CN108794475B - Alcohol-sensing fluorescent carbon dot, and preparation method and application thereof - Google Patents
Alcohol-sensing fluorescent carbon dot, and preparation method and application thereof Download PDFInfo
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- CN108794475B CN108794475B CN201810842372.7A CN201810842372A CN108794475B CN 108794475 B CN108794475 B CN 108794475B CN 201810842372 A CN201810842372 A CN 201810842372A CN 108794475 B CN108794475 B CN 108794475B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The invention provides a fluorescent carbon dot for sensing alcohol, a preparation method and application thereof, wherein the chemical structural formula of the fluorescent carbon dot is as follows:
the preparation method comprises the steps of taking N-methyl-1, 2-phenylenediamine dihydrochloride as a raw material, taking absolute ethyl alcohol as a solvent, reacting for 12 hours in a high-pressure reaction kettle with a polytetrafluoroethylene inner container at the temperature of 180 ℃ for synthesis of carbon dots, purifying a crude product by a silica gel column chromatography, taking ethyl acetate as an eluent, removing the solvent in vacuum, and further drying to finally obtain the purified carbon dots. The invention can quickly, efficiently and specifically identify the ethanol, and the fluorescent carbon dots can be used for detecting the alcohol content in different white spirits.
Description
Technical Field
The invention relates to the field of fluorescent nano material preparation, in particular to a fluorescent carbon dot for sensing alcohol, a preparation method and application thereof.
Background
Alcohol (ethanol) is a necessary medicine for medical units and household medicine boxes, and is one of the most commonly used external preparations. Alcohol can be used as disinfectant, and is also a component of cosmetics, and is also an important component of wine for human. The data show that nearly one third of the serious traffic accidents in recent years in China are caused by drunk driving. Detection, monitoring of alcohol leakage and monitoring of drunk driving are important for human safety. Therefore, the development of a carbon spot for rapidly, efficiently and specifically recognizing alcohol is urgently needed. The carbon dots synthesized by the method can be used for measuring alcohol.
At the end of the 20 th century, nanotechnology began to enter the sight of people, and as time goes on, different subjects crossed, fused and permeated, nanotechnology also began to be continuously integrated into modern scientific technology. Through the deep understanding of nanotechnology, the unique optical, electromagnetic, thermodynamic properties of nanomaterials have attracted much scientific interest. To date, various nanomaterials have been used in many applications in the fields of chemistry, physics, medicine, life science, medicine, etc. Carbon quantum dots, called carbon dots for short, are zero-dimensional fluorescent carbon nanomaterials which are rapidly developed in recent years, and have great scientific research potential in the subject fields of molecular biology, pharmaceutical analysis, cell biology and the like due to excellent optical properties, low toxicity and good biocompatibility. The carbon dots are approximately spherical in structure, the particle size is generally about 10 nm, the molecular weight is generally only thousands, and the carbon dots are generally composed of four basic elements of carbon, hydrogen, oxygen and nitrogen. The carbon dots provided by the invention have the performance of quickly, efficiently and specifically identifying the alcohol content.
Disclosure of Invention
The invention provides a fluorescent carbon dot for sensing alcohol, a preparation method and application thereof, wherein N-methyl-1, 2-phenylenediamine dihydrochloride reacts to generate a carbon dot with nitrogen positive charge, and the carbon dot has strong response to alcohol; meanwhile, the carbon dots have strong positive charges and lipophilicity, so that the nano-particles can rapidly enter cells for detection.
The technical scheme for realizing the invention is as follows: a fluorescent carbon dot for sensing alcohol has a structural formula as follows:
the preparation method of the yellow fluorescent carbon dot comprises the following steps: n-methyl-1, 2-phenylenediamine dihydrochloride is taken as a raw material, absolute ethyl alcohol is taken as a solvent, the raw material reacts for 12 hours at the temperature of 180-plus-200 ℃ in a high-pressure reaction kettle with a polytetrafluoroethylene inner container to synthesize carbon dots, a silica gel column chromatography method is used for purifying a crude product, ethyl acetate is taken as an eluent, the solvent is removed in vacuum, and the purified carbon dots are finally obtained after further drying.
The application of the yellow fluorescent carbon dot in live cell imaging.
The living cells are Hela cells, A549 cells and the like.
The synthetic route for preparing the fluorescent carbon dots by using the N-methyl-1, 2-phenylenediamine dihydrochloride is as follows:
the concentration of the N-methyl-1, 2-phenylenediamine dihydrochloride dissolved in the absolute ethyl alcohol is 0.25 mmol.
The invention relates to a fluorescent carbon dot for detecting alcohol content.
The application specifically comprises:
respectively testing the changes of ultraviolet-visible spectra and fluorescence spectra of carbon dot storage solutions (namely carbon dots are dissolved in organic solvents such as absolute ethyl alcohol and DMSO) added with alcohols with different concentrations, wherein the excitation wavelength of fluorescence is 430 nm; and observing the change of the ultraviolet and fluorescence spectra. The change of the fluorescence imaging graph of the carbon dot incubated cells is observed.
The change in fluorescence spectrum was: when the fluorescent material is excited by light of 430nm and alcohol with different concentrations is gradually added, the fluorescence intensity is enhanced along with the increase of the alcohol content.
The changes of the fluorescence imaging map are: the carbon dot mother solution is used for incubating the cells, and a confocal microscope is used for carrying out confocal imaging by using a light source with the excitation wavelength of 488 nm for excitation.
The application specifically comprises the following steps:
(1) weighing carbon dots, dissolving with absolute ethyl alcohol or other organic solvents, and accurately preparing 10mg/ml carbon dot storage solution;
(2) adding 2 mL of absolute ethyl alcohol into the cuvette, adding carbon dot storage solutions with different concentrations, and observing changes of ultraviolet and fluorescence spectrums;
(3) B-R buffer solutions with different pH values (2-12) are prepared, 8 mu L of carbon dot storage solution is added into the solutions with different pH values, and changes of ultraviolet and fluorescence spectrums are observed;
(4) adding 2 mL of alcohol solution with different water contents (0-100%) into the cuvette, adding 8 mu L of carbon dot storage solution, and observing the change of the fluorescence spectrum
(5) Adding 2 mL of white spirit containing different alcohol concentrations into the cuvette, adding 8 muL of carbon dot storage solution, and observing the change of the fluorescence spectrum;
(6) and performing fluorescence imaging on the living cells of the incubated fluorescent carbon dots by using a confocal microscope.
The concentration of the carbon dot solution in the step (2) is 0 mu g/ml, 10 mu g/ml, 20 mu g/ml, 30 mu g/ml, 40 mu g/ml, 50 mu g/ml, 60 mu g/ml, 70 mu g/ml, 80 mu g/ml, 90 mu g/ml and 100 mu g/ml respectively.
The alcohol concentration of the white spirit in the step (5) is 32%, 42%, 52% and 75%.
The invention has the beneficial effects that: (1) the carbon dots are very simple to synthesize and convenient to operate, and have the advantages of fluorescent groups, good photostability, high quantum yield and the like; (2) the invention can realize the specific detection and the rapid recognition of the alcohol; (3) the invention can be used for detection in living cells.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a graph of the UV spectrum of absolute ethanol solution with increasing carbon spot concentration under 430nm excitation.
FIG. 2 is a graph showing fluorescence spectra with increasing carbon spot concentration in an absolute ethanol solution under excitation at 430 nm.
FIG. 3 is a graph of UV emission spectra of carbon dots in B-R buffer solutions at different pH values under 430nm excitation.
FIG. 4 is a graph showing fluorescence emission spectra of carbon dots in B-R buffer solutions at different pH values under 430nm excitation.
FIG. 5 is a graph of fluorescence intensity at 565nm for carbon spots as a function of pH under 430nm excitation.
FIG. 6 is a fluorescence emission spectrum of carbon dots in different solvents under 430nm excitation.
FIG. 7 is a graph of fluorescence emission spectra of carbon dots in ethanol solutions of different concentrations (different ratios of ethanol to water) under 430nm excitation.
FIG. 8 is a dot line graph and linear relationship of fluorescence intensity at 540 nm for carbon added dots with 430nm excitation as a function of alcohol concentration.
FIG. 9 is a fluorescence emission spectrum of carbon dots in white spirit with different alcohol contents as a function of concentration under 430nm excitation.
FIG. 10 is a graph of a study of a cell experiment using fluorescent carbon spots under excitation at 430nm, and the bright and dark fields of group (A) and group (B) were imaged after 4 hours of incubation with the carbon spots.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
The carbon dots are synthesized by the following steps:
0.0500 g (0.256 mmol) of N-methyl-1, 2-phenylenediamine dihydrochloride solid powder is weighed and dissolved in 5mL of absolute ethyl alcohol, the solution is transferred to a polytetrafluoroethylene-lined high-pressure reaction kettle, the reaction kettle is placed in an oven to be heated and refluxed for 12 h at 180 ℃, and then the reaction kettle is naturally cooled to room temperature to obtain a brownish black solution. The crude product was then purified by silica gel column chromatography. And using ethyl acetate as an eluent, and finally obtaining the purified carbon dots after removing the solvent in vacuum and further drying.
Example 2
The preparation method of this example is the same as that of the example, except that the reaction temperature of the reaction kettle is 190 ℃.
Example 3
The preparation method of this example is the same as that of the example, except that the reaction temperature of the reaction kettle is 200 ℃.
1. Change in fluorescence intensity of carbon point in reaction with different pH values
B-R solutions with different pH values are prepared: 7.83g of phosphoric acid, 4.81g of acetic acid and 4.94g of boric acid are respectively weighed, and a small amount of distilled water is added respectively to be mixed and dissolved to be constant volume of 2L. 8.0g of sodium hydroxide solution was weighed and dissolved in 1L of distilled water to prepare a solution having a concentration of 0.2 mol/L. Different volumes of 0.2mol/L NaOH solution were added to 50ml of the triacid mixture to adjust the pH to different pH values.
Adding 2 mL of B-R buffer solutions with different pH values into the cuvette, adding 8 muL of carbon dot storage solution, and measuring ultraviolet and fluorescence spectra. The experimental data show that: as shown in FIG. 5, the fluorescence intensity increased with increasing pH and was very sensitive at pH between 2 and 7.
2. Reaction of carbon points to different alcohol contents
Adding 2 mL of alcohol with different concentrations into the cuvette respectively, adding 8 muL of carbon dot storage solution, and measuring a fluorescence spectrum. The experimental results show that: as shown in FIG. 7, the fluorescence intensity tends to increase with the degree of white spirit (i.e., alcohol content).
3. Reaction of carbon point on alcohol content in white spirit
2 mL of commercial white spirit with 32 degrees, 42 degrees, 52 degrees and 75 degrees is added into the cuvette respectively, 8 muL of carbon dot storage liquid is added, and a fluorescence spectrum is measured. The experimental results show that: as shown in fig. 8, the fluorescence intensity tends to increase with the increase of the alcohol content (i.e., alcohol content).
4. Bioimaging studies of carbon dots
Hela cells were inoculated into a laser confocal special culture dish containing 10% fetal calf serum in a 37 ℃ air-95% carbon dioxide incubator with 5% carbon dioxide. After 4 hours of incubation, confocal imaging was performed by excitation with light sources having excitation wavelengths of 488 nm and 552 nm. As shown in FIG. 9, cellular fluorescence responses were observed at both 488 nm and 552nm excitation wavelengths. Cell imaging data indicate that the carbon dots are excellent in cell permeability.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (4)
1. A fluorescent carbon dot for sensing alcohol is characterized by having the following structural formula:
2. the method for preparing a fluorescent carbon dot for sensing alcohol according to claim 1, characterized by comprising the steps of: n-methyl-1, 2-phenylenediamine dihydrochloride is used as a raw material, absolute ethyl alcohol is used as a solvent, the raw material reacts for 12 hours at the temperature of 180 ℃ in a high-pressure reaction kettle to synthesize the carbon quantum dots, a silica gel column chromatography method is used for purifying a crude product, ethyl acetate is used as an eluent, the solvent is removed in vacuum, and the purified fluorescent carbon dots are obtained after further drying.
3. The method for preparing a fluorescent carbon dot for sensing alcohol according to claim 2, wherein: the concentration of the N-methyl-1, 2-phenylenediamine dihydrochloride dissolved in the absolute ethyl alcohol is 0.25 mmol.
4. Use of the alcohol sensing fluorescent carbon dot of claim 1 for detecting alcohol content.
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| CN110057804B (en) * | 2019-05-24 | 2021-11-26 | 郑州大学 | Application of N-methyl o-phenylenediamine hydrochloride-based fluorescent carbon dots in lysosome targeting |
| CN111351822B (en) * | 2020-03-23 | 2021-04-06 | 哈尔滨学院 | AZO/ZnTAP (t-Bu)4Compound gas-sensitive film of/benzyl isoquinoline alkaloid and preparation method thereof |
| CN114621101A (en) * | 2020-12-11 | 2022-06-14 | 李冰坚 | Refining method of 3, 5-dimethyl-1, 2-phenylenediamine dihydrochloride |
| 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 |
| 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 |
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