CN108593618B - Method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry - Google Patents

Method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry Download PDF

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CN108593618B
CN108593618B CN201810421888.4A CN201810421888A CN108593618B CN 108593618 B CN108593618 B CN 108593618B CN 201810421888 A CN201810421888 A CN 201810421888A CN 108593618 B CN108593618 B CN 108593618B
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nitrite ions
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polymer carbon
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CN108593618A (en
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刘金华
赵朵朵
陈灿
李林
张承武
于海东
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Nanjing Tech University
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Abstract

The invention belongs to the field of nanotechnology, and discloses preparation of a polymer carbon dot and a detection method of the polymer carbon dot applied to nitrite ion colorimetric fluorescence. When nitrite ions with different concentrations exist in a buffer system containing a certain amount of polymer carbon dots, the absorption peak at 610nm of an absorption spectrum is obviously reduced, and the absorption peak at 380nm is gradually enhanced; the fluorescence spectrum gradually decreases the intensity of the fluorescence emission peak at 625nm with the increase of nitrite ions. Therefore, according to the change of the fluorescence spectrum and the absorption spectrum of the polymer carbon dots in the system, the high-sensitivity and high-selectivity detection of nitrite ions is realized through the analysis of a fluorescence colorimetric multi-output signal. Further, detection of nitrite ions in complex systems such as urine is also achieved. The polymer-based carbon dot fluorescent colorimetric probe is a new development of the original analysis method, and is expected to be used for analyzing and detecting nitrite ions in complex systems such as food, environment and the like.

Description

Method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry
Technical Field
The invention relates to a method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry and application thereof, belonging to the field of nanotechnology.
Background
Nitrite is a chemical substance whose residual quantity is required to be strictly controlled by national, industrial and local standards, and has been widely used as a preservative and an additive in the fields of food, natural water sources, environment and service industries, etc. Nitrite, however, presents a serious environmental and human health hazard. On the one hand, excess nitrite in the human body can cause irreversible oxidation of hemoglobin, and reduce blood volume; on the other hand, nitrite interacts with amines and is converted into carcinogenic nitrosamines, which are potentially toxic, mutagenic and carcinogenic. In addition, nitrite can cause enterogenous cyanosis, teratogenesis and other hazards. So develop aGu equals 2016 and published a method for detecting nitrite ion by using aniline fluorescent probe formed by combining two-step reaction with imidazole and aniline, the probe uses amine group as electron-donating group and has strong fluorescence, when it reacts with nitrite ion, intramolecular cyclization leads amine group diazotization to generate multi-electron heterocyclic structure derivative, intramolecular charge transfer leads probe fluorescence quenching, Xue equals 2012 published a method for detecting nitrite ion by colorimetry on royiety of Chemistry, this method is stirred for one week at room temperature and generates diazo salt with strong dark fluorescence after diazotization of nitrite ion, simple instrument and naked eye are used to realize quantitative detection of nitrite ion, the detection method has the characteristics of simple rapid and visual method, L equals 2017, Acyto equals to 201alalia complex is used as a rare earth NO complex and reported a method for detecting nitrite ion by using Chiacta NO complex+A method for detecting nitrite ions by the trapping agent through visualization and spectrum. The method can realize rapid detection and make up for the defect of slow color development of diazotization reaction. However, these methods have some disadvantages, such as complicated synthesis route, relatively single output signal, harsh reaction conditions, and low detection sensitivity. Therefore, it is a challenge to develop a method for detecting nitrite ions easily, rapidly and with high sensitivity.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry. The method can polymerize dopamine and o-phenylenediamine by a one-step hydrothermal method to form polymer carbon dots with strong red fluorescence. The prepared polymer has high carbon point, high sensitivity and high selectivity for detecting nitrite ions, and has good biocompatibility and low toxic and side effects on cells and organisms.
The technical scheme of the invention is as follows: a method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry comprises the following steps: weighing dopamine hydrochloride and o-phenylenediamine hydrochloride at room temperature, preparing a mixed solution by using ultrapure water in a beaker, adding concentrated hydrochloric acid to adjust the pH of the solution, transferring the obtained solution to a reaction kettle, heating the solution in an oven for a certain time to obtain a blue polymer carbon dot solution, and testing the formed polymer carbon dots by using an ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer.
Preferably, the method comprises the following steps of weighing 5-150 mg of dopamine hydrochloride and 10mg of o-phenylenediamine at room temperature, preparing 10m L mixed solution by using ultrapure water in a 50m L beaker, enabling the molar ratio of the dopamine hydrochloride to the o-phenylenediamine in the mixed solution to be 1:4-8:1, transferring the obtained solution to a 20m L reaction kettle, heating the obtained solution in an oven at the temperature of 150-180 ℃ for 8 hours to obtain blue polymer carbon dot solution, and testing the formed polymer carbon dots by using an ultraviolet visible spectrophotometer and a fluorescence spectrophotometer.
Preferably, the polymer carbon dot solution is added into a Tris-HCl buffer solution, and nitrite ions are added to make the polymer carbon dots in the buffer solution generate changes of absorption spectra and fluorescence spectra.
Preferably, the Tris-HCl buffer solution is a buffer solution with the concentration of 20mM and the pH value of 7, the concentration of the used nitrite ion solution is 10mM, and the concentration of the polymer carbon dots is 0.2-0.4mg/m L.
Preferably, the amount of Tris-HCl buffer solution is 400-2000 mu L, the concentration of the polymer carbon dots is 0.2-0.4mg/M L, and the concentration of the nitrite ion solution is 0-500 mu M.
Preferably, the Tris-HCl buffer solution is a 20mM buffer solution with pH 7, 5% human urine is added to the buffer solution, the concentration of the used nitrite ion solution is 10mM, and the concentration of the polymer carbon dot is 0.4mg/m L.
Preferably, the dosage of the Tris-HCl buffer solution is 380 mu L, the dosage of the human urine is 20-100 mu L, the concentration of the polymer carbon dots is 0.2-0.4mg/M L, and the concentration of the nitrite ion solution is 0-500 mu M.
Preferably, PBS buffer solution is added into a culture dish for culturing adherent cells Hela, polymer carbon dots and nitrite ion solution are added into the culture dish, after incubation, the culture dish is washed three times by using fresh PBS buffer solution, and the culture dish is placed under a fluorescence confocal fluorescence microscope for imaging to obtain the fluorescence detection nitrite ion of the polymer carbon dots in the Hela cells.
Preferably, the PBS buffer solution is 10mM Mg2+，50mM K+pH 7.4 buffer solution, concentration of nitrite ion used 200 μ M, concentration of polymer carbon dot solution 1mg/M L, incubation time 3 hours.
Preferably, the PBS buffer solution is 1m L, the polymer carbon dot solution is 100 μ L, and the sulfite ion solution is 20 μ L.
The invention has the beneficial effects that:
the method of the invention is to polymerize dopamine and o-phenylenediamine by a one-step hydrothermal method to form polymer carbon dots with strong red fluorescence. Adding a certain amount of polymer carbon dots into a Tris-HCl buffer system, wherein when nitrite ions with different concentrations exist in the system, the absorption spectrum of the polymer carbon dots has the absorption peak at 610nm obviously reduced and the absorption peak at 380nm gradually enhanced; the fluorescence spectrum gradually decreases the intensity of the fluorescence emission peak at 625nm with the increase of nitrite ions. And through the analysis of a fluorescence colorimetric multi-output signal, the high-sensitivity and high-selectivity detection on nitrite ions is realized. The prepared polymer carbon dot has the characteristics of simple synthesis process, no toxic or side effect on cells and organisms, good sensitivity, good chemical stability, good biocompatibility, good selectivity and the like on nitrite ion detection. In addition, the fluorescent probe is successfully applied to detection of nitrite ions in complex environment systems such as human urine, and further expands application and realizes imaging detection of nitrite ions in living cells. These studies provide a new approach to the realization of highly sensitive and highly selective detection of nitrite ions in organisms.
The invention is further explained and illustrated below:
on the basis of the technical scheme, the influence of variables of different factors on the invention is examined:
1. the influence of different molar ratios of dopamine hydrochloride and o-phenylenediamine on the carbon point of the polymer was examined and is shown in examples 1, 2, 3, 4, 5, 6 and 7.
2. The influence of the pH (1, 3, 5, 7, 9) synthesis conditions on the carbon point of the polymer was examined, see examples 8, 9, 10, 11, 12, 13.
3. The influence of temperature (150 ℃, 180 ℃, 200 ℃) on the carbon point of the polymer was examined and is shown in examples 14, 15 and 6.
4. The effect of peracid conditions (30, 100, 300 μ L concentrated HCl added, respectively) on the carbon point of the polymer was examined, see examples 16, 17, 18.
5. The effect of different test conditions (varying pH from 1 to 11) on the carbon point of the polymer was examined, see example 19.
6. The fluorescence and absorption changes of the polymer carbon dots after adding nitrite ions with different concentrations into a Tris-HCl buffer solution are considered, and the nitrite ions are quantitatively detected, see examples 20 and 22.
7. Ion selectivity, the effect of common anions on the carbon sites of the polymer, was examined, see examples 21, 23.
8. The color change of the polymer carbon dot solution after adding nitrite ions with different concentrations is examined, and the nitrite ions are detected by colorimetry, which is shown in example 24.
9. The fluorescence spectrum and absorption of polymer carbon dots after adding nitrite ions with different concentrations into Tris-HCl buffer solution (simulated biological environment) containing 5% urine are examined, and the nitrite ions are quantitatively detected, see examples 25 and 26.
10. The toxicity profile of the carbon dots of the polymer in Hela cells was examined and found in example 27.
11. The fluorescence imaging properties of the polymer carbon dots in Hela cells were examined, see example 28.
Drawings
The embodiments of the present invention will be further described with reference to the accompanying drawings.
FIG. 1 is an absorption spectrum of carbon dots of the polymer prepared in example 1;
FIG. 2 is a graph showing a fluorescence spectrum of carbon dots of the polymer prepared in example 1;
FIG. 3 is an absorption spectrum of a carbon dot of the polymer prepared in example 2;
FIG. 4 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 2;
FIG. 5 is an absorption spectrum of carbon dots of the polymer prepared in example 3;
FIG. 6 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 3;
FIG. 7 is an absorption spectrum of carbon dots of the polymer prepared in example 4;
FIG. 8 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 4;
FIG. 9 is an absorption spectrum of carbon dots of the polymer prepared in example 5;
FIG. 10 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 5;
FIG. 11 is an absorption spectrum of carbon dots of the polymer prepared in example 6;
FIG. 12 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 6;
FIG. 13 is an absorption spectrum of carbon dots of the polymer prepared in example 7;
FIG. 14 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 7;
FIG. 15 is an absorption spectrum of carbon dots of the polymer prepared in example 8;
FIG. 16 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 8;
FIG. 17 is an absorption spectrum of carbon dots of the polymer prepared in example 9;
FIG. 18 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 9;
FIG. 19 is an absorption spectrum of carbon dots of the polymer prepared in example 10;
FIG. 20 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 10;
FIG. 21 is an absorption spectrum of carbon dots of the polymer prepared in example 11;
FIG. 22 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 11;
FIG. 23 is an absorption spectrum of a carbon dot of the polymer prepared in example 12;
FIG. 24 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 12;
FIG. 25 is an absorption spectrum of carbon dots of the polymer prepared in example 13;
FIG. 26 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 13;
FIG. 27 is an absorption spectrum of carbon dots of the polymer prepared in example 14;
FIG. 28 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 14;
FIG. 29 is an absorption spectrum of carbon dots of the polymer prepared in example 15;
FIG. 30 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 15;
FIG. 31 is an absorption spectrum of carbon dots of the polymer prepared in example 16;
FIG. 32 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 16;
FIG. 33 is an absorption spectrum of carbon dots of the polymer prepared in example 17;
FIG. 34 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 17;
FIG. 35 is an absorption spectrum of carbon dots of the polymer prepared in example 18;
FIG. 36 is a graph showing a fluorescence spectrum of carbon dots of the polymer obtained in example 18;
FIG. 37 is a line graph showing the fluorescence intensities of carbon dots of the polymer prepared in example 6 in different pH test environments;
FIG. 38 is a combination graph of a fluorescence scattergram and a standard curve of the carbon dot of the polymer prepared in example 6 after adding nitrite ions at different concentrations to a Tris-HCl (20mM, pH 7) buffer solution, which is an abstract figure;
FIG. 39 is a bar graph of the fluorescence ion selectivity of the carbon dots of the polymer prepared in example 6 with 400 μ M of a common anion in Tris-HCl (20mM, pH 7) buffer;
FIG. 40 is a combination graph of an absorption scattergram and a standard curve of the carbon dot of the polymer prepared in example 6 after adding nitrite at various concentrations to a Tris-HCl (20mM, pH 7) buffer solution;
FIG. 41 is a bar graph of the absorbent ion selectivity of the carbon dots of the polymer prepared in example 6 in Tris-HCl (20mM, pH 7) buffer solution with the addition of 400. mu.M of common anions;
FIG. 42 is a graph of carbon dots of the polymer prepared in example 6 incubated with nitrite ions at different concentrations in Tris-HCl (20mM, pH 7) buffer for half an hour before irradiation with fluorescent light;
FIG. 43 is a combination of a fluorescence scattergram and a standard curve of the polymer carbon dot prepared in example 6 after adding nitrite ions at different concentrations to Tris-HCl (20mM, pH 7) buffer solution containing 5% urine;
FIG. 44 is a combination graph of an absorption scattergram and a standard curve of the polymer carbon dot prepared in example 6 after adding nitrite ions at different concentrations to Tris-HCl (20mM, pH 7) buffer solution containing 5% urine;
FIG. 45 is a graph showing the toxicity of carbon dots of the polymer prepared in example 6 to Hela cells;
FIG. 46 is a graph of fluorescence images of polymer carbon quantum dots prepared in example 6 in Hela cells.
Detailed Description
The embodiments of the present invention will be described in detail below with reference to the accompanying drawings: the present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a process are given, but the scope of the present invention is not limited to the following embodiments.
Example 1 weighing 5mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 1:4) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue polymer carbon dot at a concentration of 10mg/m L. a 0.4mg/m L carbon dot solution was prepared in a Tris-HCl (20mM, pH 7) buffer solution and the uv-vis spectrophotometer test was performed and the absorption spectrum recorded, a 0.2mg/m L carbon dot solution was prepared in a Tris-HCl (20mM, pH 7) buffer solution and the fluorescence spectrophotometer test was performed and the emission spectrum recorded, the absorption wavelength was 380nm, 560nm, 610nm and the emission wavelength was 625nm (Ex 580nm), as shown in fig. 1 and fig. 2, respectively.
Example 2 weighing 10mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 1:2) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths 380nm, 560nm, 610nm and emission wavelengths 625nm (Ex 580nm) were measured as shown in fig. 3 and 4, respectively.
Example 3 weighing 20mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 1:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 c for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum was recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum was recorded.a measurement gave an absorption wavelength of 380nm, 560nm, 610nm and an emission wavelength of 625nm (Ex 580nm), as shown in fig. 5 and 6, respectively.
Example 4 weighing 40mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 2:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were measured as shown in fig. 7 and 8, respectively.
Example 5 weighing 70mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 4:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were measured as shown in fig. 9 and 10, respectively.
Example 6 weighing 90mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum was recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum was recorded.a measurement gave an absorption wavelength of 380nm, 560nm, 610nm and an emission wavelength of 625nm (Ex 580nm) as shown in fig. 11 and 12, respectively.
Example 7 weighing 150mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 8:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 c for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were measured as shown in fig. 13 and 14, respectively.
Example 8 weighing 90mg of dopamine hydrochloride in 10ml of water, adding 10mg of o-phenylenediamine (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), adding concentrated hydrochloric acid to adjust the pH to 1, transferring the mixture to a reaction kettle (20ml), heating in an oven at 200 ℃ for 8 hours to obtain a blue solution with a concentration of 10mg/m L, preparing a 0.4mg/m L carbon dot solution with a Tris-HCl (20mM, pH 7) buffer solution, performing an ultraviolet-visible spectrophotometer test, recording the absorption spectrum, preparing a 0.2mg/m L carbon dot solution with a Tris-HCl (20mM, pH 7) buffer solution, performing a fluorescence spectrophotometer test, recording the emission spectrum, testing to obtain an absorption wavelength of 380nm, 560nm, 610nm, and an emission wavelength of 625nm (Ex-580 nm), as shown in fig. 15 and 16, respectively.
Example 9 weighing 90mg of dopamine hydrochloride in 10ml of water, adding 10mg of o-phenylenediamine (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), adding concentrated hydrochloric acid to adjust the pH of the solution to 3, transferring the mixture to a reaction kettle (20ml), heating in an oven at 200 ℃ for 8 hours to obtain a blue solution with a concentration of 10mg/m L, performing uv-vis spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.4mg/m L carbon dot solution, recording the absorption spectrum, performing fluorescence spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.2mg/m L carbon dot solution, recording the emission spectrum, measuring the absorption wavelength of 380nm, 560nm, 610nm, and the emission wavelength of 625nm (Ex-580 nm), as shown in fig. 17 and 18, respectively.
Example 10 weighing 90mg of dopamine hydrochloride in 10ml of water, adding 10mg of o-phenylenediamine (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), adding concentrated hydrochloric acid to adjust the pH of the solution to 5, transferring the mixture to a reaction kettle (20ml), heating in an oven at 200 ℃ for 8 hours to obtain a blue solution with a concentration of 10mg/m L, performing uv-vis spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.4mg/m L carbon dot solution, recording the absorption spectrum, performing fluorescence spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.2mg/m L carbon dot solution, recording the emission spectrum, measuring the absorption wavelength of 380nm, 560nm, 610nm, and the emission wavelength of 625nm (Ex-580 nm), as shown in fig. 19 and fig. 20, respectively.
Example 11 weighing 90mg of dopamine hydrochloride in 10ml of water, adding 10mg of o-phenylenediamine (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), adding concentrated hydrochloric acid to adjust the pH of the solution to 7, transferring the mixture to a reaction kettle (20ml), heating in an oven at 200 ℃ for 8 hours to obtain a blue solution with a concentration of 10mg/m L, performing uv-vis spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.4mg/m L carbon dot solution, recording the absorption spectrum, performing fluorescence spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.2mg/m L carbon dot solution, recording the emission spectrum, measuring the absorption wavelength of 380nm, 560nm, 610nm, and the emission wavelength of 625nm (Ex-580 nm), as shown in fig. 21 and 22, respectively.
Example 12 weighing 90mg of dopamine hydrochloride in 10ml of water, adding 10mg of o-phenylenediamine (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), adding concentrated hydrochloric acid to adjust the pH 9. the mixture was transferred to a reaction kettle (20ml) and heated in an oven at 200 ℃ for 8 hours to obtain a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum was recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum was recorded. the measurement gave an absorption wavelength of 380nm, 560nm, 610nm, and an emission wavelength of 625nm (Ex 580nm), as shown in fig. 23 and 24, respectively.
Example 13 weighing 90mg of dopamine hydrochloride in 10ml of water, adding 10mg of o-phenylenediamine (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), adding concentrated hydrochloric acid to adjust the pH of the solution to 11, transferring the mixture to a reaction kettle (20ml), heating in an oven at 200 ℃ for 8 hours to obtain a blue solution with a concentration of 10mg/m L, performing uv-vis spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.4mg/m L carbon dot solution, recording the absorption spectrum, performing fluorescence spectrophotometry with a Tris-HCl (20mM, pH 7) buffer solution to prepare a 0.2mg/m L carbon dot solution, recording the emission spectrum, measuring the absorption wavelength of 380nm, 560nm, 610nm, and the emission wavelength of 625nm (Ex-580 nm), as shown in fig. 25 and 26, respectively.
Example 14 weighing 90mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml) and heated in an oven at 150 ℃ for 8h to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were measured as shown in fig. 27 and 28, respectively.
Example 15 weighing 90mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml) and heated in an oven at 180 ℃ for 8h to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were obtained as shown in fig. 29 and 30, respectively.
Example 16 weighing 90mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 30 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were measured as shown in fig. 31 and 32, respectively.
Example 17 weighing 90mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 100 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20m L) and heated in an oven at 200 ℃ for 8 hours to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with a Tris-HCl (20mM, pH 7) buffer solution was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were measured as shown in fig. 33 and 34, respectively.
Example 18 weighing 90mg of dopamine hydrochloride in 10m L water, adding 10mg of o-phenylenediamine and 300 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml) and heated in an oven at 200 ℃ for 8h to give a blue solution with a concentration of 10mg/m L. a 0.4mg/m L carbon spot solution prepared with Tris-HCl (20mM, pH 7) buffer was subjected to uv-vis spectrophotometer measurement and its absorption spectrum recorded, a 0.2mg/m L carbon spot solution prepared with Tris-HCl (20mM, pH 7) buffer was subjected to fluorescence spectrophotometer measurement and its emission spectrum recorded, absorption wavelengths of 380nm, 560nm, 610nm and emission wavelengths of 625nm (Ex 580nm) were obtained as shown in fig. 35 and 36, respectively.
Example 19 weighing 90mg dopamine hydrochloride dissolved in 10m L water, adding 10mg o-phenylenediamine and 500 u L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml) at 200 c and heated in an oven for 8h to obtain a blue solution with a concentration of 10mg/m L. Tris-HCl (20mM) buffer solution with pH 1-11 was used to prepare 0.4mg/m L carbon spot solution for fluorescence spectrometer test, excitation at 580nm to obtain an emission wavelength of 625nm, and data were recorded for fluorescence intensity at 625nm, as shown in FIG. 37.
Example 20 weighing 90mg dopamine hydrochloride dissolved in 10M L water, adding 10mg o-phenylenediamine and 500 u L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml), the reaction temperature was 200 ℃, heating in an oven for 8h, obtaining a blue solution with a concentration of 10mg/M L. Tris-HCl (20mM, pH 7) buffer solution was used to prepare 0.2mg/M L carbon dot solution for fluorescence spectrophotometer test, nitrite ions of different concentrations were added to this solution, fluorescence intensity was measured by a fluorescence spectrometer, signal to noise ratio was used as ordinate, final concentration of nitrite ions was used as abscissa to plot, a standard curve of nitrite was obtained after fitting, the lower limit of detection of nitrite ions by fluorescence quantitative determination was 0.5 u M, there was an online relationship in the range of 0-2 u M, R is R20.9972, as shown in fig. 38, which is the left drawing of the abstract.
Example 21 weighing 90mg dopamine hydrochloride dissolved in 10M L water, adding 10mg o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml) at 200 ℃, heated in an oven for 8h to obtain a blue solution with a concentration of 10mg/M L. preparing a 0.2mg/M L carbon dot solution with Tris-HCl (20mM, pH 7) buffer solution, adding 400 μ M common anions separately for ion selectivity examination, recording the emission spectra (Ex 580nm, Em 625nm) as shown in fig. 39 (blank 1, 2-18 in sequence P in fig. 39)2O7 4-，H2PO4 -，HPO4 2-，PO4 3-，CO3 2-，HCO3 -，SO3 2-，SO4 2-，SCN-，F-，Cl-，Br-，I-，S2-，Ac-，NO3 -，NO2 -)。
Example 22 weighing 90mg dopamine hydrochloride dissolved in 10m L water, adding 10mg o-phenylenediamine and 500 u L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) and transferring the mixture to a reaction kettle (20ml) for reactionHeating in an oven at 200 ℃ for 8h to obtain a blue solution with the concentration of 10mg/M L, preparing 0.4mg/M L carbon dot solution by using Tris-HCl (20mM, pH 7) buffer solution for absorption spectrophotometer test, recording the absorption spectrum of the solution, adding nitrite ions with different concentrations into the solution, uniformly mixing the solution, recording the absorption spectrum of the solution, taking the ratio of the absorption intensity at 380nm to 610nm as a vertical coordinate, taking the final concentration of the nitrite in a reaction system as a horizontal coordinate, and obtaining a standard curve of the nitrite after fitting, wherein the lower limit of the detection of the nitrite ions by ultraviolet-visible absorption quantitative detection is 5 mu M, and the linear relation R is stored in the range of 0-25 mu M20.9669, as shown in fig. 40, namely the right drawing of the abstract drawing.
Example 23 weighing 90mg dopamine hydrochloride dissolved in 10M L water, adding 10mg o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) the mixture was transferred to a reaction kettle (20ml) and heated in an oven at 200 ℃ for 8h to obtain a blue solution with a concentration of 10mg/M L. a 0.4mg/M L carbon spot solution was prepared with Tris-HCl (20mM, pH 7) buffer solution and subjected to an absorption spectrophotometer test, 400 μ M different kinds of anions were added respectively for ion selectivity investigation, and the absorption spectra were recorded, as shown in fig. 41 (1 in the figure is a blank, and 2-18 are P in sequence)2O7 4-，H2PO4 -，HPO4 2-，PO4 3-，CO3 2-，HCO3 -，SO3 2-，SO4 2-，SCN-，F-，Cl-，Br-，I-，S2-，Ac-，NO3 -，NO2 -)。
Example 24 weighing 90mg of dopamine hydrochloride dissolved in 10m L water, adding 10mg of o-phenylenediamine and 500 μ L concentrated hydrochloric acid (molar ratio of dopamine hydrochloride to o-phenylenediamine is 5:1), transferring the mixture into a reaction kettle (20ml), heating in an oven at 200 ℃ for 8h to obtain a blue solution with a concentration of 10mg/m L, preparing 0.625mg/m L carbon-point solutions respectively with Tris-HCl (20mM, pH 7) buffer solutions, adding nitrite ions respectively in an amount such that the concentrations of nitrite ions in the final reaction system are 0, 10, 30, 40, 60, 80, 100, 130, 160, 200 μm, shaking and mixing uniformly, standing for half an hour, recording the color of the solution, and realizing quantitative detection of nitrite ions by naked eyes by photographing, as shown in fig. 42.
Example 25 weighing 90mg dopamine hydrochloride dissolved in 10M L water, adding 10mg o-phenylenediamine and 500 μ L concentrated hydrochloric acid (molar ratio of dopamine hydrochloride to o-phenylenediamine is 5:1), transferring the mixture to a reaction kettle (20M L), heating in an oven at 200 deg.C for 8h to obtain a blue solution with a concentration of 10mg/M L. preparing a 0.4mg/M L carbon dot solution using a Tris-HCl (20mM, pH 7) buffer solution containing 5% urine, performing a fluorescence spectroscopy test, recording emission spectra (Ex 580nm, Em 625nm), adding nitrite ions with different concentrations to the solution, incubating, detecting fluorescence intensity by a fluorescence spectrometer, plotting the signal-to-noise ratio as ordinate and the final concentration of nitrite ions as abscissa, and fitting to obtain a standard curve of nitrite ions20.9801, as in fig. 43.
Example 26 weighing 90mg dopamine hydrochloride dissolved in 10M L water, adding 10mg o-phenylenediamine and 500 μ L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1), transferring the mixture to a reaction kettle (20M L), heating in an oven at 200 deg.C for 8h to obtain a blue solution with a concentration of 10mg/M L. preparing a 0.4mg/M L carbon-point solution with a Tris-HCl (20mM, pH 7) buffer solution containing 5% urine, performing an absorption spectrophotometer test, recording the absorption spectrum, fitting a standard curve of nitrite after using the ratio of the absorption intensities at 380nm and 610nm as ordinate, using the final concentration of nitrite in the reaction system as abscissa, quantitatively detecting the nitrite ion with a lower limit of 2.4 μ M in UV-visible absorption quantitative detection, storing an online relationship in the range of 0-10 μ M, and storing R in the range of 0-10 μ M20.9747, as in fig. 44.
Example 27 weighing 90mg dopamine hydrochloride dissolved in 10ml water, adding 10mg o-phenylenediamine and 500. mu. L concentrated hydrochloric acid (dopamine hydrochloride to o-phenylenediamine molar ratio 5:1) and mixingTransferring into a reaction kettle (20ml), heating in an oven at 200 deg.C for 8 hr to obtain blue solution with concentration of 10mg/m L, detecting sample toxicity, adding into 1m L culture medium (containing 5 × 10. mu.g/m L) at culture medium to stock solution volume ratio of 5000:1, 2000:1, 1000:1, 500:1, and 100:1 (concentration of 2, 5, 10, 50, and 100. mu.g/m L in sequence)3Hela cells) it was confirmed by MTT analysis that the cell activity was still 90% when the amount of the polymer carbon dots added was 50 μ g/m L, indicating that the entry of the polymer carbon dots into the interior of the cells did not significantly decrease the cell activity, as shown in fig. 45.
Example 28: PBS buffer (10mM Mg) was added to the culture dish for culturing adherent cells (Hela)2+，50mM K+pH 7.4)1m L, adding 40 μ L (10mg/m L) of the polymer carbon quantum dot solution obtained in example 6 into a culture dish, incubating for 2 hours, washing twice with a newly prepared PBS buffer solution, and imaging under a fluorescence confocal microscope to obtain a fluorescence imaging picture (excitation wavelength is 594nm, emission fluorescence collection range is 609 and 760nm) of the polymer carbon dots in Hela cells, as shown in fig. 46.
The invention is not limited to the specific technical solutions described in the above embodiments, and all technical solutions formed by equivalent substitutions are within the scope of the invention as claimed.

Claims (4)

1. A method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry is characterized by comprising the following steps of weighing 5-150 mg of dopamine hydrochloride and 10mg of o-phenylenediamine at room temperature, adding 10m L ultrapure water, preparing a mixed solution in a beaker, adding concentrated hydrochloric acid to adjust the pH of the solution, transferring the obtained solution to a reaction kettle, heating the obtained solution in an oven at 180 ℃ for 8 hours to obtain a blue polymer carbon dot solution, testing the formed polymer carbon dots by using an ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer, adding the polymer carbon dot solution into a Tris-HCl buffer solution with the concentration of 20mM and the pH of 7, enabling the polymer carbon dots in the Tris-HCl buffer solution to generate absorption spectra and fluorescence spectrum changes, enabling the absorption peaks of the absorption spectra at 610nm to be obviously reduced and the absorption peaks at 380nm to be gradually enhanced along with the increase of the concentration of the nitrite ions, enabling the fluorescence spectra in the buffer solution to generate absorption spectra and fluorescence spectrum changes along with the increase of the concentration of the nitrite ions to gradually reduce the intensity of the colorimetric ions, and realizing high fluorescence emission sensitivity of the nitrite ions to 625 nm.
2. The method for detecting nitrite ions based on polymer carbon dot fluorescence colorimetry according to claim 1, wherein the solution containing nitrite ions is human urine, and the concentration of the polymer carbon dots in a Tris-HCl buffer solution is 0.4mg/m L.
3. The method for colorimetric detection of nitrite ion based on polymer carbon dot fluorescence according to claim 2, wherein the amount of Tris-HCl buffer solution is 380 μ L and the amount of human urine is 20-100 μ L.
4. An imaging detection method of nitrite ions in living cells is characterized by comprising the following steps of weighing 5-150 Mg of dopamine hydrochloride and 10Mg of o-phenylenediamine at room temperature, adding 10m L ultrapure water, preparing a mixed solution in a beaker, adding concentrated hydrochloric acid to adjust the pH value of the solution, transferring the obtained solution to a reaction kettle, heating the solution in an oven at 180 ℃ for 8 hours at 150 ℃ to obtain a blue polymer carbon dot solution, adding 1m L PBS buffer solution into a culture dish for culturing adherent Hela cells, wherein the pH value of the PBS buffer solution is 7.4 and contains 10mM Mg2+、50mM K+Adding 40 mu L10 mg/m L blue polymer carbon dot solution into a culture dish, incubating for 2 hours, washing twice by using the newly prepared PBS buffer solution, and placing under a fluorescence confocal microscope for imaging to obtain a fluorescence imaging picture of the polymer carbon dot in Hela cells, thereby realizing the imaging detection of nitrite ions in living cells.
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