2-Dodecanoylaminonaphtho[2,1-d]thiazole in Fe 3+ or Hg 2+ Application of fluorescent probes for detection

By using 2-dodecanoylaminonaphthalene[2,1-d]thiazole as a fluorescent probe, combined with its coordination reaction with Fe3+ or Hg2+, simultaneous detection of two metal ions is achieved, solving the problem of only one metal ion in the prior art, and expanding the application of optical properties of naphthiazole substances.

CN115449367BActive Publication Date: 2025-03-18CHIZHOU UNIV
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Patent Information

Application Number
CN202211164394.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-09-23
Publication Date
2025-03-18
Estimated Expiration
2042-09-23

AI Technical Summary

Technical Problem

Existing fluorescent probes can only detect one of Fe3+ or Hg2+, and few studies have been conducted on the optical properties of naphtho[2,1-d]thiazoles.

Method used

The detection of two metal ions is achieved through its coordination reaction with Fe3+ or Hg2+. When the probe is present, the fluorescence intensity decreases and is detected using the "turn off" mode.

Benefits of technology

Simultaneous detection of Fe3+ and Hg2+ is achieved, and the optical properties of naphthiazoles are broadened, and the detection sensitivity and selectivity are high.

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Abstract

The invention discloses a method for preparing 2-dodecanoylaminonaphtho[2,1-d]thiazole in Fe 3+ or Hg 2+ The application of fluorescent probes for detection belongs to the technical field of application of naphthothiazole derivatives. 2-Dodecanoylaminonaphtho[2,1-d]thiazole is used as a fluorescent probe to detect Fe 3+ The detection of Hg 2+ Detection.
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Description

Technical Field

[0001] The present invention relates to the technical field of application of naphthothiazole derivatives, and more specifically to the application of 2-dodecanoylaminonaphtho[2,1-d]thiazole in Fe 3+ or Hg 2+ Application of fluorescent probes for detection. Background Art

[0002] Heavy metals mainly refer to mercury (Hg), cadmium (Cd), lead (Pb), chromium (Cr), arsenic (As), copper (Cu), zinc (Zn), cobalt (Co), nickel (Ni) and other heavy metals. They exist in the environment in different forms, migrate and accumulate in the environment. Mining, metallurgy, chemical industry and other industries are the main sources of man-made pollution in water bodies. Excessive enrichment of heavy metals in the food chain will cause great harm to the natural environment and human health. Hg is a silvery-white liquid metal. Hg and its compounds are toxic substances that can invade the human body through various channels and accumulate in the body. Among them, Hg 2+ It can cause irreversible damage to the human respiratory system, nervous system, kidneys, blood, skin and other systems and organs. 3+ Although it is an essential chemical element for the human body and plays an important role in human metabolism, Fe 3+ Excess or deficiency will cause biological disorder and seriously affect human health. 3+ and Hg 2+ Detection is very important.

[0003] In recent years, the detection of Fe 3+ and Hg 2+ There are many reports. For example, Pei Chang's group used π-extended rhodamine hydrazides to complete the 2+ Wang Dong's team used functionalized Janus microspheres to detect Hg 2+ Ou Panpan's group used M-TiO2-CdSe QDs composite material photoelectrochemical sensor equipment to achieve Hg 2+ Detection of Hg; Yang Zhi's team used thiol-β-cyclodextrin protected red light copper nanoclusters to achieve 2+ Xue Songsong's group used a sulfonylhydrazone probe that can rapidly and selectively identify mercury (II) ions to detect Hg 2+ Zhou Kaili's group used organosilicon grafted with profloxacin to detect iron ions; Meng Qingjun's group used multi-element quantum dot fluorescence sensing to detect Fe 3+ Han Xiaohong's group used copper nitrate to react with gallic acid to generate a new complex and achieved the detection of Fe 3+ However, existing fluorescent probes can only detect Fe 3+ and Hg2+ There are few reports on the optical properties of naphtho[2,1-d]thiazoles. Summary of the invention

[0004] In view of the above problems, the present invention uses 2-dodecanoylaminonaphtho[2,1-d]thiazole as a fluorescent probe for Fe 3+ or Hg 2+ Detection.

[0005] The purpose of this application is to provide 2-dodecanoylaminonaphtho[2,1-d]thiazole in the preparation of Fe 3+ or Hg 2+ Application of fluorescent probes for detection.

[0006] Preferably, anhydrous ethanol is used as a solvent to 3+ or Hg 2+ The solution was added to the anhydrous ethanol solution of 2-dodecanoylaminonaphtho[2,1-d]thiazole for detection.

[0007] Preferably, 2-dodecanoylaminonaphtho[2,1-d]thiazole is 2+ The minimum detection limit is 8.08×10 -6 mol / L, for Hg 2+ The response range is 2×10 -5 mol / L-2×10 -4 mol / L.

[0008] Preferably, 2-dodecanoylaminonaphtho[2,1-d]thiazole is Fe 3+ The response range is also 2×10 -5 mol / L-2×10 -4 mol / L, the minimum detection limit is 3.15×10 -6 mol / L.

[0009] Preferably, the 2-dodecanoylaminonaphtho[2,1-d]thiazole is prepared according to the following method:

[0010] 2-Dodecanoylaminonaphtho[2,1-d]thiazole was synthesized by free radical ring-closure reaction using glacial acetic acid as solvent, manganese acetate as catalyst and 3-(2-naphthyl)-1-dodecanoylthiourea as raw material.

[0011] Preferably, the free radical ring-closing reaction occurs by microwave reaction, and the heating temperature of the microwave reaction is 100-110° C., the power is 600-800 W, and the heating time is 25-30 min.

[0012] Preferably, the ratio of 3-(2-naphthyl)-1-dodecanoylthiourea, manganese acetate and glacial acetic acid is 0.78-0.82 mmol:1.95-2.03 mmol:15 mL.

[0013] Preferably, after the free radical ring-closure reaction is completed, the reaction solution is cooled to room temperature, deionized water and dichloromethane are added for extraction, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, and the filtrate is concentrated and purified to obtain 2-dodecanoylaminonaphtho[2,1-d]thiazole.

[0014] Compared with the prior art, the present invention has the following beneficial effects:

[0015] The present invention uses 2-dodecanoylaminonaphtho[2,1-d]thiazole as a fluorescent probe and utilizes Hg 2+ The coordination effect with 2-dodecanoylaminonaphtho[2,1-d]thiazole caused the aggregation of 2-dodecanoylaminonaphtho[2,1-d]thiazole, which weakened its fluorescence intensity. 2+ In addition, Fe 3+ The fluorescence intensity of 2-dodecanoylaminonaphtho[2,1-d]thiazole can be quenched, realizing the "turn off" mode for detecting Fe 3+ . It can realize "one needle for multiple purposes", which can be used for Fe 3+ The detection of Hg 2+ If Hg is detected in the actual sample later 2+ When Fe 3+ , you can try adding NaF to mask Fe 3+ . It broadens the application of the optical properties of 2-dodecanoylaminonaphtho[2,1-d]thiazole, a naphthothiazole. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1A Fe 3+ Effects on the fluorescence spectrum of NH01;

[0017] Figure 1B Hg 2+ Effects on the fluorescence spectrum of NH01;

[0018] Figure 1C Ag + Effects on the fluorescence spectrum of NH01;

[0019] Figure 1D For Al 3+ Effects on the fluorescence spectrum of NH01;

[0020] Figure 1E Ca 2+Effects on the fluorescence spectrum of NH01;

[0021] Figure 1F For Ba 2+ Effects on the fluorescence spectrum of NH01;

[0022] Figure 1G Cd 2+ Effects on the fluorescence spectrum of NH01;

[0023] Figure 1H For Co 2+ Effects on the fluorescence spectrum of NH01;

[0024] Fig. 1I Cu 2+ Effects on the fluorescence spectrum of NH01;

[0025] Figure 1J Zn 2+ Effects on the fluorescence spectrum of NH01;

[0026] Figure 1K K + Effects on the fluorescence spectrum of NH01;

[0027] Figure 1L Mg 2+ Effects on the fluorescence spectrum of NH01;

[0028] Figure 1M Mn 2+ Effects on the fluorescence spectrum of NH01;

[0029] Figure 1N for Na + Effects on the fluorescence spectrum of NH01;

[0030] Fig.1O For you 2+ Effects on the fluorescence spectrum of NH01;

[0031] Figure 1P Pb 2+ Effects on the fluorescence spectrum of NH01;

[0032] Figure 2 Testing Fe for other ions NH01 3+ System coexistence interference test bar graph;

[0033] Figure 3 For other ion pairs NH01 tests Hg 2+ System coexistence interference test bar graph;

[0034] Figure 4a NH01 to Fe 3+ Detection chart;

[0035] Figure 4b Fe 3+ Working curve diagram;

[0036] Figure 5a NH01 to Hg 2+ Detection chart;

[0037] Figure 5b Hg 2+ Working curve diagram;

[0038] Figure 6 NaF to Fe 3+ The influence of mixed solution with NH01;

[0039] Figure 7 is NaF to Hg 2+ and NH01 mixed solution. DETAILED DESCRIPTION

[0040] The following will be combined with the drawings in the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0041] Example 1

[0042] The synthesis method of 2-dodecanoylaminonaphtho[2,1-d]thiazole, the synthesis route is as follows:

[0043]

[0044] The specific steps include:

[0045] 0.30g (i.e. 0.78mmol) 3-(2-naphthyl)-1-dodecanoylthiourea, 0.52g (i.e. 1.95mmol) manganese acetate and 15mL glacial acetic acid were added to a 50mL round-bottom flask in sequence, and then placed in a microwave synthesizer, with the heating temperature set to 100°C, the power set to 700W, the heating time set to 25min, and the magnetic stirring set to start. After the reaction was completed, the reaction solution was cooled to room temperature, 30mL deionized water and dichloromethane (20mL×3) were added for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain a light yellow solid, which was then purified by silica gel column [eluent was dichloromethane / petroleum ether (60-90°C), V / V=2:1] to obtain 253mg of 2-dodecanoylaminonaphtho[2,1-d]thiazole, with a yield of 85%. 2-dodecanoylaminonaphtho[2,1-d]thiazole was recorded as NH01.

[0046] Melting point: 130~131℃.

[0047] 1 H NMR (400MHz, CDCl3): δ11.06(s,1H),8.04(d,J=8.10Hz,1H),7.96(d,J=8.00Hz,1H),7.88(d,J=8.90Hz,1H),7.85(d,J=8.80Hz,1 H),7.65-7.58(m,1H),7.56-7.50(m,1H),2.50(t,J=7.60Hz,2H),1.76-1.69(m,2H),1.28-1.18(m,16H),0.87(t,J=7.00Hz,3H).

[0048] 13 C NMR (101MHz, CDCl3): δ171.7,158.6,145.8,130.5,129.0,128.3,127.9,127.4,127.2, 125.4,124.1,119.7,36.6,31.9,29.6,29.6,29.4,29.3,29.2,29.1,25.1,22.7,14.1.

[0049] HRMS(ESI)calcd for C 23 H 31 N2OS[M+H] + :383.2157, found 383.2152.

[0050] Example 2

[0051] The synthesis method of 2-dodecanoylaminonaphtho[2,1-d]thiazole specifically comprises the following steps:

[0052] 0.80mmol 3-(2-naphthyl)-1-dodecanoylthiourea, 1.99mmol manganese acetate and 15mL glacial acetic acid were added to a 50mL round-bottom flask in sequence, and then placed in a microwave synthesizer, and the heating temperature was set to 110°C, the power was 800W, the heating time was 27min, and magnetic stirring was turned on. After the reaction was completed, the reaction solution was cooled to room temperature, 30mL deionized water and dichloromethane (20mL×3) were added for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain a light yellow solid, which was then purified by silica gel column [eluent was dichloromethane / petroleum ether (60-90°C), V / V=2:1] to obtain 2-dodecanoylaminonaphtho[2,1-d]thiazole.

[0053] Example 3

[0054] The synthesis method of 2-dodecanoylaminonaphtho[2,1-d]thiazole specifically comprises the following steps:

[0055] 0.82mmol 3-(2-naphthyl)-1-dodecanoylthiourea, 2.03mmol manganese acetate and 15mL glacial acetic acid were added to a 50mL round-bottom flask in sequence, and then placed in a microwave synthesizer, and the heating temperature was set to 105°C, the power was 600W, the heating time was 30min, and magnetic stirring was turned on. After the reaction was completed, the reaction solution was cooled to room temperature, 30mL deionized water and dichloromethane (20mL×3) were added for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain a light yellow solid, which was then purified by silica gel column [eluent was dichloromethane / petroleum ether (60-90°C), V / V=2:1] to obtain 2-dodecanoylaminonaphtho[2,1-d]thiazole.

[0056] The performance of 2-dodecanoylaminonaphtho[2,1-d]thiazole prepared in Examples 2 to 3 is similar to that of 2-dodecanoylaminonaphtho[2,1-d]thiazole prepared in Example 1. We only take 2-dodecanoylaminonaphtho[2,1-d]thiazole prepared in Example 1 as an example and use 2-dodecanoylaminonaphtho[2,1-d]thiazole to detect Fe 3+ and Hg 2+ .

[0057] (1) Preparation of NH01 solution

[0058] Weigh 0.0038 g of NH01 solid, dissolve it in anhydrous ethanol, and adjust the volume to 50 mL. The concentration is 4×10 - 4 mol / L NH01 solution. The concentration of metal ions used in the experiment was 2×10 -2 mol / L, and the solutions of these metal ions are all aqueous solutions.

[0059] (2) Effect of adding different metal ions on the fluorescence spectrum of NH01

[0060] Take 200 μL (4×10 -4 mol / L) NH01 solution, add 1800μL of anhydrous ethanol to the NH01 solution, first measure a blank sample, then add 1μL (2×10 -2 mol / L) of Fe 3+ The solution was measured each time it was added (a total of 10 times), and the data for each time was recorded and processed into a spectrum after sorting. 2+ , Ca 2+ , Cd 2+ ,Co 2+ , Cu 2+, K + , Mn 2+ , Ni 2+ , Pb 2+ , Zn 2+ , Al 3+ , Ag + ,Mg 2+ , Na + , Hg 2+ ) on the fluorescence spectrum of NH01, using the same steps as above. Figure 1A -P, where the top curve in Figure 1 represents NH01 (concentration of 4×10 -5 mol / L, using ethanol as solvent). The remaining curves from top to bottom are the concentrations of metal ions in the mixed solution of 1×10 -5 mol / L、2×10 -5 mol / L、3×10 -5 mol / L、4×10 -5 mol / L、5×10 -5 mol / L、6×10 -5 mol / L、7×10 -5 mol / L、8×10 -5 mol / L、9×10 -5 mol / L、1×10 -4 mol / L, the concentration of NH01 in the mixed solution was 4×10 -5 mol / L, Figure 1A The metal ions in -P are Fe 3+ , Hg 2+ 、Ag + 、Al 3+ , Ca 2+ , Ba 2 、Cd 2+ 、Co 2+ , Cu 2 + 、Zn 2+ , K + Mg 2+ , Mn 2+ 、Na + 、Ni 2+ , Pb 2+ .

[0061] Figure 1A It can be seen that when Fe 3+ When added to NH01, its fluorescence intensity increases with Fe 3+ It gradually weakens with the increase of concentration. Figure 1B It can be obtained that when Hg 2+When added to NH01, its fluorescence intensity increases with the 2+ The concentration gradually decreases. Figures 1C to 1P It can be seen that when these ions are added to NH01, their fluorescence spectrum has almost no effect. This shows that this method can simultaneously identify two metal ions: Fe 3+ and Hg 2+ .

[0062] (3) Coexistence interference test (other ions on Fe 3+ Impact of

[0063] Take 200 μL (4×10 -4 mol / L) NH01 solution, add 1800 μL of anhydrous ethanol to the NH01 solution, shake well and record the fluorescence spectrum of the blank sample, then add 10 μL (2×10 -2 mol / L) of Fe 3+ After the solution is shaken, the test is performed again, and finally 10 μL (2×10 -2 mol / L) of some other metal ion (such as Na + ) and then shaken and tested. The remaining 14 metal ions (Ba 2+ , Ca 2+ , Cd 2+ ,Co 2+ , Cu 2+ , K + , Mn 2+ , Ni 2+ , Pb 2+ , Zn 2+ , Al 3+ , Ag + ,Mg 2+ , Hg 2+ ) Detection of Fe on NH01 3+ The coexistence interference detection steps are the same as those of Na + The results are as follows Figure 2 shown. Figure 2 The concentration of NH01 used in the experiment was 4×10 -5 mol / L, the metal ion concentration used was 1×10 -4 mol / L, Figure 2 Ag in + 、Al is Al 3+ , Ba is Ba 2+ , Ca is Ca 2+ , Cd is Cd 2+ 、Co is Co 2 + 、Cu is Cu 2+ , Hg is Hg 2+ , K is K +Mg is Mg 2+ 、Mn is Mn 2+ 、Na is Na + , Ni for Ni 2+ 、Pb is Pb 2+ 、Zn is Zn 2+ .

[0064] Figure 2 where I is Fe 3+ After adding other ions (such as Ag) to the mixed solution with NH01 + ), I0 is the fluorescence intensity of NH01 and Fe 3+ Fluorescence intensity of the mixture, other ions for NH01 test Fe 3+ The interference experiment is the same as the above Ag + It can be seen from the figure that I / I0 basically hovers around 1.0, indicating that when Fe 3+ The fluorescence intensity after adding NH01 is almost the same as that after adding other ions to the mixed solution. Therefore, it can be determined that other metal ions have little effect on the Fe test of NH01. 3+ No interference in the system.

[0065] (4) Coexistence interference test (other ions to Hg 2+ Impact of

[0066] Take 200 μL (4×10 -4 mol / L) NH01 solution, add 1800 μL of anhydrous ethanol to the NH01 solution, shake well and record the fluorescence spectrum of the blank sample, then add 10 μL (2×10 -2 mol / L) of Hg 2+ After the solution is shaken, the test is performed again, and finally 10 μL (2×10 -2 mol / L) of some other metal ion (such as Na + ) and then shaken and tested. The remaining 14 metal ions (Ba 2+ , Ca 2+ , Cd 2+ ,Co 2+ , Cu 2+ , K + , Mn 2+ , Ni 2+ , Pb 2+ , Zn 2+ , Al 3+ , Ag + ,Mg 2+ , Fe 3+ ) Detection of Hg in NH01 2+ The coexistence interference detection steps are the same as those of Na + The results are as follows Figure 3shown.

[0067] Figure 3 The concentration of NH01 used in the experiment was 4×10 -5 mol / L, the metal ion concentration used was 1×10 -4 mol / L, Figure 3 Ag in + 、Al is Al 3+ , Ba is Ba 2+ , Ca is Ca 2+ , Cd is Cd 2+ 、Co is Co 2+ 、Cu is Cu 2+ , Fe is Fe 3+ , K is K + Mg is Mg 2+ 、Mn is Mn 2+ 、Na is Na + , Ni for Ni 2+ 、Pb is Pb 2+ 、Zn is Zn 2+ .

[0068] Figure 3 I2 is Hg 2+ After adding other ions (such as Ag) to the mixed solution with NH01 + ), I1 is the fluorescence intensity of NH01 and Hg 2+ Fluorescence intensity of the mixture, other ions NH01 test Hg 2+ The interference experiment is the same as the above Ag + .Depend on Figure 3 It can be seen that I2 / I1 is basically hovering around 1.0 (except Fe 3+ ), indicating that when Hg 2+ The fluorescence intensity after adding NH01 is almost the same as that after adding other ions to the mixed solution, which can be used to determine the fluorescence intensity of other metal ions (except Fe 3+ ) Test Hg for NH01 2+ There is no interference in the system. 3+ When present, it will affect the determination of mercury ions.

[0069] (5) NH01 to Fe 3+ and Hg 2+ Response test

[0070] Take 200 μL (4×10 -5 mol / L) NH01 solution, add 1800μL of anhydrous ethanol to the NH01 solution to obtain a blank sample. First measure the blank sample 20 times to obtain the standard deviation of the blank sample, and then add 2μL (2×10 -2mol / L) of Fe 3+ The solution was measured each time it was added (a total of 10 times), and the data for each time was recorded and processed into a spectrum after being sorted, as shown in a and b in Figure 4.

[0071] Take 200 μL (4×10 -5 mol / L) NH01 solution, add 1800μL of anhydrous ethanol to the NH01 solution to obtain a blank sample. First measure the blank sample 20 times to obtain the standard deviation of the blank sample, and then add 2μL (2×10 -2 mol / L) of Hg 2+ The solution was measured each time it was added (a total of 10 times), and the data for each time was recorded and processed into a spectrum after being sorted, as shown in a and b in Figure 5.

[0072] like Figure 4a As shown, when NH01 is used as the probe solution, as Fe 3+ As the concentration increases (from 0 μM to 200 μM), the intensity of the probe fluorescence spectrum gradually decreases. Figure 4a Some data in (Fe 3+ The five data of concentrations of 20 μmol / L, 40 μmol / L, 60 μmol / L, 80 μmol / L, and 100 μmol / L, respectively, can obtain the linear regression equation y=-2.9411x+445.58, the correlation coefficient R=0.9852, and the standard deviation of the blank sample is: 3.0889, Fe 3+ The minimum detection limit is 3.15 μmol / L (the minimum detection limit is 3 times the standard deviation of the blank sample divided by the slope), and its linear range is 20 μmol / L to 100 μmol / L. Figure 4b As shown, a certain response trend is shown in the range of 0 μmol / L to 200 μmol / L.

[0073] Depend on Figure 5a It can be seen that with the increase of Hg 2+ With the increase of concentration (from 0μM to 200μM), the fluorescence intensity of NH01 gradually weakened (from 505.438 to 203.016), combined with Figure 5a It can be seen that when Hg 2+ When the concentration was 100 μM, the fluorescence intensity of NH01 decreased slightly, and from 160 μM, its fluorescence intensity remained basically the same. Figure 5a Some data in (Hg 2+The concentrations of 20 μmol / L, 40 μmol / L, 60 μmol / L, and 80 μmol / L, respectively, can be used to obtain the linear regression equation y = -2.3054x + 464.35, the correlation coefficient R = 0.9983, and the standard deviation of the blank sample is: 6.21271, Hg 2+ The minimum detection limit is 8.08 μmol / L (the minimum detection limit is 3 times the standard deviation of the blank sample divided by the slope), and its linear range is 20 μmol / L to 80 μmol / L. Figure 5b As shown, a certain response trend is shown in the range of 0 μmol / L to 200 μmol / L.

[0074] (6) NaF was added to Fe 3+ and NH01 mixed solution, Hg 2+ and NH01 mixed solution

[0075] Take 200 μL (4×10 -4 mol / L) NH01 solution, add 1800μL of anhydrous ethanol to the NH01 solution, and perform fluorescence spectrum test; then add 10μL of 1mol / L NaF to the solution, and perform fluorescence spectrum test; finally, add 20μL of 2×10 -2 mol / LFe 3+ , perform fluorescence spectrum test and organize it into a spectrum, such as Figure 6 shown.

[0076] Take 200 μL (4×10 -4 1800 μL of anhydrous ethanol was added to the NH01 solution for fluorescence spectrum test; then 10 μL of 1 mol / L NaF was added to the solution for fluorescence spectrum test; finally, 20 μL of 2×10 -2 mol / LHg 2+ , perform fluorescence spectrum test and organize it into a spectrum, such as Figure 7 .

[0077] Depend on Figure 6 It can be seen that when NaF is added to NH01 solution, its fluorescence intensity is not affected. 3+ Adding it into a mixed solution of NaF and NH01 does not affect its fluorescence intensity.

[0078] Depend on Figure 7 It can be seen that when NaF is added to NH01 solution, its fluorescence intensity is not affected. 2+When added to the mixed solution of NaF and NH01, the fluorescence intensity weakened normally, indicating that NaF can indeed be used to detect Fe in this system. 3+ Masking is performed without affecting the detection of mercury ions by NH01.

[0079] Although the preferred embodiments of the present invention have been described, those skilled in the art may make other changes and modifications to these embodiments once they have learned the basic creative concept. Therefore, the appended claims are intended to be interpreted as including the preferred embodiments and all changes and modifications that fall within the scope of the present invention.

[0080] Obviously, those skilled in the art can make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. Thus, if these modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include these modifications and variations.

Claims

1. 2-Dodecanoylaminonaphtho[2,1-d]thiazole in the preparation of Fe 3+ or Hg 2+ Application of fluorescent probes for detection.

2. The 2-dodecanoylamino naphtho[2,1-d]thiazole according to claim 1 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that Using anhydrous ethanol as solvent, 3+ or Hg 2+ The solution was added to the anhydrous ethanol solution of 2-dodecanoylaminonaphtho[2,1-d]thiazole for detection.

3. The 2-dodecanoylamino naphtho[2,1-d]thiazole according to claim 2 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that 2-Dodecanoylaminonaphtho[2,1-d]thiazole for Hg 2+ The minimum detection limit is 8.08×10 -6 mol / L, for Hg 2+ The response range is 2×10 -5 mol / L-2×10 -4 mol / L.

4. The 2-dodecanoylamino naphtho[2,1-d]thiazole according to claim 2 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that 2-Dodecanoylaminonaphtho[2,1-d]thiazole for Fe 3+ The response range is 2×10 - 5 mol / L-2×10 -4 mol / L, the minimum detection limit is 3.15×10 -6 mol / L.

5. The 2-dodecanoylaminonaphtho[2,1-d]thiazole according to claim 4 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that The 2-dodecanoylaminonaphtho[2,1-d]thiazole is prepared according to the following method: 2-Dodecanoylaminonaphtho[2,1-d]thiazole was synthesized by free radical ring-closure reaction using glacial acetic acid as solvent, manganese acetate as catalyst and 3-(2-naphthyl)-1-dodecanoylthiourea as raw material.

6. The 2-dodecanoylaminonaphtho[2,1-d]thiazole according to claim 5 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that The free radical ring-closing reaction occurs through microwave reaction, wherein the heating temperature of the microwave reaction is 100-110° C., the power is 600-800 W, and the heating time is 25-30 min.

7. The 2-dodecanoylaminonaphtho[2,1-d]thiazole according to claim 6 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that The ratio of 3-(2-naphthyl)-1-dodecanoylthiourea, manganese acetate and glacial acetic acid is 0.78-0.82 mmol:1.95-2.03 mmol:15 mL.

8. The 2-dodecanoylaminonaphtho[2,1-d]thiazole according to claim 7 is used in the preparation of Fe 3+ or Hg 2+ Application in fluorescent probe for detection, characterized in that After the free radical ring-closure reaction is completed, the reaction solution is cooled to room temperature, deionized water and dichloromethane are added for extraction, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, and the filtrate is concentrated and purified to obtain 2-dodecanoylaminonaphtho[2,1-d]thiazole.

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