CN112852418B - Double-emission-ratio fluorescent carbon dot and preparation method and application thereof - Google Patents

Double-emission-ratio fluorescent carbon dot and preparation method and application thereof Download PDF

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CN112852418B
CN112852418B CN202110042028.1A CN202110042028A CN112852418B CN 112852418 B CN112852418 B CN 112852418B CN 202110042028 A CN202110042028 A CN 202110042028A CN 112852418 B CN112852418 B CN 112852418B
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fluorescent carbon
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carbon dot
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CN112852418A (en
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梁彩珍
谢小保
施庆珊
王玲玲
董鹏
冯劲
孙廷丽
李素娟
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Guangdong Detection Center of Microbiology of Guangdong Institute of Microbiology
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    • C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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    • C01B32/15—Nano-sized carbon materials
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    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"

Abstract

The invention discloses a double-emission-ratio fluorescent carbon dot and a preparation method and application thereof. The preparation method of the double-emission-ratio fluorescent carbon dot comprises the step of carrying out hydrothermal carbonization or solvent thermal carbonization on sodium alginate and glutathione to prepare the double-emission-ratio fluorescent carbon dot. The method has the advantages of simple and easy operation, low cost and good repeatability. The prepared carbon dot has an excitation wavelength of 420nm and dual emission wavelengths of 480nm and 650nm respectively. In addition, the double-emission ratio fluorescent carbon dots have high light stability, good water solubility, low cytotoxicity and good biocompatibility, and can be used for Fe3+The specificity detection is good in selectivity and high in sensitivity; and can be used in environmental waters such as tap water for Fe3+Sensitive detection of (3).

Description

Double-emission-ratio fluorescent carbon dot and preparation method and application thereof
Technical Field
The invention belongs to the technical field of fluorescent carbon nano materials, and particularly relates to a double-emission-ratio fluorescent carbon dot and a preparation method and application thereof.
Background
Iron ion (Fe)3+) Is an essential trace element in human body, and is used in physiological process,Plays an indispensable role in diagnosis and ecological environment. Fe3+Oxygen may also be carried to transport electrons and catalyze redox reactions in proteins. In environmental quality evaluation, Fe3+The content is one of the important indexes for evaluating the water quality grade, and the Fe in domestic drinking water3+The content should not exceed 5.4. mu. mol/L. In the human system, Fe3+Is suitably present in a total amount of about 4 g. In recent years, research reports have indicated that Fe3+Excessive content can cause coronary heart disease, cancer, methemoglobinemia, immune system dysfunction and other serious diseases. Fe3+Deficiency can lead to severe diseases such as anemia and physical dysfunction. Therefore, the development of a low-cost technology using sensitive fluorescent nano-materials can rapidly and sensitively detect Fe in environmental water or biological samples3+Has important significance in environment and biomedicine. Fluorescence spectroscopy has the advantages of high sensitivity, short response time, simple and convenient detection process and the like and is widely concerned.
In recent years, the design and synthesis of novel fluorescent materials to replace organic dyes and semiconductor quantum dots in the fields of ion detection, biological labeling and the like is one of the research hotspots of fluorescent nano materials. The carbon dots have good application prospects in the aspects of fluorescence sensing, environment monitoring, biological imaging, drug delivery, photocatalysis, photoelectronic devices and the like due to the characteristics of small particle size, high fluorescence stability, good photobleaching resistance, adjustable emission spectrum, easy surface functionalization, low toxicity, good biocompatibility and the like, so that the carbon dots are concerned. However, many of the carbon dots reported at present mainly emit fluorescence in blue, green or yellow regions, and are easily interfered by the autofluorescence emission of biomass, limiting further applications in photoelectric devices, biomedicine, and the like. Carbon dots with long-wavelength fluorescence emission are highly concerned by researchers because the interference of self-emitted fluorescence of biological substrates can be effectively avoided. They synthesized carbon dots having long wavelength emission by surface structure modification, increasing the degree of conjugation, changing the position of substituents, etc., but these carbon dots exhibited only a single emission state, and were quantified based on the change in intensity of a single emission peak during detection. The fluorescent probe is used in the detection processThe method is easily influenced by probe concentration change, laser fluctuation, instrument efficiency, local microenvironment change and the like, so that the sensitivity and the accuracy of a determination result are reduced. Compared with a single-emission carbon dot, the ratiometric fluorescent probe based on the carbon dot can effectively eliminate the adverse effect on the quantitative analysis result by simultaneously measuring the fluorescence intensity of two or more emission peaks and taking the change of the ratio of the two or more emission peaks as a fluorescence response signal of the determination target analysis. The existing ratiometric fluorescent probe is mainly constructed by combining two nano materials with different fluorescence emission wavelengths by a chemical bonding or physical method, and has the disadvantages of complex, fussy, time-consuming and high cost in operation and treatment processes. Therefore, the method with simple and easy design and low cost is used for synthesizing the dual-emission fluorescent carbon dot with long-wavelength emission for Fe3+The detected ratiometric fluorescent probes are of great significance.
Disclosure of Invention
Aiming at the preparation bottleneck of the prior double-emission-ratio fluorescent carbon dot with long-wavelength emission, the invention overcomes the defects of the prior art and provides a method which can be used for simply synthesizing and reacting Fe3+Double-emission-ratio fluorescent carbon dots with specific response function and long-wavelength emission characteristic, and preparation method and application thereof.
The invention discloses a preparation method of a double-emission-ratio fluorescent carbon dot.
Preferably, sodium alginate and glutathione are dissolved in a reaction solvent, then the mixture is placed in a microwave synthesizer for hydrothermal or solvothermal reaction, and then the mixture is filtered, dialyzed, and dialyzate is collected and dried to obtain the double-emission-ratio fluorescent carbon dots.
The preparation method specifically comprises the following steps:
adding sodium alginate and glutathione into a reaction solvent, stirring for dissolving, transferring to a reaction tank, placing in a microwave synthesizer, heating to 100-220 ℃ at a heating speed of 4-20 ℃/min for reacting for 0.5-24 h, filtering, dialyzing the obtained filtrate for 12-120 h by using a dialysis bag, collecting dialysate, and freeze-drying to obtain the double-emission-ratio fluorescent carbon dots;
the mass ratio of the sodium alginate to the glutathione is 1-30: 1-30, and the mass volume ratio of the sodium alginate to the reaction solvent is 1g of sodium alginate: 5-200 mL of reaction solvent.
Preferably, the preparation method comprises the following steps:
adding sodium alginate and glutathione into a reaction solvent, stirring for dissolving, transferring to a reaction tank, placing in a microwave synthesizer, heating to 190 ℃ at a heating speed of 10 ℃/min for reacting for 8h, filtering, dialyzing the obtained filtrate for 90h by using a dialysis bag, collecting dialysate, and freeze-drying to obtain the double-emission-ratio fluorescent carbon dots;
the mass ratio of the sodium alginate to the glutathione is 1:1, and the mass volume ratio of the sodium alginate to the reaction solvent is 1g of sodium alginate: 20mL of reaction solvent.
Preferably, the filtration is vacuum filtration with a 0.22 μm microporous membrane, and the dialysis bag has a molecular weight cutoff of 1000Da or 3500 Da.
Preferably, the reaction solvent is deionized water, N-Dimethylformamide (DMF) or a mixed solution of the deionized water and the DMF, and the volume ratio of the deionized water to the DMF in the mixed solution is 1-20: 1-10.
The second purpose of the invention is to provide the double-emission-ratio fluorescent carbon dot prepared by the preparation method.
The third purpose of the invention is to provide the double-emission ratio fluorescent carbon dot for detecting Fe3+The use of (1).
Preferably, the application comprises the following steps:
a. the gradient concentration of Fe is known3+Respectively adding the aqueous solution into the double-emission-ratio fluorescent carbon dot solution for reaction, measuring the fluorescence spectrum under the excitation condition of 420nm, and calculating the fluorescence intensity ratio F at the 650nm emission wavelength and the 480nm emission wavelength of each sample650/F480Drawing F650/F480With Fe3+Standard curve between concentrations;
b. fe to be detected3+Adding the solution sample into the double-emission ratio fluorescent carbon dot solution, carrying out the same reaction as in the step a, and determining to obtain the corresponding F650/F480Is a reaction of the compound F650/F480Substituting into the standard curve of the step a to obtain Fe to be detected3+Fe in solution samples3+And (4) concentration.
Preferably, the dual emission ratio fluorescent carbon dot to Fe3+The fluorescence response interval of (a) is 0-200. mu.M.
Preferably, the double-emission-ratio fluorescent carbon dot solution is a double-emission-ratio fluorescent carbon dot solution which is prepared by dissolving double-emission-ratio fluorescent carbon dots in a Tris-HCl buffer solution and has a concentration of 50-500 mu g/mL.
The method can realize the aim of Fe3+The specificity quantitative detection and the application in practical samples.
Compared with the prior art, the invention has the following advantages and effects:
(1) the preparation process is simple and feasible, the reaction condition is mild, the cost is low, the repeatability is good, the dual-emission-ratio fluorescent carbon dots can be obtained by one-step hydrothermal or solvothermal treatment, and surface structure modification and passivation are not needed or other fluorescent materials are not needed for hybridization. The prepared carbon dots have small and uniform particle size, good water dispersibility and excellent fluorescence performance, and the absolute fluorescence quantum yield is 6.8-15%.
(2) The double-emission-ratio fluorescent carbon dot prepared by the invention has the characteristic of long-wave emission, and has the advantages of good photobleaching resistance, high fluorescence stability, good water solubility, low cytotoxicity and good biocompatibility.
(3) The double-emission-ratio fluorescent carbon dots prepared by the method have rich surface functional groups and are Fe-tolerant3+Has specific recognition ability, and can be used for treating Fe3+The kit realizes ratiometric fluorescence response, has good selectivity and high sensitivity, and can realize detection of the kit on environmental water and biomass samples.
(4) The invention expands the types of the long-wave dual-emission-ratio type carbon dots and provides technical support for preparing novel dual-emission-ratio fluorescent carbon dots.
Drawings
FIG. 1 is an infrared spectrum of a dual emission ratio fluorescent carbon dot prepared in example 3 of the present invention.
FIG. 2 is an XRD spectrum of a dual emission ratio fluorescent carbon dot prepared in example 3 of the present invention.
FIG. 3 is a diagram of the UV-VIS absorption spectrum and fluorescence excitation-emission spectrum of a dual emission ratio fluorescent carbon dot prepared in example 3 of the present invention.
FIG. 4 is a graph of fluorescence intensity F of dual emission ratio fluorescent carbon dots prepared in example 3 of the present invention for different ions650/F480Selective experiments under the ratio, the black bars represent the fluorescence intensity change of the double-emission ratio fluorescent carbon dots in different ions, and the gray bars represent the double-emission ratio fluorescent carbon dots in different ions to Fe3+Change in fluorescence response.
FIG. 5 is a graph of the fluorescence intensity F of amino acids and anions versus dual emission ratio fluorescent carbon dots prepared in example 3 of the present invention650/F480Selective experiments under the ratio, the black column represents the fluorescence intensity change of the double-emission ratio fluorescent carbon dots in different molecules, and the gray column represents the double-emission ratio fluorescent carbon dots in different molecules to Fe3+Change in fluorescence response.
FIG. 6 shows different concentrations of Fe3+When present, the fluorescence intensity of the dual emission ratio fluorescent carbon dot changes.
FIG. 7 is F650/F480Ratio to Fe3+And its standard curve.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof.
Example 1
For detecting Fe3+The preparation method of the double-emission ratio fluorescent carbon dot comprises the following steps:
respectively weighing 30g of sodium alginate and 1g of glutathione, dissolving in 150mL of deionized water, magnetically stirring at room temperature for 30min to completely dissolve the solid, transferring the obtained mixed system into a microwave synthesizer with a polytetrafluoroethylene inner container, heating to 100 ℃ at a heating speed of 4 ℃/min, reacting for 24h, cooling to room temperature after the reaction is stopped, vacuum-filtering the obtained product through a 0.22 mu m filter membrane, dialyzing the obtained filtrate for 120h by using a 3500Da dialysis bag, collecting dialysate, and finally freeze-drying to obtain the dual-emission-ratio fluorescent carbon dot. And (3) measuring the absolute fluorescence quantum yield of the prepared double-emission-ratio fluorescent carbon dots by using a fluorescence spectrometer, wherein the fluorescence quantum yield is 15%.
Example 2
For detecting Fe3+The preparation method of the double-emission ratio fluorescent carbon dot comprises the following steps:
respectively weighing 1g of sodium alginate and 30g of glutathione to dissolve in 200mL of DMF, magnetically stirring for 5min at room temperature to completely dissolve the solid, transferring the obtained mixed system into a microwave synthesizer with a polytetrafluoroethylene inner container, heating to 220 ℃ at a heating speed of 20 ℃/min, reacting for 0.5h, cooling to room temperature after the reaction is stopped, vacuum-filtering the obtained product through a 0.22 mu m filter membrane, dialyzing the obtained filtrate for 12h by adopting a 1000Da dialysis bag, collecting dialysate, and finally freeze-drying to obtain the dual-emission-ratio fluorescent carbon dot. And (3) measuring the absolute fluorescence quantum yield of the prepared double-emission-ratio fluorescent carbon dots by using a fluorescence spectrometer, wherein the fluorescence quantum yield is 6.8%.
Example 3
For detecting Fe3+The preparation method of the double-emission ratio fluorescent carbon dot comprises the following steps:
respectively weighing 10g of sodium alginate and 10g of glutathione, dissolving the sodium alginate and the glutathione in 200mL of deionized water/DMF (volume ratio of 3/1) mixed solution, magnetically stirring the mixture at room temperature for 10min to completely dissolve the solid, transferring the obtained mixed system into a microwave synthesizer with a polytetrafluoroethylene inner container, heating the mixed system to 190 ℃ at the heating speed of 10 ℃/min, reacting for 8h, cooling the program to room temperature after the reaction is stopped, then carrying out vacuum filtration on the obtained product through a 0.22 mu m filter membrane, dialyzing the obtained filtrate for 90h by using a 3500Da dialysis bag, collecting dialysate, and finally carrying out freeze drying to obtain the dual-emission ratio fluorescent carbon dot. And (3) measuring the absolute fluorescence quantum yield of the prepared double-emission-ratio fluorescent carbon dots by using a fluorescence spectrometer, wherein the fluorescence quantum yield is 10.6%.
Example 4
The characterization of the dual emission ratio fluorescent carbon dots prepared in example 3 of the present invention is shown in FIGS. 1 and 2. The infrared spectrum of fig. 1 shows that the carbon dot has a large number of amino and carboxyl functional groups and demonstrates C-O, C-N and C-N/C-O structures. The XRD spectrum of fig. 2 confirms that the carbon dots have a graphite-like lattice structure.
Example 5
The optical spectrum of the dual emission ratio fluorescent carbon dot prepared in example 3 of the present invention is shown in fig. 3. The ultraviolet-visible absorption spectrum of the carbon dot has absorption peaks at 270nm, 399nm, 425nm, 643nm and 692 nm. Meanwhile, dual-wavelength emission of 480nm and 650nm occurs under the excitation of 420nm wavelength, and yellow green fluorescence is formed under the irradiation of 365nm ultraviolet light.
Example 6
In this example, the dual emission ratio fluorescent carbon dots prepared in example 3 were used to realize Fe contrast3+Specific ratio fluorescence detection of (2).
(1) Dissolving Fe (NO) in Tris-HCl buffer (pH 6.0)3)3·9H2O solid, preparing Fe with different concentrations in sequence3+An aqueous solution. And other ions and molecules were formulated at a concentration of 4mM (the other ion being NH)4 +、Na+、Mg2+、Al3+、K+、Ca2+、Cr3+、Mn2+、Fe2+、Fe3+、Co2+、Ni2+、Cu2+、Zn2+、Cd2+、Pb2+、Ag+、ClO-、S2-、SO3 2-、S2O3 2-、CO3 2-、Br-、I-、CH3COO-、H2PO4 -Etc.; the other molecules are glycine (Gly), isoleucine (Isoleu), valine (Val), threonine (Thr), proline (Pro), leucine (Leu), serine (Ser), arginine (Arg), cysteine (Cys), aspartic acid (Asp), tyrosine (Tyr), glutamic acid (Glu), phenylalanine (Phe), Glutathione (GSH)(GSH), Glucose (Glucose), hydrogen peroxide (H)2O2) Disodium ethylene diamine tetraacetate (Na)2-EDTA)) aqueous solution. The two-emission-ratio fluorescent carbon dots prepared in example 3 were dissolved in Tris-HCl buffer solution at pH 6.0 to prepare a two-emission-ratio fluorescent carbon dot solution having a concentration of 120 μ g/mL.
(2) 0.5mL of 4mM Fe prepared as described above3+Respectively adding the aqueous solution and 4mM different ion/molecule aqueous solution into 1.0mL of the prepared double-emission-ratio fluorescent carbon dot solution, reacting at room temperature for a period of time, measuring the fluorescence spectrum under the excitation condition of 420nm, and calculating the fluorescence intensity ratio F at the 650nm emission wavelength and the 480nm emission wavelength650/F480。
(3) 1mL of Fe prepared as described above at various concentrations3+The aqueous solution was added to 1.0mL of the dual emission ratio fluorescent carbon dot solution prepared above to prepare a solution having different Fe3+Reacting the mixed solution with a concentration (final concentration of 0-200 μ M) at room temperature for a period of time, measuring the fluorescence spectrum under the excitation condition of 420nm, and drawing F650/F480With Fe3+Standard curves between concentrations and fit linear relationships.
Example 3 Dual emission ratio fluorescent carbon dot to Fe3+The ratio response of (c) is shown in fig. 4, 5, 6, 7. FIGS. 4 and 5 show that this carbon point is opposite to Fe3+Has high selective response and can be used for Fe in complex samples3+Detection of (3). FIG. 6 shows that with Fe3+The fluorescence intensity at 650nm of the carbon spot gradually decreases while the fluorescence intensity at 480nm is substantially unchanged with increasing concentration. FIG. 7 shows the carbon point F650/F480Ratio to Fe3+Correlation of concentration (F)650/F480＝-0.0053C(Fe3+)+0.58689，R20.992), linear range 0.1-50 μ M, detection limit 0.56 μ M.
Example 7
Application of double-emission-ratio fluorescent carbon dots prepared in embodiments 1, 2 and 3 of the invention to detection of Fe in tap water in laboratory3+The detection method refers to the step (3) in the example 6, and the calculation formula refers to the factLinear regression Curve (F) in example 6650/F480＝-0.0053C(Fe3+)+0.58689，R20.992), the results are shown in table 1 below. It can be seen from Table 1 that the carbon dots detect Fe in tap water3+The recovery rate is 95.6-105.4%, and the recovery rate meets the detection standard, which indicates that the carbon dots can be used for Fe in environmental water3+Detection of (3).
TABLE 1 detection of Fe in tap water using dual emission ratio fluorescent carbon dots3+Results of concentration
Figure BDA0002896274520000061

Claims (7)

1. Double emission ratio fluorescent carbon spot in detection of Fe3+The double-emission ratio fluorescent carbon dot is prepared by carrying out hydrothermal carbonization or solvent thermal carbonization on sodium alginate and glutathione;
the method comprises the following steps: the double-emission-ratio fluorescent carbon dots are obtained by dissolving sodium alginate and glutathione in a reaction solvent, then placing the reaction solvent in a microwave synthesizer to carry out hydrothermal or solvothermal reaction, filtering, dialyzing, collecting dialysate and drying;
the reaction solvent is deionized water, N-dimethylformamide or a mixed solution of the two.
2. Use according to claim 1, characterized in that it comprises the following steps:
adding sodium alginate and glutathione into a reaction solvent, stirring for dissolving, transferring to a reaction tank, placing in a microwave synthesizer, heating to 100-220 ℃ at a heating speed of 4-20 ℃/min for reacting for 0.5-24 h, filtering, dialyzing the obtained filtrate for 12-120 h by using a dialysis bag, collecting dialysate, and freeze-drying to obtain the double-emission-ratio fluorescent carbon dots;
the mass ratio of the sodium alginate to the glutathione is 1-30: 1-30, and the mass volume ratio of the sodium alginate to the reaction solvent is 1g of sodium alginate: 5-200 mL of reaction solvent.
3. The use according to claim 2, wherein the filtration is vacuum filtration using a 0.22 μm microfiltration membrane and the dialysis bag is a dialysis bag with a molecular weight cut-off of 1000Da or 3500 Da.
4. The use according to claim 1, wherein the reaction solvent is a mixed solution of deionized water and N, N-dimethylformamide, and the volume ratio of the deionized water to the N, N-dimethylformamide in the mixed solution is 1-20: 1-10.
5. Use according to claim 1, characterized in that it comprises the following steps:
a. the gradient concentration of Fe is known3+Respectively adding the aqueous solution into the double-emission-ratio fluorescent carbon dot solution for reaction, measuring the fluorescence spectrum under the excitation condition of 420nm, and calculating the fluorescence intensity ratio F at the 650nm emission wavelength and the 480nm emission wavelength of each sample650/F480Drawing F650/F480With Fe3+A standard curve between concentrations;
b. fe to be detected3+Adding the solution sample into the double-emission ratio fluorescent carbon dot solution, carrying out the same reaction as in the step a, and determining to obtain the corresponding F650/F480Is a reaction of the compound F650/F480Substituting into the standard curve of the step a to obtain Fe to be detected3+Fe in solution samples3+And (4) concentration.
6. The use of claim 5, wherein the dual emission ratio fluorescent carbon dot solution is a 50-500 μ g/mL dual emission ratio fluorescent carbon dot solution prepared by dissolving a dual emission ratio fluorescent carbon dot in a Tris-HCl buffer.
7. The use of claim 5, wherein said dual emission ratio fluorescent carbon dot to Fe3+The fluorescence response interval of (a) is 0-200. mu.M。
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