CN106588844A - Water-soluble coumarin fluorescent probe as well as preparation method and application thereof - Google Patents
Water-soluble coumarin fluorescent probe as well as preparation method and application thereof Download PDFInfo
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- CN106588844A CN106588844A CN201611029585.5A CN201611029585A CN106588844A CN 106588844 A CN106588844 A CN 106588844A CN 201611029585 A CN201611029585 A CN 201611029585A CN 106588844 A CN106588844 A CN 106588844A
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- fluorescent probe
- water
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- mercury ion
- fluorescence
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- C—CHEMISTRY; METALLURGY
- 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
- C07D311/16—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 7
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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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- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
Abstract
The invention discloses a water-soluble coumarin fluorescent probe as well as a preparation method and application thereof. The structure of the fluorescent probe is represented by a formula (I) (shown in the description). The probe is capable of selectively identifying mercury ions; and after the probe acts with the mercury ions in a pure water buffer solution, the fluorescence emission at a 450nm site is changed from a hardly any state to 100-time enhanced blue fluorescence, the detection limit to the mercury ions is 0.12mu mol/L, and furthermore, the probe has very strong selectivity and can be used for the naked eye qualitative identification and fluorescent quantitative determination of trace mercury ions.
Description
Technical field
The invention belongs to fluorescence chemical field of sensing technologies, and in particular to one kind is based on coumarin fluorescent compound, with hydrargyrum
Ionic catalysises hydrolysed ethylene ehter bond is means of identification, the fluorescent probe for having the Fluorescence Increasing detection of high selectivity to mercury ion.
Background technology
Heavy metal ion has very strong toxic to environmental and biological materials, is constantly subjected to the concern of people.In numerous heavy metals
In ion, mercury ion can in vivo be enriched with and gather, so as to the serious harm mankind's as one of toxicity strongest element
The mercury ion of health, such as inorganic form can change into the organic mercuries such as methyl mercury under microbial action, and methyl mercury is once entered
After human body, special damage can be produced to brain neuroblastoma, conduct disorder and nerve injury can be caused.However, industrial processes
In would generally be related to the use of mercury metal such as salt electrolysis, precious metal smelting, therefore, it is efficiently fixed for realizing in environmental water sample
The technology of property and quantitative trace detection mercury ion has realistic meaning and application prospect.
At present the technology of detection mercury ion mainly has：Atomic absorption method, atomic emissions method, inductively coupled plasma method,
Although these technologies are advantageous, the shortcomings of need the cost of more complicated pre-treatment, skilled operation and costliness, it is compared
Under, fluorescent probe detection method has the advantages that sensitivity is high, selectivity is good, fast response time, becomes research worker extensive concern
One of focus.In the last few years, many mercury ion fluorescence probe reports, detection mercury ion is based primarily upon two big class, probe and hydrargyrum
Ion generation coordination [referring to：(a)Jha AK,Umar S,Arya RK,Datta D and Goel A.J Mater
Chem B 2016:4:4934；(b)Kao SL,Wu SP,Sens Actuators B Chem 2015:212:382], it is and chemical
Reaction [referring to：(a)Hu J,Hu Z,Liu S,Zhang Q,Gao HW,Uvdal K.Sens Actuators B Chem
2016:230:639；(b)Atta AK,Kim SB,Heo J,Cho DG..Org Lett 2013:15:1072].With the former phase
Than the probe based on the specific reaction of mercury ion has advantage in ion selectivity.
Coumarin compound becomes ion to have the advantages that high light heat and chemical stability, high-fluorescence quantum yield
One of field fluorescent probe system of greatest concern such as identification and bioanalysiss [referring to：(a)Inorganica Chimica
Acta 2012:381:2；(b)Org Let 2008:10:5015.].The mercury ion probe applied research of Coumarinses is increasingly
Concern [referring to：(a)Chem.Commun.2011,47,5073；(b)Chem.Commun.2009,3560；(c)Tetrahedon
Lett 2010,51,3852].Having some limitations property such as water solublity is bad in these probes, fluorescent quenching, ion selectivity not
It is good etc., and EPA specifies the content of Mercury in Drinking Water ion less than 2ppb, therefore, it is necessary go to study a kind of good water solubility,
Selectivity is high, Coumarinses fluorescent probe to trace amount mercury ion detection.
The content of the invention
The invention provides a kind of water-soluble coumarin class fluorescent probe preparation method and applications, the water-soluble coumarin
Class fluorescent probe can efficiently be detected to mercury ion.
A kind of water-soluble coumarin class fluorescent probe, the structural formula of fluorescent probe is as follows：
The water-soluble coumarin class fluorescent probe of the present invention, introduces in the molecule ethylene ehter bond, can be catalyzed by mercury ion
Hydrolysed ethylene ehter bond, realizes probe alternative recognition detection mercury ion.In pure water buffer solution, the probe is at 450nm
Almost without fluorescence, and after acting on mercury ion, then very strong blue-fluorescence is produced, the detection to mercury ion is limited to 0.12 μ
Mol/L, and with very strong selectivity, can be used for bore hole qualitative identification and fluorogenic quantitative detection.
Present invention also offers a kind of preparation method of described water-soluble coumarin class fluorescent probe, including following step
Suddenly：
3- Methyl-7-hydroxy-coumarins and glycol dibromide are dissolved in DMF (DMF), carbon is added
Sour potassium, reacting by heating, intermediate 3- methyl -7- bromine oxethyl coumarins, then with the carbon -7- alkene of 1,8- diazabicylos 11
(DBU) reacting by heating in acetonitrile, reacts and process after Jing after terminating the water-soluble coumarin class fluorescent probe described in obtaining.
Reaction equation is as follows：
Concrete preparation method is as follows：
By compound 1 (3- Methyl-7-hydroxy-coumarins) and glycol dibromide amine in molar ratio 1:1～1:It 1.5 is dissolved in
In DMF, the potassium carbonate quantitative with glycol dibromide etc. is added, heat 90 degree of reactions, stirring is no less than
24 hours；After reaction terminates, filter, filtrate decompression is spin-dried for grease, and with silica gel column chromatography purification is carried out, with ethyl acetate and
Petroleum ether=1:5～1:8 (v/v) are separated as eluant, obtain intermediate 2 (3- methyl -7- bromine oxethyl coumarins).
Intermediate 3- methyl -7- bromine oxethyls coumarin is with the carbon -7- alkene (DBU) of 1,8- diazabicylos 11 in molar ratio
1:1～1:1.5 are dissolved in acetonitrile, heat 90 degree of reactions, and stirring is no less than 12 hours；After reaction terminates, decompression is spin-dried for oily
Thing, adds ethyl acetate extraction, anhydrous sodium sulfate drying to filter, be spin-dried for grease, and purification is carried out with silica gel column chromatography, uses
Ethyl acetate and petroleum ether=1:4～1:6 (v/v) are separated as eluant, obtain fluorescent probe.
Present invention also offers a kind of application of described water-soluble coumarin class fluorescent probe in mercury ion detecting.
Qualitative detection can be carried out to mercury ion using the water-soluble coumarin class fluorescent probe of the present invention, concrete grammar is such as
Under：Prepare liquid is added in the HEPES buffer solution of water-soluble coumarin class fluorescent probe, is then shone using exciting light
Penetrate, observe the change in fluorescence of probe solution, and according to probe solution change in fluorescence judging whether containing mercury ion.When probe it is molten
Liquid illustrates, containing a certain amount of mercury ion, otherwise, to illustrate to be substantially free of mercury ion when no fluorescence is changed into strong blue.
Detection by quantitative can be carried out to mercury ion using the water-soluble coumarin class fluorescent probe of the present invention, method is as follows：
Prepare liquid is added in water-soluble coumarin class fluorescent probe acetonitrile solution, fluorescence emission spectrum is then determined, addition is obtained and is treated
The probe surveyed before and after liquid fluorescence change at 450nm, is then contrasted ratio fluorescent changing value and standard curve, is obtained
Mercury ion content in prepare liquid.
Compared with the existing technology, beneficial effects of the present invention are：The probe can be used in pure water, direct detection Trace Mercury
Ion, after acting on mercury ion in pure water, fluorescent emission has 110 times of increase at 450nm, and the detection to mercury ion is limited to
0.25 μm of ol/L, meanwhile, other metal ions are not interfered with to identification, and the probe is applicable to the qualitative mirror of the bore hole to mercury ion
Other and fluorogenic quantitative detection trace amount mercury ion.
Description of the drawings
Fig. 1 is fluorescent emission spectrogram of the fluorescent probe of the present invention to mercury ion.
Fig. 2 is fluorescent probe of the present invention and the mass spectrogram after mercury ion effect.
Fig. 3 is that fluorescent probe of the present invention changes (F/ to the fluorescence ratio at 450nm after the effect of variable concentrations mercury ion
F0) spectrogram.
Fig. 4 is in 450nm Fluorescence emission values after fluorescent probe of the present invention is acted on mercury ion under condition of different pH.
Fig. 5 is in 450nm Fluorescence emission values after fluorescent probe of the present invention is acted on different metal ions.
Fig. 6 is fluorescent emission response value of the fluorescent probe of the present invention to mercury ion under different metal ions existence condition.
Specific embodiment
Embodiment 1
Weigh 3- Methyl-7-hydroxy-coumarins (1.0g, 5.7mmol) and glycol dibromide (1.17g, 6.2mmol) is molten
In DMF (20ml), potassium carbonate (1.0g, 7.4mmol) is added, 90 degree are heated under nitrogen atmosphere
Reaction 24 hours；After reaction terminates, filtrate is filtrated to get, decompression is spin-dried for grease, and with silica gel column chromatography purification is carried out, and uses second
Acetoacetic ester and petroleum ether=1:5 (v/v) are separated as eluant, obtain intermediate 2 (yield 57%, purity 98%).
Embodiment 2
Weigh intermediate 3- methyl -7- bromine oxethyl coumarins (0.4g, 1.4mmol) to be dissolved in acetonitrile (20ml), then add
Enter the carbon -7- alkene (DBU) (0.26g, 1.7mmol) of 1,8- diazabicylos 11,90 degree of reactions 12 are heated under nitrogen atmosphere
Hour；After reaction terminates, filtrate is filtrated to get, decompression is spin-dried for acetonitrile, adds 20ml water, then is extracted with ethyl acetate, and is associated with
Machine phase, anhydrous sodium sulfate drying is filtered, and filtrate decompression is spin-dried for grease, and with silica gel column chromatography purification is carried out, and uses ethyl acetate
With petroleum ether=1:5 (v/v) are separated as eluant, obtain fluorescent probe 2 (yield 46%, purity 98%).1H NMR
(400MHz,CDCl3):δ 7.55 (d, J=8.4Hz, 1H), 6.94-6.97 (m, 2H), 6.67 (dd, J1=13.6Hz, J2=
6.0Hz,1H),6.19(s,1H),6.67(dd,J1=13.6Hz, J2=1.6Hz, 1H), 6.67 (dd, J1=6.0Hz, J2=
1.6Hz,1H),2.42(s,3H).13C NMR(100MHz,CDCl3):δ160.8,159.5,154.9,152.2,146.3,
125.8,115.3,113.4,113.0,104.2,98.1,18.7.FTMS(ESI)calcd for[M+H]+C12H11O3:
203.0703,found 203.0706.
Embodiment 3
The fluorescent emission spectrogram that probe is responded to mercury ion：Probe is dissolved in into configuration in HEPES buffer solution (pH=7.0)
Into the solution that concentration is 2.5 μm of ol/L, then the aqueous solution of Deca 0-15 μm ol/L mercury ions, after ready to balance, determines fluorescence and sends out
Spectrum is penetrated, Fig. 1 is as a result seen.
Embodiment 4
Mass spectrogram after fluorescent probe of the present invention and mercury ion effect：We determine probe and hydrargyrum with high resolution mass spectrum
The molecular weight of the product 3- Methyl-7-hydroxy-coumarins after ionization, as shown in Fig. 2 the theoretical mass spectra value of the molecule is
177.0473, measured value is 177.0553, illustrates that probe obtains high fluorescent material 3- methyl -7- with the catalysis of mercury ion association reaction
Hydroxycoumarin, as a result as shown in Figure 3.
Embodiment 5
Fluorescent probe of the present invention changes (F/F to the fluorescence ratio at 450nm after the effect of variable concentrations mercury ion0) spectrum
Figure：Probe is dissolved in HEPES buffer solution (pH=7.0) and is configured to the solution that concentration is 2.5 μm of ol/L, then Deca 0-
The aqueous solution of 1.8 μm of ol/L mercury ions, after ready to balance, determines fluorescence emission spectrum, arranges result and sees Fig. 4.
As shown in Figure 4, the fluorescence ratio (F/F at 450nm0) can be with the linear change of the concentration of trace amount mercury ion
Change, therefore, it can carry out quantitatively the mercury ion of trace in Environmental Water sample according to ratio fluorescent value.
Embodiment 6
Probe under condition of different pH to mercury ion effect after in 450nm Fluorescence emission values：Probe is dissolved in into different pH to delay
The solution for being configured to that concentration is 2.5 μm of ol/L is rushed in solution, then 10 μm of ol/L mercury ions of Deca, after ready to balance, determine fluorescence
Emission spectrum, arranges result and sees Fig. 5.
As shown in Figure 5, when pH is in acid and neutrality, mercury ion catalyzing hydrolysis alkene ehter bond, fluorescence response ratio are conducive to
It is more apparent, therefore, the suitable pH scopes of the probe in detecting mercury ion are acid and neutral.
Embodiment 7
Probe to different metal ions effect after in 450nm Fluorescence emission values (F450nm)：Probe is dissolved in into HEPES bufferings
The solution that concentration is 2.5 μm of ol/L is configured in solution (pH=7.0), then 10 μm of ol/L different metal ions of Deca is water-soluble
Liquid, after ready to balance, determines fluorescence emission spectrum, and exists under interference in different metal ions, determines probe to the glimmering of mercury ion
Light transmitting response, arranges result and sees Fig. 6.
It will be appreciated from fig. 6 that the Fluorescence emission values of probe are only varied widely to mercury ion, and other metal ions are not received
Detection interference.
Claims (5)
1. a kind of water-soluble coumarin class fluorescent probe, it is characterised in that the structural formula of fluorescent probe is as follows：
2. a kind of preparation method of Coumarinses class fluorescent probe as claimed in claim 1, it is characterised in that including following step
Suddenly：
(1) 3- Methyl-7-hydroxy-coumarins and glycol dibromide are dissolved in acetonitrile, add potassium carbonate, reacting by heating to obtain
Compound 3- methyl -7- bromine oxethyl coumarins；
(2) the 3- methyl -7- bromine oxethyls coumarin that step (1) is obtained exists with the carbon -7- alkene of organic base 1,8- diazabicylos 11
Reacting by heating in acetonitrile, reacts and process after Jing after terminating the water-soluble coumarin class fluorescent probe described in obtaining.
3. application of a kind of water-soluble coumarin class fluorescent probe as claimed in claim 1 in mercury ion detecting.
4. application of the water-soluble coumarin class fluorescent probe according to claim 3 in mercury ion detecting, its feature exists
In detection method is as follows：Prepare liquid is added in the aqueous solution of water-soluble coumarin class fluorescent probe, is then shone using light
Penetrate, observe the change in fluorescence of probe solution, and according to the change in fluorescence of probe solution judging whether containing mercury ion.
5. application of the water-soluble coumarin class fluorescent probe according to claim 3 in mercury ion detecting, its feature exists
In detection method is as follows：Prepare liquid is added in the aqueous solution of water-soluble coumarin class fluorescent probe, fluorescent emission is then determined
Spectrum, obtains adding the fluorescence change before and after prepare liquid, is then contrasted fluorescence change with standard curve, is treated
The mercury ion content surveyed in liquid.
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Cited By (2)
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| CN113406049A (en) * | 2021-06-16 | 2021-09-17 | 安徽大学 | CdTe quantum dot-benzocoumarin-3-formic acid ratiometric fluorescent probe and preparation method and application thereof |
| CN114805272A (en) * | 2022-05-13 | 2022-07-29 | 济南市规划设计研究院 | Aryl coumarin probe, probe molecule compound and Hg in urban planning sewage system 2+ Applications in assays |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113406049A (en) * | 2021-06-16 | 2021-09-17 | 安徽大学 | CdTe quantum dot-benzocoumarin-3-formic acid ratiometric fluorescent probe and preparation method and application thereof |
| CN113406049B (en) * | 2021-06-16 | 2023-02-03 | 安徽大学 | CdTe quantum dot-benzocoumarin-3-formic acid ratiometric fluorescent probe and preparation method and application thereof |
| CN114805272A (en) * | 2022-05-13 | 2022-07-29 | 济南市规划设计研究院 | Aryl coumarin probe, probe molecule compound and Hg in urban planning sewage system 2+ Applications in assays |
| CN114805272B (en) * | 2022-05-13 | 2024-04-16 | 济南市规划设计研究院 | Arylcoumarin probe, probe molecule complex and Hg of urban sewage planning system 2+ Application in detection |
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