CN102876323A - Cadmium ion fluorescence probe, preparation method and application - Google Patents
Cadmium ion fluorescence probe, preparation method and application Download PDFInfo
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- CN102876323A CN102876323A CN2012104110815A CN201210411081A CN102876323A CN 102876323 A CN102876323 A CN 102876323A CN 2012104110815 A CN2012104110815 A CN 2012104110815A CN 201210411081 A CN201210411081 A CN 201210411081A CN 102876323 A CN102876323 A CN 102876323A
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Abstract
The invention relates to a cadmium ion fluorescence probe and a preparation method thereof. The cadmium ion fluorescence probe consists of a derivative of quinoline with a position 2 which is modified by aza-crown ether. An aza-crown ether group is bonded onto a quinoline chromophoric group with an auxiliary coordination function to synthesize the cadmium ion fluorescence probe with a specific response function. As homologous transition metal ions, the interaction of cadmium and zinc with S, O and N donors is very close. Comparatively, the connection of the cadmium with the S and N donors is closer than the connection of the zinc with the S and N donors. The novel fluorescence probe is designed by using the characteristics. The influence of zinc ions on the unique response of the cadmium ion fluorescence probe is overcome. The fluorescence probe can be used for the selective rapid fluorescence detection of the cadmium ions in water bodies, the selectivity is very good, the resistance to interference of other metal ions is strong and the cadmium ion fluorescence probe consists of ideal sensing molecules for the field detection of the cadmium ions.
Description
Technical field
The present invention relates to environmental analysis, bioanalysis detection field, relate generally to a kind of cadmium ion fluorescent probe and preparation method thereof, this probe molecule can highly selective, the cadmium ion in the qualitative and even semiquantitative detection water body.
Background technology
Cadmium is used very extensive in industrial production.Because its good alkali-resistivity material corrosive power is applied to plastic cement manufacturing and Metal plating, also is used to make battery, produces pigment and fluorescent material etc.But the problem of consequent cadmium pollution is also day by day serious.Cadmium is not the essential element of human body, and the cadmium in the human body is to enter body accumulation by Shi Wu ﹑ water and air to get off.As the easiest toxicant of accumulating in human body, the velocity of discharge of cadmium is very slow, and be 10-30 the biological half time of people's renal cortex cadmium.The biological toxicity Journal of Sex Research of relevant cadmium shows, causes easily in the low-dosage cadmium environmental exposure in the population that renal dysfunction, bone mineral density reduce, CaE increases and genotoxicity.Cadmium pollution soil can cause the nuisance disease itai-itai.Therefore, the environmental health standards of relevant cadmium are very strict.Environmental Protection Agency restriction enters lake, river, throw aside and the cadmium amount in farmland and forbid containing in the sterilant cadmium.Environmental Protection Agency allows tap water to contain the cadmium of 10ppb.The cadmium content of food and drug administration's regulation food dye must not be more than 15ppm.
Therefore study the method that can fast and effeciently detect the cadmium ion content in ecotope and the organism all significant to chemistry, biology, environmental chemistry, medical science.Up to now, people have worked out multiple detection method, mainly contain atomic absorption spectrometry (Atomic Absorption Spectroscopy) such as traditional cadmium ion detection method, ultraviolet spectrophotometry (Ultra-violet Spectroscopy), anodic stripping voltammetry (Anodic Stripping Voltammetr), oscilloscopic polarography (Oscillopolarography) and various Instrument crosslinking technology are such as inductively coupled plasma mass spectrometry (Inductively Coupled Plasma Mass Spectrometry), inductively coupled plasma atomic emission spectrum analysis (Inductively Coupled Plasma Atomic Emission Spectrometry) etc.But mostly need large-scale instrument, cost is higher, and sample will can only be measured single heavy metal species concentration one by one through clearing up, and detecting step is loaded down with trivial details simultaneously, is not suitable for scene, on-line analysis detection.And the characteristics such as fluorescent probe is highly sensitive because having, selectivity good, good resolution and in situ detection are fit to be applied to the detection of cadmium ion in the environmental and biological materials system very much.
The topmost problem of design cadmium ion fluorescent probe is distinguished Zn exactly at present
2+With Cd
2+Very difficult, zinc and cadmium are positioned at same gang, and the cationic chemical property of their responses is also very approaching.So the minority fluorescent probe is only arranged have been realized for Cd
2+Detection, yet also there are many drawbacks in these probes, little etc. such as poorly water-soluble, burst of ultraviolel and complex ability, this also impels people to go to address these problems.
Summary of the invention
The object of the invention is to provide a kind of cadmium ion fluorescent probe and preparation method thereof, this cadmium ion fluorescent probe is the derivative at the assorted Modified with Crown Ether of 2 warps of quinoline, employing will be mixed the crown ether group bonding to the quinoline chromophoric group with auxiliary coordination function, synthesize the cadmium ion fluorescent probe with specificly-response, utilize cadmium, zinc very tight as the interaction of transition metal ion of the same clan and S, O and N donor, compare cadmium and S and be connected with the N donor and be connected closelyr than zinc, these characteristics design new fluorescent probe.Overcome zine ion to the impact of cadmium ion fluorescent probe specificity response.This fluorescent probe can be applicable to the selectivity fluorescence rapid detection of Cadmium In The Water Body ion, and selectivity is fine, anti-other metal ion disturbance ability is strong, is a kind of desirable sensor molecules that can be applicable to the cadmium ion Site Detection.
A kind of cadmium ion fluorescent probe of the present invention, this fluorescent probe are that its structure formula I is at the derivative of the assorted Modified with Crown Ether of 2 warps of quinoline:
（Ⅰ）。
The preparation method of described cadmium ion fluorescent probe follows these steps to carry out:
A, be solvent with 1,2-ethylene dichloride, adding intermediate I is 8-ethoxyacetic acid ethyl ester quinoline-2-formaldehyde and assorted crown ether, at room temperature stirs 10 minutes, adds NaBH (OAc) in batches again
3, room temperature reaction spends the night, and wherein the mol ratio of 8-ethoxyacetic acid ethyl ester quinoline-2-formaldehyde, assorted crown ether and sodium triacetoxy borohydride is 1:1:1.1;
After b, reaction finish, to pH=4-5, then be neutralized to pH=7-8 with the 1N sodium hydroxide solution with the hcl acidifying of 1N, use again ethyl acetate extraction 3 times, collect organic phase, use anhydrous sodium sulfate drying, the underpressure distillation desolventizing is through silica gel chromatographic column, purify with methylene chloride/25% ethyl acetate, obtaining the intermediate II is 2-methylene radical-(Isosorbide-5-Nitrae dioxy-7,13 two sulphur-azepine 15 hats 5)-(quinoline-8-oxygen base) ethyl acetate;
C, intermediate II that step b is obtained add 10 mg NaOH take ethanol as solvent, stir under the room temperature and spend the night;
D, the complete rear dichloromethane extraction of using of reaction, organic phase anhydrous sodium sulfate drying after the extraction, the underpressure distillation desolventizing, can obtain cadmium ion fluorescent probe is 2-methylene radical-(1,4 dioxies-7,13, two sulphur-azepine 15 hats 5)-(quinoline-8-oxygen base) sodium acetate.
The purposes of described cadmium ion fluorescent probe, this cadmium ion fluorescent probe is used for the sensing detection of the cadmium ion of water environment system or biomass cells system, analyzes and spike.
A kind of cadmium ion fluorescent probe of the present invention and preparation method and purposes, the synthetic route of this cadmium ion fluorescent probe is as follows:
A kind of cadmium ion fluorescent probe of the present invention and preparation method and purposes, this cadmium ion fluorescent probe strengthen numerical value F/F0 by simple fluorescence and can effectively detect Cd in neutral buffered solution
2+, and the impact of rejecting zine ion; The zygotic induction system fluorescence of fluorescent probe and cadmium ion strengthens 8 times; The dissociation constant of this metal ion match is 3.61 ± 0.24 pM; Have very high detection sensitivity, the fluorescence emission spectrum test result shows the detection cadmium ion that this fluorescent probe can rapid sensitive in the scope of pH=6 10, and more stable.This explanation probe molecule can detect cadmium ion in more wide in range environment.Therefore, the present invention is a kind of simple, quick, sensitive cadmium ion specificity detection reagent, and its performance will be in an embodiment by reference to the accompanying drawings based on detailed description.
Description of drawings
Fig. 1 is fluorescence emission spectrogram of the present invention, utilizes F-4600 spectrophotofluorometer (HIT), (25 mM HEPES, 0.1 M NaClO in buffer solution system
4, pH=7.4) test.The concentration of fluorescent probe molecule is 5 μ M, and concentration of cadmium ions is followed successively by 0,1.25,2.5,3.75,5,6,8,10,20 μ M, and excitation wavelength is 310nm, slit is wide be 5nm 5nm, X-coordinate is that wavelength, ordinate zou are relative intensity of fluorescence.
Fig. 2 is probe selective light spectrogram of the present invention, and wherein 1 for adding the equivalent cadmium ion; 2 for adding equivalent competition metal ion; 3 for adding equivalent competition metal ion and cadmium ion, configures certain density probe solution, then adds respectively the different metal ion A g of equivalent in the solution
+, K
+, Ca
2+, Mg
2+, Mn
2+, Fe
2+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Cd
2+, Hg
2+, Pb
2+, under each metal ion existence condition, the fluorescence emission spectrum of probe molecule, subsequently continuation drips the cadmium ion of equivalent, is determined at the immunity from interference that there is lower probe in detecting cadmium ion in the different metal ion.
Fig. 3 is probe molecule of the present invention and the variation of metal complex fluorescent emission spectrum under different pH values thereof, configuration finite concentration probe molecule solution, add respectively the hydrochloric acid of different concns or sodium hydroxide solution with the pH value of regulator solution, (upper curve is the fluorescence of metal complexes to measure the fluorescence emission spectrum of every group of corresponding pH value solution; Lower curve is the fluorescence of probe molecule).
Embodiment
The preparation method of cadmium ion fluorescent probe of the present invention:
A, at room temperature be 8-ethoxyacetic acid ethyl ester quinoline-2-formaldehyde (25.9 mg with intermediate I, 0.1 mmol) be dissolved in 1, the 2-ethylene dichloride (10 mL) with assorted crown ether (25.1 mg, 0.1mmol), stirred 10 minutes, and added again NaBH (OAc) in batches
3(0.22 g, 0.11 mmol), room temperature reaction spends the night;
After b, reaction finish, with the hcl acidifying of 1N to pH=4-5, then be neutralized to pH=7-8 with the 1N sodium hydroxide solution, use again ethyl acetate extraction 3 times, collect organic phase, use anhydrous sodium sulfate drying, the underpressure distillation desolventizing, obtaining the intermediate II through silica gel chromatographic column with (methylene dichloride/25% ethyl acetate) purification is 2-methylene radical-(Isosorbide-5-Nitrae dioxy-7,13 2 sulphur-azepine 15 hats 5)-and (quinoline-8-oxygen base) ethyl acetate, productive rate 46%;
C, with step b obtains intermediate II (0.45 g, 1.0 mmol) is dissolved in the ethanol (5 mL), add 10 mg NaOH, stirred overnight at room temperature;
D, the complete rear adding methylene dichloride of reaction (10 mL * 3) extraction, organic phase anhydrous sodium sulfate drying after the extraction, the underpressure distillation desolventizing, can obtain cadmium ion fluorescent probe is 2-methylene radical-(1,4 dioxies-7,13 2 sulphur-azepine 15 hats 5)-and (quinoline-8-oxygen base) sodium acetate, productive rate 96%.
The purposes of cadmium ion fluorescent probe of the present invention:
In buffered soln (25 mM HEPES, 0.1 M NaClO4, pH=7.4), the concentration of fluorescent probe is 5 μ M, concentration of cadmium ions is followed successively by 0,1.25,2.5,3.75,5,6,8,10,20 μ M, and excitation wavelength is 310nm, slit is wide be 5nm 5nm;
(25 mM HEPES, 0.1 M NaClO in buffered soln
4, pH=7.4), the maximum absorption band of fluorescent probe self has a wide absorption band at 241 nm at long wavelength's direction 270 330 nm, when add Cd in solution
2+After (0 1.5 equiv), 241 nm absorption peaks weaken gradually, and a little red shift, and because Cd
2+With the coordination of quinoline, long wave strong point absorption band a little red shift to 300-350 nm; Simultaneously, dripping Cd
2+After, they produce 3 isosbestic points at 245 nm, 257 nm, 310nm place, and this explanation has only formed a kind of cadmium ion title complex in solution, and when dripping 1.0 equivalent Cd
2+Rear continuation drips Cd
2+, absorption spectrum is substantially unchanged, and fluorescent probe molecule and Cd are described
2+Complexing is than being 1:1;
In buffered soln, with 310 nm optical excitation (excite with the emission wavelength slit and be respectively 5 nm), fluorescent probe molecule presents weak fluorescence emission peak at 360 550 nm, and quantum yield lower (Ф=0.022) is when drip Cd in solution
2+(0 1.6 equiv), the fluorescence intensity of system has produced obvious enhancing, the corresponding cadmium ion title complex of formation after dropping is saturated, its quantum yield has reached 0.21, obviously, such fluorescence strengthens owing to cadmium ion and tertiary amine coordination, makes on the tertiary amine the effectively fluorescence of Quenching System of lone-pair electron, is typical PET process of inhibition;
By being K with the change curve of free concentration of cadmium ions through the dissociation constant that least square curve fit obtains this metal ion match to fluorescence intensity
d=3.61 ± 0.24 pM(R=0.99), the fluorescence emission spectrum test result shows: the detection cadmium ion (Fig. 1) that cadmium ion fluorescent probe of the present invention can rapid sensitive.
Configure 5 μ M fluorescent probe solution, then add respectively the different metal ion A g of equivalent in the solution
+, K
+, Ca
2+, Mg
2+, Mn
2+, Fe
2+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Cd
2+, Hg
2+, Pb
2+, be determined at each metal ion existence lower, the fluorescence emission spectrum of fluorescent probe molecule;
With reference to the fluorescence spectrum titration experiments of cadmium ion to probe molecule, the present invention judges probe to the selectivity of cadmium ion by competition metal ion titration experiments, adds respectively the Ag of equivalent in solution
+, Mn
2+, Fe
2+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Hg
2+, Pb
2+And the K of 100 equivalents
+, Ca
2+, Mg
2+After, fluorescence spectrum does not have considerable change yet, only has adding Cd
2+After, fluorescence spectrum has just produced very large enhancing, and show by the ratio F/F0 monitoring to the fluorescent emission intensity integral area: the present invention extremely is suitable as cadmium ion fluorescent probe (Fig. 2).
Configure 5 μ M fluorescent probe solution, then add respectively the different metal ion A g of equivalent in the solution
+, K
+, Ca
2+, Mg
2+, Mn
2+, Fe
2+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Cd
2+, Hg
2+, Pb
2+, subsequently continuation drips the cadmium ion of equivalent, is determined at the immunity from interference that there is lower probe in detecting cadmium ion in the different metal ion, and its result shows: metal ion such as K
+, Ca
2+, Mg
2+, Mn
2+, Fe
2+, Co
2+, Ni
2+, Zn
2+, Cd
2+Fluorescent signal enhancing degree impact on probe identification silver ions is very little, but Hg
2+, Cu
2+, Pb
2+, Ag
+Can cause interference (Fig. 2) to a certain degree.
The variation of fluorescence emission spectrum under different pH values configures 5 μ M fluorescent probe solution, adds respectively the hydrochloric acid of different concns or sodium hydroxide solution with the pH value of regulator solution, measures the fluorescence emission spectrum of every group of corresponding pH value solution.
In order to investigate the pH value to the impact of probe molecule and cadmium ion complex fluorescent emmission spectrum thereof, the integral area of probe molecule and cadmium ion complex fluorescent emission peak thereof is with shown in the variation (Fig. 3) of pH value, this result shows: all have fine cadmium ion response in the scope of pH=6 10, and more stable, this illustrates that cadmium ion fluorescent probe of the present invention can detect cadmium ion in more wide in range environment.
Claims (3)
1. cadmium ion fluorescent probe is characterized in that this fluorescent probe is that its structure formula I is at the derivative of the assorted Modified with Crown Ether of 2 warps of quinoline:
（Ⅰ）。
2. the preparation method of cadmium ion fluorescent probe according to claim 1 is characterized in that following these steps to carrying out:
A, be solvent with 1,2-ethylene dichloride, adding intermediate I is 8-ethoxyacetic acid ethyl ester quinoline-2-formaldehyde and assorted crown ether, at room temperature stirs 10 minutes, adds NaBH (OAc) in batches again
3, room temperature reaction spends the night, and wherein the mol ratio of 8-ethoxyacetic acid ethyl ester quinoline-2-formaldehyde, assorted crown ether and sodium triacetoxy borohydride is 1:1:1.1;
After b, reaction finish, to pH=4-5, then be neutralized to pH=7-8 with the 1N sodium hydroxide solution with the hcl acidifying of 1N, use again ethyl acetate extraction 3 times, collect organic phase, use anhydrous sodium sulfate drying, the underpressure distillation desolventizing is through silica gel chromatographic column, purify with methylene chloride/25% ethyl acetate, obtaining the intermediate II is 2-methylene radical-(Isosorbide-5-Nitrae dioxy-7,13 two sulphur-azepine 15 hats 5)-(quinoline-8-oxygen base) ethyl acetate;
C, intermediate II that step b is obtained add 10 mg NaOH take ethanol as solvent, stir under the room temperature and spend the night;
D, the complete rear dichloromethane extraction of using of reaction, organic phase anhydrous sodium sulfate drying after the extraction, the underpressure distillation desolventizing, can obtain cadmium ion fluorescent probe is 2-methylene radical-(1,4 dioxies-7,13, two sulphur-azepine 15 hats 5)-(quinoline-8-oxygen base) sodium acetate.
3. the purposes of cadmium ion fluorescent probe according to claim 1 is characterized in that this cadmium ion fluorescent probe is used for the sensing detection of the cadmium ion of water environment system or biomass cells system, analyzes and spike.
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| CN103245646A (en) * | 2013-04-25 | 2013-08-14 | 山西大学 | Application of 1, 3, 4-oxadiazole derivative fluorescent probe in test of cadmium ions |
| CN103265539A (en) * | 2013-04-19 | 2013-08-28 | 浙江大学 | Fluorescent probe: benzothiazole-terpyridine compound used for distinguishing and detecting zinc ions and cadmium ions, preparation method and application method thereof |
| CN103436251A (en) * | 2013-07-16 | 2013-12-11 | 安徽大学 | Ratiometric two-photon cadmium ion fluorescent probe and synthetic method thereof |
| CN103592276A (en) * | 2013-11-19 | 2014-02-19 | 东南大学 | Quantum dot fluorescence sensor for cadmium ion detection, and detection method of fluorescence sensor |
| CN104327843A (en) * | 2014-10-17 | 2015-02-04 | 中国科学院新疆理化技术研究所 | Mercury ion fluorescent probe as well as preparation method and application thereof |
| CN104673279A (en) * | 2015-03-24 | 2015-06-03 | 郑州大学 | Water-soluble cadmium ion fluorescence probe molecule as well as preparation method and application thereof |
| CN106442440A (en) * | 2016-08-31 | 2017-02-22 | 新奥生态环境治理有限公司 | Device for rapid detection of heavy metal cadmium in river runway and lake mud |
| CN109134452A (en) * | 2018-09-05 | 2019-01-04 | 东华大学 | A kind of fluorescence probe and its preparation and application |
| CN109897628A (en) * | 2019-03-25 | 2019-06-18 | 四川大学 | A kind of fluorescence probe and its preparation method and application for detecting cadmium ion |
| CN110746444A (en) * | 2019-10-25 | 2020-02-04 | 华东理工大学 | Crown ether compound, preparation method thereof and application thereof in ion recognition |
| CN112011597A (en) * | 2020-07-24 | 2020-12-01 | 南京师范大学 | Cadmium ion sensing method combining induced allosteric probe with rolling circle amplification |
| CN113358619A (en) * | 2021-06-05 | 2021-09-07 | 中国科学院新疆理化技术研究所 | Preparation method and application of fluorescent sensing analysis card for semi-quantitative detection of potassium permanganate solution |
| CN115112617A (en) * | 2022-05-31 | 2022-09-27 | 永春县产品质量检验所(福建省香产品质量检验中心、国家燃香类产品质量监督检验中心(福建)) | Fluorescence detection method for content of burning heavy metal cadmium |
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2012
- 2012-10-25 CN CN201210411081.5A patent/CN102876323B/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| LUCA PRODI ET AL.: "Characterization of 5-chloro-8-methoxyquinoline appended diaza-18-crown-6 as a chemosensor for cadmium", 《TETRAHEDRON LETTERS》 * |
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| CN103265539B (en) * | 2013-04-19 | 2015-09-02 | 浙江大学 | For distinguishing fluorescent probe benzothiazole-terpyridyl compounds and the methods for making and using same thereof of detection zine ion and cadmium ion |
| CN103245646A (en) * | 2013-04-25 | 2013-08-14 | 山西大学 | Application of 1, 3, 4-oxadiazole derivative fluorescent probe in test of cadmium ions |
| CN103436251A (en) * | 2013-07-16 | 2013-12-11 | 安徽大学 | Ratiometric two-photon cadmium ion fluorescent probe and synthetic method thereof |
| CN103592276A (en) * | 2013-11-19 | 2014-02-19 | 东南大学 | Quantum dot fluorescence sensor for cadmium ion detection, and detection method of fluorescence sensor |
| CN103592276B (en) * | 2013-11-19 | 2016-04-13 | 东南大学 | Cadmium ion detects by quantum dot fluorescent optical sensor and detection method thereof |
| CN104327843A (en) * | 2014-10-17 | 2015-02-04 | 中国科学院新疆理化技术研究所 | Mercury ion fluorescent probe as well as preparation method and application thereof |
| CN104327843B (en) * | 2014-10-17 | 2016-03-30 | 中国科学院新疆理化技术研究所 | A kind of mercury ion fluorescence probe and preparation method and purposes |
| CN104673279A (en) * | 2015-03-24 | 2015-06-03 | 郑州大学 | Water-soluble cadmium ion fluorescence probe molecule as well as preparation method and application thereof |
| CN104673279B (en) * | 2015-03-24 | 2016-06-22 | 郑州大学 | A kind of water-soluble cadmium ion fluorescent probe molecule and preparation method thereof and application |
| CN106442440A (en) * | 2016-08-31 | 2017-02-22 | 新奥生态环境治理有限公司 | Device for rapid detection of heavy metal cadmium in river runway and lake mud |
| CN109134452A (en) * | 2018-09-05 | 2019-01-04 | 东华大学 | A kind of fluorescence probe and its preparation and application |
| CN109134452B (en) * | 2018-09-05 | 2021-07-20 | 东华大学 | Fluorescent probe and preparation and application thereof |
| CN109897628A (en) * | 2019-03-25 | 2019-06-18 | 四川大学 | A kind of fluorescence probe and its preparation method and application for detecting cadmium ion |
| CN110746444A (en) * | 2019-10-25 | 2020-02-04 | 华东理工大学 | Crown ether compound, preparation method thereof and application thereof in ion recognition |
| CN110746444B (en) * | 2019-10-25 | 2021-12-17 | 华东理工大学 | Crown ether compound, preparation method thereof and application thereof in ion recognition |
| CN112011597A (en) * | 2020-07-24 | 2020-12-01 | 南京师范大学 | Cadmium ion sensing method combining induced allosteric probe with rolling circle amplification |
| CN112011597B (en) * | 2020-07-24 | 2023-03-21 | 南京师范大学 | Cadmium ion sensing method combining induced allosteric probe with rolling circle amplification |
| CN113358619A (en) * | 2021-06-05 | 2021-09-07 | 中国科学院新疆理化技术研究所 | Preparation method and application of fluorescent sensing analysis card for semi-quantitative detection of potassium permanganate solution |
| CN113358619B (en) * | 2021-06-05 | 2023-05-19 | 中国科学院新疆理化技术研究所 | Preparation method and application of fluorescence sensing analysis card for semi-quantitatively detecting potassium permanganate solution |
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