CN114805272B - Arylcoumarin probe, probe molecule complex and Hg of urban sewage planning system 2+ Application in detection - Google Patents
Arylcoumarin probe, probe molecule complex and Hg of urban sewage planning system 2+ Application in detection Download PDFInfo
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- CN114805272B CN114805272B CN202210532625.7A CN202210532625A CN114805272B CN 114805272 B CN114805272 B CN 114805272B CN 202210532625 A CN202210532625 A CN 202210532625A CN 114805272 B CN114805272 B CN 114805272B
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- 239000000523 sample Substances 0.000 title claims abstract description 77
- 238000001514 detection method Methods 0.000 title claims abstract description 21
- 239000010865 sewage Substances 0.000 title claims abstract description 14
- -1 aryl coumarin Chemical compound 0.000 claims abstract description 61
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims abstract description 59
- 229960000956 coumarin Drugs 0.000 claims abstract description 50
- 235000001671 coumarin Nutrition 0.000 claims abstract description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 229920001661 Chitosan Polymers 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052753 mercury Inorganic materials 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 10
- 239000011259 mixed solution Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 8
- 238000004090 dissolution Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical group [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 abstract description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000686 lactone group Chemical group 0.000 description 2
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003968 anodic stripping voltammetry Methods 0.000 description 1
- 238000001391 atomic fluorescence spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- CIJQGPVMMRXSQW-UHFFFAOYSA-M sodium;2-aminoacetic acid;hydroxide Chemical compound O.[Na+].NCC([O-])=O CIJQGPVMMRXSQW-UHFFFAOYSA-M 0.000 description 1
- QXADHXQCAQTNGW-UHFFFAOYSA-M sodium;boric acid;hydroxide Chemical compound [OH-].[Na+].OB(O)O QXADHXQCAQTNGW-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- OAEZRJNGCVFHCM-UHFFFAOYSA-M tetramethylazanium hydroxide tetrahydrate Chemical compound O.O.O.O.[OH-].C[N+](C)(C)C OAEZRJNGCVFHCM-UHFFFAOYSA-M 0.000 description 1
- KIDNPGPIDAWJED-UHFFFAOYSA-M tetramethylazanium;hydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].C[N+](C)(C)C KIDNPGPIDAWJED-UHFFFAOYSA-M 0.000 description 1
- YNIRKEZIDLCCMC-UHFFFAOYSA-K trisodium;phosphate;hydrate Chemical compound [OH-].[Na+].[Na+].[Na+].OP([O-])([O-])=O YNIRKEZIDLCCMC-UHFFFAOYSA-K 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The invention discloses an aryl coumarin probe, a probe molecule complex and Hg of a sewage system in urban planning 2+ Application in detection. Compared with the prior art, the aryl coumarin probe and the probe molecule complex have good stability to Hg 2+ Very sensitive, high detection sensitivity and good popularization and application value.
Description
Technical Field
The invention relates to the field of fluorescence detection under urban planning environment evaluation, and particularly provides an aryl coumarin probe, a probe molecule complex and Hg (Hg) of an urban planning sewage system 2+ Application in detection.
Background
Under the background of rapid urban treatment, heavy metal ion pollution in urban sewage causes great harm to the environment and human health. It is counted that heavy metal pollution has become one of the important factors for carcinogenesis. Among the heavy metal pollution, the pollution of mercury ions is the most serious and the harm is the greatest. In urban environments, mercury exists in three forms of elemental mercury, mercury ions and organic mercury, which become potential factors threatening the health of citizens, and once excessive intake occurs, serious damage is caused to our perception system and nervous system, even so-called "water sickness" occurs, and this risk is especially serious for pregnant women and minors.
The current methods for detecting and analyzing mercury ions are as follows: atomic absorption emission spectroscopy, inductively coupled plasma mass spectrometry, cold atomic fluorescence spectroscopy, gas chromatography, electrochemical methods such as anodic stripping voltammetry, redox potential methods, and the like, but can be used as a fast low-cost detection means in the first line of work, and is preferably a small-molecule fluorescent probe with selectivity for mercury ions.
Coumarin compounds are one of the most interesting fluorescent probe molecules in the fields of ion identification, drug analysis and the like, and have the advantages of higher photo-thermal and chemical stability, high fluorescence quantum yield and the like. However, the mercury ion probe of single coumarin has some limitations such as poor water solubility, fluorescence quenching, poor ion selectivity and the like, and cannot be widely used.
Disclosure of Invention
The invention aims at the defects of the prior art, provides an aryl coumarin probe which has the characteristics of stable structure, high sensitivity and the like, and can be used for Hg in urban sewage 2+ Detection is carried out to promote sustainable development of urban health.
It is a further technical task of the present invention to provide an arylcoumarin probe molecule complex.
It is a still further technical task of the present invention to provide a process for the preparation of the above-mentioned compounds.
The invention further aims to provide the application of the coumarin-based probe and the compound in Hg & lt2+ & gt detection of urban planning sewage systems.
In order to achieve the technical task, the invention provides the following technical scheme.
Aryl coumarin probe shown in structural formula (I),
the preparation method of the aryl coumarin probe shown in the structural formula (I) comprises the following steps:
dissolving 2, 4-dihydroxybenzaldehyde and 1, 2-dibromoethane in N, N-Dimethylformamide (DMF), adding potassium carbonate, heating for reaction, heating with 1, 8-diazabicyclo undec-7-ene (DBU) in acetonitrile for reaction, condensing with p-hydroxybenzaldehyde, and performing aftertreatment after the reaction is finished to obtain the aryl coumarin probe shown in the structural formula (I). The reaction equation is as follows:
aryl coumarin probe molecular compound shown in structural formula (II),
the preparation method of the aryl coumarin probe molecular compound shown in the structural formula (II) is characterized by comprising the following steps:
s1, adding chitosan into a mixed solution of acetic acid and absolute methanol for dissolution to form a chitosan dispersion liquid, and then adding an aryl coumarin probe shown in a structural formula (I) for full dissolution to obtain a mixed solution;
s2, heating the mixed solution to 70-90 ℃ (preferably 75-85 ℃), adding a proper amount of pH regulator to adjust the pH to 9-12 (preferably 10-12) to obtain the aryl coumarin probe molecular compound, wherein the grafting rate of chitosan is 5-20%.
The reaction equation is as follows:
preferably, the molecular weight of the chitosan is 4 to 10 ten thousand, and the concentration of chitosan in the chitosan dispersion is 0.1 to 1.5g/L (particularly preferably 0.5 to 1 g/L).
Preferably, the pH regulator is a tetramethylammonium hydroxide nonpolar reagent, particularly preferably tetramethylammonium hydroxide tetrahydrate, tetramethylammonium hydroxide pentahydrate and/or tetramethylammonium hydroxide hexahydrate.
Preferably, the ratio of chitosan, arylcoumarin probe, acetic acid and anhydrous methanol is 1g (0.01-0.5 g) (5-50 ml) (300-3000 ml), particularly preferably 1g (0.05-0.2 g) (10-30 ml) (800-1500 ml).
According to the invention, the aryl coumarin probe shown in the structural formula (I) and the aryl coumarin probe molecular compound shown in the structural formula (II) can generate fluorescent molecules under the action of mercury ions, so that the selective recognition and detection of mercury ions can be realized.
In pure water or PBS buffer solution, the probe or the compound does not have fluorescence at 365nm, and generates strong blue fluorescence under the irradiation of an ultraviolet lamp after the probe or the compound reacts with mercury ions, the detection limit of the mercury ions is 0.01 mu mol/L, and the probe or the compound has strong selectivity and sensitivity and can be used for qualitative identification and fluorescence quantitative detection.
The aryl coumarin probe shown in the structural formula (I) and the aryl coumarin probe molecular compound shown in the structural formula (II) have stable molecular structure and high sensitivity, so that the method can be suitable for the complex environment of urban sewage and realize the accurate detection of mercury ions in the urban sewage.
Preferably, the method for detecting mercury ions by using the aryl coumarin probe shown in the structural formula (I) or the aryl coumarin probe molecular complex shown in the structural formula (II) comprises the following steps:
and adding a liquid to be detected into the aqueous solution of the probe molecular compound, then irradiating with ultraviolet light, observing the fluorescence change of the probe solution, and judging whether mercury ions are contained according to the fluorescence change of the probe solution.
Or is:
adding a to-be-detected liquid into an aqueous solution of a water-soluble coumarin fluorescent probe, then measuring a fluorescence emission spectrum to obtain fluorescence change values before and after adding the to-be-detected liquid, and then comparing the fluorescence change values with a standard curve to obtain the mercury ion content in the to-be-detected liquid.
Compared with the prior art, the aryl coumarin probe, the probe molecular compound, the preparation method and the Hg of the urban planning sewage system are provided 2+ The application in detection has the following outstanding beneficial effects:
the aryl coumarin probe molecule shown in the structural formula (I) is a novel compound, and the molecular skeleton of the aryl coumarin probe molecule belongs to a generalized flavonoid compound, and has great difference with the nature of the general coumarin probe molecule. Because of the substituted aryl, a large conjugated system is formed, the fluorescence intensity is improved, the lactone ring is changed to be very stable, and the whole molecule is not influenced by acid, alkali and corrosive chemical substances in the sewage, so that the method is favorable for being used as a detection reagent;
secondly, chitosan is used as a carrier, so that the aryl coumarin probe molecule compound shown in the structural formula (II) has enhanced water solubility, and the chitosan has a certain enrichment effect on mercury ions in water, so that the sensitivity can be improved, and even dispersion and inactivation of probe molecules in a large-volume water sample can be avoided in a short time, so that the application range is further expanded;
and (III) the aryl coumarin probe shown in the structural formula (I) and the aryl coumarin probe molecular compound shown in the structural formula (II) are convenient to use, low in production cost, suitable for being matched with a portable ultraviolet lamp at any place and suitable for further product development of a detection kit.
Drawings
FIG. 1 is a fluorescence emission spectrum of a chitosan-arylcoumarin probe molecular complex in response to mercury ions;
FIG. 2 is a fluorescence emission spectrum of a chitosan-arylcoumarin probe molecular complex responsive to mercury ions at different pH values.
Detailed Description
The invention will now be further described with reference to the drawings and specific examples, which are not intended to limit the invention.
Example 1
Preparation of aryl coumarin probes of formula (I):
0.1mol of 2, 4-dihydroxybenzaldehyde and 0.12mol of 1, 2-dibromoethane are dissolved in 200ml of N, N-Dimethylformamide (DMF), 60g of potassium carbonate is added, the mixture is heated and reacted, poured into ice water with 3 times of volume, filtered off with suction and dried. Then carrying out heating reaction with 0.1mol of 1, 8-diazabicyclo undec-7-ene (DBU) in 200ml of acetonitrile, adding 0.1mol of p-hydroxybenzaldehyde, 50ml of triethylamine and 50ml of acetic anhydride after spin drying, heating to reflux for condensation, pouring into ice water after the reaction is finished, and carrying out suction filtration to obtain the aryl coumarin probe shown in the structural formula (I).
Example 2
Preparation of arylcoumarin probe molecular complexes represented by structural formula (II):
firstly, 100mg of chitosan (molecular weight: 8 ten thousand) was weighed, 2mL of acetic acid was added dropwise for dissolution, and then 98mL of anhydrous methanol was added for further dissolution to form a methanol dispersion (1.0 g/L) of chitosan. Then, 10mg of coumarin probe molecules shown in the structural formula (I) are added and fully dissolved, the temperature of the mixed solution is raised to 80 ℃, tetramethyl ammonium hydroxide pentahydrate is added dropwise to adjust the pH to 12, and the magnetic stirring is kept for 1h, so that the chitosan-aryl coumarin probe molecule compound with the grafting rate of 15.5% is obtained.
Example 3
Drawing a fluorescence-concentration standard curve:
the chitosan-aryl coumarin probe molecular compound is prepared into a solution with the concentration of 10mg/L, then the aqueous solution of mercury acetate is added dropwise to the final concentration of 1, 5, 10, 15 and 20 mu mol/L, and after balancing, the fluorescence emission spectrum of the response of the fluorescent probe molecular compound to mercury ions is measured (see figure 1).
Example 4
Effects of different pH values:
the chitosan-arylcoumarin probe molecular complex was prepared into a solution with a concentration of 10mg/L in PBS buffer solution with pH=4, 5, 6, 7, 8 and 9, then mercury ions were added dropwise to 10. Mu. Mol/L, after equilibration, 365nm ultraviolet irradiation was performed to determine fluorescence intensity, and the result is shown in FIG. 2. The results indicate that the probe is effective in the pH range where mercury ions are soluble.
Example 5
Comparison of the stability of fluorescent molecules and classical coumarin fluorescent molecules produced by the invention
Preparing a solution with a specified pH value (boric acid-sodium hydroxide buffer solution is used for pH10, glycine-sodium hydroxide is used for pH11, disodium hydrogen phosphate-sodium hydroxide is used for pH12, sodium hydroxide is used for pH13 and 14), respectively preparing the aryl coumarin probe obtained in the example 1 and the classical coumarin fluorescent molecule into solutions with the concentration of 10mg/L, stirring at 50 ℃ for one hour, after balancing, irradiating with 365nm ultraviolet, observing fluorescence and recording:
from the detection results, the aryl coumarin probe molecule provided by the invention is obviously more stable to strong alkali, and the lactone ring is not easy to open.
Example 6
The aryl coumarin probe and the aryl coumarin probe molecular complex used in the invention are compared with the detection range of the classical coumarin probe
The arylcoumarin probe obtained in example 1, the arylcoumarin probe complex described in example 2 and the classical coumarin probe are prepared into a solution with the concentration of 10mg/L, mercury acetate is added to the solution with the final concentration of 0.01, 0.05, 0.1, 0.5 and 1 mu mol/L, after balancing, ultraviolet irradiation is performed at 365nm, fluorescence is observed and recorded:
as can be seen from the detection results, the aryl coumarin probe and the compound provided by the invention are specific for Hg 2+ The detection limit of the aryl coumarin probe complex on mercury ions can reach 0.01 mu mol/L.
Claims (6)
1. Aryl coumarin probe shown in structural formula (I),
2. an arylcoumarin probe molecule complex represented by the structural formula (II), the preparation method of which comprises the following steps:
s1, adding chitosan into a mixed solution of acetic acid and absolute methanol for dissolution to form a chitosan dispersion liquid, then adding an aryl coumarin probe shown in a structural formula (I) for full dissolution to obtain a mixed solution,
the molecular weight of the chitosan is 4-10 ten thousand, the concentration of the chitosan in the chitosan dispersion liquid is 0.1-1 g/L,
the dosage ratio of chitosan, aryl coumarin probe, acetic acid and absolute methanol is 1g (0.01-0.5 g) (5-50 ml) (300-3000 ml);
s2, heating the mixed solution to 70-90 ℃, adding a proper amount of pH value regulator to regulate the pH value to 9-12, obtaining the aryl coumarin probe molecular compound,
the pH value regulator is tetramethylammonium hydroxide nonpolar reagent,
3. the method for preparing the arylcoumarin probe molecular complex shown in the structural formula (II) in claim 2, which is characterized by comprising the following steps:
s1, adding chitosan into a mixed solution of acetic acid and absolute methanol for dissolution to form a chitosan dispersion liquid, then adding an aryl coumarin probe shown in a structural formula (I) for full dissolution to obtain a mixed solution,
the molecular weight of the chitosan is 4-10 ten thousand, the concentration of the chitosan in the chitosan dispersion liquid is 0.1-1 g/L,
the dosage ratio of chitosan, aryl coumarin probe, acetic acid and absolute methanol is 1g (0.01-0.5 g) (5-50 ml) (300-3000 ml);
s2, heating the mixed solution to 70-90 ℃, adding a proper amount of pH value regulator to regulate the pH value to 9-12, obtaining the aryl coumarin probe molecular compound,
the pH value regulator is tetramethylammonium hydroxide nonpolar reagent,
4. the application of the compound shown in the structural formula (I) in the detection of mercury ions in sewage,
5. the use of the aryl coumarin probe molecular complex shown in the structural formula (II) in claim 2 in detection of mercury ions in sewage.
6. The use according to claim 5, characterized in that: adding a sewage to-be-detected liquid into the aqueous solution of the probe molecular compound, then irradiating with ultraviolet light, observing the fluorescence change of the probe solution, and judging whether mercury ions are contained according to the fluorescence change of the probe solution.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588844A (en) * | 2016-11-15 | 2017-04-26 | 嘉兴学院 | Water-soluble coumarin fluorescent probe as well as preparation method and application thereof |
| CN113666898A (en) * | 2021-07-01 | 2021-11-19 | 长春工业大学 | Selective recognition Hg of coumarin-containing2+Fluorescent probe and preparation method thereof |
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2022
- 2022-05-13 CN CN202210532625.7A patent/CN114805272B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588844A (en) * | 2016-11-15 | 2017-04-26 | 嘉兴学院 | Water-soluble coumarin fluorescent probe as well as preparation method and application thereof |
| CN113666898A (en) * | 2021-07-01 | 2021-11-19 | 长春工业大学 | Selective recognition Hg of coumarin-containing2+Fluorescent probe and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 基于香豆素骨架的Hg2 + 荧光探针的研究进展;高京硕等;化学通报;20211231;第84卷(第5期);440-449 * |
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