CN107033158A - A kind of colorimetric fluorescence probe of hypersensitive analysis mercury ion and preparation method thereof - Google Patents
A kind of colorimetric fluorescence probe of hypersensitive analysis mercury ion and preparation method thereof Download PDFInfo
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- CN107033158A CN107033158A CN201611246359.2A CN201611246359A CN107033158A CN 107033158 A CN107033158 A CN 107033158A CN 201611246359 A CN201611246359 A CN 201611246359A CN 107033158 A CN107033158 A CN 107033158A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
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- 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"
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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Abstract
The present invention relates to colorimetric fluorescence probe of a kind of hypersensitive analysis mercury ion and preparation method thereof.Specifically, probe of the invention is a kind of thiocarbonic acid benester compound, and it can be used for the detection of mercury ion as mercury ion colorimetric fluorescence probe.This kind of probe can realize at least one in following technique effect：Mercury ion is recognized with high selectivity；Quickly mercury ion can be realized and responded；The High Sensitive Analysis to mercury ion can be realized；Property is stable, can for a long time preserve and use；And with stronger antijamming capability.
Description
Technical field
, can be rapidly to mercury ion Gao Xuan the present invention relates to thiocarbonic acid benester compound as mercury ion fluorescence probe
Select the quick identification of personality, or its can in determination sample mercury ion concentration.
Background technology
Mercury is a kind of metallic element with serious physiological-toxicity, because it has persistence, easy migration and height
Bioconcentration, becomes one of most noticeable environmental contaminants at present.Inorganic mercury ion in environment can be certain
Under the conditions of by organism conversion for severe toxicity methyl mercury.Inorganic mercury mainly influences kidney, and methyl mercury is mainly invaded after entering human body
Evil nervous system, especially central nervous system.Both of which can by food chain in biological tissue it is highly enriched so as to people
Huge harm is caused with nature.Mercury poisoning can produce extremely ill effect to entire society, and present mercury is existed by dominated column
On global environment monitoring system inventory, therefore, to the in situ, real-time, online of the Selective recognition of mercury ion, especially mercury ion
Monitoring is all significant for medical science, biology and environmental science.
In consideration of it, the analysis method that effective detection mercury ion is capable of in development is of crucial importance and significant.Nowadays
The analysis method of the detection mercury ion of report include Atomic absorption-emission spectrometry, high performance liquid chromatography, inductive etc. from
(such as anodic stripping voltammetry, oxidation are also for daughter mass spectrum, nuclear magnetic resonance, colorimetric method (such as traditional dithizone method), electrochemical method
Former current potential method etc.), colorimetric fluorescence probe turns into researcher due to its distinctive advantage in these numerous detection methods
Focus of attention.However, the colorimetric and fluorescence probe reported at present still suffer from some problems, including selectivity is not good enough, response
Speed is not fast enough, synthesis is complicated.Due to other ions such as bicarbonate ion in life entity, sulfate ion, bromide ion, chlorine
Other metal ions such as ion, nitrate ion, nitrite ion and phosphate anion, it can be constituted to the detection of mercury ion
Potential interference, therefore, development can the analysis method of mercury ion be necessary in high sensitivity detection life entity.In a word, develop
Quickly, high selectivity, high sensitivity, the simple mercury ion colorimetric fluorescence binary channels probe of synthesis are that those skilled in the art are badly in need of
Solve.
The content of the invention
This area is badly in need of one kind and prepares simple high sensitivity mercury ion colorimetric fluorescence probe, so as to effective detection mercury
Ion.Therefore, the present invention has synthesized the colorimetric fluorescence probe of the novel detection mercury ion of a class, its synthesis is simple, selectivity is high,
Sensitivity is high, can recognize mercury ion at once.Specifically, the invention provides a kind of mercury ion fluorescence probe, it is fluorescence
Chlorins compound, its structure is as follows：
It is preferred that, fluorescence probe of the invention is：
Present invention also offers the preparation method of mercury ion fluorescence probe, it is by by corresponding to the phase of probe of the present invention
Answer fluoresceins compound and thio phenyl chloroformate in dichloromethane solution stirring at normal temperature 6 hours and synthesize and be made.It is preferred that
, the corresponding fluoresceins compound corresponding to probe of the present invention of the invention is the fluorescein of rhodamine B hydridization.
Present invention also offers the detection preparation or kit for detecting ion concentration of mercury in sample, it includes the present invention
Probe.Preferably, detection preparation of the invention or kit also include the operation instructions of product.It is further preferred that of the invention
Kit also include the buffer for being used for determining ion concentration of mercury in sample.
Present invention also offers the method for ion concentration of mercury in detection sample, it includes the probe of the present invention and treats test sample
The step of this contact.
Prepared present invention also offers the probe of the present invention for detecting the use in sample in the preparation of ion concentration of mercury
On the way.
Present invention also offers the probe of the present invention, mercury ion is dense in preparing for detecting sample (such as water sample sample)
Purposes in the kit of degree.
The mercury ion colorimetric fluorescence probe of the present invention can be acted on mercury ion, produce fluorescence spectrum and UV absorption light
The change of spectrum, so as to realize the quantitative detection to mercury ion.
Specifically, mercury ion colorimetric fluorescence probe of the invention respectively with aluminium ion, copper ion, magnesium ion, potassium ion,
Zinc ion, nickel ion, sodium ion, nitrite ion, bicarbonate ion, sulfate ion, carbanion, chlorion,
Other ions such as nitrate ion, fluorine ion, which are acted on, can not cause fluorescence spectrum and the obvious of ultra-violet absorption spectrum to change
Become, so as to realize the Selective recognition to mercury ion, and then can be optionally used for excluding in these ions and human body other from
Interference of the presence of son to the quantitative determination of mercury ion.
Selectively, the stability of mercury ion fluorescence probe of the invention is good, and then can for a long time preserve and use.
Further, mercury ion colorimetric fluorescence probe of the invention is the high mercury ion colorimetric fluorescence probe of sensitivity,
And synthesis is simple, is conducive to commercialized popularization and application.
Brief description of the drawings
Fig. 1 is (5 μM) addition Hg of probe2+Fluorescence spectrum before and after (10 μM).
Fig. 2 a are various concentrations Hg2+The influence of (0-0.8 μM) to probe (5 μM) fluorescence spectrum；Fig. 2 b are various concentrations Hg2 +The influence of (0-10 μM) to probe (10 μM) absorption spectrum.
Fig. 3 a and Fig. 3 b are Hg2+(5 μM) and other different ions analytes (50 μM) are to the fluorescence intensity of probe (5 μM)
Influence, wherein：A. probe, b. mercury ions, c. aluminium ions, d. copper ions, e. magnesium ions, f. potassium ions, h. zinc ions, i. nickel from
Son, j. sodium ions, k. nitrite ions, l. bicarbonate ions, m. sulfate ions, n. carbanions, o. chlorions,
P. nitrate ion, q. fluorine ions.
Embodiment：
The invention provides synthetic route, method and its spectrum of above-mentioned quick high-selectivity mercury ion fluorescence probe
Energy.
The mercury ion colorimetric fluorescence probe of the present invention is a class fluoresceins compound, and it has following general structure
In above formula：R1, R2, R3, R4, R5, R6And R7For hydrogen atom, straight or branched alkyl, straight or branched alkoxyl, sulphur
Acidic group, ester group, carboxyl；R1, R2, R3, R4, R5, R6And R7Can be with identical or different.
The synthetic route and method of such mercury ion colorimetric Fluorescence Fluorescence probe are as follows：
Specifically, colorimetric fluorescence probe of the invention can be prepared via a method which, by certain mol proportion (example 1:1.5-
1:3) fluoresceins compound (such as fluorescein of rhodamine B hydridization) with thio phenyl chloroformate in dichloromethane, two
The mol ratio of person is (1:2) then stirring at normal temperature for a period of time (such as 6h), then rotated using rotating instrument, after being spin-dried for plus
Enter a small amount of dichloromethane to be dissolved, obtain product after crossing post, if to obtain purer product, dichloromethane can be used
With mixed system (such as v/v, 1 of petroleum ether:5) carry out being recrystallized to give sterling.
Therefore, prepared present invention also offers thio phenyl chloroformate for detecting in the colorimetric fluorescence probe of mercury ion
Purposes.
Prepared present invention also offers fluoresceins compound (such as the fluorescein of rhodamine B hydridization) for detecting mercury
Purposes in the colorimetric fluorescence probe of ion.
The highly sensitive identification mercury ion colorimetric fluorescence probe of quick high-selectivity of the present invention is noteworthy characterized by can be quick
High selectivity is sensitive to be recognized mercury ion and accurately can carry out quantitative analysis to mercury ion in the presence of other ions.
Below will be by the way that the present invention be described in more detail by following examples.Following examples are merely illustrative,
It should be understood that the present invention is not limited by following embodiments.
Embodiment 1
The fluorescein of 387mg (1mmol) rhodamine B hydridization is dissolved in 15mL dichloromethane by (scheme 1), adds
The thio phenyl chloroformate stirring at normal temperature 6h of 337mg (2mmol), are then rotated using rotating instrument, obtain crude product.If will
Obtain purer product, can by its dichloromethane and petroleum ether mixed system (such as v/v, 1:5) recrystallized in
Obtain sterling.Red pure product 364mg is obtained, yield is 64%.
The fluorescein of 387mg (1mmol) rhodamine B hydridization is dissolved in 15mL dichloromethane by (scheme 2), adds
The thio phenyl chloroformate stirring at normal temperature 6h of 252.7mg (1.5mmol), are then rotated using rotating instrument, obtain crude product.Such as
Fruit to obtain purer product, can by its dichloromethane and petroleum ether mixed system (such as v/v, 1:5) weighed in
Crystallization obtains sterling.Red pure product 297mg is obtained, yield is 52%.
The fluorescein of 387mg (1mmol) rhodamine B hydridization is dissolved in 15mL dichloromethane by (scheme 3), then adds
The thio phenyl chloroformate stirring at normal temperature 6h of 421.3mg (2.5mmol), are then rotated using rotating instrument, obtain crude product.Such as
Fruit to obtain purer product, can by its dichloromethane and petroleum ether mixed system (such as v/v, 1:5) weighed in
Crystallization obtains sterling.Red pure product 483mg is obtained, yield is 85%.
The fluorescein of 500mg (1mmol) rhodamine B hydridization is dissolved in 20mL dichloromethane by (scheme 4), adds
The thio phenyl chloroformate stirring at normal temperature 6h of 505.5mg (3mmol), are then rotated using rotating instrument, obtain crude product.If
Obtain purer product, can by its dichloromethane and petroleum ether mixed system (such as v/v, 1:5) tied again in
Crystalline substance obtains sterling.Red pure product 503mg is obtained, yield is 89%.
The fluorescein and 173mg (1mmol) of 500mg (1mmol) rhodamine B hydridization are dissolved in 15mL dichloromethanes by (scheme 5)
In alkane, the thio phenyl chloroformate stirring at normal temperature 10h of 421.3mg (2.5mmol) are added, are then rotated using rotating instrument,
Obtain crude product.If obtaining purer product, can by its dichloromethane and petroleum ether mixed system (such as v/v,
1:5) carry out being recrystallized to give sterling in.Red pure product 497mg is obtained, yield is 88%.
1H-NMR(400MHz,DMSO-d6)δ(*10-6):1.20 (t, J=6Hz, 6H), 3.36-3.45 (m, 4H), 6.39-
6.49(m,2H),6.59-6.62(m,1H),6.86-6.91(m,2H),7.22-7.29(m,3H),7.32-7.38(m,1H),
(d, J=8Hz, the 1H) of 7.49 (t, J=8Hz, 2H), 7.63-7.73 (m, 3H), 8.05
Embodiment 2
Fig. 1 is (5 μM) addition Hg of probe2+Fluorescence spectrum before and after (10 μM).As can clearly be seen from Figure, mercury ion
Addition causes fluorescence intensity to strengthen.
Embodiment 3
Fig. 2 a are various concentrations Hg2+The influence of (0-0.8 μM) to probe (5 μM) fluorescence spectrum；Fig. 2 b are various concentrations Hg2 +The influence of (0-10 μM) to probe (10 μM) ultra-violet absorption spectrum.
Along with Hg in probe solution it can be seen from Fig. 2 a2+The increase of concentration, fluorescence intensity gradually strengthens, and in (0-
0.8μM)Hg2+In concentration range, Hg2+Concentration and fluorescence intensity good linear relationship is presented.This is proved by means of the fluorescence
Probe can be to Hg2+Quantitative analysis is carried out, and with higher sensitivity.Hg in Drinking Water in China standard2+Standard limited value be
Therefore, probe of the invention can relatively accurately determine Hg in sample to be tested to 0.001mg/L2+Content.In addition, with Hg2+Concentration
Increase, absorption spectrum also gradually strengthens therewith, and this shows that using the probe colorimetric method for determining to mercury ion can be realized.
Embodiment 4
Fig. 3 is Hg2+The influence of (5 μM) and other different ions analytes (50 μM) to the fluorescence intensity of probe (5 μM).Point
Analysis thing includes：Concentration is 50 μM of aluminium ions, copper ion, magnesium ion, potassium ion, zinc ion, nickel ion, sodium ion, nitrous acid
Radical ion, bicarbonate ion, sulfate ion, carbanion, chlorion, nitrate ion, fluorine ion, and concentration is
5 μM of mercury ion.All test conditions are completed in pure water, and used probe is prepared probe in embodiment 1, and
All spectrum are measured all at 25 DEG C after analyte is added.Specifically, the 1mM probe storing solutions for pipetting 50 μ L put 10mL into
In colorimetric cylinder, the PBS cushioning liquid of 5mL pure water and 0.5mL pH=7.4 is then added, 10mL is settled to pure water, then pipette
The above-mentioned 10mM analytes storing solutions of 50 μ L are added in colorimetric cylinder, are shaken up, and are determined after 30min.As a result it is as shown in Figure 3.
The other common ions existed in organism are can be seen that from Fig. 3 a will not obvious response to probe；From figure
3b, which can be seen that the other common ions existed in organism, will not significantly interfere with measure of the probe to mercury ion, therefore probe
With good selectivity.
Although with above embodiments describing the present invention, it should be appreciated that before the spirit without departing substantially from the present invention
Put, the present invention further can be modified and changed, and these modification and variation belong to protection scope of the present invention it
It is interior.
Claims (10)
1. compound, it has following structure
Wherein：R1, R2, R3, R4, R5, R6And R7For independently selected from by hydrogen atom, straight or branched alkyl, straight or branched alcoxyl
The group that base, sulfonic group, ester group and hydroxyl are constituted；And R therein1, R2, R3, R4, R5, R6And R7Can be with identical or different.
2. compound according to claim 1, it is the compound of following structure：
3. preparation or kit for detecting mercury ion content in sample, it includes the compound of claim 1 or 2.
4. preparation according to claim 3 or kit, wherein described sample is water sample sample.
5. the compound of claim 1 or 2 is being prepared for detecting the use in sample in the preparation or kit of ion concentration of mercury
On the way.
6. purposes according to claim 5, wherein described sample is water sample sample.
7. preparing the method for the compound of claim 1 or 2, it comprises the following steps：
The fluorescein of rhodamine B hydridization is dissolved in dichloromethane with thio phenyl chloroformate and reacted.
8. method according to claim 7, wherein the mol ratio of the fluorescein of the rhodamine B hydridization and thio phenyl chloroformate
For 1:1.5-1:3.
9. method according to claim 7, wherein the time of the reaction is 6-10 hour.
10. method according to claim 9, wherein the time of the reaction is 6 hours.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746406A (en) * | 2017-11-22 | 2018-03-02 | 济南大学 | A kind of preparation and application of hypersensitive high selectivity hypochlorous acid fluorescence probe |
| CN108918482A (en) * | 2018-05-07 | 2018-11-30 | 济南大学 | A kind of kit of the highly selective mercury ion fluorescence probe based on fluorescein |
| CN109438426A (en) * | 2018-11-05 | 2019-03-08 | 湖北大学 | A kind of response type Hg based on half flower cyanines2+Fluorescence probe Cy-PT and its preparation method and application |
| CN110938051A (en) * | 2019-12-19 | 2020-03-31 | 济南大学 | Probe for efficiently detecting mercury ions, preparation method and application |
| CN115477657A (en) * | 2022-10-06 | 2022-12-16 | 中国药科大学 | Coumarin prodrug and preparation method and application thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746406A (en) * | 2017-11-22 | 2018-03-02 | 济南大学 | A kind of preparation and application of hypersensitive high selectivity hypochlorous acid fluorescence probe |
| CN107746406B (en) * | 2017-11-22 | 2021-02-09 | 济南大学 | Preparation and application of ultrasensitive high-selectivity hypochlorous acid fluorescent probe |
| CN108918482A (en) * | 2018-05-07 | 2018-11-30 | 济南大学 | A kind of kit of the highly selective mercury ion fluorescence probe based on fluorescein |
| CN109438426A (en) * | 2018-11-05 | 2019-03-08 | 湖北大学 | A kind of response type Hg based on half flower cyanines2+Fluorescence probe Cy-PT and its preparation method and application |
| CN109438426B (en) * | 2018-11-05 | 2021-04-27 | 湖北大学 | Half-cyanine-based reactive type Hg2+ fluorescent probe Cy-PT and preparation method and application thereof |
| CN110938051A (en) * | 2019-12-19 | 2020-03-31 | 济南大学 | Probe for efficiently detecting mercury ions, preparation method and application |
| CN110938051B (en) * | 2019-12-19 | 2022-05-10 | 济南大学 | Probe for efficiently detecting mercury ions, preparation method and application |
| CN115477657A (en) * | 2022-10-06 | 2022-12-16 | 中国药科大学 | Coumarin prodrug and preparation method and application thereof |
| CN115477657B (en) * | 2022-10-06 | 2023-10-31 | 中国药科大学 | Coumarin prodrug and preparation method and application thereof |
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