A detection probe based on naphthalene imide derivatives, preparation method and application thereof

Abstract

The present invention provides a detection probe based on naphthalimide derivatives, a preparation method thereof and applications thereof. The preparation method of the detection probe is as follows: S1. A mixture of compound I, imidazole and anhydrous potassium carbonate is added to a solvent and stirred to dissolve, and then heated and reacted under nitrogen protection, and cooled to room temperature to obtain a mixed solution; S2. The mixed solution is filtered, and then the obtained crude product solution is distilled under reduced pressure to remove the solvent to obtain a solid product; S3. The solid product is separated by column chromatography silica gel and then purified with an eluent to obtain a solid compound II, which is the detection probe based on naphthalimide derivatives. The detection probe in the present invention is used for the detection of ClO-, Fe3+, Cr3+, Al3+, has high selectivity and high sensitivity, realizes in-situ, real-time and ratio response, the detection limit can reach the order of 10-9 mol / L, and the preparation method of the detection probe is simple and easy to operate, and the cost is low, which can meet the simultaneous detection of multiple ions.

Description

Technical Field

[0001] The present invention belongs to the technical field of optical sensing imaging detection, and in particular relates to a detection probe based on naphthaleneimide derivatives, a preparation method and application thereof. Background Art

[0002] In the field of environmental monitoring and life health, heavy metal detection is of great significance. Trivalent metal ions (such as Fe 3+ ,Cr 3+ , Al 3+ ) will eventually enter the human body through various channels. Imbalance in the body will cause a series of diseases, such as brain damage, cancer and kidney disease. Both the lack and excess of iron in the human body will induce biological disorders and lead to a series of diseases related to iron metabolism. This requires an effective means to quickly detect such heavy metal ions.

[0003] Hypochlorite ion is an important small molecule among active oxides. As an unstable weak acid, it is widely used in bleaching agents and disinfectants in life. In biological systems, hypochlorite, as an indispensable biologically active oxide, plays an important role in the redox balance in cells. Since the fluorescence analysis method has the advantages of good selectivity, high sensitivity and small sample size, it has a wide range of applications in scientific fields such as chemistry, medicine and environmental science. The use of fluorescent probe technology for the detection of hypochlorite ions and various heavy metals is of great significance, but the fluorescent probes in the prior art cannot well meet the needs of simultaneous detection of multiple ions.

[0004] Therefore, it is necessary to provide an improved technical solution to address the above-mentioned deficiencies in the prior art. Summary of the invention

[0005] In view of the above-mentioned shortcomings of the prior art, the object of the present invention is to provide a detection probe based on naphthalene imide derivatives, a preparation method and application thereof, so as to solve the problem that the fluorescent probe in the prior art cannot meet the requirements of simultaneous detection of multiple ions.

[0006] To achieve the above objectives and other related objectives, the present invention provides a detection probe based on naphthalene imide derivatives, the chemical structure of the detection probe is as follows:

[0007]

[0008] Preferably, the preparation method comprises the following steps:

[0009] S1. Add a mixture of compound I, imidazole and anhydrous potassium carbonate into a solvent, stir and dissolve, then heat and react for a period of time under nitrogen protection, and then cool to room temperature to obtain a mixed solution, wherein the chemical structure of compound I is as follows:

[0010]

[0011] S2, filtering the mixed solution, and then distilling the obtained crude product solution under reduced pressure to remove the solvent to obtain a solid product;

[0012] S3. Separate the solid product by column chromatography on silica gel, and then purify it with an eluent to obtain a solid compound II, which is a detection probe based on naphthaleneimide derivatives.

[0013] Preferably, in step S1, the molar ratio of the compound I to the imidazole is 1:3 to 1:5.

[0014] Preferably, in step S1, the molar ratio of the imidazole to the anhydrous potassium carbonate is 1:1 to 1:1.5.

[0015] Preferably, in step S1, the mass ratio of the total mass of the compound I, the imidazole and the anhydrous potassium carbonate to the mass ratio of the solvent is 1:3 to 1:8.

[0016] Preferably, the solvent in step S1 is acetonitrile.

[0017] Preferably, the temperature of the heating reaction in step S2 is 85-100° C., and the time of the heating reaction is 48-80 hours.

[0018] Preferably, the eluent in step S3 is a mixture of ethyl acetate / dichloromethane, or a mixture of methanol / ethyl acetate / dichloromethane.

[0019] Preferably, the volume ratio of ethyl acetate to dichloromethane in the ethyl acetate / dichloromethane mixture is 1:1; and the volume ratio of methanol, ethyl acetate and dichloromethane in the methanol / ethyl acetate / dichloromethane mixture is 1:2:3 to 1:2:4.

[0020] The present invention also provides an application of a detection probe based on a naphthalene imide derivative, wherein the detection probe is used for ClO - , Fe 3+ Cr 3+ 、Al 3+ The detection comprises the following steps: preparing the detection probe to a concentration of 1×10 -5 mol / L solution, to which different concentrations of ClO - , Fe 3+ Cr 3+ or Al 3+ ions, and measuring the fluorescence intensity of the solution at different wavelengths to obtain the detection probe for ClO - , Fe 3+ Cr 3+or Al 3+ Fluorescence emission spectra of ions.

[0021] As described above, the detection probe based on naphthalene imide derivatives, the preparation method and the application thereof of the present invention have the following beneficial effects:

[0022] The detection probe based on naphthalene imide derivatives of the present invention is for ClO - , Fe 3+ Cr 3+ 、Al 3+ The detection of ions is highly selective and sensitive, and can achieve in-situ, real-time, and ratio response, with a detection limit of 10 -9 The order of mol / L.

[0023] The preparation method of the detection probe based on naphthalene imide derivatives in the present invention is simple, easy and low-cost. The use of naphthalene imide dyes as optical signal reporting groups can meet the requirements of simultaneous detection of multiple ions, not only for ClO - It has fast ion response, high selectivity, high detection sensitivity, and can also be used for the detection of trivalent heavy metal ions. The method is simple and easy to promote and apply. Naphthalimide derivatives can be used as a platform to design probes for the recognition of a variety of molecules or ions. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 The detection probe based on naphthalene imide derivatives in the specific embodiment of the present invention is shown as ClO - , Fe 3+ Cr 3 + 、Al 3+ Diagram of the detection and recognition mechanism.

[0025] Figure 2 Shown is the mass spectrum of the detection probe prepared in Example 1 of the present invention.

[0026] Figure 3 The detection probe prepared in Example 1 of the present invention is shown 1 H NMR (400MHz) nuclear magnetic spectrum.

[0027] Figure 4 The detection probe prepared in Example 1 of the present invention is shown 13 C NMR (100MHz) nuclear magnetic spectrum.

[0028] Figure 5 It shows that the detection probe in Application Example 1 of the present invention is ClO at different concentrations - Fluorescence emission spectra of .

[0029] Figure 6It is shown that the detection probe pair ClO in Application Example 1 of the present invention - Detection limit test data plot in .

[0030] Figure 7 It is shown that the detection probe of the present invention in Application Example 2 is different in Fe concentration. 3+ Fluorescence emission spectra of .

[0031] Figure 8 It is shown that the detection probe of Fe in Application Example 2 of the present invention 3+ Detection limit test data plot in .

[0032] Fig. 9 The results show that the detection probe in Application Example 3 of the present invention is different in concentration of Cr 3+ Fluorescence emission spectra of .

[0033] Fig.10 It is shown that the detection probe of Cr in Application Example 3 of the present invention 3+ Detection limit test data plot in .

[0034] Fig.11 It shows that the detection probe in Application Example 4 of the present invention is different in concentration of Al 3+ Fluorescence emission spectra of .

[0035] Fig.12 It is shown that the detection probe is Al in Application Example 4 of the present invention 3+ Detection limit test data plot in . DETAILED DESCRIPTION

[0036] The following describes the embodiments of the present invention through specific examples, and those skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and the details in this specification can also be modified or changed in various ways based on different viewpoints and applications without departing from the spirit of the present invention.

[0037] The present invention provides a detection probe based on naphthalene imide derivatives, and the chemical structural formula of the detection probe is as follows:

[0038]

[0039] The present invention provides a method for preparing a detection probe based on naphthaleneimide derivatives, and the preparation method comprises the following steps:

[0040] S1. Add a mixture of compound I, imidazole and anhydrous potassium carbonate into a solvent, stir and dissolve, then heat and react for a period of time under nitrogen protection, and then cool to room temperature to obtain a mixed solution, wherein the chemical structure of compound I is as follows:

[0041]

[0042] S2, filtering the mixed solution, and then distilling the obtained crude product solution under reduced pressure to remove the solvent to obtain a solid product;

[0043] S3. The solid product is separated by column chromatography on silica gel and then purified by an eluent to obtain a solid compound II, which is a detection probe based on naphthaleneimide derivatives.

[0044] Specifically, the column chromatography silica gel in step S3 is white uniform particles, the main component of which is silicon dioxide. It is a colloidal system with solid characteristics and is composed of colloidal particles that form an agglomerated structure. The colloidal particles are condensation products of hydrated silica gel (polysilicic acid) and are amorphous substances. The gaps between the aggregates of the colloidal particles form a microporous structure inside the reagent column chromatography silica gel particles. It is a high-quality adsorption material with rich microporous structure, high specific surface area, high purity and high activity. The column chromatography silica gel can be those known to those skilled in the art and is not excessively restricted herein.

[0045] As an example, the molar ratio of compound I to imidazole in step S1 is 1:3 to 1:5.

[0046] Specifically, the molar ratio of compound I to imidazole in step S1 may include values ​​within any range such as 1:3, 1:3.5, 1:4, 1:4.5, 1:5, etc., and may be adjusted according to actual conditions.

[0047] As an example, the molar ratio of imidazole to anhydrous potassium carbonate in step S1 is 1:1 to 1:1.5.

[0048] Specifically, the molar ratio of imidazole to anhydrous potassium carbonate in step S1 may include values ​​within any range such as 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, etc., and may be adjusted according to actual conditions.

[0049] As an example, in step S1, the mass ratio of the total mass of compound I, imidazole and anhydrous potassium carbonate to the solvent is 1:4 to 1:8.

[0050] Specifically, the mass ratio of the total mass of compound I, imidazole and anhydrous potassium carbonate to the solvent in step S1 may include values ​​within any range such as 1:4, 1:5, 1:6, 1:7, 1:8, etc., and can be adjusted according to actual conditions.

[0051] As an example, the solvent in step S1 is acetonitrile.

[0052] As an example, the temperature of the heating reaction in step S2 is 85-100° C., and the time of the heating reaction is 48-80 hours.

[0053] Specifically, the temperature of the heating reaction in step S2 may include a value within any range such as 85°C, 90°C, 95°C, 100°C, etc., which can be adjusted according to actual conditions; the time of the heating reaction may include a value within any range such as 48h, 54h, 60h, 66h, 72h, 80h, etc., which can be adjusted according to actual conditions.

[0054] As an example, the eluent in step S3 is a mixture of ethyl acetate / dichloromethane, or a mixture of methanol / ethyl acetate / dichloromethane.

[0055] As an example, the volume ratio of ethyl acetate to dichloromethane in a mixture of ethyl acetate / dichloromethane is 1:1; the volume ratio of methanol, ethyl acetate and dichloromethane in a mixture of methanol / ethyl acetate / dichloromethane is 1:2:3 to 1:2:4.

[0056] Specifically, the volume ratio of methanol, ethyl acetate and dichloromethane in the mixture of methanol / ethyl acetate / dichloromethane may include values ​​within any range such as 1:2:3, 1:2:3.2, 1:2:3.4, 1:2:3.6, 1:2:3.8, 1:2:4, etc., and may be adjusted according to actual conditions.

[0057] The present invention also provides an application of a detection probe based on a naphthalene imide derivative, the detection probe is used for ClO - , Fe 3+ Cr 3+ 、Al 3+ The detection comprises the following steps: preparing the detection probe to a concentration of 1×10 -5 mol / L solution, to which different concentrations of ClO - , Fe 3+ Cr 3+ or Al 3+ ions, measure the fluorescence intensity of the solution at different wavelengths, and obtain the detection probe to detect ClO - , Fe 3+ Cr 3+ or Al 3+ Fluorescence emission spectra of ions.

[0058] Specifically, the detection probe based on naphthalene imide derivatives was first prepared to a concentration of 5×10 -3 mol / L DMF solution, save it for later use, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L detection solution.

[0059] The detection mechanism of the detection probe is shown in Figure 1 When the detection probe is 3+ (Fe 3+ Cr3+ 、Al 3+ ), the carbonyl O atom and N atom on the naphthalene imide and the N atom on the imidazole are used to participate in the coordination to form a complex, which can cause the charge distribution in the probe molecule to change; when the detection probe is combined with ClO - After the reaction, ClO - It combines with the N atom on imidazole to form a complex and can cause changes in the charge distribution within the probe molecule.

[0060] In order to better understand the detection probe based on naphthalene imide derivatives, the preparation method and the application thereof in the present invention, the detection probe based on naphthalene imide derivatives, the preparation method and the application thereof in the present invention are described below with reference to specific examples. It should be noted that these examples are merely descriptive and do not limit the present invention in any way.

[0061] Example 1

[0062] This embodiment provides a detection probe based on naphthalene imide derivatives and a preparation method thereof. The chemical structure of the detection probe is as follows:

[0063]

[0064] The preparation method comprises the following steps:

[0065] S1. Add a mixture of compound I (2.75 g, 7.09 mmol), imidazole (1.50 g, 22.05 mmol) and anhydrous potassium carbonate (3.04 g, 22.05 mmol) into acetonitrile (30 mL) and stir to dissolve. Then, heat to 90° C. under nitrogen protection for 72 h, and cool to room temperature to obtain a mixed solution. The chemical structure of compound I is as follows:

[0066]

[0067] S2, filtering the mixed solution, and then distilling the obtained crude product solution under reduced pressure to remove the solvent to obtain a solid product;

[0068] S3. The solid product is separated by column chromatography on silica gel, and then purified using ethyl acetate / dichloromethane (v / v=1 / 1) as an eluent to obtain a yellow solid compound II, which is a detection probe based on naphthaleneimide derivatives.

[0069] After testing, the yield of the detection probe based on naphthalene imide derivative prepared in this embodiment is 64.35%, the melting point is 158°C~159°C, and the nuclear magnetic hydrogen spectrum is 1H NMR (400MHz, CDCl3) δ (ppm) 8.67 (dd, J=7.2,4.8Hz,2H), 8.08 (d, J=8.3Hz,1H), 7.84-7.80 (m,2H), 7.72 (d, J=7.7Hz,1H), 7.36 (s,1H), 7.33 (s,1H), 4.35 (t, J=6.8Hz,2H), 3.66 (m,4H), 2.71 (t, J=6.8Hz,2H), 2.58 (s,4H).

[0070] Application Example 1

[0071] This application example provides an application of a detection probe based on naphthalene imide derivatives, and the detection probe prepared in Example 1 is used for ClO - The detection method comprises the following steps: preparing the detection probe prepared in Example 1 to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L probe solution, to which different concentrations of ClO - Ions (0~33×10 -6 mol / L), and record the fluorescence intensity of the probe solution at different wavelengths (345nm~635nm) to obtain the detection probe to detect ClO - The fluorescence emission spectrum of ions is Figure 5 As described above, 330 nm is used as the excitation wavelength.

[0072] according to Figure 5 The probe was detected at different concentrations of ClO - As can be seen from the fluorescence emission spectrum, as ClO is added to the probe solution - As the concentration of ions gradually increased, the fluorescence intensity of the probe solution at an emission wavelength of 473 nm gradually increased.

[0073] The detection probe prepared in Example 1 was prepared to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L probe solution, ClO - The detection was carried out in 6 3mL concentrations of 1×10 -5 0 μM, 0.4 μM, 0.8 μM, 1.2 μM, 1.6 μM, and 2.0 μM ClO were added to the 1.5 μM probe solution. -ions, the fluorescence emission spectrum was measured using an excitation wavelength of 330 nm, and then the ratio of the fluorescence emission intensity of the probe solution at emission wavelengths of 473 nm and 394 nm was compared with that of ClO - The detection limit curve was obtained by plotting the concentration of

[0074] like Figure 6 The detection probe is shown for ClO - The detection limit test data in the figure shows that σ = 0.010128, and the detection limit is calculated to be 86.22nM, indicating that the detection probe can quantitatively detect ClO - Ion levels, available for intracellular ClO - Detection of ions.

[0075] Application Example 2

[0076] This application example provides an application of a detection probe based on naphthalene imide derivatives, and the detection probe prepared in Example 1 is used for Fe 3+ The detection method comprises the following steps: preparing the detection probe prepared in Example 1 to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L probe solution, to which different concentrations of Fe 3+ Ions (0~33×10 -6 mol / L), and record the fluorescence intensity of the probe solution at different wavelengths (345nm~635nm) to obtain the detection probe for Fe 3+ The fluorescence emission spectrum of ions is Figure 7 As described above, 330 nm is used as the excitation wavelength.

[0077] according to Figure 7 The probe was detected at different concentrations of Fe 3+ As can be seen from the fluorescence emission spectrum, as Fe is added to the probe solution 3+ As the concentration of ions gradually increased, the fluorescence intensity of the probe solution at an emission wavelength of 402 nm gradually increased.

[0078] The detection probe prepared in Example 1 was prepared to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L probe solution, Fe 3+ The detection was carried out in 6 3mL concentrations of 1×10 -5 0 μM, 0.4 μM, 0.8 μM, 1.2 μM, 1.6 μM, and 2.0 μM Fe were added to the mol / L probe solution. 3+ions, the fluorescence emission spectrum was measured using an excitation wavelength of 330 nm, and then the fluorescence emission intensity change (I-I0) of the probe solution at 402 nm and the Fe 3+ The concentration of Fe is plotted to obtain the detection limit curve, where I0 is the concentration of Fe 3+ The fluorescence emission intensity of the detection probe is 3+ The fluorescence emission intensity during the reaction.

[0079] like Figure 8 The detection probe is shown for Fe 3+ The detection limit test data in the figure shows that σ = 0.007642, and the detection limit is calculated to be 0.5321nM, indicating that the detection probe can quantitatively detect Fe 3+ Ion changes can be used for Fe 3+ Rapid detection of ions.

[0080] Application Example 3

[0081] This application example provides an application of a detection probe based on naphthalene imide derivatives, and the detection probe prepared in Example 1 is used for Cr 3+ The detection method comprises the following steps: preparing the detection probe prepared in Example 1 to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 3 mL of the probe solution with a concentration of Cr 3+ Ions (0~33×10 -6 mol / L), and record the fluorescence intensity of the probe solution at different wavelengths (345nm~635nm) to obtain the detection probe to detect Cr 3+ The fluorescence emission spectrum of ions is Fig. 9 As described above, 330 nm is used as the excitation wavelength.

[0082] According to the detection probe at different concentrations of Cr 3+ Fluorescence emission spectra of Fig. 9 ) It can be seen that as Cr is added to the probe solution 3+ As the concentration of ions gradually increased, the fluorescence intensity of the probe solution at an emission wavelength of 402 nm gradually increased.

[0083] The detection probe prepared in Example 1 was prepared to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L probe solution, Cr 3+ The detection was carried out in 6 3mL concentrations of 1×10 -50 μM, 0.4 μM, 0.8 μM, 1.2 μM, 1.6 μM, and 2.0 μM Cr were added to the 1.5 μM probe solution. 3+ ions, the fluorescence emission spectrum was measured using an excitation wavelength of 330 nm, and then the fluorescence emission intensity change (I-I0) of the probe solution at 402 nm and the Cr 3+ The concentration of Cr is plotted to obtain the detection limit curve, where I0 is the concentration of Cr in the absence of Cr. 3+ The fluorescence emission intensity of the detection probe is 3+ The fluorescence emission intensity during the reaction.

[0084] like Fig.10 The detection probe is shown for Cr 3+ The detection limit test data in the figure shows that σ = 009116, and the calculated detection limit is 27.87nM, indicating that the detection probe can quantitatively detect Cr 3+ Ion changes can be used for Cr 3+ Rapid detection of ions.

[0085] Application Example 4

[0086] This application example provides an application of a detection probe based on naphthalene imide derivatives, and the detection probe prepared in Example 1 is used for Al 3+ The detection method comprises the following steps: preparing the detection probe prepared in Example 1 to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5 mol / L probe solution, to which different concentrations of Al 3+ Ions (0~33×10 -6 mol / L), and record the fluorescence intensity of the probe solution at different wavelengths (345nm~635nm) to obtain the detection probe to detect Al 3+ The fluorescence emission spectrum of ions is Fig.11 As described above, 330 nm is used as the excitation wavelength.

[0087] According to the detection probe at different concentrations of Al 3+ Fluorescence emission spectra of Fig.11 ) It can be seen that as Al is added to the probe solution 3+ As the concentration of ions gradually increased, the fluorescence intensity of the probe solution at an emission wavelength of 402 nm gradually increased.

[0088] The detection probe prepared in Example 1 was prepared to a concentration of 5×10 -3 mol / L DMF solution, and then dissolve the detection probe solution in water to prepare 1×10 -5mol / L probe solution, Al 3+ The detection was carried out in 6 3mL concentrations of 1×10 -5 0 μM, 0.4 μM, 0.8 μM, 1.2 μM, 1.6 μM, and 2.0 μM Al were added to the mol / L probe solution. 3+ ions, the fluorescence emission spectrum was measured using an excitation wavelength of 330 nm, and then the fluorescence emission intensity change of the probe solution at 402 nm (I-I0) and Al 3+ The concentration of Al is plotted to obtain the detection limit curve, where I0 is the concentration of Al 3+ The fluorescence emission intensity of the detection probe is 3+ The fluorescence emission intensity during the reaction.

[0089] like Fig.12 The detection probe is shown for Al 3+ The detection limit test data in the figure shows that σ = 0.008547, and the calculated detection limit is 32.03nM, indicating that the detection probe can quantitatively detect Al 3+ Ion changes can be used for Al 3+ Rapid detection of ions.

[0090] In summary, the detection probe based on naphthalene imide derivatives in the present invention is effective for ClO - , Fe 3+ Cr 3+ 、Al 3+ The detection of ions is highly selective and sensitive, and can achieve in-situ, real-time, and ratio response, with a detection limit of 10 -9 mol / L; the preparation method of the detection probe based on naphthalene imide derivatives in the present invention is simple and easy, low-cost, and uses naphthalene imide dyes as optical signal reporting groups, which can meet the requirements of simultaneous detection of multiple ions, not only for ClO - The invention has fast ion response, high selectivity, high detection sensitivity, and can also be used for the detection of trivalent heavy metal ions. The method is simple and easy to promote and apply. The naphthalene imide derivative can be used as a platform to design probes for the recognition of various molecules or ions. Therefore, the invention effectively overcomes various shortcomings in the prior art and has high industrial utilization value.

[0091] The above embodiments are merely illustrative of the principles and effects of the present invention, and are not intended to limit the present invention. Anyone familiar with the art may modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by a person of ordinary skill in the art without departing from the spirit and technical concept disclosed by the present invention shall still be covered by the claims of the present invention.

Claims

1. A detection probe based on naphthalimide derivatives, characterized in that: The chemical structural formula of the detection probe is as follows:

2. A method for preparing a detection probe based on naphthalimide derivatives according to claim 1, characterized in that: The preparation method comprises the following steps: S1. Add a mixture of compound I, imidazole and anhydrous potassium carbonate into a solvent, stir and dissolve, then heat and react for a period of time under nitrogen protection, and then cool to room temperature to obtain a mixed solution, wherein the chemical structure of compound I is as follows: S2, filtering the mixed solution, and then distilling the obtained crude product solution under reduced pressure to remove the solvent to obtain a solid product; S3. Separate the solid product by column chromatography on silica gel, and then purify it with an eluent to obtain a solid compound II, which is a detection probe based on naphthaleneimide derivatives.

3. The method for preparing a detection probe based on naphthaleneimide derivatives according to claim 2, characterized in that: In step S1, the molar ratio of the compound I to the imidazole is 1:3 to 1:

5.

4. The method for preparing a detection probe based on naphthaleneimide derivatives according to claim 2, characterized in that: The molar ratio of the imidazole to the anhydrous potassium carbonate in step S1 is 1:1 to 1:1.

5.

5. The method for preparing a detection probe based on naphthaleneimide derivatives according to claim 2, characterized in that: In step S1, the mass ratio of the total mass of the compound I, the imidazole and the anhydrous potassium carbonate to the mass ratio of the solvent is 1:3 to 1:

8.

6. The method for preparing a detection probe based on naphthaleneimide derivatives according to claim 2, characterized in that: The solvent in step S1 is acetonitrile.

7. The method for preparing a detection probe based on naphthaleneimide derivatives according to claim 2, characterized in that: The temperature of the heating reaction in step S1 is 85-100° C., and the time of the heating reaction is 48-80 hours.

8. The method for preparing a detection probe based on naphthalimide derivatives according to claim 2, characterized in that: The eluent in step S3 is a mixture of ethyl acetate / dichloromethane, or a mixture of methanol / ethyl acetate / dichloromethane.

9. The method for preparing a detection probe based on naphthalimide derivatives according to claim 8, characterized in that: The volume ratio of ethyl acetate to dichloromethane in the ethyl acetate / dichloromethane mixture is 1:1; the volume ratio of methanol, ethyl acetate and dichloromethane in the methanol / ethyl acetate / dichloromethane mixture is 1:2:3 to 1:2:

4.

10. A use of the detection probe based on naphthalimide derivatives according to claim 1, characterized in that: The detection probe is used for non-diagnostic and non-therapeutic purposes. - Detection.

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