CN112625676B - Ratio type fluorescent carbon dot, preparation method thereof and method for detecting dopamine - Google Patents

Ratio type fluorescent carbon dot, preparation method thereof and method for detecting dopamine Download PDF

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CN112625676B
CN112625676B CN202011277807.1A CN202011277807A CN112625676B CN 112625676 B CN112625676 B CN 112625676B CN 202011277807 A CN202011277807 A CN 202011277807A CN 112625676 B CN112625676 B CN 112625676B
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fluorescent carbon
carbon dot
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dopamine
ratio
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CN112625676A (en
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任丽丽
陈许
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Southeast University
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Abstract

The invention discloses a ratio type fluorescent carbon dot, a preparation method thereof and a method for detecting dopamine, wherein the fluorescent carbon dot comprises the following raw materials in parts by mole: 0.1-1 part of p-phenylenediamine and 1 part of triethylamine. The preparation method of the fluorescent carbon dots comprises the following steps: dissolving p-phenylenediamine and triethylamine in a solvent and then carrying out hydrothermal reaction; and filtering and dialyzing the solution obtained after the reaction to obtain the ratio type fluorescent carbon dots. The method for detecting dopamine by using the fluorescent carbon dots comprises the steps of adding dopamine into the ratio type fluorescent carbon dot solution, exciting by using exciting light, and measuring the spectrum of the emission wavelength of the carbon dot solution. The ratio-type fluorescent carbon dots are prepared by taking p-phenylenediamine and triethylamine as raw materials, and can simultaneously emit double-emission fluorescent carbon dots with different fluorescent colors; the fluorescent sensor as a ratio can effectively eliminate the interference of background signals; the synthetic method is simple, and the raw materials are economical and easily available; the method is simple to operate when detecting dopamine and has intuitive color change.

Description

Ratio type fluorescent carbon dot, preparation method thereof and method for detecting dopamine
Technical Field
The invention relates to a preparation method and application of carbon dots, in particular to a preparation method of ratio-type fluorescent carbon dots and application of ratio-type fluorescent carbon dots in dopamine detection.
Background
Dopamine (DA) is an important catecholamine neurotransmitter in humans and animals, is located mainly in the central nervous system, and plays an important role in the control of central nervous system-related diseases such as parkinson's disease, schizophrenia and depression. Accurate and sensitive detection of dopamine can play an important role in clinical diagnosis of neurological diseases. However, problems such as sample pre-treatment and complex instrumentation greatly affect the process of detecting dopamine.
As a novel nano carbon material, the carbon dot has the characteristics of excellent photoluminescence performance, abundant precursor sources, easy surface functionalization, good biocompatibility, water solubility and the like. In recent years, the proportional fluorescent probe based on carbon dots has a wide prospect in chemical monitoring and identification by virtue of the advantages of high sensitivity, low cost, simple operation and the like. However, conventional ratiometric fluorescent probes based on carbon dots generally require the bonding of different nanomaterials by chemical or physical methods and the manufacturing process is more cumbersome.
Disclosure of Invention
The purpose of the invention is as follows: it is a first object of the present invention to provide a ratiometric fluorescent carbon dot having a dual emission fluorescent carbon dot;
the second purpose of the invention is to provide a preparation method of the ratio type fluorescent carbon dots, which has simple synthesis method and easily obtained and economic raw materials and can obtain the double-emission fluorescent carbon dots;
the third purpose of the invention is to provide a method for detecting dopamine by using ratio type fluorescent carbon dots.
The technical scheme is as follows: the ratio type fluorescent carbon dots comprise the following raw materials in parts by mole: 0.1-1 part of p-phenylenediamine and 1 part of triethylamine.
The preparation method of the ratio type fluorescent carbon dot comprises the following steps:
(1) dissolving p-phenylenediamine and triethylamine in a solvent and then carrying out hydrothermal reaction;
(2) and filtering and dialyzing the solution obtained after the reaction to obtain the ratio type fluorescent carbon dots.
Preferably, in step (1), the solvent is an alcohol solution. More preferably an ethanol solution.
Preferably, in the step (1), the molar ratio of the p-phenylenediamine to the triethylamine is 0.1-1: 1.
Preferably, in the step (1), the temperature of the hydrothermal reaction is 100-250 ℃; the reaction time is 6-24 h.
The method for detecting dopamine by using the ratiometric fluorescent carbon dots comprises the steps of adding dopamine into a ratiometric fluorescent carbon dot solution, exciting by using exciting light, and measuring the spectrum of the emission wavelength of the carbon dot solution.
Preferably, the carbon dot solution has a measured spectrum of emission wavelengths between 300-600 nm.
The surface of the fluorescent carbon dot obtained by taking p-phenylenediamine and triethylamine as raw materials and adopting a hydrothermal one-step method contains rich nitrogen-doped functional groups, mainly comprises pyridine nitrogen, amino and pyrrole nitrogen, and the functional groups and dopamine generate electron transfer, so that the fluorescence quenching effect of the carbon dot is induced, and the specific mechanism is shown in figure 5.
Has the advantages that: compared with the prior art, the invention has the following remarkable effects: 1. the ratio-type fluorescent carbon dots are prepared by taking p-phenylenediamine and triethylamine as raw materials, and when the ratio-type fluorescent carbon dots are excited by a single wavelength, the ratio-type fluorescent carbon dots can simultaneously emit double-emission fluorescent carbon dots with different fluorescent colors; the carbon dots are used as a ratio fluorescence sensor, so that the interference of background signals can be effectively eliminated; 2. the synthetic method is simple, and the raw materials are economical and easily available; 3. when the carbon dot is excited by an excitation wavelength of 360nm, the carbon dot has fluorescence emission at 435nm and 595nm, and when dopamine exists, the fluorescence of the carbon dot can be remarkably quenched, so that the dopamine can be accurately detected. 4. Compared with the existing dopamine detection method, the method is simple to operate, has more intuitive color change, and can be used for the quantitative detection of dopamine.
Drawings
FIGS. 1(a) and 1(b) are a transmission electron micrograph and a particle size distribution of a ratiometric fluorescent carbon dot according to example 1 of the present invention, respectively;
FIG. 2 is an infrared spectrum of a ratiometric fluorescent carbon dot of example 1 of the present invention;
FIGS. 3(a) and 3(b) are respectively an ultraviolet absorption spectrum and a fluorescence excitation emission spectrum of a ratiometric fluorescent carbon dot according to example 1 of the present invention;
FIGS. 4(a) and 4(b) are a fluorescence spectrum and a linear relationship between fluorescence intensity and dopamine concentration of the ratio-type fluorescent carbon dot-detected dopamine in example 1 of the present invention, respectively;
FIG. 5 is a schematic diagram of the mechanism of detecting dopamine by using a ratiometric fluorescent carbon dot in example 1 of the present invention;
FIG. 6 is a diagram illustrating the selectivity of the ratiometric fluorescent carbon dot of example 1 of the present invention to common substances.
Detailed Description
The invention is described in further detail below with reference to the drawings.
Example 1
Step 1, 0.03g of p-phenylenediamine and 100. mu.L of triethylamine are dissolved in 10mL of ethanol at room temperature, and the solution is fully stirred to obtain a transparent solution.
Step 2, the solution was transferred to a 20mL hydrothermal reaction kettle.
And 3, placing the reaction kettle in an oven, and reacting for 8 hours at 180 ℃ to obtain a crude product.
And 4, naturally cooling the crude product, centrifuging the crude product solution at 5000rpm for 10min, and removing insoluble substances to obtain a light brown transparent solution.
And 5, dialyzing the solution in distilled water for 24 hours by using a dialysis bag of 500Da, and changing the water every 4 hours to obtain the blue fluorescent ratio type fluorescent carbon dot.
The carbon dots prepared in example 1 are characterized by TEM, infrared spectrum, ultraviolet absorption spectrum and fluorescence spectrum as shown in fig. 1(a) -4(b), wherein fig. 1(a) is a transmission electron microscope image of the ratiometric fluorescent carbon dots of the present example, and fig. 1(b) is a particle size distribution diagram, and it can be seen that the particle sizes of the carbon dots prepared in the present invention are all less than 10nm, and the surface of the carbon dots contains functional groups such as amino groups and hydroxyl groups.
FIGS. 3(a) and 3(b) are UV absorption spectrum and fluorescence excitation emission spectrum of the carbon dots prepared in example 1; from the above spectra, it can be seen that when 360nm is selected as the excitation wavelength, the difference between the fluorescence intensities of the two emission peaks is large. Therefore, in order to ensure the sensitivity of the proportional fluorescence method, 360nm is selected as the optimal excitation wavelength during the later detection.
FIG. 4(a) is a fluorescence spectrum of dopamine detected at carbon spots prepared in example 1; from FIG. 4(b), it can be seen that the ratio of the fluorescence intensities of the solutions is I595nm/I435 nmThe ratio is shown to be gradually increased along with the increase of the concentration of the dopamine, the ratio of two-peak fluorescence intensity is in a better linear relation with the dopamine in the range of 50-80 mu M, and therefore the carbon dot can sensitively detect the dopamine through a dual-signal sensing model.
FIG. 5 is a schematic diagram of the mechanism of detecting dopamine by using a ratio-type fluorescent carbon dot according to the present invention; as can be seen, the surface of the fluorescent carbon dot contains abundant nitrogen-doped functional groups, and the functional groups and dopamine undergo electron transfer, so that the fluorescence quenching effect of the carbon dot is induced.
FIG. 6 shows the selectivity of carbon sites to common substances prepared in example 1; the results indicate that the prepared carbon dots have a higher specific response to dopamine than other competitive substances.
Example 2
Step 1, 0.03g of p-phenylenediamine and 100. mu.L of triethylamine are dissolved in 10mL of ethanol at room temperature, and the solution is fully stirred to obtain a transparent solution.
Step 2, the solution was transferred to a 20mL hydrothermal reaction kettle.
And 3, placing the reaction kettle in an oven, and reacting for 6 hours at 250 ℃ to obtain a crude product.
And 4, naturally cooling the crude product, centrifuging the crude product solution at 5000rpm for 10min, and removing insoluble substances to obtain a light brown transparent solution.
And 5, dialyzing the solution in distilled water for 24 hours by using a dialysis bag of 500Da, and changing the water every 4 hours to obtain the blue fluorescent ratio type fluorescent carbon dot.
Example 3
Step 1, 0.03g of p-phenylenediamine and 100. mu.L of triethylamine are dissolved in 10mL of ethanol at room temperature, and the solution is fully stirred to obtain a transparent solution.
Step 2, the solution was transferred to a 20mL hydrothermal reaction kettle.
And 3, placing the reaction kettle in an oven, and reacting for 24 hours at 100 ℃ to obtain a crude product.
And 4, naturally cooling the crude product, centrifuging the crude product solution at 5000rpm for 10min, and removing insoluble substances to obtain a light brown transparent solution.
And 5, dialyzing the solution in distilled water for 24 hours by using a dialysis bag of 500Da, and changing the water every 4 hours to obtain the blue fluorescent ratio type fluorescent carbon dot.
Example 4
Step 1, 0.03g of p-phenylenediamine and 40. mu.L of triethylamine are dissolved in 10mL of ethanol at room temperature, and the solution is fully stirred to obtain a transparent solution.
Step 2, the solution was transferred to a 20mL hydrothermal reaction kettle.
And 3, placing the reaction kettle in an oven, and reacting for 8 hours at 180 ℃ to obtain a crude product.
And 4, naturally cooling the crude product, centrifuging the crude product solution at 5000rpm for 10min, and removing insoluble substances to obtain a light brown transparent solution.
And 5, dialyzing the solution in distilled water for 24 hours by using a dialysis bag of 500Da, and changing the water every 4 hours to obtain the blue fluorescent ratio type fluorescent carbon dot.
Example 5
Step 1, 0.015g of p-phenylenediamine and 200. mu.L of triethylamine are dissolved in 10mL of ethanol at room temperature, and the solution is fully stirred to obtain a transparent solution.
Step 2, the solution was transferred to a 20mL hydrothermal reaction kettle.
And 3, placing the reaction kettle in an oven, and reacting for 8 hours at 180 ℃ to obtain a crude product.
And 4, naturally cooling the crude product, centrifuging the crude product solution at 5000rpm for 10min, and removing insoluble substances to obtain a light brown transparent solution.
And 5, dialyzing the solution in distilled water for 24 hours by using a dialysis bag of 500Da, and changing the water every 4 hours to obtain the blue fluorescent ratio type fluorescent carbon dot.
Example 6
Step 1, 0.04g of p-phenylenediamine and 140. mu.L of triethylamine are dissolved in 10mL of ethanol at room temperature, and the solution is fully stirred to obtain a transparent solution.
Step 2, the solution was transferred to a 20mL hydrothermal reaction kettle.
And 3, placing the reaction kettle in an oven, and reacting for 6 hours at 160 ℃ to obtain a crude product.
And 4, naturally cooling the crude product, centrifuging the crude product solution at 5000rpm for 10min, and removing insoluble substances to obtain a light brown transparent solution.
And 5, dialyzing the solution in distilled water for 24 hours by using a dialysis bag of 500Da, and changing the water every 4 hours to obtain the blue fluorescent ratio type fluorescent carbon dot.
Fig. 5 is a diagram of dopamine detection using ratiometric fluorescent carbon spots. 2mL of the carbon dot solution prepared in example 1 was added to a fluorescence cuvette, and 0 to 80. mu.M of dopamine solutions with different concentrations were added by pipette, respectively, and after reaction for 20min, the fluorescence intensity of the solution was measured at an excitation wavelength of 360 nm. The experimental results show that: as shown in fig. 4(a) and 4(b), the fluorescence intensity of the carbon dots at 435nm and 595nm gradually decreased with the increase of the dopamine concentration.
Adding 2mL of carbon dot solution into a fluorescence cuvette, respectively adding 10 common substances with the concentration of 100 mu M by using a pipette, reacting for 20min, and measuring the fluorescence intensity of the solution at the excitation wavelength of 360 nm. As shown in fig. 6, the experimental results show that: the carbon dot has good selectivity to dopamine, and the dopamine can cause fluorescence quenching of a carbon dot solution. And to a certain extent, dopamine can be visually detected.

Claims (6)

1. The ratio type fluorescent carbon dot is characterized by comprising the following raw materials in parts by mole: 0.1-1 part of p-phenylenediamine and 1 part of triethylamine;
the preparation method of the ratio type fluorescent carbon dot comprises the following steps:
(1) dissolving p-phenylenediamine and triethylamine in a solvent and then carrying out hydrothermal reaction;
(2) and filtering and dialyzing the solution obtained after the reaction to obtain the ratio type fluorescent carbon dots.
2. A ratiometric fluorescent carbon dot of claim 1, wherein in step (1), the solvent is an alcohol solution.
3. A ratiometric fluorescent carbon dot of claim 1, wherein in step (1), the molar ratio of p-phenylenediamine to triethylamine is in the range of 0.1 to 1: 1.
4. The ratiometric fluorescent carbon dot of claim 1, wherein in step (1), the hydrothermal reaction is carried out at a temperature of 100 to 250 ℃; the reaction time is 6-24 h.
5. A method for detecting dopamine by using a ratiometric fluorescent carbon dot according to claim 1, wherein dopamine is added to the ratiometric fluorescent carbon dot solution, and excitation is performed with excitation light to measure the spectrum of the emission wavelength of the carbon dot solution.
6. The method for detecting dopamine by using the ratio-type fluorescent carbon dot as claimed in claim 5, wherein the spectrum of the emission wavelength of the carbon dot solution between 300-600nm is determined.
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CN113607702B (en) * 2021-07-21 2022-09-23 南京工业大学 Method for detecting activities of alkaline phosphatase and cardiac troponin based on manganese ion-induced ratio-type fluorescence reaction and application
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CN106970061A (en) * 2017-05-10 2017-07-21 青岛大学 The preparation method of carbon point/copper nano-cluster compound ratio fluorescent dopamine probe
CN107573931A (en) * 2017-10-17 2018-01-12 南京理工大学 A kind of preparation method of zinc doping carbon quantum dot

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106970061A (en) * 2017-05-10 2017-07-21 青岛大学 The preparation method of carbon point/copper nano-cluster compound ratio fluorescent dopamine probe
CN107573931A (en) * 2017-10-17 2018-01-12 南京理工大学 A kind of preparation method of zinc doping carbon quantum dot

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