CN114014301B - Synthetic method of fluorescent carbon nano onion - Google Patents

Synthetic method of fluorescent carbon nano onion Download PDF

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CN114014301B
CN114014301B CN202111363645.8A CN202111363645A CN114014301B CN 114014301 B CN114014301 B CN 114014301B CN 202111363645 A CN202111363645 A CN 202111363645A CN 114014301 B CN114014301 B CN 114014301B
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秦卫东
孟昭
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Beijing Normal University
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    • C09K11/65Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon

Abstract

The invention provides a synthesis method of fluorescent carbon nano-onions, belonging to the technical field of carbon nano-materials. The method comprises the following steps: (1) preparing carbon nano onion by a pyrolysis method; (2) Processing the carbon nano onion for 0.5 to 3 hours at the temperature of between 600 and 1000 ℃ under the protection of nitrogen gas of between 50 and 500mL/min; (3) passivating for 1-3 h by using 8-14.5 mol/L nitric acid at the temperature of 120-200 ℃; (4) Dialyzing for 16-32 h by using a dialysis membrane with the molecular weight cutoff of 3-10 kD, and drying. The fluorescence quantum efficiency of the carbon nano onion synthesized by the method is 10.6 times of that of the prior art, and the carbon nano onion has higher detection sensitivity when used as a probe and lower biological toxicity when used for biological imaging.

Description

Synthetic method of fluorescent carbon nano onion
Technical Field
The invention belongs to the technical field of carbon nano materials, and particularly relates to a preparation method of fluorescent carbon nano onions.
Background
Carbon nano-onions (CNOs) are a special form of carbon nanotubes, which are sleeve-spherical in structure, resembling carbon nanotubes with an aspect ratio of about 1: 1. The structure of the carbon nano onion is discovered for the first time by Iijima as early as 1980; in 1992, ugarte converted polyhedral graphite in carbon soot produced by arc discharge into carbon nano-onions under HRTEM electron beam irradiation. Then, xu and Tanaka also use HRTEM low-energy electron beam irradiation to convert the amorphous carbon film into onion-shaped nanometer material under the catalytic action of metal nanometer particles Al, pt and Au. The carbon nano onion has a plurality of special and excellent physical and chemical properties due to the special bent and closed graphite layer structure, and is widely applied to the fields of electronics, energy storage, friction, catalysis, biosensing and the like.
Methods for synthesizing CNO include arc discharge, plasma, electron beam irradiation, heat treatment, pyrolysis, chemical Vapor Deposition (CVD), and the like. CNO is passivated to have carboxyl, amino and other groups on the surface, so that the CNO has the fluorescent characteristic and is used for biological imaging (Small 2011,7, no.22, 3170-3177). In recent years, kim topic group reported a simple synthesis method of Fluorescent Carbon Nano Onion (FCNO) (ACS curable chem. Eng.2017,5, 3982-3992), which uses linseed oil as a carbon source of FCNO, and prepares fluorescent carbon nano onion by burning linseed oil, collecting soot, and passivating with nitric acid. However, the FCNO prepared by the prior art has low fluorescence quantum efficiency, and thus, when the FCNO is used as a probe, the detection sensitivity is low; when the FCNO is used for biological imaging research, the ideal result can be obtained by using FCNO with higher concentration, and the cytotoxicity of FCNO seriously restricts the application (ACS appl. Nano mater.2018,1, 662-674). Therefore, the synthesis of FCNO with high fluorescence quantum efficiency is an urgent technical problem to be solved.
Disclosure of Invention
The invention aims to provide a method for synthesizing FCNO with high fluorescence quantum efficiency. The inventor finds that the fluorescence emission intensity of the CNO can be obviously improved by passivating the CNO prepared by the pyrolysis method with nitric acid after the CNO is treated at high temperature under the protection of nitrogen. In view of the above, the present invention provides a method for preparing a fluorescent carbon nano onion, which is characterized by comprising the following steps:
(1) Preparing carbon nano onion by a pyrolysis method;
(2) Treating carbon nano onion at high temperature under the protection of nitrogen;
(3) Treating the product obtained in the step (2) with nitric acid;
(4) And (4) dialyzing the product obtained in the step (3), removing nitric acid, and drying to obtain the fluorescent nano onion.
And (3) treating the soot in the step (2) in an atmosphere furnace, wherein the purity of nitrogen is more than or equal to 99.5%, the flow rate is 50-500 mL/min, and the preferred flow rate is 100-300 mL/min.
The treatment temperature in the step (2) is 600-1000 ℃, and the treatment time is 0.5-3 h.
The concentration of the nitric acid in the step (3) is 8-14.5 mol/L, the treatment temperature is 120-200 ℃, and the treatment time is 1-3 h.
The cut-off molecular weight of the dialysis membrane in the step (4) is 3-10 kD, the dialysate is deionized water and is replaced once every 2 hours, and the dialysis time is 16-32 hours.
The FCNO provided by the application not only keeps the composition and the appearance of the original carbon nano onion, but also greatly improves the fluorescence efficiency, and the fluorescence emission intensity is improved by 10.6 times compared with the prior art. The FCNO can be applied to detection to obviously improve the sensitivity, and the application of the FCNO to biological imaging can greatly reduce the dosage and further reduce the biological toxicity.
Drawings
Fig. 1 is a TEM image of FCNO synthesized in example 1.
FIG. 2 shows the resultant FCNO fluorescence emission spectra (excitation wavelength 350 nm) of example 1 (line A) and example 2 (line B).
Fig. 3 is a TEM image of FCNO synthesized in example 2.
Detailed Description
The patent provides a preparation method of a fluorescent carbon nano onion, which comprises the following steps:
(1) Preparing carbon nano onion by a pyrolysis method;
(2) Processing the carbon nano onion in a high-temperature furnace filled with nitrogen; the purity of the used nitrogen is more than or equal to 99.5 percent, the flow rate is 50-500 mL/min, and the preferred flow rate is 100-300 mL/min; the temperature of the high-temperature furnace is 600-1000 ℃, and the processing time is 0.5-3 h;
(3) Passivating the carbon nano onion treated at high temperature by using nitric acid; the concentration of the nitric acid is 8-14.5 mol/L, the treatment temperature is 120-200 ℃, and the treatment time is 1-3 h;
(4) Dialyzing the passivated carbon nano onion with deionized water, wherein the cut-off molecular weight of a dialysis membrane is 3-10 kD, and the deionized water is replaced every 2 hours for 16-32 hours; and removing nitric acid and drying to obtain the fluorescent nano onion.
For further understanding of the present invention, the following examples are provided to illustrate the preparation method of the fluorescent carbon nano-onion provided by the present invention, and the scope of the present invention is not limited by the following examples.
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
Fluorescent nano onions were synthesized using literature reported methods (ACS sustamable chem. Eng.2017,5, 3982-3992), the morphology and fluorescence properties of the products were studied and compared as comparative examples with the products of this scheme.
1.1 Preparation of FCNO
1.1.1 preparation of Nano onion Ash
Pouring about 200mL of linseed oil into an alcohol burner, after the linseed oil is ignited, putting a 200mL glass beaker upside down above the alcohol burner, enabling the outer boundary of flame outer flame to be about 10cm away from the bottom of the beaker, and collecting soot in the combustion process. After firing the sinter the collected soot was carefully scraped off with a stainless steel spatula.
1.1.2 passivation
0.1g of soot is weighed, added into a polytetrafluoroethylene digestion tank with a volume of 50mL, added with 30mL of nitric acid with a concentration of 14.5M, stirred uniformly by a glass rod, sealed and treated at 170 ℃ for 1.5h.
1.1.3 purification
After cooling to normal temperature, large particles were first filtered out with qualitative filter paper (Xinxing brand, hangzhou specialty paper industries, ltd.), the filtrate was put into a dialysis bag (Millipore, 3 kD) for dialysis, deionized water was changed every 2 hours, after dialysis for 24 hours, FCNO solution was transferred into a beaker, which was first put in an oil bath at 100 ℃ to completely evaporate water, and then the beaker was placed in an oven at 120 ℃ to be dried for 6 hours.
1.2 TEM characterization of FCNO
FCNO prepared in 1.1 was characterized by TEM (Talos F200S, hillsboro, OR, USA) with an acceleration voltage of 200kV. As can be seen from FIG. 1, the synthesized product is onion-shaped with a diameter of 5-15 nm. The interlayer spacing is about 0.36nm, and the carbon nano material meets the characteristics of the carbon nano material with the onion structure (ACS appl. Nano mater.2018,1, 662-674).
1.3 Fluorescence characterization of FCNO
0.23g of FCNO was weighed and dissolved in 10mL of 10mM phosphoric acid buffer solution, dispersed uniformly by ultrasound for 10 minutes, and placed in a 1cm fluorescence cell, and subjected to fluorescence analysis using an FLS980 fluorescence spectrometer (Edinburgh Instruments Ltd., livingston, UK) with both incident and exit slit widths of 5nm during measurement. FIG. 2A shows that FCNO has a fluorescence emission peak at 520nm with an intensity of 4.8X 10 at an excitation wavelength of 350nm 4
Example 2
FCNO was synthesized and characterized using the method of the invention.
2.1 Preparation of FCNO
2.1.1 preparation of nanometer onion soot
The same as 1.1.1 in example 1.
2.1.2 high temperature treatment
The CNO soot is carefully poured into a quartz boat, the quartz boat is placed in a tubular heating furnace, 99.995 percent high-purity nitrogen is introduced into the furnace at the flow rate of 200mL/min, the temperature is raised after 10min, and the temperature is kept for 1.5h after reaching 800 ℃. And taking out the CNO after cooling to the normal temperature.
2.1.3 passivation
This procedure is the same as procedure 1.1.2 in example 1.
2.1.4 purification
Same as step 1.1.3 in example 1.
2.2 TEM characterization of FCNO
The experimental conditions were the same as in step 1.2 of example 1.
As can be seen from FIG. 3, the shapes and sizes of the nano onions are not significantly changed after high-temperature treatment during the synthesis process.
2.3 Fluorescence characterization of FCNO
The experimental conditions were the same as in step 1.3 of example 1.
FIG. 2B shows that FCNO has a fluorescence emission peak at 520nm with an intensity of 5.1X 10 when the excitation wavelength is 350nm 5 The fluorescence intensity was increased by 10.6 times compared to the comparative example.
Example 3
This example explores the effect of nitrogen flow rate during heat treatment.
The preparation process parameters of the nano onion ash are the same as 2.1.1.
0.1g CNO soot is weighed, carefully poured into a quartz boat, pushed into a tube-type heating furnace, and introduced with 99.995% high-purity nitrogen gas at flow rates of 10, 50, 100, 200, 300, 400, 500, 600 and 700mL/min, respectively. Except that the flow rate needs to be stabilized for 30min when the flow rate is 10mL/min, the temperature is raised after the system is stabilized for 10min at the other flow rates, and the temperature is kept for 1.5h after the temperature is raised to 800 ℃. And taking out the CNO after cooling to the normal temperature.
After passivation and purification of the product using the steps 2.1.3 and 2.1.4, respectively, fluorescence characterization studies were performed using the conditions 2.3 (excitation wavelength 350nm, scanning emission spectrum, and recording emission intensity at 520 nm), the results are shown in table 1.
TABLE 1 influence of Nitrogen flow Rate on FCNO fluorescence emission intensity during Heat treatment
Figure BDA0003360159220000041
Table 1 shows that the nitrogen flow rate is in the range of 50-500 mL/min, and the fluorescence emission intensity of FCNO is stabilized at 4.6-5.7X 10 5 Taking the process time and the material cost into consideration, the flow rate is 50-500 mL/min; table 1 also shows that, when the flow rate is 100-300 mL/min, not only high-purity nitrogen can be saved, but also the light emission intensity of FCNO is high.
Example 4
The effect of the temperature and the time of the heat treatment on the fluorescence emission intensity of the nano onion is realized in the embodiment. The heating temperature and time were varied during the experiment, and the nitrogen flow rate was maintained at 200mL/min, and the rest of the experimental conditions were the same as in example 3.
TABLE 2 Effect of Heat treatment temperature and time on FCNO fluorescence emission intensity
Temperature (. Degree.C.) 500 600 700 800 900 1000 1100
Time (h) 3 3 2 2 1 0.5 0.5
Fluorescence emission intensity (. Times.10) 5 ) 3.9 4.5 5.3 5.1 5.7 4.3 2.0
As can be seen from Table 2, the fluorescence emission intensity of FCNO is greater than 4.0X 10 in the time range of 0.5-3 h and the temperature is 600-1000 deg.C 5 And the requirement of sensitive detection is met.
Example 5
This example examines the effect of nitric acid concentration, passivation temperature and passivation time on the fluorescence emission intensity of the product during the FCNO passivation process. In the heat treatment process, the nitrogen flow rate is 200mL/min, and the temperature is kept at 800 ℃ for 2h. The remaining process conditions were the same as in example 3.
TABLE 3 influence of nitric acid concentration, passivation temperature and time
Nitric acid concentration (mol/L) Temperature (. Degree. C.) Time (h) Fluorescence emission intensity (. Times.10) 5 )
6 120 1 1.7
6 170 1.5 1.5
6 200 3 3.1
8 120 1 2.7
8 170 1.5 3.8
8 200 3 4.4
10 120 1 3.2
10 170 1.5 3.1
10 200 3 4.7
12 120 1 3.8
12 170 1.5 4.9
12 200 3 4.6
14.5 120 1 5.1
14.5 170 1.5 4.9
14.5 200 3 2.0
The passivation process of the invention is that oxidation reaction is carried out between strong acid and carbon atoms on the surface of the nano onion at high temperature, carboxyl is generated on the surface, and the electronic valence state of the surface of the nano structure is changed by introducing heteroatom, thereby enhancing the fluorescence emission. The experimental results in Table 3 show that the concentration of nitric acid affects the passivation, and when the concentration is 6mol/L, satisfactory results cannot be obtained by increasing the passivation time and the passivation temperature, which is shown in that the fluorescence emission intensity of the final product is between that of the final product1.5~3.1×10 5 Less than 4X 10 5 And (6) counting. While concentrated nitric acid (concentration of 14.5 mol/L) has strong passivation effect, but destroys the structure of carbon nano onion, and when the carbon nano onion is treated in the concentrated nitric acid at 200 ℃ for 3h, the fluorescence emission intensity is reduced to 2.0 multiplied by 10 5 Counting shows that the strong oxidation reaction breaks the outer layer structure of the carbon nano onion, thereby affecting the fluorescence performance of the whole material. The passivation time can strengthen the passivation effect on the whole, although the change trend of the fluorescence intensity is not obvious after 1 hour and 1.5 hours of passivation, when nitric acid (6-12 mol/L) with lower concentration is used, the FCNO fluorescence emission intensity after 3 hours of passivation is obviously stronger than the effect after 1 hour of passivation.
Example 6
This example investigates the effect of dialysis membrane molecular weight cut-off and dialysis time on the intensity of fluorescence emission from the product. Molecular weight cut-off (M) of dialysis membranes T ) 3, 7, 10kD, respectively, dialysis time (T) D ) 4, 8, 16, 24 and 32h respectively. In the heat treatment process, the nitrogen flow rate is 200mL/min, and the temperature is kept at 800 ℃ for 2h. The other process conditions were the same as in example 3.
Table 4 shows that dialysis purification is an important step due to high concentration of nitric acid for inactivating FCNO, 3, 7 and 10kD dialysis bags are adopted, the dialysis time is 16-32 hours, the obtained product can generate a sensitive fluorescent signal when dissolved in a buffer solution, and the fluorescence emission intensity is 4.9-5.7 x 10 5 And (6) counting.
TABLE 4 molecular weight cut-off of dialysis membrane vs. dialysis time vs. FCNO fluorescence intensity (. Times.10) 5 ) Influence of (2)
Figure BDA0003360159220000061
The above examples show that the FCNO prepared by the method of the present invention has higher fluorescence quantum efficiency than the products prepared by the prior art, and can provide higher sensitivity for fluorescence detection, while the dosage of FCNO is greatly reduced when used for in vivo imaging, thereby effectively reducing the biological toxicity of the material.
The above embodiments are only intended to help the understanding of the method of the present invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.

Claims (5)

1. A synthetic method of a fluorescent carbon nano onion is characterized by comprising the following steps:
(1) Preparing carbon nano onion by a pyrolysis method;
(2) Carrying out heat treatment on the carbon nano-onions under the protection of nitrogen with the purity of more than or equal to 99.5%, wherein the treatment temperature is 600-1000 ℃, and the treatment time is 0.5-3 h;
(3) Treating the product obtained in the step (2) by using nitric acid with the concentration of 10-12 mol/L, wherein the treatment temperature is 120-200 ℃, and the treatment time is 1-3 h;
(4) And (3) dialyzing the product obtained in the step (3) by using a dialysis membrane with the molecular weight cutoff of 3-10 kD, wherein the dialysate is deionized water and is replaced every 2 hours for 16-32 hours, and removing nitric acid and drying to obtain the fluorescent nano onion.
2. The method for synthesizing fluorescent carbon nano-onions according to claim 1, wherein the carbon nano-onions in step (2) are heat-treated in an atmosphere furnace.
3. The method for synthesizing fluorescent carbon nano-sized onions according to claim 1, wherein the flow rate of nitrogen in step (2) is 50-500 mL/min.
4. The method for synthesizing fluorescent carbon nano-onions according to claim 3, wherein the flow rate of nitrogen is 100 to 300mL/min.
5. The fluorescent carbon nano-onions prepared according to any one of claims 1 to 4.
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