of autoclave of polytetrafluoroethylliner liner, use
Silica gel column chromatography purifies crude product, using ethyl acetate as eluant, eluent, through vacuum except solvent and after being further dried, most
The carbon dots purified eventually.
Application of the yellow fluorescence carbon dots in living cells imaging.
The living cells is Hela cells, A549 cells etc..
Using N- methyl-1s, the synthetic route that 2- phenylenediamine dihydrochlorides prepare fluorescent carbon point is as follows：
；
The N- methyl-1s, 2- phenylenediamine dihydrochlorides are dissolved in a concentration of 0.25mmol in absolute ethyl alcohol.
The present invention is the fluorescent carbon point for detecting alcohol content.
Above application specifically includes：
Carbon dots storing liquid is tested respectively（I.e. carbon dots are dissolved in the organic solvents such as absolute ethyl alcohol, DMSO）Various concentration alcohol is added
The excitation wavelength of the variation of uv-vis spectra and fluorescence spectrum, fluorescence is 430nm；Observe ultraviolet and fluorescence pattern variation.
Observe the variation for the cell fluorescence image that carbon dots are incubated.
The variation of fluorescence spectrum is：When being excited with 430nm light, when being gradually added into various concentration alcohol, fluorescence intensity with
The increase of alcohol content and enhance.
The variation of fluorescence imaging figure is：With carbon dots mother liquor incubated cell, Laser Scanning Confocal Microscope is used in combination, is with excitation wavelength
488 nm light source activations carry out co-focusing imaging.
Above application, specifically, including the following steps：
（1）Carbon dots are weighed, are dissolved with absolute ethyl alcohol or other organic solvents, the accurate carbon dots storing liquid for preparing 10mg/ml；
（2）The absolute ethyl alcohol of 2 mL is added into cuvette, the carbon dots storing liquid of various concentration is added, observes ultraviolet and fluorogram
The variation of spectrum；
（3）Configure different pH value（2-12）B-R buffer solutions, the carbon dots storing liquid of 8 μ L is added into the solution of different pH, see
Examine ultraviolet and fluorescence pattern variation；
（4）The different moisture content of 2 mL is added into cuvette（0-100%）Alcoholic solution, add 8 μ L carbon dots storage
Liquid observes the variation of fluorescence pattern
（5）The white wine containing different alcohol concentrations of 2 mL is added into cuvette, adds the carbon dots storing liquid of 8 μ L, observes
The variation of fluorescence pattern；
（6）Fluorescence imaging is carried out to the living cells for the fluorescent carbon point being incubated by Laser Scanning Confocal Microscope.
The step（2）The concentration of middle carbon dots solution is respectively 0 μ g/ml, 10 μ g/ml, 20 μ g/ml, 30 μ g/ml, 40 μ g/
ml、50μg/ml、60μg/ml、70μg/ml、80μg/ml、90μg/ml、100μg/ml。
The step（5）The alcohol concentration of middle white wine is 32%, 42%, 52% and 75%.
The beneficial effects of the invention are as follows：（1）The synthesis very simple of carbon dots, it is easy to operation, and there is fluorophor, have
The advantages that good light stability, high quantum yield；（2）The present invention can realize specific detection and quickly identification to alcohol；（3）This
Invention can be detected in living cells.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
Obtain other attached drawings according to these attached drawings.
Fig. 1 is under 430nm excitations, with the increased ultraviolet spectrogram of carbon dots concentration in ethanol solution.
Fig. 2 is under 430nm excitations, with the increased fluorescence spectra of carbon dots concentration in ethanol solution.
Fig. 3 is ultraviolet emission spectrogram of the carbon dots in the B-R buffer solutions of different pH value under 430nm excitations.
Fig. 4 is fluorescence emission spectrogram of compound of the carbon dots in the B-R buffer solutions of different pH value under 430nm excitations.
Fig. 5 be 430nm excitation under, carbon dots at 565nm fluorescence intensity with pH value variation diagram.
Fig. 6 is fluorescence emission spectrogram of compound of the carbon dots in different solvents under 430nm excitations.
Fig. 7 is ethanol solution of the carbon dots in various concentration under 430nm excitations（Ethyl alcohol and water different proportion）In fluorescence
Launching light spectrogram.
Fig. 8 be 430nm excitation under, add carbon dots at 540 nm fluorescence intensity with the increased point and line chart of alcohol concentration and line
Sexual intercourse.
Fig. 9 is under 430nm excitations, and carbon dots are in the white wine containing different alcohol contents, with the fluorescence of concentration variation
Launching light spectrogram.
Figure 10 is the cell experiment research figure of fluorescent carbon point under 430nm excitations, (A) group and (B) group, is that carbon dots are added
The imaging of light field and details in a play not acted out on stage, but told through dialogues after being incubated 4 hours.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical scheme of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
The every other embodiment that those of ordinary skill in the art are obtained under the premise of not making the creative labor, belongs to this hair
The range of bright protection.
Embodiment 1
The synthesis of carbon dots, steps are as follows：
First weigh N- methyl-1s, 0.0500 g of 2- phenylenediamine dihydrochlorides solid powder（0.256 mmol）, be dissolved in 5 mL without
In water-ethanol, its solution is transferred in the autoclave of polytetrafluoroethyllining lining, reaction kettle is placed in baking oven at 180 DEG C
Under the conditions of be heated to reflux 12 h, reaction kettle cooled to room temperature is obtained into the solution of brownish black later.Then silica gel column layer is used
Analysis method purifies crude product.Using ethyl acetate as eluant, eluent, except solvent and after being further dried, finally obtained pure through vacuum
The carbon dots of change.
Embodiment 2
The same embodiment of the present embodiment preparation method, the difference is that the reaction temperature of reaction kettle is 190 DEG C.
Embodiment 3
The same embodiment of the present embodiment preparation method, the difference is that the reaction temperature of reaction kettle is 200 DEG C.
1. the fluorescence intensity change that carbon dots are reacted from different pH value
Prepare the B-R solution of different pH value：Phosphoric acid 7.83g, acetic acid 4.81g, boric acid 4.94g are weighed respectively, it is each that a small amount of steam is added
It is settled to 2L after distilled water mixed dissolution.It weighs 8.0g sodium hydroxide solutions and is dissolved in 1L distilled water and be configured to a concentration of 0.2mol/
L.The NaOH solution of the 0.2mol/L of different volumes is added in the sour mixed liquors of 50ml tri-, adjusts pH value to different pH.
The B-R buffer solutions of the different pH value of 2 mL are added into cuvette, the carbon dots storing liquid of 8 μ L is added, measure purple
Outer and fluorescence pattern.Experimental data shows：As shown in figure 5, pH, between 2-7, fluorescence intensity increases as pH increases, and
It is very sensitive.
2. reaction of the carbon dots to different alcohol contents
It is separately added into the alcohol that 2 mL contain various concentration into cuvette, the carbon dots storing liquid of 8 μ L is added, measures fluorogram
Spectrum.The experimental results showed that：As shown in fig. 7, with the white wine number of degrees（That is alcohol content）Increase, fluorescence intensity becomes in incremental
Gesture.
3. reaction of the carbon dots to alcohol content in white wine
Commercially available 32 degree of 2 mL are separately added into cuvette, 42 degree, 52 degree, the carbon dots storage of 8 μ L is added in 75 degree of white wine
Liquid measures fluorescence pattern.The experimental results showed that：As shown in figure 8, with the white wine number of degrees（That is alcohol content）Increase, fluorescence is strong
Degree is in incremental trend.
4. the bio-imaging of carbon dots is studied
At 37 DEG C, 95 % air, in 5 % carbon dioxide incubators, by Hela cell inoculations to swashing containing 10 % fetal calf serums
It is cultivated in the burnt special culture dish of light copolymerization.After cultivating 4 hours, with excitation wavelength for 488 nm and 552nm light source activations, into
Row co-focusing imaging.As shown in figure 9, being 488 nm and 552nm equal it is observed that cell fluorescence response in excitation wavelength.Cell at
As statistics indicate that, the carbon dots cell permeability is excellent.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (8)
1. a kind of fluorescent carbon point of sensing alcohol, it is characterised in that structural formula is as follows：
。
2. the preparation method of the fluorescent carbon point of sensing alcohol described in claim 1, it is characterised in that steps are as follows：With N- first
Base -1,2- phenylenediamine dihydrochloride is raw material, and absolute ethyl alcohol is solvent, in 180-200 DEG C of reaction 12 h synthesis of autoclave
Carbon quantum dot purifies to crude product with silica gel column chromatography, using ethyl acetate as eluant, eluent, through vacuum except solvent and into one
After step is dry, purifying fluorescent carbon point is finally obtained.
3. the preparation method of the fluorescent carbon point of sensing alcohol according to claim 2, it is characterised in that：The N- methyl-
1,2- phenylenediamine dihydrochlorides are dissolved in a concentration of 0.25mmol in absolute ethyl alcohol.
4. in application of the fluorescent carbon point of sensing alcohol described in claim 1 in detection alcohol content and living cells imaging
Using.
5. the application of fluorescent carbon point according to claim 4, it is characterised in that steps are as follows：
（1）Fluorescent carbon point is weighed, is dissolved with organic solvent, the carbon dots storing liquid of 10mg/ml is prepared；
（2）The absolute ethyl alcohol of 2 mL is added into cuvette, carbon dots storing liquid is added, prepares the carbon dots solution of various concentration, sees
Examine ultraviolet and fluorescence pattern variation；
（3）The B-R buffer solutions for configuring different pH value, the carbon dots storing liquid of 8 μ L is added into the solution of different pH, and observation is ultraviolet
And the variation of fluorescence pattern；
（4）The alcoholic solution of the different moisture content of 2 mL is added into cuvette, adds the carbon dots storing liquid of 8 μ L, observation is glimmering
The variation of light collection of illustrative plates；
（5）The white wine containing different alcohol concentrations of 2 mL is added into cuvette, adds the carbon dots storing liquid of 8 μ L, observes
The variation of fluorescence pattern；
（6）Fluorescence imaging is carried out to the living cells for the fluorescent carbon point being incubated by Laser Scanning Confocal Microscope.
6. the application of fluorescent carbon point according to claim 5, it is characterised in that：The step（2）Middle carbon dots solution it is dense
Degree is respectively 0 μ g/ml, 10 μ g/ml, 20 μ g/ml, 30 μ g/ml, 40 μ g/ml, 50 μ g/ml, 60 μ g/ml, 70 μ g/ml, 80 μ g/
ml、90μg/ml、100μg/ml。
7. the application of fluorescent carbon point according to claim 5, it is characterised in that：The step（5）The alcohol of middle white wine is dense
Degree is 32%, 42%, 52% and 75%.
8. the application of fluorescent carbon point according to claim 5, it is characterised in that：The step（6）Middle living cells is Hela
Cell or A549 cells.
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Cited By (6)
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|---|---|---|---|---|
| CN110057804A (en) * | 2019-05-24 | 2019-07-26 | 郑州大学 | Application of the fluorescent carbon point based on N- methyl-o-phenylenediamine hydrochloride in lysosome targeting |
| CN111351822A (en) * | 2020-03-23 | 2020-06-30 | 哈尔滨学院 | AZO/ZnTAP (t-Bu)4Compound gas-sensitive film of/benzyl isoquinoline alkaloid and preparation method thereof |
| CN112858236A (en) * | 2021-01-14 | 2021-05-28 | 浙江工业大学 | Double-channel fluorescence sensor based on carbon quantum dots and application thereof |
| CN113388389A (en) * | 2021-07-23 | 2021-09-14 | 齐鲁工业大学 | Fluorescent carbon nanodot, preparation method and application thereof in cell nucleus targeted imaging |
| CN114621101A (en) * | 2020-12-11 | 2022-06-14 | 李冰坚 | Refining method of 3, 5-dimethyl-1, 2-phenylenediamine dihydrochloride |
| CN116790249A (en) * | 2023-06-07 | 2023-09-22 | 湖北第二师范学院 | Ultraviolet A wave band carbon dot and preparation method thereof |
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Cited By (11)
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| CN111351822A (en) * | 2020-03-23 | 2020-06-30 | 哈尔滨学院 | AZO/ZnTAP (t-Bu)4Compound gas-sensitive film of/benzyl isoquinoline alkaloid and preparation method thereof |
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| CN112858236A (en) * | 2021-01-14 | 2021-05-28 | 浙江工业大学 | Double-channel fluorescence sensor based on carbon quantum dots and application thereof |
| CN112858236B (en) * | 2021-01-14 | 2023-09-29 | 浙江工业大学 | Binary channels fluorescence sensor based on carbon quantum dots and application thereof |
| CN113388389A (en) * | 2021-07-23 | 2021-09-14 | 齐鲁工业大学 | Fluorescent carbon nanodot, preparation method and application thereof in cell nucleus targeted imaging |
| CN113388389B (en) * | 2021-07-23 | 2022-03-29 | 齐鲁工业大学 | Fluorescent carbon nanodot, preparation method and application thereof in cell nucleus targeted imaging |
| CN116790249A (en) * | 2023-06-07 | 2023-09-22 | 湖北第二师范学院 | Ultraviolet A wave band carbon dot and preparation method thereof |
| CN116790249B (en) * | 2023-06-07 | 2024-05-31 | 湖北第二师范学院 | Ultraviolet A wave band carbon dot and preparation method thereof |
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