CN108218880B - Mercury ion optical probe and preparation method and application thereof - Google Patents
Mercury ion optical probe and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a mercury ion optical probe and a preparation method and application thereof, wherein the structural formula of the mercury ion optical probe is as follows:
(ii) a The preparation method comprises preparing rhodamine B acyl chloride from rhodamine B, and reacting with rhodamine B acyl chlorideN,NReacting dimethylthiourea in a solvent containing triethylamine, removing the solvent through reduced pressure distillation, extracting, rotary evaporating and separating by column chromatography to obtain the mercury ion optical probe. The invention takes rhodamine B as a fluorescent group,N,Nthe-dimethylthiourea is used as a recognition group to synthesize the mercury ion optical probe, has strong selectivity and high sensitivity to mercury ions and strong anti-interference capability to other metal ions, can be used as a basis for qualitative and quantitative detection of the mercury ions, is applied to mercury ion detection and in-situ online quantitative analysis, and has wide application prospects.
Description
Technical Field
The invention relates to a mercury ion optical probe, in particular to a mercury ion optical probe and a preparation method and application thereof.
Background
Mercury is mainly expressed as mercury simple substance (Hg) and mercury ion (Hg) in nature2+) And methyl mercury (MeHg)+) And the like. Elemental mercury in liquid form is very low in toxicity because it cannot be absorbed by the human body through skin contact or the gastrointestinal tract. The gaseous mercury has great toxicity, and can easily enter human body through alveolar membrane, and can be oxidized into virulent Hg by catalase in erythrocytes and liver cells2+. The mercury in the atmosphere can be oxidized into Hg by ozone, hydroxyl free radical and the like in the air2+Then, the water enters the ground and the soil along with rainfall, and finally is accumulated in various water bodies. Hg in a portion of a water body2+Absorbed by aquatic microorganisms and converted into MeHg with higher toxicity to human body+Finally, the medicine is absorbed by human beings, causes cardiovascular diseases such as heart disease and hypertension, can affect the functions of liver, thyroid gland and skin of human beings, and even causes serious damage to the central nervous system and endocrine system, thereby threatening the health of human beings"Water preferentially" in Japan is caused by methylmercury poisoning. Therefore, China requires that the mercury content in drinking water and farmland irrigation water is not more than 0.001 mg/L, and the mercury content in fishery water is not more than 0.005 mg/L. However, in recent years, environmental pollution is increased, water body pollution is serious, and the content of mercury in the water body is possibly over standard, so that a method for efficiently, simply, quickly and sensitively detecting and identifying trace mercury in the environment and organisms is urgently needed to be established.
The currently commonly used methods for detecting mercury ions include atomic absorption/emission spectrometry, inductively coupled plasma mass spectrometry, electrochemical methods, chemiluminescence methods, and the like, but these methods still have many disadvantages in practical use, such as expensive instruments, complex operation, and inability to realize real-time in-situ detection. In recent years, the molecular optical probe has the advantages of high efficiency, rapidness, high sensitivity, realization of in-situ visual detection and the like, so that the research and the application of the molecular optical probe are increasingly concerned. Nevertheless, many reported mercury ion optical probes still have the problems of complex synthesis steps, poor selectivity, harsh test conditions and the like. Therefore, the development of a novel mercury ion optical probe which is simple in preparation method, good in selectivity, high in sensitivity, convenient and practical has important significance in the fields of biochemistry, environmental science, medicine and the like.
Disclosure of Invention
The invention aims to provide a mercury ion optical probe to solve the problems of poor selectivity, low sensitivity, harsh test conditions and the like of the conventional mercury ion optical probe.
The second objective of the present invention is to provide a method for preparing a mercury ion optical probe, so as to solve the problem of complicated preparation steps of the existing mercury ion optical probe.
The invention also aims to provide the application of the mercury ion optical probe in the aspects of mercury ion detection and quantitative analysis so as to realize the high-selectivity and high-sensitivity detection of mercury ions and the quantitative determination of the content of mercury ions.
One of the objects of the invention is achieved by:
a mercury ion optical probe has a structural formula as follows:
the second purpose of the invention is realized by the following steps:
the preparation method of the mercury ion optical probe comprises the steps of preparing rhodamine B acyl chloride by adopting rhodamine B, and reacting the rhodamine B acyl chloride with the rhodamine B acyl chlorideN,NReacting dimethylthiourea in a solvent containing triethylamine, removing the solvent through reduced pressure distillation, extracting, rotary evaporating and separating by column chromatography to obtain the mercury ion optical probe.
Rhodamine B andN,Nthe mol ratio of the dimethyl thiourea to the dimethyl thiourea is 1: 1-1.5.
The solvent is one or a mixture of tetrahydrofuran and acetonitrile.
The volume of triethylamine is 1.2-2.0 mL, and the volume of the used solvent is 10-12 mL.
Rhodamine B acyl chloride andN,Nthe reaction temperature of the dimethylthiourea in the solvent containing triethylamine is 10-35 ℃.
Rhodamine B acyl chloride andN,Nthe reaction time of the dimethylthiourea in the solvent containing triethylamine is 5-12 h.
The eluent used for column chromatography separation is a mixed solution of ethyl acetate and petroleum ether.
Heating, refluxing and stirring rhodamine B and phosphorus oxychloride in 1, 2-dichloroethane at 90-100 ℃, reacting for 4-5 h, and distilling under reduced pressure to remove 1, 2-dichloroethane to obtain rhodamine B acyl chloride; mixing the obtained rhodamine B acyl chloride withN,NReacting dimethylthiourea in a solvent containing triethylamine, removing the solvent through reduced pressure distillation, extracting, rotary evaporating and separating by column chromatography to obtain the mercury ion optical probe.
The molar volume ratio of rhodamine B to phosphorus oxychloride is 0.5 mmol: 0.3-0.5 mL, and the volume of 1, 2-dichloroethane is 10-13 mL.
The third purpose of the invention is realized by the following steps:
the mercury ion optical probe is applied to the aspects of mercury ion detection and content analysis, has high selectivity to mercury ions, and has high reaction speed with mercury ions and good detection sensitivity.
The invention takes rhodamine B as a fluorescent group,N,Nthe mercury ion optical probe is synthesized by using dimethylthiourea as a recognition group, and the method has the advantages of simple synthesis steps, readily available raw materials and convenience in preparation. Mercury ions can act with-C = S group in the optical probe, so that ring-opening reaction of lactam ring is induced, strong fluorescence is generated, a remarkable absorption peak is generated at 557 nm, the color of the solution is changed from colorless to purple red, fluorescence at 582 nm is remarkably enhanced, and the fluorescence intensity and the mercury ion concentration have excellent linear relation in a certain range, and the optical probe can be used as Hg2+And (5) the basis of qualitative and quantitative detection.
The optical probe has specific recognition on mercury ions, has high reaction speed with the mercury ions, can tend to be stable in fluorescence intensity within 1 min, has high sensitivity, longer absorption and emission wavelengths, small background interference, almost no response to other metal ions and strong anti-interference capability to other metal ions, can be widely applied to mercury ion detection and in-situ online quantitative analysis, and has wide application prospects in the fields of biochemistry, environmental science, medicine and the like.
Drawings
FIG. 1 is an absorption spectrum of an optical probe of the present invention as a function of mercury ion concentration.
FIG. 2 is a fluorescence emission spectrum of the optical probe of the present invention as a function of mercury ion concentration.
FIG. 3 is a graph of the fluorescence increase versus mercury ion concentration for the optical probe of the present invention reacted with mercury ions.
FIG. 4 is a selective response absorption spectrum of an optical probe of the present invention for mercury ions.
FIG. 5 is a fluorescence spectrum of the selective response of the optical probe of the present invention to mercury ions.
FIG. 6 is a bar graph showing the change in fluorescence intensity of the optical probe of the present invention after reaction with mercury ions in the presence of different interfering metal ions.
Detailed Description
The present invention will be described in further detail with reference to examples.
In the following examples, the procedures and methods not described in detail are conventional methods well known in the art, and the reagents used are commercially available, analytically pure or chemically pure. The following examples all achieve the objects of the present invention.
Example 1
239.5 mg of rhodamine B (0.5 mmol) is weighed, dissolved in 10mL of 1, 2-dichloroethane, 0.3 mL of phosphorus oxychloride is added dropwise, and the mixture is heated and refluxed for reaction for 4 hours at 90 ℃. And after the reaction is finished, removing the solvent by reduced pressure distillation to obtain a red rhodamine B acyl chloride intermediate.
Weighing 52.1 mgN,NDimethylthiourea (0.5 mmol), dissolved in 5 mL of tetrahydrofuran, was added dropwise with stirring to 1.2 mL of triethylamine. Dissolving the rhodamine B acyl chloride prepared in the previous step in 5 mL of tetrahydrofuran, dropwise adding the solution, and reacting for 10 h at 20 ℃. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain a purple red substance, 10mL of secondary distilled water was added thereto, extraction was carried out three times (20 mL. times.3) with methylene chloride, and the extract was distilled off under reduced pressure to remove the solvent to obtain a crude product. And (3) separating the obtained crude product by adopting column chromatography (silica gel G, 200-300 meshes), wherein an eluant is a mixed solution of ethyl acetate and petroleum ether, the volume ratio of the ethyl acetate to the petroleum ether is 1:3, and the pure product of the rhodamine B optical probe is 129.9 mg, and the yield is 49.2%. The product was obtained as a pale yellow solid with a molecular weight of 528.3.
And performing mass spectrum and nuclear magnetism characterization on the obtained optical probe, wherein the results are as follows:
mass spectrum: MS (ESI) M/z 529.3 [ M + H ]]+；
Nuclear magnetic hydrogen spectrum:1H NMR (500 MHz, CDCl3, 298 K):(ppm), 7.97 (d, J = 7.0 Hz,1H ), 7.50-7.57 (m, 2H), 7.18 (d, J = 7.5 Hz, 1H ), 6.38-6.45 (m, 4H), 6.27-6.29 (m, 2H), 3.34 (q, J = 7.0 Hz, 8H), 3.24 (s, 3H), 2.94 (s, 3H), 1.16 (t,J = 7.0 Hz, 12H)；
nuclear magnetic carbon spectrum:13C NMR (125 MHz, CDCl3, 298 K):(ppm), 180.2, 164.5,154.3, 153.0, 149.0, 133.5, 130.3, 129.1, 128.5, 124.6, 123.6, 107.5, 98.1,69.2, 44.3, 12.6。
the reaction equation for this synthesis is as follows:
example 2
239.5 mg of rhodamine B (0.5 mmol) is weighed, dissolved in 12 mL of 1, 2-dichloroethane, 0.4 mL of phosphorus oxychloride is added dropwise, and the mixture is heated and refluxed for reaction for 5 hours at 95 ℃. And after the reaction is finished, removing the solvent by reduced pressure distillation to obtain a red rhodamine B acyl chloride intermediate.
72.9 mg of N, N-dimethylthiourea (0.7 mmol) were weighed out, dissolved in 6 mL of acetonitrile and 1.6 mL of triethylamine was added dropwise with stirring. Dissolving the rhodamine B acyl chloride prepared in the previous step in 5 mL of tetrahydrofuran, dropwise adding the solution, and reacting for 5 h at 35 ℃. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain a purple red substance, 10mL of secondary distilled water was added thereto, extraction was carried out three times (20 mL. times.3) with methylene chloride, and the extract was distilled off under reduced pressure to remove the solvent to obtain a crude product. And (3) separating the obtained crude product by adopting column chromatography (silica gel G, 200-300 meshes), wherein an eluant is a mixed solution of ethyl acetate and petroleum ether, the volume ratio of the ethyl acetate to the petroleum ether is 1:3, and the pure product of the rhodamine B optical probe, namely 137.5 mg, is obtained, and the yield is 52.1%.
Example 3
239.5 mg of rhodamine B (0.5 mmol) is weighed, dissolved in 13 mL of 1, 2-dichloroethane, 0.5 mL of phosphorus oxychloride is added dropwise, and the mixture is heated and refluxed for 5 hours at 100 ℃. And after the reaction is finished, removing the solvent by reduced pressure distillation to obtain a red rhodamine B acyl chloride intermediate.
Weighing 78.2 mgN,NDimethylthiourea (0.75 mmol), dissolved in 7 mL acetonitrile, was added dropwise with stirring to 2.0 mL triethylamine. Dissolving the rhodamine B acyl chloride prepared in the previous step in 5 mL of acetonitrile, dropwise adding the solution, and reacting at 10 ℃ for 12 h. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain a purple red substance, 10mL of secondary distilled water was added thereto, extraction was carried out three times (20 mL. times.3) with methylene chloride, and the extract was distilled off under reduced pressure to remove the solvent to obtain a crude product. Will be describedThe crude product is separated by column chromatography (silica gel G, 200-300 meshes), the eluent is a mixed solution of ethyl acetate and petroleum ether, the volume ratio of the ethyl acetate to the petroleum ether is 1:3, and 144.1 mg of a pure product of the rhodamine B optical probe can be obtained, and the yield is 54.6%.
Example 4
The optical probe of the invention is researched by adopting a mixed system of acetonitrile and phosphate buffer solution with pH =7.20 and a volume ratio of 1:1 for different concentrations of Hg2+In response to (2).
Adding the optical probe of the present invention to a mixed system of acetonitrile and phosphate buffer solution (pH = 7.20) in a volume ratio of 1:1 to make the final concentration thereof 5 μ M; hg is added at a concentration of 0 μ M, 0.5 μ M, 1 μ M, 1.5 μ M, 2 μ M, 2.5 μ M, 3 μ M, 3.5 μ M, 4 μ M, 4.5 μ M, 5 μ M, 10 μ M, 15 μ M, 20 μ M, 25 μ M, 30 μ M, 35 μ M, 40 μ M, 45 μ M, or 50 μ M2+After the volume of the mixture of acetonitrile and water is constant to the same volume by using the volume ratio of 1:1, the Hg added is measured2+Before and after the absorption spectrum and fluorescence spectrum (excitation with excitation light having a wavelength of 520 nm) of the optical probe of the present invention.
FIGS. 1 and 2 show the absorption spectrum and fluorescence emission spectrum of the optical probe according to the present invention as a function of the concentration of mercury ions, respectively, and FIG. 3 shows the working curve of the fluorescence increment of the optical probe according to the present invention reacting with mercury ions versus the concentration of mercury ions. The above results show that the optical probe of the present invention has the following characteristics: (1) the optical probe has no absorption and almost no fluorescence in the solution, but generates absorption at 557 nm and yellow fluorescence at 582 nm along with the addition of mercury ions; (2) the absorption spectrum and the fluorescence intensity are enhanced along with the increase of the concentration of mercury ions; (3) when the optical probe with the thickness of 5 mu M is used, the fluorescence increment and mercury ions in the range of 0.5-3.5 mu M form an excellent linear relation.
Example 5
The selectivity of the optical probe of the invention for mercury ions was studied using a mixed system of acetonitrile and phosphate buffer solution with a pH =7.20, volume ratio of 1: 1.
A mixed system of acetonitrile and phosphate buffer solution in a volume ratio of 1:1 (pH = 7.20) was added to the optical probe of the present invention to make a final concentration of 5 μ M; then adding different metal ions (Ag) with 10 times of molar equivalent respectively+、Cu2+、Fe3+、Fe2 +、K+、Mg2+、Ca2+、Ba2+、Cr3+、Mn2+、Co2+、Ni2+、Zn2+、Cd2+、Pb2+、Al3+、Hg2+) And after reacting for 5 min, detecting the absorption spectrum and the fluorescence intensity of the mixture.
Fig. 4 and 5 show selective response absorption spectra and fluorescence spectra of the optical probe of the present invention for mercury ions, respectively, and the results show that the absorption and fluorescence intensities are significantly enhanced only after the mercury ions are added, and the absorption and fluorescence spectra are almost unchanged after other metal ions are added, which indicates that the optical probe has specific recognition for mercury ions, i.e. has high selectivity.
Example 6
The interference research of other common metal ions on the detection of mercury ions by the optical probe is researched by adopting a mixed system of acetonitrile and phosphate buffer solution with the pH =7.20 and the volume ratio of 1: 1.
Adding the optical probe of the present invention to a mixed system of acetonitrile and phosphate buffer solution (pH = 7.20) in a volume ratio of 1:1 to make the final concentration thereof 5 μ M; then adding different metal ions (Ag) with 10 times of molar equivalent respectively+、Cu2+、Fe3+、Fe2 +、K+、Mg2+、Ca2+、Ba2+、Cr3+、Mn2+、Co2+、Ni2+、Zn2+、Cd2+、Pb2+、Al3+) Then, 10 times of molar equivalent of mercury ions are added dropwise, and after 5 min of reaction, the fluorescence intensity is detected.
FIG. 6 is a bar graph showing the change of fluorescence intensity of the optical probe of the present invention after reacting with mercury ions in the presence of different interfering metal ions, and the result shows that the presence of other metal ions has little interference on the identification of mercury ions by the optical probe of the present invention.
Claims (9)
1. A mercury ion optical probe is characterized in that the structural formula is as follows:
2. the preparation method of the mercury ion optical probe as claimed in claim 1, wherein rhodamine B and phosphorus oxychloride are heated, refluxed and stirred in 1, 2-dichloroethane at 90-100 ℃ for reaction for 4-5 hours, and the 1, 2-dichloroethane is removed by reduced pressure distillation to obtain rhodamine B acyl chloride; reacting rhodamine B acyl chloride withN,NReacting dimethylthiourea in a solvent containing triethylamine, removing the solvent through reduced pressure distillation, extracting, rotary evaporating and separating by column chromatography to obtain the mercury ion optical probe.
3. The method according to claim 2, wherein the rhodamine B is a compound of rhodamine andN,Nthe mol ratio of the dimethyl thiourea to the dimethyl thiourea is 1: 1-1.5.
4. The method according to claim 2, wherein the solvent is one of tetrahydrofuran and acetonitrile, or a mixture thereof.
5. The method according to claim 2, wherein the rhodamine B chloride is reacted withN,NThe reaction temperature of the dimethylthiourea in the solvent containing triethylamine is 10-35 ℃.
6. The method according to claim 2, wherein the rhodamine B chloride is reacted withN,NThe reaction time of the dimethylthiourea in the solvent containing triethylamine is 5-12 h.
7. The preparation method according to claim 2, wherein the eluent used for column chromatography is a mixture of ethyl acetate and petroleum ether.
8. The preparation method of claim 2, wherein the molar volume ratio of rhodamine B to phosphorus oxychloride is 0.5 mmol: 0.3-0.5 mL.
9. The application of the mercury ion optical probe in claim 1 in the aspects of mercury ion detection and content analysis.
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| CN102093372A (en) * | 2011-01-14 | 2011-06-15 | 青岛科技大学 | N-(rhodamine 6G) lactam-N'-phenylthiourea derivative fluorescent probe and preparation method |
| WO2014144561A2 (en) * | 2013-03-15 | 2014-09-18 | The Oregon State Board Of Higher Education Acting By And Through Portland State University | Lysophosphatidic acid detection |
| CN106083870A (en) * | 2016-06-07 | 2016-11-09 | 青岛科技大学 | A kind of Novel phosphoric acid two hydrogen radical fluorescent ion probe and preparation method and application |
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| CN106117230B (en) * | 2016-06-29 | 2018-07-06 | 河南师范大学 | Replace rhodamine B amide groups Thiourea fluorescent probe compounds and its preparation method and application |
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| CN102093372A (en) * | 2011-01-14 | 2011-06-15 | 青岛科技大学 | N-(rhodamine 6G) lactam-N'-phenylthiourea derivative fluorescent probe and preparation method |
| WO2014144561A2 (en) * | 2013-03-15 | 2014-09-18 | The Oregon State Board Of Higher Education Acting By And Through Portland State University | Lysophosphatidic acid detection |
| CN106083870A (en) * | 2016-06-07 | 2016-11-09 | 青岛科技大学 | A kind of Novel phosphoric acid two hydrogen radical fluorescent ion probe and preparation method and application |
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| Highly sensitive and selective turn-on fluorescent chemosensor for Pb2+ and Hg2+ based on a rhodamine-phenylurea conjugate;Zhi-Qiang Hu, 等;《Chemical Communications》;20100416;第46卷(第21期);第3765页图1，第3767页第1段 * |
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