CN109385276B - High-performance red-light carbon quantum dot material, preparation method and biological imaging application thereof - Google Patents
High-performance red-light carbon quantum dot material, preparation method and biological imaging application thereof Download PDFInfo
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Abstract
The invention discloses a high-performance red-light carbon quantum dot material, a preparation method and a biological imaging application thereof, wherein the carbon quantum dot is a product obtained by taking 4, 4' -triamino Triphenylamine (TAPA) as a main raw material and reacting at a certain temperature and pressure. The preparation method comprises the following steps: simultaneously dissolving or dispersing a certain amount of TAPA, a selected initiator and a catalyst in a pure solvent or a mixed solvent to obtain a precursor solution, then initiating the reaction liquid to react for a period of time under the solvothermal condition of a reaction kettle to obtain a crude product dispersion liquid, and further purifying and drying the obtained crude product dispersion liquid to obtain the carbon quantum dot material. The carbon quantum dot has the characteristics of red light emission (lambda max: 580-800 nm), narrow half-peak width (FWHM <50nm) and high quantum yield (> 50%), and can be suitable for biological imaging application.
Description
Technical Field
The invention belongs to the field of chemistry and nano material science, and relates to a high-performance red light carbon quantum dot material, a preparation method and a biological imaging application thereof.
Background
The carbon quantum dot is a novel nano luminescent material which is mainly composed of light elements such as carbon elements and has nano size and obvious photoluminescence effect. Compared with inorganic semiconductor quantum dots, the carbon quantum dots do not contain heavy metal elements, have the outstanding advantages of good biocompatibility, environmental friendliness and low toxicity, and are therefore considered as potential substitutes of the semiconductor quantum dots in the field of biological imaging and detection, and are widely concerned.
Due to the outstanding advantages of carbon quantum dots in the bio-related field, the synthesis processes and methods of carbon quantum dots have been extensively explored and have made considerable progress in the diversity of the methods and processes. At present, the synthesis of carbon quantum dots mainly depends on more severe chemical and physical processes including high-temperature hydrothermal, high-temperature solvothermal, microwave synthesis, laser lift-off, pyrolysis, acid reflux and the like. Generally, the synthesis methods still have insufficient control on the morphology, surface properties and spectral properties of the product, and the formed carbon quantum dots often have more structural defects. Therefore, most of the carbon quantum dots have wide and unfixed emission wavelength, the half-peak width of a main emission peak is usually more than 100nm, and the deep application of the carbon quantum dots in the aspects of display and imaging is limited. Another problem is that under severe reaction conditions, many side reactions occur simultaneously, resulting in the introduction of a large number of structural defects, such that the carbon quantum dots undergo a large amount of non-radiative decay during luminescence, resulting in generally low quantum yields (< 30% in large part). In addition, most of the obtained carbon quantum dots have small effective conjugate areas, the main luminescence is concentrated in a blue-green light (400-550 nm) range, and the carbon quantum dots which emit red light and near infrared light (lambda max is greater than 580nm) required by biological imaging application are relatively rare. In conclusion, the preparation of the high-performance red light carbon quantum dot with high quantum yield and narrow half-peak width has important practical value and important fundamental research significance.
Disclosure of Invention
The purpose of the invention is as follows: in view of the defects of the prior art, the main object of the present invention is to provide a high-performance red light carbon quantum dot material with high quantum yield, narrow half-peak width and red light emission.
The invention also aims to provide a preparation method for preparing the high-performance red-light carbon quantum dot material.
The invention further aims to provide application of the high-performance red-light carbon quantum dot material in the field of biological imaging
The technical scheme is as follows: the preparation method of the red light carbon quantum dot material comprises the following steps: dispersing a TAPA compound in a solvent to obtain a dispersion liquid with the concentration of 1-5 mM; adding an initiator and an acid catalyst into the dispersion liquid to ensure that the molar concentration ratio of the TAPA compound to the initiator is 1: 5-2: 1, and the concentration of the acid catalyst is 2.5-250 mM to obtain a reaction solution; sealing the reaction solution in a reaction kettle, and reacting at 80-200 ℃ for 2-24 h to obtain a crude product containing red light carbon quantum dots; and purifying and drying the crude product to obtain the red light carbon quantum dot material.
Further, the initiator added comprises one or a mixture of more than one of commercial or synthetic free radical initiators such as potassium persulfate, ammonium persulfate, hydrogen peroxide, Fenton reagent, benzoyl peroxide tert-butyl peroxide, methyl ethyl ketone peroxide, di-tert-butylperoxyisopropyl, azobisisobutyronitrile, azobisisoheptonitrile, azobisisobutyronitrile and the like in any proportion.
Further, the acid catalyst includes, but is not limited to, inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, perchloric acid, periodic acid, and one or more organic acids such as formic acid, acetic acid, citric acid, and the like, which are mixed in any proportion.
Further, the purification means includes, but is not limited to, one or a combination of several of filtration, dialysis, and column chromatography separation; the drying means includes but is not limited to drying under normal pressure, vacuum drying, rotary evaporation, freeze drying and the like, or a combination of several drying means.
Further, the solvent comprises one or more of water, methanol, ethanol, acetone, tetrahydrofuran, dichloromethane, chloroform, N-hexane, toluene, N-dimethylformamide, and N-methylpyrrolidone.
Further, the solvent comprises methanol or ethanol, and the molar concentration ratio of the TAPA compound to the initiator is 1: 2-2: 1, the concentration of the acid catalyst is 10-100 mM, and the reaction liquid reacts in a reaction kettle for 2-24 hours at 130-180 ℃. The red light carbon quantum dot material prepared by the preparation method of the red light carbon quantum dot material has the quantum yield of more than 50.7%, the half-peak width of less than 50nm, the central wavelength of 580-800 nm and no change with exciting light, and the particle size of the carbon quantum dot is 1-10 nm. The application of the red light carbon quantum dot material in biological imaging uses visible light with the wavelength of 400 nm-800 nm or near infrared light with the wavelength of 800 nm-1700 nm as an excitation light source, and fluorescence signals are collected in a visible light red light wave band of 580 nm-800 nm to mark and image biological targets. The imaging target includes an organelle, a cell mass, a tissue, an organ, or an animal.
Has the advantages that: compared with the prior art, the invention has the advantages that:
(1) high quantum yield, narrow half-peak width and red emission are all considered. Particularly, through condition optimization, the fluorescence quantum yield of the obtained carbon quantum dots can be higher than 80%, the half-peak width can be narrower than 30nm, and the carbon quantum dots have outstanding advantages compared with most of carbon quantum dots, are superior to most of common dyes, are similar to semiconductor quantum dots, and are suitable for imaging and display application.
(2) Has very low biological toxicity and good photobleaching resistance, so that the photobleaching inhibitor is very suitable for practical biological imaging application.
(3) The synthesis method has high controllability, and the obtained carbon quantum dot luminescence spectrum can be finely adjusted by adjusting reaction conditions (temperature, time, initiator and catalyst).
(4) The synthesis method is simple and easy to implement, has high yield and is suitable for expanded production.
(5) Through optimization, the carbon quantum dots can be imaged by using near-infrared two-region excitation light (>1000nm), and the imaging depth is favorably improved.
Drawings
FIG. 1 is the emission spectra at 550nm excitation of the products of examples 1 to 3;
FIG. 2 is a 3D fluorescence spectrum of the product of example 2;
FIG. 3 is a graph showing the experimental principle and effect of example 2;
FIG. 4 is TEM morphology and particle size statistics of the product of example 2;
FIGS. 5(a) to 5(c) are two-photon excitation and emission spectra of the product of example 2;
FIGS. 6(a) to 6(c) are 3D fluorescence spectra of the products of examples 4 to 6;
FIG. 7 is a comparison of integrated fluorescence intensities for the control products of different temperatures in example 7;
FIGS. 8(a) and 8(b) are photographs of single-photon and two-photon imaging, respectively, of the product of example 2 for lysosomal staining of NIH3T3 cells under the conditions of example 8;
FIGS. 9(a) and 9(b) are photographs of single and two-photon images of the product of example 2 stained 96hpf zebrafish under the conditions of example 8.
Detailed Description
The present invention will be described in detail below with reference to the accompanying drawings.
Example 1
0.1mmol (. about.29 mg) of 4, 4' -Triaminotriphenylamine (TAPA) was weighed out and dispersed in 20mL of absolute ethanol, and ultrasonically dispersed to a 5mM concentration solution. 200 mu L of 10M sulfuric acid and 0.2mmol of tert-butyl hydroperoxide are added into the solution, the mixture is packaged in a 20mL hydrothermal reaction kettle, and the reaction is carried out for 12h at 150 ℃ to obtain a crude product. Collecting the crude product, performing rotary evaporation to remove the solvent, purifying by using a silica gel column chromatography to collect a red fluorescent component, wherein a developing agent is 1: 5 methanol/dichloromethane mixed solvent. Collecting the purified components, dispersing the components in deionized water after removing the solvent by rotary evaporation, filtering and freeze-drying to obtain the target product solid powder. The fluorescence spectrogram of the obtained product is shown in figure 1, and the TEM morphology test shows that the particle size of the carbon quantum dots is 1-10 nm.
Example 2
0.2mmol (. about.58 mg) of TAPA was weighed out and dispersed in 200mL of absolute ethanol and sonicated to a 1mM concentration solution. 200 mu L of 10M hydrochloric acid and 0.2mmol of tert-butyl hydroperoxide are added into the solution, the mixture is packaged in a 200mL hydrothermal reaction kettle, and the reaction is carried out for 2h at 130 ℃ to obtain a crude product. Collecting the crude product, performing rotary evaporation to remove the solvent, purifying by using a silica gel column chromatography to collect a red fluorescent component, wherein a developing agent is 1: 5 methanol/dichloromethane mixed solvent. Collecting the purified components, and removing the solvent by rotary evaporation to obtain the target product solid powder. The fluorescence spectra of the obtained product are shown in FIG. 1 and FIG. 2. As can be seen from FIG. 4, the particle size of the carbon quantum dots is 1 to 5nm, and the average particle size is 2.75 nm. As can be seen from FIG. 5a, the obtained carbon quantum dots have significant two-photon excitation effects in the first near-infrared region (800-1000 nm) and the second near-infrared region (1000-1300 nm), and are suitable for two-photon imaging application of near-infrared region excitation; as can be seen from FIG. 5b, the obtained two-photon fluorescence emission center of the carbon quantum dot is located at 620nm, is similar to single-photon fluorescence spectrum, is red light emission and does not change with the power of excitation light; as can be seen from fig. 5c, the intensity of the two-photon fluorescence emission of the carbon quantum dots increases linearly with the square of the excitation light intensity.
Example 3
0.1mmol (. about.29 mg) of TAPA was weighed out and dispersed in 50mL of methanol, and dissolved in a 2mM concentration solution with stirring. Adding 0.5mmol perchloric acid and 0.05mmol hydrogen peroxide into the solution, packaging the solution in a 50mL hydrothermal reaction kettle, and reacting at 180 ℃ for 24h to obtain a crude product. Collecting crude product, rotary evaporating to remove solvent, dispersing in water solution, filtering, and purifying by dialysis (molecular weight cut-off of 500D). Collecting the purified components, and removing the solvent by rotary evaporation to obtain the target product solid powder. The fluorescence spectrogram of the obtained product is shown in figure 1, and the TEM morphology test shows that the particle size of the carbon quantum dots is 1-10 nm.
TABLE 1
Table 1 shows a numerical comparison of the carbon quantum dots prepared in examples 1 to 3 and the commercial semiconductor quantum dot QD625 in terms of maximum emission wavelength, quantum yield, and half-width. As can be seen from table 1, the carbon quantum dots prepared in examples 1 to 3 all had higher quantum yields (greater than 50%) and narrower half-peak widths (less than 40 nm). In particular, the quantum yield of the carbon quantum dot prepared in example 2 is as high as 89.79%, the half-peak width is only 25, and the quantum yield can be compared with that of the commercial semiconductor quantum dot QD 625.
Example 4
0.05mmol (. about.14.5 mg) of TAPA was weighed out and dispersed in 20mL of acetone and sonicated to a 2mM concentration dispersion. Adding 0.5mmol of nitric acid and 0.05mmol of azobisisobutyronitrile into the dispersion, packaging in a 20mL hydrothermal reaction kettle, and reacting at 150 ℃ for 6h to obtain a crude product. Filtering to remove insoluble substances, and blowing to dry the solvent to obtain the product.
Example 5
0.05mmol (. about.14.5 mg) of TAPA was weighed out and dissolved in 20mL of 75% ethanol (ethanol: water: 3: 1) with stirring to obtain a 2.5mM dispersion. And adding 5 mu mol of ammonium persulfate and 0.05mmol of phosphoric acid into the solution, packaging the solution in a 20mL hydrothermal reaction kettle, and reacting at 200 ℃ for 4h to obtain a crude product. After insoluble substances are removed by centrifugation, the target product is obtained by evaporation, concentration, filtration and freeze-drying.
Example 6
0.2mmol (. about.58 mg) of TAPA was weighed out and dispersed in 40 mM N-methylpyrrolidone and sonicated to a 5mM concentration dispersion. To this dispersion, 1mmol of di-t-butylperoxycumene and 10mmol of acetic acid were added, followed by packaging in 50 mL. Reacting at 160 ℃ for 12h to obtain a crude product, drying to remove the solvent, dispersing in an aqueous solution, washing with diethyl ether, collecting an aqueous phase solution, and freeze-drying to obtain a target product.
The fluorescence spectra of examples 4 to 6 are shown in FIGS. 6(a) to 6 (c). As can be seen from fig. 6(a) to 6(c), red carbon quantum dots can be obtained in examples 4 to 6.
Example 7
A set of parallel experiments was designed for example 2, and the crude product was obtained by reacting in a reaction kettle at 80, 105, 130, 155 and 180 degrees celsius for 2 hours, all other conditions being the same as in example 2. The resulting products were dispersed in 100mL of deionized water, respectively, and the integrated fluorescence intensity of the solution was compared as shown in FIG. 7. As can be seen from FIG. 7, the red-light carbon quantum dots can be obtained at the reaction temperature of 80-180 ℃, and the better fluorescence intensity can be obtained within the range of 105-180 ℃.
Example 8
The carbon quantum dot product obtained in example 2 was dispersed in a 0.9% sodium chloride solution (physiological saline) to obtain a solution having a concentration of 2.5 g/mL. Weighing 20 mu L of the solution, adding 1mL of DMEM medium containing 10% FBS, adding into a 35mm confocal culture dish with 3X105NIH3T3 cells growing adherently, staining for 15min, washing with PBS, and performing fluorescence imaging on cell lysosomes under the condition of soaking in 1mL of PBS solution.
Imaging conditions are as follows:
single photon imaging:
the excitation wavelength is 561nm, and the receiving wavelength is 590-650 nm;
two-photon imaging:
the excitation wavelength is 1100nm, and the receiving wavelength is 590-650 nm;
as can be seen from fig. 8a, the carbon quantum dot fluorescence in both single photon and two-photon imaging modes exhibits selective labeling of lysosomes, indicating that the carbon quantum dot is simultaneously suitable for both imaging modes.
Example 9
The carbon quantum dot product obtained in example 2 was dispersed in deionized water to give a solution having a concentration of 100. mu.g/mL. After the 96hpf zebra fish is bred for one hour, the zebra fish is replaced in clear water to wash away carbon quantum dots attached to the surface, and then in-vivo fluorescence imaging is carried out under the conditions of tricaine anesthesia and low-melting-point agarose immobilization.
Imaging conditions are as follows:
single photon imaging:
the excitation wavelength is 561nm, and the receiving wavelength is 590-650 nm;
two-photon imaging:
the excitation wavelength is 1100nm, and the receiving wavelength is 590-650 nm;
comparing fig. 9a (single photon imaging mode) and fig. 9b (two photon imaging mode), it can be seen that the limit penetration depth to the animal body is low (<400nm) in the single photon imaging mode and high (>500nm) in the two photon imaging mode.
Claims (9)
1. A preparation method of a red light carbon quantum dot material is characterized in that a TAPA compound, namely a 4, 4' -triaminotriphenylamine compound, is dispersed in a solvent to obtain a dispersion liquid with the concentration of 1-5 mM; adding an initiator and an acid catalyst into the dispersion liquid to ensure that the molar concentration ratio of the TAPA compound to the initiator is 1: 5-2: 1, and the concentration of the acid catalyst is 2.5-250 mM to obtain a reaction solution; sealing the reaction solution in a reaction kettle, and reacting at 80-200 ℃ for 2-24 h to obtain a crude product containing red light carbon quantum dots; and purifying and drying the crude product to obtain the red light carbon quantum dot material.
2. The method for preparing the red-light carbon quantum dot material according to claim 1, wherein the solvent comprises one or more of water, methanol, ethanol, acetone, tetrahydrofuran, dichloromethane, chloroform, N-hexane, toluene, N-dimethylformamide and N-methylpyrrolidone.
3. The method for preparing the red-light carbon quantum dot material according to claim 2, wherein the solvent comprises methanol or ethanol, and the molar concentration ratio of the TAPA compound to the initiator is 1: 2-2: 1, the concentration of the acid catalyst is 10-100 mM, and the reaction liquid reacts in a reaction kettle for 2-24 hours at 130-180 ℃.
4. The method for preparing the red-light carbon quantum dot material according to claim 1, wherein the added initiator comprises one or more of potassium persulfate, ammonium persulfate, hydrogen peroxide, Fenton reagent, benzoyl peroxide tert-butyl peroxide, methyl ethyl ketone peroxide, di-tert-butylperoxyisopropyl, azobisisobutyronitrile, azobisisoheptonitrile, and commercially or synthetically prepared free radical initiator of azobisisobutyronitrile formamide.
5. The method for preparing red-light carbon quantum dot material according to claim 1, wherein the added acid catalyst includes but is not limited to hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, perchloric acid, inorganic acids of periodic acid, and one or more of formic acid, acetic acid and organic acids of citric acid.
6. The method for preparing the red light carbon quantum dot material according to claim 1, wherein the purification means includes but is not limited to one or a combination of filtration, dialysis and column chromatography separation; drying means includes but is not limited to drying under normal pressure, vacuum drying, rotary evaporation and freeze drying.
7. The red-light carbon quantum dot material prepared by the preparation method of the red-light carbon quantum dot material according to claim 3, wherein the quantum yield of the red-light carbon quantum dot material is more than 50.7%, the half-peak width is less than 50nm, the central wavelength is 580-800 nm and is not changed with excitation light, and the particle size of the carbon quantum dot is 1-10 nm.
8. The application of the red-light carbon quantum dot material in biological imaging according to claim 7, wherein visible light with the wavelength of 400 nm-800 nm or near infrared light with the wavelength of 800 nm-1700 nm is used as an excitation light source, and fluorescence signals are collected in a visible light red wave band of 580 nm-800 nm to mark and image a biological target.
9. The red-light carbon quantum dot material for use in biological imaging according to claim 7, wherein the imaging target comprises an organelle, a cell mass, a tissue, an organ, or an animal.
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| CN112175611B (en) * | 2020-09-22 | 2023-03-31 | 陕西科技大学 | Application of free radical initiator in adjusting and controlling maximum emission wavelength of carbon point fluorescence |
| CN112574744B (en) * | 2020-12-31 | 2023-01-03 | 苏州国纳思新材料科技有限公司 | Preparation method of photoluminescence blue-light carbon quantum dots |
| CN112730330B (en) * | 2021-01-19 | 2022-11-01 | 中南大学 | Carbon point waveguide-based benzoyl peroxide gas sensor |
| CN112898968B (en) * | 2021-01-26 | 2022-09-02 | 临沂大学 | Preparation method of red fluorescent carbon dots |
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| CN113861973B (en) * | 2021-10-29 | 2023-03-07 | 山西大学 | Nitrogen-phosphorus co-doping ratio fluorescent carbon dot and preparation method and application thereof |
| CN116554867B (en) * | 2022-11-03 | 2024-04-09 | 中国科学院苏州生物医学工程技术研究所 | Carbon quantum dot with aggregation-induced fluorescence effect and application thereof |
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