CN113563878A - Multi-emission carbon spot fluorescent probe with large Stokes displacement and preparation method and application thereof - Google Patents

Multi-emission carbon spot fluorescent probe with large Stokes displacement and preparation method and application thereof Download PDF

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CN113563878A
CN113563878A CN202110844180.1A CN202110844180A CN113563878A CN 113563878 A CN113563878 A CN 113563878A CN 202110844180 A CN202110844180 A CN 202110844180A CN 113563878 A CN113563878 A CN 113563878A
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CN113563878B (en
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孔荣梅
吕燕玲
李佩华
梁娜
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Qufu Normal University
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Abstract

The invention belongs to the field of ratio type fluorescent probes, and particularly relates to a multi-emission carbon spot fluorescent probe with large Stokes displacement, and a preparation method and application thereof. The ratiometric fluorescent probe compounds of the invention are novel multiple-emitting Carbon Spots (CDs) with large Stokes shifts, the CDs having a size of 3-7 nm. The invention prepares CDs by a simple one-step solvothermal method. The preparation method is simple and convenient, the materials are easy to obtain, and the prepared CDs have good dispersibility and high stability in aqueous solution and show excellent luminescence characteristics. The invention also provides the application of the CDs in zinc ion detection, which can effectively avoid the interference of the external environment on the detection result and has high sensitivity and selectivity. The ratiometric fluorescent probe successfully realizes the sensitive detection of zinc ions in a serum sample.

Description

Multi-emission carbon spot fluorescent probe with large Stokes displacement and preparation method and application thereof
Technical Field
The invention belongs to the field of ratio type fluorescent probes, and particularly relates to a multi-emission carbon spot fluorescent probe with large Stokes displacement, and a preparation method and application thereof.
Background
Zn2+Quantitative detection has a crucial role in both environmental and biological systems. Zn2+The second major trace element with the content second to that of iron in human body plays an important role in regulating various physiological processes. The traditional method has the defects of expensive instrument, complex operation, difficult maintenance and difficulty in meeting the requirement of large-scale Zn detection2+Compared with the conventional ratiometric fluorescence method, the method has the advantages of convenient operation, high sensitivity and high selectivity, and the fluorescence output signal is hardly interfered by the intensity of a light source, the inherent sensitivity of an instrument and the fluctuation of the background of a matrix, so that the method can be used as a good choice.
CDs are of great interest because of their unique optical properties. CDs have the characteristics of strong light stability, large Stokes displacement, longer fluorescence life and the like, and are widely applied to the fields of biosensing, biological imaging, biomedicine and photoelectric materials. Compared with fluorescent nano materials composed of other elements, CDs have low toxicity and good biocompatibility.
Some CDs-based nanoprobes require the introduction of organic molecules or other nanomaterials as recognition or output signals through covalent linkage, which raises many problems such as complexity of probe structure, toxicity and increased cost. In addition, most nanoprobes are based on a single signal output mode, which generally results in poor selectivity of the nanoprobe and is susceptible to light source intensity fluctuations, probe concentration, background fluorescence and environmental changes.
Disclosure of Invention
According to the defects in the prior art and the combination with the current research frontier, the invention provides the multi-emission carbon spot fluorescent probe with large Stokes displacement and the preparation method and the application thereof, the synthesis method is simple and convenient, the invention has the advantages of easy synthesis, low cost and the like, and the invention can also be used for Zn2+Sensitive detection of (3).
The invention is realized by adopting the following technical scheme:
the invention provides a preparation method of a multi-emission carbon spot fluorescent probe with large Stokes displacement, which specifically comprises the following steps:
1) adding glutathione powder into formamide solution, and fully mixing;
2) heating the solution to 160 ℃ for 2-6 h; cooling to room temperature to obtain a dark green CDs solution;
3) filtering to remove particles with the particle size of more than 0.22 mu m in the CDs solution, and storing at 0-4 ℃ in a shading mode.
Wherein the mass-volume ratio of the glutathione to the formamide solution in the step 1) is 0.03-0.04 g/mL.
Specifically, the solution in the step 2) is heated in a reaction kettle for reaction.
The invention also provides a multi-emission carbon spot fluorescent probe with large Stokes displacement, which is prepared by the preparation method, wherein the particle size of the carbon spot is 3-7nm, and the average particle size is 5.0 nm.
Meanwhile, the invention also provides application of the carbon spot multiple-emitting fluorescent probe, wherein the mass concentration of the carbon spot multiple-emitting fluorescent probe is 0.0174g/mL, and the carbon spot multiple-emitting fluorescent probe is used for Zn with the concentration range of 0-2 mu M2+And (5) detecting the solution.
Further, as a preferred embodiment of the present invention, the CDs solution is mixed with Zn2+Uniformly mixing the standard substance solution, reacting at room temperature for 15-30 min, wherein the pH range is 5-8, and then reacting according to F650/F685Establishing a standard curve equation for Zn according to the change of the fluorescence intensity ratio2+And (4) quantitatively detecting the solution.
Further, as a preferable embodiment of the present invention, the reaction time is 20min, and the pH range is 7.
Compared with the prior art, the invention has the beneficial effects that:
the CDs are prepared by a simple one-step solvothermal method, as shown in figure 1. The preparation method is simple and convenient, the materials are easy to obtain, and the prepared CDs have good dispersibility and high stability in aqueous solution and show excellent luminescence characteristics. Based on CDs and Zn2+Designed by chelation between them, excitation at 420nmAt wavelength, CDs were prepared with three emission peaks at 470, 650 and 685nm, respectively. In the long wavelength emission region (Stokes shift 230nm), Zn2+Not only can effectively quench the fluorescence intensity at 685nm, but also can obviously enhance the fluorescence intensity at 650 nm. Furthermore, the ratio of fluorescence intensity at emission peaks of 650nm and 685nm (F)650/F685) With Zn2+The concentration increases. The application of the CDs in zinc ion detection can effectively avoid the interference of the external environment on the detection result, and has high sensitivity and selectivity.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention.
In the drawings:
FIG. 1 is a schematic diagram of the preparation and application process of a multi-emission carbon spot fluorescent probe with large Stokes shift provided by the present invention;
FIG. 2 is a fluorescence emission spectrum of CDs synthesized at different times in examples 1-3;
FIG. 3 is a high power transmission electron micrograph of CDs in example 1;
FIG. 4 is a graph showing the particle size distribution of CDs in example 1;
FIG. 5 is an X-ray single crystal diffractogram of CDs in example 1;
FIG. 6 is an X-ray photoelectron spectrum of CDs of example 1;
FIG. 7 is an X-ray photoelectron spectrum of C1s of CDs of example 1;
FIG. 8 is an X-ray photoelectron spectrum of N1s of CDs of example 1;
FIG. 9 is an X-ray photoelectron spectrum of O1s of CDs in example 1;
FIG. 10 is an X-ray photoelectron spectrum of S2 p of CDs in example 1;
FIG. 11 is a fluorescence excitation (Ex), emission (Em) spectrum of CDs in example 1;
FIG. 12 shows CDs, CDs + Zn in example 12+Fluorescence emission and excitation spectra of (a);
FIG. 13 is the response of CDs to different ions in example 1, wherein the concentrations of the metal ions are all 1. mu.M;
FIG. 14 is Zn2+Fluorescence lifetime plots of CDs before and after addition;
FIG. 15 is Zn2+Adding the ultraviolet-visible absorption spectra of the CDs before and after adding;
FIG. 16 is Zn2+Adding fluorescence emission spectrum and excitation spectrum of CDs before and after adding;
FIG. 17 is a concentration optimization curve for CDs;
FIG. 18 is a pH conditioning optimization curve for CDs;
FIG. 19 is a time optimized plot of CDs;
FIG. 20 shows application of CDs fluorescent probe to Zn2+Detection, fluorescence intensity ratio (F)650/F685) For Zn2+A concentration response curve; wherein, F650And F685The fluorescence intensities of CDs at 650nm and 685nm, respectively.
FIG. 21 is F650/F685With Zn2+A linear plot of concentration;
FIG. 22 is Zn2+The concentration is in the range of 0-2. mu.M with F650/F685Is shown in linear relationship.
Detailed Description
In order to make the purpose and technical solution of the present invention more apparent, the present invention is further described in detail below with reference to the accompanying drawings. The experimental methods described in the following examples are all conventional methods unless otherwise specified; the specific techniques or conditions are not indicated in the examples, and the techniques or conditions are described in the literature in the field or according to the product specification; the reagents and materials are commercially available, unless otherwise specified.
Firstly, preparing a multi-emission carbon spot fluorescent probe with large Stokes shift:
example 1
0.68g of reduced Glutathione (GSH) was dissolved in 20mL of formamide, sonicated at room temperature for 2min, and mixed well. After mixing uniformly, the solution is transferred to a hydrothermal reaction kettle. The reaction was heated to 160 ℃ and the reaction time lasted 4 h. After cooling at room temperature, a dark green solution was finally obtained. The large particle size spots in the CDs were removed by filtration through a cylindrical membrane filter (0.22 μm) and finally the CDs were prepared to completion, giving an original carbon spot concentration of 1.174 g/mL.
Example 2
In contrast to example 1, the heating time of the reaction lasted 2 h.
Example 3
In contrast to example 1, the heating time of the reaction lasted 6 h.
Second, property detection analysis of fluorescent probe
As can be seen from FIG. 2, the fluorescence emission spectra of CDs synthesized in examples 1-3 at different times are the best in optical performance of CDs synthesized in 4h, and then the CDs synthesized in example 1 are subsequently detected.
FIG. 3 is a high-power Transmission Electron Micrograph (TEM) of CDs prepared in example 1, from which it is clear that the synthesized CDs have good dispersibility in aqueous solution and uniform particle size of 3-7 nm. FIG. 4 is a graph showing a distribution of the particle diameters of CDs, and the average particle diameter is 5.0nm as a result of counting the sizes of hundreds of particles of CDs. Fig. 5 is an XRD pattern of CDs, with the broad peak at 23.88 ° 2 θ corresponding to the (002) plane of graphite, indicating the presence of graphitic carbon domains in the prepared CDs.
FIGS. 6-10 are XPS plots of CDs showing the presence of C, N, O, S four elements, the high resolution spectra of C1S showing C-C/C-C, C-S, N-C-O, respectively, the high resolution spectra of N1S showing C-N-C, pyrrole N and graphite N, respectively, the high resolution spectra of S2 p corresponding to thiolate, 2p of S, respectively3/2And 2p1/2The high resolution spectrum of S ═ O, O1S of (a) shows C-O, C ═ O, C-O-C/C-OH.
FIG. 11 is an excitation and emission spectrum of CDs prepared in example 1, from which it is clear that the excitation wavelength of CDs is about 420nm, and there are three fluorescence emission peaks at 470nm, 650nm and 685nm, respectively.
Thirdly, the fluorescent probe is used for the zinc ion (Zn) in the solution2+) Detection of (2):
100 mu L of Zn with different concentrations2+Adding the solution into 400 μ L CDs solution (diluted 100 times with PBS), mixing, reacting at room temperature for 25minF650/F685Change of fluorescence intensity ratio by Zn2+And (4) carrying out quantitative detection.
As can be seen from FIG. 12, the fluorescence intensity of CDs at 650nm is weak, and the fluorescence intensity at 685nm is strong; zn at a concentration of 2. mu.M2+The fluorescence intensity at 650nm can be increased and the fluorescence intensity at 685nm can be decreased.
As shown in FIG. 13, the CDs have different response degrees to different ions, wherein the concentration of metal ions is 1 μ M, and the fluorescent nanoprobe based on CDs can detect Zn with ultra-sensitivity2+。
As can be seen from FIG. 14, Zn2+When present, the intensity at 423nm, the maximum excitation wavelength for the emission peak at 650nm, is significantly increased, while the intensity at 416nm, the maximum excitation wavelength for the emission peak at 685nm, is decreased. As can be seen from FIG. 15, Zn compared to CDs alone2+The UV-Vis absorption spectrum of CDs in the presence of the fluorescent dye has an increased absorption at 423nm, which is well matched with the fluorescence excitation and emission spectra. As shown in FIG. 16, the fluorescence lifetime was slightly changed in the average fluorescence lifetime, and it was confirmed that CDs-Zn was present2+And (4) forming a complex.
FIGS. 17-19 are CDs + Zn concentration optimization curves for examples of the present invention2+Incubation time and pH were optimized. As can be seen in FIG. 17, the fluorescence intensity increased and then decreased with increasing dilution factor of CDs. FIG. 18 shows the fluorescence response of CDs in various pH environments (pH 5.0-pH 9.0). The dual emission intensity of CDs remained almost constant over the pH range of 5.0 to 8.0, but as the pH increased from 8.0 to 9.0, the fluorescence intensity at 685nm decreased significantly and increased significantly at 650 nm. As can be seen from FIG. 19, F650/F685Increases with increasing reaction time and remains almost unchanged after 15 min. The optimal CDs concentration is 0.01174g/mL, the optimal incubation time is 20min, and the optimal pH condition is 7.0.
FIG. 20 is a graph of novel multi-emission CDs with large Stokes shifts versus Zn concentration range of 0-4 μ M for example 1 of the present invention2+The response curve of (c). Zn is carried out under optimum conditions2+With quantitative detection of Zn2+The concentration is increased, the fluorescence intensity of CDs at 650nm is gradually increased,and gradually decreases at 685 nm. Accordingly, F650/F685Following Zn2+The concentration increases gradually, indicating that the proposed method is for Zn2+The detection of fluorescence of (2) is feasible. FIG. 21 shows Zn2+Concentration and F650/F685(ratio of fluorescence intensity at 650nm to 685nm emission peak) and the CDs vs Zn can be seen in FIG. 222+Has good linearity, and the linearity range is 0 to 2 mu M. It is shown that the novel multi-emission CDs with large Stokes shift in the present example can be successfully applied in the ratiometric fluorescence detection of Zn2+。
As shown in table 1, the recovery rate ranged from 95.0% to 105.0% at a Relative Standard Deviation (RSD) of less than 5.0%. The results show that the CDs-based ratiometric fluorescent nanoprobes can realize Zn in human serum samples2+The great potential of quantitative determination.
Table 1 results of recovery of zinc ions in serum samples.
Figure BDA0003179893450000051
It should be understood that the above description is only a preferred embodiment of the present invention, and not intended to limit the present invention, and although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications and equivalents may be made in the technical solutions described in the foregoing embodiments, or some technical features may be substituted. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (7)

1. A preparation method of a multi-emission carbon spot fluorescent probe with large Stokes displacement is characterized by comprising the following steps:
1) adding glutathione powder into formamide solution, and fully mixing;
2) heating the solution to 160 ℃ for 2-6 h; cooling to room temperature to obtain a dark green CDs solution;
3) filtering to remove particles with the particle size of more than 0.22 mu m in the CDs solution, and storing at 0-4 ℃ in a shading mode.
2. The preparation method according to claim 1, wherein the mass-to-volume ratio of the glutathione to the formamide solution in the step 1) is in a range of 0.03 to 0.04 g/mL.
3. The preparation method according to claim 2, wherein the solution in the step 2) is heated in a reaction kettle for reaction.
4. A multi-emission carbon spot fluorescent probe having a large Stokes shift prepared by the preparation method of any one of claims 1 to 3, wherein the carbon spot has a particle diameter of 3 to 7nm and an average particle diameter of 5.0 nm.
5. Use of the carbon multi-emission-spot fluorescent probe according to claim 4, wherein the carbon spot mass concentration of the carbon multi-emission-spot fluorescent probe is 0.0174g/mL, and the carbon multi-emission-spot fluorescent probe is used for Zn with the concentration range of 0-2 μ M2+And (5) detecting the solution.
6. Use of the multiple-emission carbon-spot fluorescent probe according to claim 5, wherein the CDs solution is mixed with Zn2+Uniformly mixing the standard substance solution, reacting at room temperature for 15-30 min, wherein the pH range is 5-8, and then reacting according to F650/F685Establishing a standard curve equation for Zn according to the change of the fluorescence intensity ratio2+And (4) quantitatively detecting the solution.
7. The use of the carbon multi-emission spot fluorescent probe according to claim 6, wherein the reaction time is 20min and the pH range is 7.
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