CN110982514A - Preparation method of carbon dot fluorescent probe, product and application thereof - Google Patents

Preparation method of carbon dot fluorescent probe, product and application thereof Download PDF

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CN110982514A
CN110982514A CN201911290128.5A CN201911290128A CN110982514A CN 110982514 A CN110982514 A CN 110982514A CN 201911290128 A CN201911290128 A CN 201911290128A CN 110982514 A CN110982514 A CN 110982514A
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fluorescent probe
carbon dot
dot fluorescent
amino acid
preparation
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叶李薇
彭华乔
李林
刘曦非
张亚博
王强
张帆
王天明
苏正良
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Second Research Institute of CAAC
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    • 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"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
    • G—PHYSICS
    • 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"
    • G01N2021/6432—Quenching

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Abstract

The invention discloses a preparation method of a carbon dot fluorescent probe, which comprises the steps of stirring and dispersing umbelliferone derivatives and amino acid in an aqueous solution, reacting for 12-15 hours at 180-200 ℃, centrifuging suspension to remove large particles, filtering supernate through a filter membrane of 0.22-0.25 mu m, completely removing the large particles, dialyzing, and freeze-drying to obtain a product. The material can realize the aim of Fe3+High sensitivity and high selectivity. The invention not only provides a synthesis strategy of the carbon dot hybrid material, but also opens up a new way for ion detection, and realizes high selectivity and specific identification of iron ions in the water phase.

Description

Preparation method of carbon dot fluorescent probe, product and application thereof
Technical Field
The invention belongs to the field of organic small-molecule fluorescent probes, and relates to a preparation method of a carbon dot fluorescent probe, and a product and application thereof.
Technical Field
Iron element is inevitably introduced in the transportation and storage processes of aviation oil, and is ionized into iron ions in the presence of trace water, so that irreversible slow corrosion is caused to pipelines and containers. The existence of iron ions cannot be observed from the appearance, the time for adding the corrosion inhibitor again cannot be intuitively judged by adding the corrosion inhibitor, and the experience period for adding the corrosion inhibitor can be obtained only by repeated sampling test and data analysis for many times. However, the transportation condition is influenced by various conditions, the experience period cannot well match the actual condition, the corrosion condition is often more serious than the expected corrosion condition, and the iron ion corrosion cannot be well prevented.
Disclosure of Invention
In view of this, the invention provides a preparation method of a carbon dot fluorescent probe, a product and an application thereof. The technical scheme is as follows:
1. a preparation method of a carbon dot fluorescent probe is characterized by comprising the following steps: stirring and dispersing the umbelliferone derivative and the amino acid in an aqueous solution, reacting for 12-15 hours at 180-200 ℃, centrifuging the suspension to remove large particles, filtering the supernatant with a 0.22-0.25 mu m filter membrane to completely remove the large particles, dialyzing, and freeze-drying to obtain the product.
Further, the umbelliferone derivative is 4-methylumbelliferone, and the amino acid is D-arginine.
Furthermore, the cut-off molecular weight of the dialysis is 200 Da-250 Da, and the time is 2-3 hours.
Further, the molar ratio of the umbelliferone to the amino acid is 0.8: 1-1: 1.3.
Further, the molar ratio of the umbelliferone to the amino acid is 1:1.
Furthermore, the rotating speed of the centrifugation is 10000-20000 revolutions per minute.
2. The carbon dot fluorescent probe is prepared according to the preparation method.
3. The carbon dot fluorescent probe is used for detecting Fe in free water of aviation oil3+The application of (1).
The invention has the beneficial effects that: the umbelliferone/carbon dot hybrid composite material (namely CDs-4-MU) is successfully prepared by a simple one-step hydrothermal synthesis method, D-arginine forms carbon dots by itself, and 4-methyl umbelliferone is used as an additive to form the hybrid material. For CD-4-MU to Fe3+The research on the fluorescent response behavior shows that the material can realize the effect on Fe3+High sensitivity and high selectivity. Because CDs-4-MU and Fe3+The electron transfer process between the two leads to CDs-4-MU-Fe3+The generation of complexes and the phenomenon of fluorescence quenching. The invention not only provides a synthesis strategy of the carbon dot hybrid material, but also opens up a new way for ion detection, and realizes high selectivity and specific identification of iron ions in the water phase.
Drawings
In order to make the object, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings for explanation:
FIG. 1 shows the stability of carbon spot fluorescent probe CDs-4-MU at different irradiation time, different solvent, different ionic strength and different temperature
FIG. 2 Effect of different metal cations (concentration. about.1 mM) on the fluorescence intensity of carbon spot fluorescence probe CDs-4-MU
FIG. 3 shows a carbon spot fluorescent probe CDs-4-MU and different concentrations of Fe3+Fluorescence spectrum at excitation wavelength λ 378nm after mixing.
Detailed Description
The following detailed description of preferred embodiments of the invention refers to the accompanying drawings.
Example 1
0.25mmol of 4-methylumbelliferone was dispersed in a solution containing 10mL of ultrapure water and 0.25mmol of D-arginine with gentle stirring. Transferring the mixture into 50ml stainless steel autoclave lined with polytetrafluoroethylene, heating the autoclave to 180 deg.C and maintaining for 12h, naturally cooling to room temperature, centrifuging the obtained suspension at 10000 rpm for 5min to remove large particles, and filtering the supernatant with 0.22 μm water film to further completely remove the large particles. Finally, the crude solution was diluted with 10ml of ultrapure water, and dialyzed for 2 hours with stirring in a cellulose ester membrane bag (molecular weight cut-off 200Da) to obtain a purified product. After lyophilization, the yellowish brown powder was collected and redissolved as a stock solution in ultrapure water at a concentration of 0.5mg/mL (referred to as CDs-4-MU).
Example 2
0.5mmol of 4-methylumbelliferone was dispersed in a solution containing 20mL of ultrapure water and 0.5mmol of D-arginine with gentle stirring. The mixture was transferred into a 100ml stainless steel autoclave lined with polytetrafluoroethylene, the temperature of the autoclave was heated to 190 ℃ and maintained for 14 hours, after naturally cooling to room temperature, the resulting suspension was centrifuged at 20000 rpm for 5 minutes to remove large particles, and then the supernatant was filtered through a 0.22 μm water membrane to further completely remove large particles. Finally, the crude solution was diluted with 20ml of ultrapure water, and dialyzed for 2 hours with stirring in a cellulose ester membrane bag (molecular weight cut-off 200Da) to obtain a purified product. After lyophilization, the yellowish brown powder was collected and redissolved as a stock solution in ultrapure water at a concentration of 0.5mg/mL (referred to as CDs-4-MU).
Example 3
1mmol of 4-methylumbelliferone was dispersed in a solution containing 40mL of ultrapure water and 1mmol of D-arginine with gentle stirring. The mixture was transferred into a 200ml stainless steel autoclave lined with polytetrafluoroethylene, the temperature of the autoclave was heated to 200 ℃ and maintained for 15 hours, after naturally cooling to room temperature, the resulting suspension was centrifuged at 15000 rpm for 5 minutes to remove large particles, and then the supernatant was filtered through a 0.22 μm water membrane to further completely remove large particles. Finally, the crude solution was diluted with 40ml of ultrapure water, and dialyzed for 2 hours with stirring in a cellulose ester membrane bag (molecular weight cut-off 200Da) to obtain a purified product. After lyophilization, the yellowish brown powder was collected and redissolved as a stock solution in ultrapure water at a concentration of 0.5mg/mL (referred to as CDs-4-MU).
Test example 1 stability analysis of CDs-4-MU
The stability of the CDs-4-MU obtained in example 1 was determined at different irradiation times (fig. 1a), different solvents (fig. 1b), ion strength (fig. 1c) and different temperatures (fig. 1d) at an excitation wavelength λ 378 nm. 0.25mL of CDs-4-MU (0.25mg/mL) is added into an aqueous solution at 10-60 ℃, and the influence of the ionic strength and the excitation time on the fluorescence intensity of the CDs-4-MU is measured. Preparing CDs-4-MU, mixing with NaCl solution of different concentration, continuously exciting for 10min, recording corresponding emission spectrum on RF-6000 instrument, and measuring the results of the above groups at least three times.
As shown in fig. 1a, stability analysis of fluorescence quenching or decay was performed by exposing the CDs-4-MU solution to continuous ultraviolet irradiation (λ 378nm), and it can be seen that the fluorescence intensity of the CDs-4-MU solution was not decreased even under 10 minutes of ultraviolet irradiation.
As shown in FIG. 1b, the fluorescence properties of CDs-4-MU dispersed in different media such as ultrapure water, PBS and tris-HCl buffer remained well consistent and stable.
As shown in FIG. 1c, the fluorescence intensity of the CDs-4-MU solution was almost unchanged in NaCl solutions of different concentrations.
As shown in FIG. 1d, the fluorescence intensity of the CDs-4-MU solution also showed no visible decay when the solution was heated from 10 ℃ to 60 ℃.
Therefore, the synthesized CDs-4-MU has obvious long-term stability under various environmental conditions, and a good fluorescent probe platform is provided for further ion relay detection.
Test example 2 ion detection and Selective analysis
250 μ L CDs-4-MU (concentration 0.25mg/mL) and 250 μ L Fe3+After the solution (concentration: 1mM) was added to 2ml tris-HCl buffer (pH: 7.0,10mM) and the like at room temperature for 2 minutes, the resulting solution was transferred to a quartz cuvette (1 × 1cm), and the fluorescence spectrum was measured at an excitation wavelength λ 378. The effect of other cations (concentration ═ 1mM) on the fluorescence intensity of CDs-4-MU solutions was measured under similar conditions as described above, and the results are shown in fig. 2.
As can be seen from FIG. 2, the fluorescence intensity of common metal ions such as silver ion, aluminum ion, calcium ion, copper ion, magnesium ion, zinc ion, etc. hardly changed, and the fluorescence intensity was changed only by adding Fe3+The later change is obvious, so that other metal ions do not generate any interference on the detection result, and the higher selectivity of the fluorescent probe on iron ions can be proved.
Test example 3 detection of sensitivity
CDs-4-MU to Fe was systematically studied by fluorescence titration3+The detection sensitivity of (3). mu.L of CDs-4-MU solution (0.25mg/mL) was mixed with 2mL of Tris-HCl buffer (pH 7.0,10mm) and then Fe was added at various concentrations3+And (3) solution, so that the total volume of the mixed solution is kept constant. All samples (in CDs-4-M-Fe)3+Meter) were measured at an excitation wavelength λ 378nm, and the results are shown in fig. 3.
As can be seen in FIG. 3a, with Fe3+Increasing the concentration (0-250 μ M), the fluorescence intensity of the CDs-4-MU solution gradually decreased at λ 483 nm. Finally, the fluorescence intensity reaches a constant value which does not follow Fe3+The concentration was changed with increasing concentration (concentration 300-.
Adding Fe with different concentrations under the irradiation of ultraviolet light (lambda is 365nm)3+Before and after, the whole fluorescence quenching process was recorded using the fluorescence quenching ratio (F0/F) q, i.e., CDs-4-MU solution in the absence of Fe3+And has Fe3+The ratio of the initial fluorescence intensity to the current fluorescence intensity in the presence of the fluorescent probe was used to study the fluorescence intensity of the CDs-4-MU probe and Fe3+Ion concentration relationship. Through computer fitting and data processing, the corresponding linear equation and correlation index are obtained, as shown in fig. 3 b. Apparently, these results confirm that (F0/F) q and Fe are in the range of 0.35-200. mu.M3+There is a good linear relationship between the concentrations.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.

Claims (8)

1. A preparation method of a carbon dot fluorescent probe is characterized by comprising the following steps: stirring and dispersing the umbelliferone derivative and the amino acid in an aqueous solution, reacting for 12-15 hours at 180-200 ℃, centrifuging the suspension to remove large particles, filtering the supernatant with a 0.22-0.25 mu m filter membrane to completely remove the large particles, dialyzing, and freeze-drying to obtain the product.
2. The method for preparing a carbon dot fluorescent probe according to claim 1, characterized in that: the umbelliferone derivative is 4-methylumbelliferone, and the amino acid is D-arginine.
3. The method for preparing a carbon dot fluorescent probe according to claim 1, characterized in that: the cut-off molecular weight of the dialysis is 200 Da-250 Da, and the time is 2-3 hours.
4. The method for preparing a carbon dot fluorescent probe according to claim 1, characterized in that: the molar ratio of the umbelliferone to the amino acid is 0.8: 1-1: 1.3.
5. The method for preparing a carbon dot fluorescent probe according to claim 1, characterized in that: the molar ratio of the umbelliferone to the amino acid is 1:1.
6. The method for preparing a carbon dot fluorescent probe according to claim 1, characterized in that: the centrifugal rotating speed is 10000-20000 revolutions per minute.
7. A carbon dot fluorescent probe prepared by the preparation method according to any one of claims 1 to 6.
8. The method for detecting free water in aviation oil by using carbon dot fluorescent probe according to claim 7Middle Fe3+The application of (1).
CN201911290128.5A 2019-12-16 2019-12-16 Preparation method of carbon dot fluorescent probe, product and application thereof Pending CN110982514A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111521594A (en) * 2020-05-13 2020-08-11 重庆工程职业技术学院 Novel nano-composite, preparation method thereof and application thereof in sewage detection
CN113295663A (en) * 2021-05-24 2021-08-24 临沂大学 Iron ion photoelectric sensor with ITO (indium tin oxide) as substrate and preparation method thereof

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KR20190071932A (en) * 2017-12-15 2019-06-25 가천대학교 산학협력단 Method of preparing carbon quantum dots from broccoli and method for detecting silver
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111521594A (en) * 2020-05-13 2020-08-11 重庆工程职业技术学院 Novel nano-composite, preparation method thereof and application thereof in sewage detection
CN113295663A (en) * 2021-05-24 2021-08-24 临沂大学 Iron ion photoelectric sensor with ITO (indium tin oxide) as substrate and preparation method thereof
CN113295663B (en) * 2021-05-24 2022-04-26 临沂大学 Iron ion photoelectric sensor with ITO (indium tin oxide) as substrate and preparation method thereof

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