CN108587619B - Luminescent carbon quantum dot and preparation method and application thereof - Google Patents

Luminescent carbon quantum dot and preparation method and application thereof Download PDF

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CN108587619B
CN108587619B CN201810734061.9A CN201810734061A CN108587619B CN 108587619 B CN108587619 B CN 108587619B CN 201810734061 A CN201810734061 A CN 201810734061A CN 108587619 B CN108587619 B CN 108587619B
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CN108587619A (en
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李占先
刘含笑
于明明
魏柳荷
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Abstract

The invention belongs to the technical field of molecular probes, and particularly relates to a luminescent carbon quantum dot, a preparation method and application thereof, and a method for detecting arginine in an aqueous solution by using the luminescent carbon quantum dot, in particular to a method for synthesizing a carbon quantum dot and detecting arginine by fluorescence by using 2-methoxy-4-methylphenol and o-phenylenediamine as raw materials through a hydrothermal method.

Description

Luminescent carbon quantum dot and preparation method and application thereof
Technical Field
The invention belongs to the technical field of molecular probes, and particularly relates to a luminescent carbon quantum dot, a preparation method and application thereof, and a method for detecting arginine in an aqueous solution by using the luminescent carbon quantum dot.
Background
Among the 20 amino acids constituting proteins, arginine is one of the amino acids that can constitute the most diverse proteins in animals, and is not only a precursor of protein synthesis, but also a precursor of generation of nitric oxide, urea, polyamine, proline, glutamic acid, creatine, agmatine, etc., and additionally, arginine plays a crucial role in vasodilation, nerve transmission, cell division, wound healing, immune function, and hormone release, and thus has received wide attention from scientists, but its strong hydrophilicity and weak interaction with receptors make its detection in aqueous solution very challenging, and currently, only a few studies report that arginine is detected using chemical sensors [ partven, s.d.s., Affrose, a., pimtcheni, k., 2015. senser B221, 521-527. He, l.; So, V.L. L.; Xin J. H.; 2014. Sens. Actuators B192, 496-; the invention discloses a water-soluble luminescent carbon quantum dot prepared by a simple hydrothermal synthesis method, which is simple in synthesis method and completely water-soluble.
Disclosure of Invention
The invention aims to provide a luminescent carbon quantum dot, a preparation method and application thereof, and a method for detecting arginine in an aqueous solution by using the luminescent carbon quantum dot, and the luminescent carbon quantum dot has the advantages of simple synthesis, convenience in use and high detection sensitivity.
In order to achieve the purpose, the invention adopts the technical scheme that:
a preparation method of luminescent carbon quantum dots comprises the following steps: (1) dissolving o-phenylenediamine and 2-hydroxy-3-methoxybenzaldehyde with the concentration of 0.8-2.0 mol/L in deionized water to obtain reaction liquid;
(2) placing the reaction solution in a polytetrafluoroethylene reaction kettle, and heating and reacting for 8-10h at the temperature of 180 ℃ and 220 ℃;
(3) naturally cooling the reaction solution to room temperature to obtain a brown yellow solution;
(4) and (3) putting the supernatant of the brown yellow solution into a dialysis bag for dialysis, and putting the solution obtained by dialysis into a freeze dryer for drying for 18 hours to obtain the carbon quantum dots.
Further, the cut-off molecular weight of the dialysis bag used for dialysis in the step (4) is 3500, the dialysis time is 24-72 hours, and water is changed every 2-6 hours.
Furthermore, the luminescent carbon quantum dot is prepared by the preparation method of the luminescent carbon quantum dot.
Further, the luminescent carbon quantum dots are used as fluorescent probes for detecting arginine in aqueous solution in the pH range of 6-11.
Further, the method for detecting arginine in the aqueous solution by using the luminescent carbon quantum dot comprises the following steps:
step 1) taking arginine with the same volume and concentration and different metal ions or different anions or different biological micromolecule solutions, respectively adding carbon quantum dots with the same volume and deionized water with the same volume to obtain a series of mixed solutions with the same volume and concentration, and respectively carrying out fluorescence intensity detection to realize qualitative detection on arginine;
and 2) taking arginine solutions in different volumes in the step 1), adding carbon quantum dots in the same volume and deionized water in different volumes respectively to prepare a series of arginine standard solutions with the same volume and different concentrations, performing fluorescence intensity detection respectively to obtain a fluorescence spectrogram of the arginine standard solution, and drawing a standard curve and calculating a linear relation by taking the fluorescence intensity of each standard solution as a vertical coordinate and the concentration as a horizontal coordinate to realize quantitative detection of arginine.
Further, the concentration of arginine and other different metal ions, anions and biomolecule solutions in the step 1) is 100 mu mol/L, wherein the metal ions are Ag+、Ca2+、K+、Mn2+、Na+、Ni2+、NH4+、Pd2+The anion is Br-、BrO3 -、C2O4 2-、CH3COO-、Cl-、F-、H2PO4 -、I-、N3 -、NO2 -、NO3 -、SO4 2-And the biological micromolecules are phenylalanine, alanine, methionine, proline, glycine, glutamine, tyrosine, leucine, glucose, serine, threonine, isoleucine and desmosine.
Further, the detection limit of the arginine concentration is 78.11 mu M.
The invention has the advantages that: the carbon quantum dot has low synthesis cost, can be prepared from simple organic compounds and other raw materials, does not contain heavy metals, has low toxicity, is completely water-soluble, can detect arginine in water, shows good light stability, and has small change of an emission spectrum under the excitation of light.
Drawings
FIG. 1 is a graph showing the change of fluorescence spectrum after adding arginine (0-100. mu.M) at different concentrations to a dispersion of carbon quantum dots (0.02 mg/mL in a pure water system) under 376 nm light excitation.
FIG. 2 carbon quantum dots (0.02 mg/mL) arginine aqueous solution was added dropwise to pure water at a concentration of 1.67X 10 from 0 mol/L-4Photos of moles/liter (final concentration of arginine from left to right 0, 16.7, 33.3, 50.1, 66.8, 83.5, 100, 117, 134, 150, 167 μ M) under 365 nm hand-held ultraviolet excitation;
FIG. 3 shows the detection of the presence of cations (concentration of 100. mu.M, blank, Ag, respectively) under 376 nm excitation+、Ca2+、K+、Mn2+、Na+、Ni2+、NH4+、Pd2+) A graph showing the change of the ratio of fluorescence intensity I430/I570 before (dark column) and after (light column) addition of arginine (100 μ M) to the dispersion of carbon quantum dots (0.02 mg/mL, pure water system).
FIG. 4 under 376 nm light excitation, the carbon quantum dot (0.02 mg/mL, pure water system) dispersion containing amino acid (100 μ M) is respectively detected and anion (100 μ M, blank and Br from left to right-、BrO3 -、C2O4 2-、CH3COO-、Cl-、F-、H2PO4 -、HPO4 2-、I-、N3 -、NO2 -、NO3 -、SO4 2-) Histogram of change of the ratio of fluorescence intensity I430/I570 before (dark bars) and after (light bars) addition of arginine (100 μ M) thereafter.
Fig. 5 is a bar graph showing changes of fluorescence intensity ratio I430/I570 before (dark column) and after (light column) arginine (100 μ M) was added after (dark column) biological small molecules (100 μ M, arginine (Arg), phenylalanine (Phe), alanine (Ala), methionine (Met), proline (Pro), glycine (Gly), glutamine (Gln), tyrosine (Tyr), leucine (Leu), glucose (Glc), serine (Ser), threonine (Thr), isoleucine (Ile), and tryptophan (Val) were added to dispersions of carbon quantum dots (0.02 mg/mL, pure water system) containing amino acids (100 μ M) respectively under 376 nm light excitation.
Fig. 6 shows changes in luminescence of a solution after adding small biological molecules (100 μ M, arginine (Arg), phenylalanine (Phe), alanine (Ala), methionine (Met), proline (Pro), glycine (Gly), glutamine (Gln), tyrosine (Tyr), leucine (Leu), glucose (Glc), serine (Ser), threonine (Thr), isoleucine (Ile), and histidine (Val) from left to right, respectively, to a carbon quantum dot dispersion (0.02 mg/mL, pure water system), and a picture taken under irradiation of a 365 nm portable ultraviolet lamp.
FIG. 7 shows fluorescence emission spectra of carbon quantum dot (0.02 mg/mL, pure water system) dispersion at different excitation wavelengths.
FIG. 8 is a graph showing the change of the fluorescence intensity ratio I430/I570 of 100 μ M arginine (round dotted line) added to a dispersion (square dotted line) of carbon quantum dots (0.02 mg/mL, pure water system) and a solution (0.02 mg/mL, pure water system) of carbon quantum dots (0.02 mg/mL, pure water system) with pH.
FIG. 9 is a graph showing the change of the fluorescence intensity ratio I430/I570 of a dispersion of carbon quantum dots (0.02 mg/mL, pure water system) with the time of illumination.
Detailed Description
Examples
A preparation method of luminescent carbon quantum dots comprises the steps of dissolving 152.2 mg of o-phenylenediamine with the concentration of 0.8-2.0 mol/L and 216.3 mg of 2-hydroxy-3-methoxybenzaldehyde with the concentration of 0.8-2.0 mol/L in 20 mL of deionized water to obtain a reaction solution, placing the reaction solution in a polytetrafluoroethylene reaction kettle, heating and reacting for 8-10h at the temperature of 180-220 ℃, and naturally cooling to room temperature to obtain a brown yellow solution; and (3) putting the supernatant of the brown yellow solution into a dialysis bag for dialysis for 24-72h, changing water every 2-6 h, wherein the cut-off molecular weight of the dialysis bag is 3500, and putting the solution obtained by dialysis into a freeze dryer for drying for 18h to obtain the carbon quantum dots.
The luminescent carbon quantum dot prepared by the preparation method of the luminescent carbon quantum dot can be used as a fluorescent probe for detecting arginine in an aqueous solution within the pH range of 6-11.
Further, the method for detecting arginine in the aqueous solution by using the luminescent carbon quantum dot comprises the following steps:
step 1) taking arginine and different metal ions or different anions or different biological micromolecule solutions with the same volume and the same concentration, respectively adding carbon quantum dots with the same volume and deionized water with the same volume to obtain a series of mixed solutions with the same volume and the same concentration, respectively carrying out fluorescence intensity detection to realize qualitative detection of arginine, wherein the concentrations of arginine and other different metal ions, anions and biological molecule solutions are all 100 mu mol/L, and the metal ion is Ag+、Ca2+、K+、Mn2+、Na+、Ni2+、NH4+、Pd2+The anion is Br-、BrO3 -、C2O4 2-、CH3COO-、Cl-、F-、H2PO4 -、I-、N3 -、NO2 -、NO3 -、SO4 2-The biological micromolecules are phenylalanine, alanine, methionine, proline, glycine, glutamine, tyrosine, leucine, glucose, serine, threonine, isoleucine and desmosine;
and step 2) taking arginine solutions in different volumes in the step 1), adding carbon quantum dots in the same volume and deionized water in different volumes respectively to prepare a series of arginine standard solutions with the same volume and different concentrations, performing fluorescence intensity detection respectively to obtain a fluorescence spectrogram of the arginine standard solution, drawing a standard curve and calculating a linear relation by taking the fluorescence intensity of each standard solution as a vertical coordinate and the concentration as a horizontal coordinate, so as to realize quantitative detection of arginine, wherein the detection limit of the arginine concentration is 78.11 mu M.
Application of luminescent carbon quantum dots prepared in the example as fluorescent probes
The luminescent carbon quantum dot is prepared by a hydrothermal method, the carbon quantum dot is well dissolved in a pure water system, and as shown in figure 1, a new emission peak appears at 430 nm along with the increase of the concentration of arginine in the fluorescence spectrum of the luminescent carbon quantum dot.
FIG. 2 is a photograph of 365 nm hand ultraviolet excited water containing pure carbon quantum dots with arginine concentration from 0 mol/L to 1.67X 10-4Significantly enhanced fluorescence at moles/liter (final arginine concentrations from left to right of 0, 16.7, 33.3, 50.1, 66.8, 83.5, 100, 117, 134, 150, 167 μ M); different metal ions (see FIG. 3, Ag)+、Ca2+、K+、Mn2+、Na+、Ni2+、NH4+、Pd2+) Anion (FIG. 4, Br)-、BrO3 -、C2O4 2-、CH3COO-、Cl-、F-、H2PO4 -、I-、N3 -、NO2 -、NO3 -、SO4 2-) Biological small molecules (see fig. 5, phenylalanine (Phe), alanine (Ala), methionine (Met), proline (Pro), glycine (Gly), glutamine (Gln), tyrosine (Tyr), leucine (Leu), glucose (Glc), serine (Ser), threonine (Thr), isoleucine (Ile), and histidine (Val)) have no effect on the detection of arginine in a pure water system for carbon quantum dots; adding biological small molecules (100 μ M) (arginine (Arg), phenylalanine (Phe), alanine (Ala), methionine (Met), proline (Pro), glycine (Gly), glutamine (Gln), tyrosine (Tyr), leucine (Leu), glucose (Glc), serine (Ser), threonine (Thr), isoleucine (Ile), and histidine (Val) from left to right respectively) into a carbon quantum dot dispersion (0.02 mg/mL, pure water system), and then, only arginine emits strong fluorescence in the solution (FIG. 6); the emission peak of 560 nm of the carbon quantum dot of the invention does not show excitation wavelength dependence under different excitation wavelengths (fig. 7); at a wide pH rangeThe carbon quantum dots of the patent (pH value is 6-11) can detect arginine (figure 8); the carbon quantum dots show better photostability, and the emission spectrum of the carbon quantum dots does not change greatly under the excitation of light (figure 9); the detection limit of the carbon quantum dots to arginine is 78.11 mu M, the fluorescence quantum yield in water is 6.3%, and the reference is quinine sulfate.
In conclusion, the invention provides a novel luminescent carbon quantum dot nanoprobe for detecting arginine, the nanoprobe can be dispersed in a pure water system, the sensor has good arginine detection property, the synthesis method is simple, and the sensor has good light stability and anti-interference performance and is suitable for detecting arginine.

Claims (6)

1. The luminescent carbon quantum dot is characterized in that the preparation method comprises the following steps: (1) dissolving o-phenylenediamine and 2-hydroxy-3-methoxybenzaldehyde with the concentration of 0.8-2.0 mol/L in deionized water to obtain reaction liquid;
(2) placing the reaction solution in a polytetrafluoroethylene reaction kettle, and heating and reacting for 8-10h at the temperature of 180 ℃ and 220 ℃;
(3) naturally cooling the reaction solution to room temperature to obtain a brown yellow solution;
(4) and (3) putting the supernatant of the brown yellow solution into a dialysis bag for dialysis, and putting the solution obtained by dialysis into a freeze dryer for drying for 18 hours to obtain the luminescent carbon quantum dots.
2. The luminescent carbon quantum dot of claim 1, wherein: the molecular weight cut-off of the dialysis bag used in the dialysis in the step (4) is 3500, the dialysis time is 24-72 hours, and the water is changed every 2-6 hours.
3. Use of the luminescent carbon quantum dots according to claim 2 as fluorescent probes for the detection of arginine in aqueous solutions at a pH in the range of 6-11.
4. The method for detecting arginine in an aqueous solution using the luminescent carbon quantum dot according to claim 1, comprising the steps of:
step 1) taking arginine with the same volume and concentration and different metal ions or different anions or different biological micromolecule solutions, respectively adding carbon quantum dots with the same volume and deionized water with the same volume to obtain a series of mixed solutions with the same volume and concentration, and respectively carrying out fluorescence intensity detection to realize qualitative detection on arginine;
and 2) taking arginine solutions in different volumes in the step 1), adding carbon quantum dots in the same volume and deionized water in different volumes respectively to prepare a series of arginine standard solutions with the same volume and different concentrations, performing fluorescence intensity detection respectively to obtain a fluorescence spectrogram of the arginine standard solution, and drawing a standard curve and calculating a linear relation by taking the fluorescence intensity of each standard solution as a vertical coordinate and the concentration as a horizontal coordinate to realize quantitative detection of arginine.
5. The method for detecting arginine in an aqueous solution using a luminescent carbon quantum dot according to claim 4, wherein: the concentration of arginine and other different metal ions, anions and biomolecule solutions in the step 1) is 100 mu mol/L, wherein the metal ions are Ag+、Ca2+、K+、Mn2+、Na+、Ni2+、NH4+、Pd2+The anion is Br-、BrO3 -、C2O4 2-、CH3COO-、Cl-、F-、H2PO4 -、I-、N3 -、NO2 -、NO3 -、SO4 2-The biological small molecules are phenylalanine, alanine, methionine, proline, glycine, glutamine, tyrosine, leucine, glucose, serine, threonine, isoleucine and desmosine.
6. The method for detecting arginine in an aqueous solution using a luminescent carbon quantum dot according to claim 5, wherein: the detection limit of the arginine concentration is 78.11 mu M.
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CN110499153B (en) * 2019-07-15 2022-08-19 郑州大学 Mitochondria-positioned carbon dot, preparation method and application of mitochondria-positioned carbon dot in silver ion detection
CN110715914B (en) * 2019-11-05 2022-07-12 鲁东大学 Multi-mode detection method of L-cysteine
CN111117608B (en) * 2019-12-05 2021-09-28 山西大学 Fluorescent probe for quantitatively detecting acidic or basic amino acid based on carbon quantum dot fluorescence quenching or enhancement method and preparation method thereof
CN111517302B (en) * 2020-04-23 2023-04-07 延边大学 Detection of amino acid by luteolin-based carbon dot as MALDI-TOF MS matrix
CN113604213B (en) * 2021-05-18 2024-05-28 深圳先进技术研究院 Nano fluorescent probe and preparation method and application thereof
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