CN111138329B - Preparation method and application of AIE fluorescent probe for detecting palladium ions - Google Patents
Preparation method and application of AIE fluorescent probe for detecting palladium ions Download PDFInfo
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- CN111138329B CN111138329B CN202010032249.6A CN202010032249A CN111138329B CN 111138329 B CN111138329 B CN 111138329B CN 202010032249 A CN202010032249 A CN 202010032249A CN 111138329 B CN111138329 B CN 111138329B
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 32
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 31
- -1 palladium ions Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229940125904 compound 1 Drugs 0.000 claims abstract description 34
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000008859 change Effects 0.000 claims abstract description 10
- OXPWNYQHSVWRES-HIXSDJFHSA-N 1-[4-[(Z)-1-cyano-2-(4-hexoxyphenyl)ethenyl]phenyl]-3-phenylthiourea Chemical compound C(#N)\C(=C/C1=CC=C(C=C1)OCCCCCC)\C1=CC=C(C=C1)NC(=S)NC1=CC=CC=C1 OXPWNYQHSVWRES-HIXSDJFHSA-N 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- 229940125782 compound 2 Drugs 0.000 claims description 8
- 229940117953 phenylisothiocyanate Drugs 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000012265 solid product Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 8
- 238000002156 mixing Methods 0.000 abstract description 2
- 230000035945 sensitivity Effects 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000011896 sensitive detection Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QENVQRYABLFZJR-UHFFFAOYSA-N biphenylene-1-carbonitrile Chemical group C12=CC=CC=C2C2=C1C=CC=C2C#N QENVQRYABLFZJR-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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- 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"
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- 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"
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Abstract
The invention relates to a preparation method and application of a fluorescent probe for detecting palladium ions. The invention firstly prepares a compound 1 (Z) -1- (4- (1-cyano-2- (4- (hexyloxy) phenyl) ethenyl) phenyl) -3-phenylthiourea; and (2) mixing the palladium ion solution with gradient change in concentration with the compound 1 solution, measuring the fluorescence intensity, then drawing by taking the concentration of palladium ions as an abscissa and the fluorescence intensity of a mixed system as an ordinate, establishing a standard line of the gradient change in the concentration of the palladium ion solution and the change value of the fluorescence intensity of the fluorescent probe solution, and reading the concentration of the palladium ions in the solution to be measured from the graph according to the fluorescence intensity during application. The detection limit of the fluorescent probe prepared by the invention is 3.64 mu M, and the fluorescent probe can be used for detecting palladium ions with high selectivity and sensitivity.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and analytical chemistry, and particularly relates to a preparation method and application of an AIE fluorescent probe for detecting palladium ions.
Background
Fluorescent probes are widely used for detecting cations and anions due to their high selectivity and sensitivity. Common organic fluorescent probes undergo fluorescence quenching due to aggregation in aqueous solution, which severely limits their practical application value. In recent years, fluorescent probes having Aggregation Induced Emission (AIE) performance have been attracting attention because they emit light efficiently in poor solvents such as water. Such AIE fluorescent probes are also easily modified to produce good environmental compatibility and test substance selectivity. The cyanobiphenyl is a fluorescent probe with aggregation-induced emission performance, and the fluorescent probe with good emission and recognition effects can be prepared by properly modifying the cyanobiphenyl.
Metallic palladium has been widely used in various industries due to its specific physicochemical properties. However, the use of palladium in large quantities inevitably causes the palladium to remain in the environment, causing the problem of heavy metal pollution to the environment and the problem of human health. Researchers have found that the maximum daily body intake of healthy people should be less than 15 μ g. In the pharmaceutical industry, the specified value of the residual amount of palladium in the medicine is 5-10 mg/kg. Therefore, the detection of palladium ions is particularly important, and the high-efficiency, high-selectivity, high-sensitivity and short-time response quantitative detection of palladium is constructed; the ion method is a problem to be solved at present, and has very important practical significance and application value.
Disclosure of Invention
The invention aims to provide an AIE fluorescent probe capable of being used for detecting palladium ions, which can sensitively and selectively detect the existence of the palladium ions through obvious fluorescence quenching and has good application prospect.
The invention relates to an AIE fluorescent probe for detecting palladium ions, which is chemically named as (Z) -1- (4- (1-cyano-2- (4- (hexyloxy) phenyl) vinyl) phenyl) -3-phenylthiourea (compound 1), and the AIE fluorescent probe is a cyanobiphenylene structure with an alkyl chain group at the chain end, and has the specific structure as follows:
another object of the present invention is to provide a method for preparing the fluorescent probe AIE (Compound 1).
The synthetic route of the compound 1 is as follows:
the preparation method of the compound 1 specifically comprises the following steps:
under the protection of nitrogen, phenyl isothiocyanate and a compound 2 are mixed and added with CH according to the molar ratio of 1-5: 12Cl2Reacting at normal temperature for 3-12 hours, adding petroleum ether to precipitate a date red solid product after the reaction is finished, and washing the product for 3 times by using the petroleum ether to obtain the fluorescent probe compound 1.
The molecular formula of the AIE fluorescent probe (compound 1) prepared by the invention is C28H29N3OS, Infrared Spectroscopy (KBr), v/cm-13433(N-H),2933,2853(C-H),2334(C ≡ N),1587,1499(C ≡ S) nuclear magnetic hydrogen spectrum (400MHz, CDCl)3)δ8.22(s,1H,NH),7.99(s,1H,NH),7.87(d,J＝12.0Hz,2H,ArH),7.87(d,J＝12.0Hz,2H,ArH),7.41-7.52(m,8H,ArH and CH),6.98(d,2H,J＝12.0Hz,ArH),4.03(t,2H,J＝4.0Hz,OCH2),1.83(t,2H,J＝4.0Hz,CH2),1.37-1.49(m,6H,CH2),0.94(t,3H,J＝4.0Hz,CH3) Nuclear magnetic carbon spectrum (100MHz, CDCl)3) Delta ppm 179.72,161.24,142.21,137.69,136.60,131.30,129.95,127.47,126.54,126.24,125.24,125.32,125.16,118.50,114.93,107.01,68.28,31.57,29.11,25.69,22.61, 14.06; high resolution mass spectrometry (m/s): calculated value C28H29N3OS 455.2031(M)+And a measured value 455.2144.
The AIE fluorescent probe (compound 1) prepared by the invention shows light green in tetrahydrofuran solution, and has weaker fluorescence emission at 420 nm. In tetrahydrofuran and water (0.5:9.5) solution, the probe has stronger fluorescence emission at 465nm, the fluorescence quantum yield is 0.76, the fluorescent probe forms a 1:1 complex with palladium ions in the solution, and causes obvious quenching of fluorescence, can be used for sensitive detection of the palladium ions in the environment, has small interference of other ions, and is an ideal palladium ion rapid detection sensor.
The pentoxylaminocyanobenzene (compound 2) of the present invention was prepared according to literature methods (master thesis of university of fujian, linglian bin, 2018). Phenyl isothiocyanate was purchased directly from alatin reagent.
Application of fluorescent probe compound 1 in detection of palladium ions
Preparing a solution with a certain concentration from the compound 1 prepared by the invention, preparing a palladium ion series solution with gradient concentration according to multiples of 0, 0.01, 0.02, 0.03, 0.05, 0.06, 0.08, 0.1, 0.2, 0.4, 0.5, 0.6, 0.8, 1.0, 2, 4, 5, 10, 20 and 40 of the concentration of the compound 1, mixing the compound 1 with the series solution one by one, measuring the fluorescence intensity of the compound 1, and establishing a palladium ion concentration gradient change standard curve with the fluorescence intensity as ordinate and the palladium ion concentration as abscissa.
The above compound 1 was mixed with a solution simulating palladium ion, and the fluorescence intensity value of the compound 1 was measured. And comparing the obtained fluorescence intensity value with the established palladium ion concentration gradient change standard curve, and reading out the palladium ion content in the simulated palladium ion-containing solution from the curve.
The invention has the following beneficial results: the fluorescence of the prepared compound 1 is obviously changed in the presence of palladium ions, the detection of the palladium ions is not interfered by the presence of other ions, the detection limit is 3.64 mu M, and the compound can be used for selectively and sensitively detecting the palladium ions, so that the compound has important practical application value for the detection of the palladium ions in a complex environment.
Drawings
FIG. 1 shows a 1X 10 solution in tetrahydrofuran-water (5:95)-5mol/L Compound 1 with 1X 10-4The fluorescence emission spectrum of each ion is mol/L;
FIG. 2 shows 1X 10 in tetrahydrofuran water (5:95)-5The fluorescence spectra of mol/L compound 1 and palladium ions with different concentrations;
FIG. 3 is a standard curve of gradient change of concentration of palladium ion solution and change of fluorescence intensity, which is established with the equivalent concentration of palladium ion as abscissa and the fluorescence intensity of the mixed system as ordinate;
FIG. 4 shows 2X 10 in tetrahydrofuran in 0.5:9.5 water-6mol/L Compound 1 with 2X 10-5mol/L Palladium ion and 2X 10-5A comparison graph of mol/L interfering ions shows that other ions do not substantially interfere with the highly sensitive detection of the fluorescent probe of the invention for palladium ions;
FIG. 5 is an infrared spectrum of Compound 1, identifying the structure of each functional group of Compound 1;
FIG. 6 is a NMR spectrum of Compound 1, identifying the structure of Compound 1;
FIG. 7 is a NMR carbon spectrum of Compound 1, identifying the structure of Compound 1;
fig. 8 is a mass spectrum of compound 1, and the strong peak at 455 identifies the structure of compound 1.
Detailed Description
The following series of specific examples are given to further illustrate the present invention, but the present invention is not limited to these specific examples, and any modification of the present invention that would be obvious to those skilled in the art to achieve similar results would also be included in the present invention.
In fig. 1, the volume ratio of tetrahydrofuran to water in the tetrahydrofuran aqueous solution is 0.5:9.5, the abscissa is the wavelength, and the ordinate is the fluorescence intensity. The figure shows that only palladium ions in test ions have obvious response and fluorescence is remarkably quenched, and the selective recognition of the palladium ions by the compound 1 is illustrated.
In fig. 2, the volume ratio of tetrahydrofuran to water in the tetrahydrofuran aqueous solution was 0.5:9.5, the abscissa was the wavelength, and the ordinate was the fluorescence intensity. The concentration of palladium ions is 0, 0.01, 0.02, 0.03, 0.05, 0.06, 0.08, 0.1, 0.2, 0.4, 0.5, 0.6, 0.8, 1.0, 2, 4, 5, 10, 20 and 40 times of that of the compound 1 in sequence. FIG. 2 shows that the fluorescence intensity of Compound 1 is significantly decreased with the increase in the concentration of palladium ion.
In fig. 4, the volume ratio of tetrahydrofuran to water in the tetrahydrofuran aqueous solution is 0.5:9.5, and the ordinate represents the fluorescence intensity, and a smaller change in fluorescence intensity indicates a smaller interfering ability of interfering ions. As can be seen from FIG. 4, other ions do not substantially interfere with the highly sensitive detection of palladium ions by the fluorescent probes of the present invention.
Example 1
0.320g (1mmol) of Compound 2 and 0.135g (1mmol) of phenylisothiocyanate were added to a three-necked flask containing 15mL of dry dichloromethane under nitrogen protection, the reaction was stirred at room temperature for 12 hours, and TLC was performed until the starting material was substantially disappeared. 30mL of petroleum ether was added and a precipitate was precipitated. Filtering, washing the precipitate with 3 × 5mL petroleum ether, and drying to obtain light green solid, i.e. target product 1 (molecular formula is C)28H29N3OS), yield was 76%.
Example 2
0.160g (0.5mmol) of Compound 2 and 0.337g (2.5mmol) of phenylisothiocyanate were added to a three-necked flask containing 10mL of dry dichloromethane under nitrogen protection, the reaction was stirred at room temperature for 3 hours, and TLC was performed until the starting material was substantially disappeared. 20mL of petroleum ether was added and a precipitate was precipitated. Filtering, washing the precipitate with 3 × 5mL petroleum ether, and drying to obtain light green solid, i.e. target product 1 (molecular formula is C)28H29N3OS) yield was 86%.
Example 3
0.160g (0.5mmol) of Compound 2 and 0.27g (2mmol) of phenylisothiocyanate were added to a three-necked flask containing 10mL of dry dichloromethane under nitrogen protection, the reaction was stirred at room temperature for 6 hours, and TLC was performed until the starting material was substantially disappeared. 20mL of petroleum ether was added and a precipitate was precipitated. Filtering, washing the precipitate with 3 × 5mL petroleum ether, and drying to obtain light green solid, i.e. target product 1 (molecular formula)Is C28H29N3OS) yield was 80%.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent flow transformations made by using the contents of the present specification and the accompanying drawings, or applied directly or indirectly to other related technical fields, are included in the scope of the present invention.
Claims (4)
1. A preparation method of an AIE fluorescent probe for detecting palladium ions is characterized in that the chemical name of the AIE fluorescent probe is (Z) -1- (4- (1-cyano-2- (4- (hexyloxy) phenyl) vinyl) phenyl) -3-phenylthiourea, namely a compound 1, and the specific structure of the AIE fluorescent probe is as follows:
the specific synthesis comprises the following steps:
under the protection of nitrogen, phenyl isothiocyanate is mixed with the compound 2, and a proper amount of CH is added2Cl2Reacting at normal temperature, adding petroleum ether to precipitate a date red solid product after the reaction is finished, and washing the product for 3 times by using the petroleum ether to obtain the AIE fluorescent probe;
the compound 2 is:
2. the preparation method of the AIE fluorescent probe for detecting palladium ions according to claim 1, wherein the phenyl isothiocyanate and the compound 2 are mixed in a molar ratio of 1-5: 1.
3. The method for preparing an AIE fluorescent probe for detecting palladium ions according to claim 1, wherein the reaction time is 3-12 hours.
4. The use of the AIE fluorescent probe for detecting palladium ions prepared according to claim 1 is characterized in that the compound 1 prepared according to claim 1 is prepared into a solution with a certain concentration, and palladium ion series solutions with gradient concentration are prepared according to multiples of 0, 0.01, 0.02, 0.03, 0.05, 0.06, 0.08, 0.1, 0.2, 0.4, 0.5, 0.6, 0.8, 1.0, 2, 4, 5, 10, 20 and 40 times of the concentration of the compound 1, the compound 1 is respectively mixed with the series solutions one by one, the fluorescence intensity of the compound 1 is measured, and a palladium ion concentration gradient change standard curve with the fluorescence intensity as ordinate and the palladium ion concentration as abscissa is established;
and comparing the obtained fluorescence intensity value with the established palladium ion concentration gradient change standard curve, and reading out the palladium ion content in the simulated palladium ion-containing solution from the curve.
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|---|---|---|---|---|
| KR20120096847A (en) * | 2011-02-23 | 2012-08-31 | 경상대학교산학협력단 | Novel stylbeneurea derivatives, pharmaceutically acceptable salts, method for preparation and composition containing thereof as an active ingredient for prevention and treatment of diseases induced by glycosidase |
| CN104962278A (en) * | 2015-05-18 | 2015-10-07 | 华东理工大学 | Palladium ion fluorescent probe, and preparation method and applications thereof |
| CN106749093A (en) * | 2016-12-07 | 2017-05-31 | 南京工业大学 | Fluorescent probe for detecting palladium ions, preparation method and application |
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2020
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