Fluorescent probe with specific detection of gold ions and sulfur dioxide and its derivatives, preparation method and application thereof

CN122958425APending Publication Date: 2026-10-23SHANGHAI UNIV OF ENG SCI
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Patent Information

Application Number
CN202611154484.4
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2026-07-31
Publication Date
2026-10-23

AI Technical Summary

Benefits of technology

[0017]本发明荧光探针X-2的分子设计兼顾了结构刚性、供电子能力、共轭长度、光物理稳定性与生物适配性,通过TCF 基团与久洛尼定醛通过不饱和双键连接,构成大的共轭体系,成功构建了一种新的近红外波长荧光探针,使其保持探针对金离子高识别性的基础上,还可检测环境中SO2及其衍生物(SO32-)的存在并通过目视直观检测结果,为后续开发具备稳定性高、溶解性好、灵敏度高、低毒性和更好的生物相容性等优势的新型荧光探针及探究金离子催化相关研究奠定了扎实的基础。

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Abstract

The application belongs to the technical field of fluorescent probes, and particularly relates to a fluorescent probe with specific detection of gold ions and sulfur dioxide and derivatives thereof, and a preparation method and application thereof. The fluorescent probe is a fluorescent probe formed by connecting a TCF group and julolidine aldehyde through an unsaturated double bond, can specifically recognize gold ions and sulfur dioxide and derivatives thereof, has the advantages of rapid response, high selectivity, anti-interference and low cost, and provides a new molecular tool for detection of gold ions, sulfur dioxide and derivatives thereof.
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Description

Technical Field

[0001] This invention belongs to the field of fluorescent probe technology, specifically relating to a fluorescent probe for the specific detection of gold ions, sulfur dioxide and their derivatives, its preparation method and application. Background Technology

[0002] Gold, as a rare and precious metal, has wide applications not only in jewelry but also plays a vital role in biomedicine and chemical engineering, making it closely related to our daily lives. Due to the unique redox chemical and biological activity of gold ions and their high electron affinity as a transition metal, gold can effectively activate carbon-carbon double and triple bonds, catalyzing and promoting reactions such as oxidation, hydrogenation, hydrogenation, and alkylation. This is crucial for the preparation of organic cationic compounds and heterocyclic compounds. Furthermore, gold ions show promising effects in electroplating and surface coating, nanomaterial preparation, and clinical anti-cancer and anti-infective applications. Given the widespread use of gold in medicine, catalysis, and optoelectronic materials, developing effective detection methods for its monitoring is essential.

[0003] Sulfur dioxide (SO2) is a toxic air pollutant; inhalation can lead to respiratory illnesses. The human body can also produce SO2 endogenously from thiol-containing amino acids, and within certain concentration ranges, SO2 plays an important role in many physiological processes, such as cardiovascular dilation and lowering blood pressure. Excessive SO2 intake can induce many respiratory responses, and imbalances in the levels of sulfur dioxide and its derivatives in the body are closely related to diseases such as cancer and nervous system disorders. Currently, commonly used methods for analyzing and detecting SO2 include spectrophotometry, capillary electrophoresis, and titration chromatography. Fluorescent probes, due to their simplicity, high selectivity, and high sensitivity, can be combined with fluorescence microscopy to achieve in-situ real-time dynamic tracking of biological samples (living cells, living tissues, etc.) with minimal biological damage, playing an increasingly important role in biological detection. SO2 is highly soluble in water, forming HSO3. - and SO3 2- Two forms are present, and their molar ratio in neutral aqueous solution is 1:3. Due to the toxicity of excess sulfite, developing more analytical techniques for its detection is of great importance.

[0004] Existing technologies have already achieved the production of precious metal gold ions, sulfur dioxide and its derivatives (HSO3). - SO3 2-Fluorescent probe technology for detection, such as CN121318934A, a 1,2,4-triazole compound and its preparation method and application, discloses a 1,2,4-triazole fluorescent probe that can detect monovalent gold ions in aqueous phase. CN120554600A, a ternary covalent organic framework (COF) material and its application as a fluorescent sensor in gold ion detection, discloses a 1,3,5-triazole fluorescent probe. Tricarboxymethyl phloroglucinol (TP), 1,5 diaminonaphthalene (DP) and 2 sulfonyl p-phenylenediamine (DB) A ternary covalent organic framework (COF) material prepared by mixing SO3H exhibits high affinity for gold ions, enabling selective detection of gold ions in electronic waste liquid. CN119192107A discloses a quenching fluorescent probe for specific detection of gold ions, its preparation method, and its application, specifically a benzofuranone-based quenching fluorescent probe capable of specifically identifying gold ions in solution. CN121045150A discloses a fluorescent probe compound, its preparation method, and its application in detecting sulfite, disclosing a ratiometric fluorescent probe designed with acenaphthene-imidazole as the parent compound for detecting bisulfite in solution. CN120623174A discloses a fluorescent probe for quantitative detection of sulfite, its preparation method, and its application, disclosing a ratiometric fluorescent probe based on rhodane fluorescent dye for sulfite detection at room temperature. CN120463673A discloses the synthesis and application of a fluorescent probe that simultaneously distinguishes between sulfite and viscosity, disclosing a quenching fluorescent probe designed based on a coumarin core to accurately distinguish between sulfite and viscosity.

[0005] Based on existing technologies, this invention aims to develop a novel fluorescent probe with high stability, high solubility, high sensitivity, low toxicity, and better biocompatibility. This probe specifically recognizes gold ions and sulfur dioxide and its derivatives, and provides detection results that can be directly observed with the naked eye without the need for special equipment or environmental settings. Summary of the Invention

[0006] To address the shortcomings of existing technologies, this invention provides a simple and efficient novel fluorescent probe, its preparation method, and its applications. This probe can specifically recognize gold ions, sulfur dioxide, and their derivatives. The detection results can be directly observed with the naked eye, exhibiting high sensitivity and good stability. It provides a novel long-wavelength fluorescent tool for monitoring gold ions and SO2, and also offers a valuable molecular engineering approach for designing probes based on gold ion colorimetric detection of SO2 in food to ensure human health.

[0007] The technical solution of this invention is a fluorescent probe with specific detection capabilities for gold ions and sulfur dioxide and its derivatives, the structure of which is shown below: .

[0008] This invention also provides a method for preparing a fluorescent probe with specific detection capabilities for gold ions and sulfur dioxide and its derivatives. The synthetic route is shown in the following formula, and the steps include: reacting compound 3 with dimethylamino-thiocarbamoyl chloride (compound 4) in an organic solvent containing an acid-binding agent to generate a fluorescent probe (X-2) that specifically recognizes gold ions and sulfur dioxide and its derivatives. Further, compound 3 is first dissolved in an organic solvent containing an acid-binding agent, and then dimethylamino-thiocarbamoyl chloride (compound 4) is slowly added to the reaction. The reaction temperature is room temperature, preferably 25°C; the reaction time is 3-4 hours, preferably 3 hours. After the reaction is complete, column chromatography is performed, with the elution solvent EA:PE = 1:3.

[0009] The ratio of compound 3 to dimethylamino-thiocarbamoyl chloride is 1-10 mmol:1 mL, preferably 4-6 mmol:1 mL, and more preferably 5 mmol:1 mL; the ratio of compound 3 to organic solvent is 0.005-0.1 mmol:1 mL, preferably 0.01-0.05 mmol:1 mL, more preferably 0.01-0.02 mmol:1 mL, and more preferably 0.015-0.016 mmol:1 mL; the organic solvent is selected from dichloromethane, acetonitrile, acetone, and dimethyl sulfoxide, preferably dichloromethane.

[0010] The ratio of compound 3 to the acid-binding agent is 10-20 mmol:1mL, preferably 15-18 mmol:1mL, and more preferably 16-17 mmol:1mL; the acid-binding agent is selected from any one of inorganic bases, organic bases, alkoxides, alkyl lithium, and amino lithium salts, preferably an organic base, and the organic base is selected from any one of N,N-diisopropylethylamine, pyridine, and triethylamine, preferably N,N-diisopropylethylamine.

[0011] The preparation method of compound 3 is shown in the following synthetic route, comprising the following steps: Compound 1 and compound 2 are refluxed in an alcohol solution containing piperidine under a nitrogen dioxide environment to obtain compound 3. After the reflux reaction is complete, the precipitate is filtered off, washed with ethanol and diethyl ether, and dried to obtain compound 3.

[0012] In the alcohol solution, the molar ratio of compound 1 to compound 2 is 1:1-2, preferably 1:1-1.5, more preferably 1:1.2-1.3; the concentration of compound 1 is 0.005-0.1 mmol / mL, preferably 0.01-0.06 mmol / mL, 0.02-0.03 mmol / mL, more preferably 0.025 mmol / mL. The volume ratio of the alcohol solution to piperidine is 10 mL:0.001-0.005 mL, preferably 10 mL:0.003 mL. The alcohol solution is selected from methanol and ethanol, preferably ethanol.

[0013] The fluorescent probe provided by the present invention can specifically recognize both gold ions and sulfur dioxide and its derivatives (HSO3). - SO3 2- This can be used to prepare detection products that specifically recognize gold ions and / or sulfur dioxide and its derivatives, including but not limited to reagents, components, devices, or equipment. Because SO2 is highly soluble in water to form HSO3... - and SO3 2- (Molar ratio 1:3) A fluorescent probe that can specifically recognize sulfite ions, and it can also recognize sulfur dioxide.

[0014] This invention provides a detection product that specifically identifies gold ions and / or sulfur dioxide and its derivatives, containing the fluorescent probe provided by this invention. The product includes, but is not limited to, reagents, components, devices, or equipment.

[0015] The present invention also provides a detection method for specifically identifying gold ions and / or sulfur dioxide and its derivatives. The method involves fully exposing or contacting the sample to be tested with a solution containing the fluorescent probe provided by the present invention, observing the color change of the solution, and / or collecting changes in fluorescence intensity at 650 nm and / or 685 nm for qualitative and / or quantitative determination of gold ions and / or sulfur dioxide and its derivatives. Further, the method involves collecting fluorescence intensity at 650 nm for qualitative and / or quantitative determination of gold ions, or collecting fluorescence intensity at 685 nm for qualitative and / or quantitative determination of sulfur dioxide and its derivatives.

[0016] The solvent used in the solution containing the fluorescent probe provided by the present invention is a mixed solution of water and DMSO, with a volume ratio of water to DMSO of 1:1.

[0017] The molecular design of the fluorescent probe X-2 in this invention balances structural rigidity, electron-donating capability, conjugation length, photophysical stability, and biocompatibility. By linking the TCF group with julonidinaldehyde via an unsaturated double bond, a large conjugated system is formed, successfully constructing a novel near-infrared fluorescent probe. This probe maintains high recognition of gold ions while also detecting SO2 and its derivatives (SO3) in the environment.2- The presence of the fluorescent probe and the visual detection results lay a solid foundation for the subsequent development of novel fluorescent probes with advantages such as high stability, good solubility, high sensitivity, low toxicity and better biocompatibility, as well as for the investigation of gold ion catalysis-related research. Attached Figure Description

[0018] Figure 1 This is a schematic diagram of the probe synthesis route described in this invention.

[0019] Figure 2 The normalized fluorescence intensity represents the result of the fluorescent probe reacting with different concentrations of AuCl3.

[0020] Figure 3 These are fluorescence images of the fluorescent probe X-2 solution before and after the addition of AuCl3, viewed under natural light. From left to right: fluorescence image before AuCl3 addition, fluorescence image 30 seconds after AuCl3 addition, and fluorescence image after the addition of AuCl3 and SO3. 2- Fluorescence image after 60 seconds.

[0021] Figure 4 For fluorescent probe X-2 and its Au 3+ Normalized fluorescence intensity after binding.

[0022] Figure 5 To demonstrate the fluorescence of probe X-2 and Au under 365nm UV light irradiation 3+ The fluorescence images before and after the addition of gold ions are compared. The left image shows the fluorescence image with gold ions added, and the right image shows the fluorescence image without gold ions added.

[0023] Figure 6 To enable the fluorescent probe X-2 to bind Au under natural light 3+ The color changes of the solution in the cuvette before and after addition of sulfite ions, and the color changes after further addition of sulfite ions. From left to right, the images are: after adding only the fluorescent probe, after adding gold ions for 30 seconds, after adding gold ions for 2 minutes, after adding both gold ions and sulfite ions for 60 seconds, and after adding both gold ions and sulfite ions for 2 minutes.

[0024] Figure 7 The fluorescence intensity changes after fluorescent probe X-2 binds to Au and is left to stand for a period of time before sulfite ions are added. X2 represents the test system containing only the fluorescent probe, and X2-au represents the test system containing 20 μL of probe stock solution and Au. 3+ Fluorescence image of 200 μL (1 mM) after 30 s, X2-au-1 is the result of adding 20 μL of probe stock solution, Au 3+ Fluorescence image of 200 μL (1 mM) after 60 s, X2-au-2 is the result of adding 20 μL of probe stock solution, Au 3+Fluorescence image of 200 μL (1 mM) after 90 s, where X2-au-2-so2 represents the addition of 20 μL of probe stock solution, Au 3+ (1mM) 200μL and SO3 2- Fluorescence image of 200 μL after 60 s.

[0025] Figure 8 The images show the color changes of the cuvette solution after the fluorescent probe X-2 binds to sulfite ions under natural light, and the color changes after further addition of gold ions. From left to right, the images show the results after adding only the fluorescent probe, after adding sulfite ions for 60 seconds, and after adding both sulfite ions and gold ions for 60 seconds, 2 minutes, and 5 minutes.

[0026] Figure 9 Au was added after the fluorescent probe X-2 bound to SO2 and allowed to stand for a period of time. 3+ The change in fluorescence intensity was then observed. X2 represents the test system with only the fluorescent probe added, and X2-so2 represents the test system with 20 μL of probe stock solution and SO3 added. 2- Fluorescence image of 200 μL (1 mM) after 60 s. X2-so2-au-1 represents the addition of 20 μL of probe stock solution and SO3. 2- (1mM) 200μL and Au 3+ Fluorescence image of 200 μL (1 mM) after 30 s, X2-so2-au-2 indicates the addition of 20 μL of probe stock solution and SO3. 2- (1mM) 200μL and Au 3+ Fluorescence image of (1mM) 200μL after 60s.

[0027] Figure 10 The fluorescent probe X-2 of the present invention 1 1H NMR spectrum, using CDCl3 as solvent.

[0028] Figure 11 The fluorescent probe X-2 of the present invention 13 C10 NMR spectrum, using CDCl3 as solvent.

[0029] Figure 12 This is the HR-MS mass spectrum of the fluorescent probe X-2 of the present invention. Detailed Implementation

[0030] The technical solution of the present invention will be clearly and completely described below with reference to the embodiments. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.

[0031] Example 1: Synthesis of fluorescent probe X-2 Synthetic routes such as Figure 1 As shown, in a 100 mL three-necked round-bottom flask, compound 1 (0.5 mmol) and compound 2 (0.6 mmol) were dissolved in anhydrous ethanol (20 mL). Piperidine (6 μL) was added, and the mixture was refluxed under nitrogen dioxide for 3 hours. After TLC observation, the reaction mixture was cooled to room temperature, and the formed green precipitate was filtered, washed with ethanol and diethyl ether, dried, and finally compound 3 as a green powder was obtained (yield: 80.2%).

[0032] Compound 3 (0.5 mmol) was dissolved in 20 mL of anhydrous dichloromethane, and 30 μL of DIPEA (N,N-diisopropylethylamine) was added. 100 µL of compound 4 was dissolved in 12 mL of dichloromethane. The solutions were added slowly dropwise in an ice-water bath and allowed to stand overnight at room temperature. Separation was performed by column chromatography with ethyl acetate (EA):petroleum ether (PE) in a 1:3 ratio to give the deep purple compound X-2 (yield: 45%). 1 HNMR (400 MHz, CDCl3) δ 7.95 (d, J=15.6 Hz, 1H), 7.30 (s, 1H), 6.45 (d, J=15.7Hz, 1H), 3.50–3.30 (m, 10H), 2.81 (q, J=5.5 Hz, 2H), 2.61 (q, J=6.1 Hz, 2H), 2.08–1.90 (m, 4H), 1.66 (d, J=3.0 Hz, 6H). 13 C NMR (400 MHz, CDCl3, ppm) δ / ppm:21.1, 26.5, 39.0, 43.5, 50.1, 53.2, 77.0, 91.1, 96.6, 107.3, 113.2, 120.1,126.0, 143.3, 149.2, 152.1, 173.7, 176.9, 185.4; HR-Mass m / z: Calcd. for[C27H27N5O2S] + 486.189, found 486.1950. Example 2: Fluorescence spectroscopy study of the reaction of fluorescent probes with gold ions of different concentrations (1) Dissolve X-2 (4.87 mg) in DMSO to prepare a probe ion stock solution with a concentration of 1 mM.

[0033] (2) Take 16 3.5 mL four-sided transparent quartz cuvettes and add 1 mL of AuCl3 solution with concentrations of 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, and 3.0 mM to each cuvette. Then add 1 mL of fluorescent probe stock solution to each cuvette and shake well. Place the cuvettes in a fluorescence spectrometer. Set the excitation wavelength to 520 nm and the detection wavelength range to 540–850 nm. Obtain the initial fluorescence spectrum of the probe and record the fluorescence intensity at 650 nm.

[0034] (3) Record the fluorescence intensity at 650 nm in the above fluorescence spectrum to obtain the changes in fluorescence intensity after the reaction of gold ions with fluorescent probes at different concentrations. The results are as follows: Figure 2 As shown.

[0035] Figure 2 This indicates that after the X-2 probe stock solution reacts with gold ions, a significant fluorescence change occurs at 650 nm, and the fluorescence intensity changes more significantly with increasing gold ion concentration.

[0036] Example 3: Fluorescence Spectroscopy Study of the Reaction of Probe Molecules with Gold Ions (1) Dissolve gold trichloride (AuCl3) in 5 mL of distilled water to prepare a gold ion test stock solution (1 mM). The stock solution is stored in a refrigerator at 4 °C away from light and has a shelf life of 3 months.

[0037] (2) Add 2 mL of system solution (H2O / DMSO (1:1, v / v)) to a 3.5 mL four-sided transparent quartz cuvette, and then add 20 μL of probe stock solution, 200 μL of AuCl3 solution (1 mM), and sodium sulfite solution (SO3) sequentially. 2- (1mM) 200μL, to obtain the test solution. Let it stand under natural light for 1 min, and observe the color change of the solution in the cuvette. The results are as follows: Figure 3 As shown.

[0038] (3) Place the working solution into a fluorescence spectrometer, set the excitation wavelength to 520 nm, and the scanning range to 540 nm~850 nm to obtain the fluorescence spectrum of gold ions in the solution system (H2O / DMSO (1:1, v / v)). The spectrum is shown in the figure. Figure 4 As shown.

[0039] Example 4: Fluorescence spectroscopy study of probe molecules binding gold ions under the influence of sulfite ions To investigate the influencing conditions suitable for the X-2-Au probe system, the effect of sulfite ion gas on the probe's fluorescence response was explored, and the ratio of fluorescence intensity before and after the addition of sulfite ions was used as the evaluation criterion. The specific procedures are as follows: (1) Dissolve X-2 in DMSO to prepare X-2 test stock solution (1mM). The stock solution is stored in a refrigerator at 4°C away from light and has a shelf life of 3 months.

[0040] (2) Take three 3.5 mL four-sided transparent quartz cuvettes and add 20 μL of 1 mM probe test stock solution to each. Add only the probe stock solution to one cuvette, add 200 μL of 1 mM AuCl3 to another cuvette, and add 200 μL each of 1 mM AuCl3 and 1 mM sodium sulfite to the third cuvette. Make up the rest with the detection system (H2O / DMSO (1:1, v / v)) to maintain a total volume of 2 mL in each cuvette. After standing for 5 min, observe the color change of the solution in the cuvettes, record the result, and then let stand for another 5 min. Observe the color change of the solution in the cuvettes. The color change of the solution in the cuvettes is as follows: Figure 6 As shown.

[0041] (3) Place the cuvette in the fluorescence spectrometer. Set the excitation wavelength to 520 nm and the detection wavelength range to 540 nm–850 nm. Obtain the fluorescence spectrum of the probe, as shown below. Figure 7 As shown.

[0042] Figure 6 The results show that under natural light, the X-2 probe stock solution is a deep lake blue. After adding AuCl3 solution, the solution color lightens. After standing for a period of time, the deep lake blue color in the cuvette further weakens, and the solution turns yellow, indicating that the probe reacts with Au. After adding sodium sulfite to the cuvette after a period of reaction, the solution color gradually changes from yellow to clear. Subsequently, as the probe reacts further, the solution becomes turbid and gray.

[0043] Figure 7 The results showed that after adding AuCl3 solution to the X-2 probe stock solution, a significant fluorescence phenomenon appeared around 650 nm. After standing for a period of time, as the probe further reacted with gold ions, a blue shift occurred and the fluorescence intensity decreased significantly. With the addition of sodium sulfite, the fluorescence phenomenon further decreased, returning to a level similar to that of the X-2 stock solution.

[0044] Example 5: Study on the reaction results of gold ions with probe molecules binding to sulfite ions To fully elucidate the effect of gold ions on the recognition behavior of probe X-2 and sulfite ions, we systematically studied its fluorescence enhancement effect in an H2O / DMSO (1:1, v / v) system. The specific procedures are as follows: (1) Dissolve X-2 in 10 mL of DMSO to prepare X-2 test stock solution (1 mM). The stock solution is stored in a refrigerator at 4°C away from light and has a shelf life of 3 days.

[0045] (2) Take three 3.5 mL four-sided transparent quartz cuvettes, add 20 μL of the prepared probe stock solution to each cuvette, and add 200 μL of sodium sulfite solution (1 mM) to two of the cuvettes to obtain a test solution with a concentration of 100 μM.

[0046] (3) Let the above cuvette stand for 5 minutes, then observe the color change of the solution in the cuvette under natural light. Take a cuvette containing sodium sulfite solution and probe stock solution, add 200 μL of AuCl3 solution (1 mM), let it stand for a period of time, and observe the color change of the solution in the cuvette. Figure 8 As shown.

[0047] (4) Place the above reaction solution into a fluorescence spectrometer, set the excitation wavelength to 520 nm, the scanning range to 540 nm ~ 850 nm, and the temperature to 25 °C. Obtain the fluorescence intensity of probe X-2 at 685 nm after the addition of sodium sulfite and AuCl3 solution. Record the fluorescence intensity of probe X-2 at 685 nm to obtain the fluorescence spectrum. The results are as follows: Figure 9 As shown.

[0048] Figure 8 The results show that under natural light, the X-2 probe stock solution is a deep lake blue. Adding sodium sulfite solution changes the solution color from lake blue to colorless, indicating that the probe reacts with sulfite ions. After a period of reaction, adding AuCl3 solution to the cuvette changes the solution color from colorless to blue. After standing for a while, the fluorescence weakens, and the solution color gradually deepens, changing from light blue to purple.

[0049] Figure 9 The results showed that after adding sodium sulfite solution to the X-2 probe stock solution, a significant fluorescence quenching phenomenon occurred at 685 nm. After adding AuCl3 solution and letting it stand for a period of time, the fluorescence phenomenon reappeared as the probe bound to SO2 reacted further with gold ions, and fluorescence appeared at 630 nm and 650 nm, with a blue shift phenomenon. After a period of reaction, the fluorescence phenomenon weakened significantly and was almost unobservable.

[0050] Finally, it should be noted that the above description of the embodiments is intended to enable those skilled in the art to understand and use them. Those skilled in the art will readily make various modifications to these embodiments and apply the general principles described herein to other embodiments without creative effort. Therefore, the present invention is not limited to the above-described embodiments, and any improvements made by those skilled in the art based on the disclosure of the present invention without departing from the scope of the invention should be within the protection scope of the present invention.

Claims

1. A fluorescent probe with specific detection capabilities for gold ions and sulfur dioxide and its derivatives, characterized in that, The structural formula is as follows: 。 2. The method for preparing the fluorescent probe according to claim 1, characterized in that, step include: Compound 3 reacts with dimethylamino-thiocarbamoyl chloride in an organic solvent with added acid-binding agent to generate a fluorescent probe X-2 that specifically recognizes gold ions and sulfur dioxide and its derivatives. 。 3. The preparation method according to claim 2, characterized in that, The ratio of compound 3 to dimethylamino-thiocarbamoyl chloride is 1-10 mmol:1 mL, the ratio of compound 3 to organic solvent is 0.005-0.1 mmol:1 mL, and the ratio of compound 3 to acid-binding agent is 10-20 mmol:1 mL.

4. The preparation method according to claim 2, characterized in that, The organic solvent is selected from dichloromethane, acetonitrile, acetone, and dimethyl sulfoxide, and the acid-binding agent is selected from inorganic base, organic base, alkoxide, alkyl lithium, and amino lithium salt.

5. The preparation method according to claim 2, characterized in that, The preparation of compound 3 includes: reacting compound 1 and compound 2 under a nitrogen dioxide atmosphere in an alcohol solution containing piperidine under reflux to obtain compound 3; 。 6. The preparation method according to claim 5, characterized in that, In the alcohol solution, the molar ratio of compound 1 to compound 2 is 1:1-2, and the concentration of compound 1 is 0.005-0.1 mmol / mL.

7. The use of the fluorescent probe of claim 1 for detecting gold ions and / or sulfur dioxide and its derivatives, or for preparing products for detecting gold ions and / or sulfur dioxide and its derivatives.

8. A detection product that specifically identifies gold ions and / or sulfur dioxide and its derivatives, characterized in that, Contains the fluorescent probe of claim 1.

9. A detection method for specifically recognizing gold ions and / or sulfur dioxide and its derivatives, characterized in that, The sample to be tested is fully exposed or fully contacted with a solution containing the fluorescent probe of claim 1, and the color change of the solution is observed and / or the fluorescence intensity change at 650 nm and / or 685 nm is collected for qualitative and / or quantitative determination of gold ions and / or sulfur dioxide and its derivatives.

10. The detection method according to claim 9, characterized in that, The solvent used in the solution containing the fluorescent probe of claim 1 is a mixture of water and DMSO.

Citation Information

Patent Citations

  • Quenching type fluorescent probe for specifically detecting gold ions as well as preparation method and application of quenching type fluorescent probe

    CN119192107A

  • Synthesis and application of fluorescent probe for simultaneously distinguishing and detecting sulfite and viscosity

    CN120463673A

  • Ternary covalent organic framework (COF) material and application thereof as fluorescence sensor in gold ion detection

    CN120554600A

  • Fluorescent probe for quantitatively detecting sulfite as well as preparation method and application of fluorescent probe

    CN120623174A

  • Fluorescent probe compound, preparation method and application of fluorescent probe compound in detection of sulfite

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