CN108285462A - A kind of detection Bi3+Symmetric double rhodamine base fluorescent probe and preparation method thereof - Google Patents
A kind of detection Bi3+Symmetric double rhodamine base fluorescent probe and preparation method thereof Download PDFInfo
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- CN108285462A CN108285462A CN201810388456.8A CN201810388456A CN108285462A CN 108285462 A CN108285462 A CN 108285462A CN 201810388456 A CN201810388456 A CN 201810388456A CN 108285462 A CN108285462 A CN 108285462A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
Abstract
The invention belongs to fluorescence probe material and its preparation fields, and in particular to a kind of detection Bi3+Symmetric double rhodamine base fluorescent probe and preparation method thereof, detection Bi is made as shown, passing through a step condensation reaction using rhodamine and urea in structural formula3+Symmetric double rhodamine base fluorescent probe, the synthesis step of the probe is simple, single step reaction, easy to operate, and has selectivity well to bismuth ion, to K+、Na+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、Fe3+、Cu2+、Pb2+Equal metal ions have good anti-interference ability, and detection sensitivity is high, resolving time is short, can be applied to environment water body example, the bismuth ion detection in living cells, have wide application prospect.
Description
Technical field
The invention belongs to fluorescence probe material and its preparation fields, and in particular to a kind of detection Bi3+Symmetric double rhodamine
Base fluorescent probe and preparation method thereof.
Background technology
Bismuth is located at periodic table of elements period 6 V A race, is in metal and nonmetallic intersection, is a kind of nontoxicity
Element, the chemical property stable element larger as relative atomic mass, mostly with free metal and mineral in nature
Matter form exists, and is usually used in manufacturing fusible alloy in the industrial production, it is considered to be safest green metal.Compound state bismuth
It is also widely used for the treatment of enterogastritis and skin injury in medical domain.Simultaneously the study found that if taking bismuth-containing for a long time
Drug can cause metallic element to be largely deposited in brain and kidney, to cause the variation of various related pathologies, as uremia,
Memory decaying, liver function disease etc..
The detection method of metal ion experienced from traditional analysis to instrument analytical method, from single detection means
The evolution being combined to multiple technologies.The method of currently used detection bismuth ion has：Flame atomic absorption spectrometry, electric heating
Atomic absorption spectrum, atomic emission spectrum, atomic fluorescence spectrophotometry, Molecular Spectroscopy, x-ray fluorescence spectrometry etc., but these methods
It is strongly professional, it takes and complicated for operation, instrument cost is high, and has destructiveness to sample, is not suitable for biological sample and life
The in situ detection of objects system.
Fluorescence method has high sensitivity, specificity strong, not damaged, can realize that efficient, " bore hole " detects to object, together
When to object carry out qualitative and quantitative analysis.The rhodamine fluorescence probe detection Bi reported at present3+Document still lack
Weary, the probe based on off-on mechanism is less.
As Patent No. CN201410247133.9 discloses a kind of symmetric double rhodamine fluorescence of detection trivalent bismuth ion
Probe and its preparation method and application makes the open loop of rhodamine generation loop coil by the complexing induction of trivalent bismuth ion so that visit
The enhancing of color change and fluorescence signal occurs for needle molecule, and the symmetric double Rhodamine fluorescent probe is used for three in solution system
The detection of valence bismuth ion, the analysis detection of living biological cell and the trivalent bismuth ion in living tissue and fluorescence imaging detection or medicine
On detection for trivalent bismuth ion.
Patent No. CN201610255292.2 discloses a kind of method detecting bismuth ion using rhodamine fluorescence probe,
Probe solution is prepared using rhodamine fluorescence probe, the probe solution is added in bismuth ion prepare liquid, utilizes solvent
Constant volume, after standing a period of time, fluorescence intensity determines that bismuth ion is to be measured according to fluorescence intensity and bismuth concentration relationship
The content of bismuth ion in liquid.Functional activity dyestuff in the present invention has good selectivity to bismuth ion, is answered in sewage disposal
Not only facilitate in but also there is preferable using effect, but the probe is influenced by chromium ion.
Patent No. CN201710372630.5 discloses a kind of colorimetric and the double response type bismuth ion detection probes of fluorescence, has
Following below formula forms：The invention also discloses the preparation method of colorimetric and the double response type bismuth ion detection probes of fluorescence, steps
1, rhodamine 6G and reacting ethylenediamine are prepared into rhodamine 6G ethylenediamine intermediate；Step 2, the rhodamine 6G for obtaining step 1
With pyromellitic dianhydride bimolecular aminolysis reaction occurs for ethylenediamine intermediate, obtains centrosymmetric probe molecule product；Step
3, then the probe molecule product for obtaining step 2 is recrystallized to give light red solid probe point through filtering using organic solvent
The double response type bismuth ion detection probes of son, i.e. colorimetric and fluorescence, the present invention solve Bi in the prior art3+Existing for detection technique
Blank, providing a kind of having the characteristics that good, high sensitivity, fast response time the organic molecule class Bi of selectivity3+Colorimetric/fluorescence
Probe, but the synthesis step of the probe is cumbersome.
Therefore high, strongly professional, time-consuming, complicated for operation in order to solve instrument cost, and have destructiveness to sample, it is uncomfortable
The problems such as the in situ detection of biological sample and biosystem and fluorescence probe poor anti jamming capability, synthesis step is cumbersome etc. to ask
Topic, while the deficiency of detection bismuth ion fluorescence probe is supplemented, a kind of Rhodamine fluorescent probe tool of detection bismuth ion of design synthesis
There is important meaning.
Invention content
In order to solve fluorescence probe poor anti jamming capability, the problems such as synthesis step is cumbersome, the present invention provides a kind of detection Bi3+
Symmetric double rhodamine base fluorescent probe and preparation method thereof, reaction equation formula is as shown in Figure 1.
Further, Bi is detected3+Symmetric double Rhodamine fluorescent probe structural formula in group R1, R2, R3, R4 be H, or
Group R1, R2, R3 or R4 are selected from hydrogen, 1-5 carbon atom alkyl.
Further, above-mentioned detection Bi is prepared3+Symmetric double rhodamine base fluorescent probe, synthetic method is as follows：
1-2mmol rhodamines are weighed, organic solvent is dissolved in, be separately added into acid binding agent and are dissolved in organic solvent
Thiourea solution heats, and reflux, TLC, which is monitored to raw material point, not to be changed, cooling, is spin-dried for, inorganic solution washing, organic solution extraction
It takes, desiccant dryness, column chromatographic isolation and purification obtains detection Bi3+Symmetric double rhodamine base fluorescent probe.
Further, organic solvent is absolute methanol, absolute ethyl alcohol, acetonitrile, THF.
Further, acid binding agent is triethylamine or pyridine.
Further, rhodamine, thiocarbamide, acid binding agent molar ratio be 1:0.5-0.8:1.0-1.3.
Further, inorganic solution 5%Na2CO3Solution.
Further, extraction organic solution is CHCl3Solution.
Further, drier is anhydrous MgSO4。
Further, column chromatographic isolation and purification solvent is ethyl alcohol and dichloromethane, volume ratio 1：180-230.
A kind of detection Bi is made by a step condensation reaction in present invention application rhodamine and urea3+Symmetric double rhodamine
Base fluorescent probe, the synthesis step of the probe is simple, single step reaction, easy to operate, and has selection well to bismuth ion
Property, to K+、Na+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、Fe3+、Cu2+、Pb2+Equal metal ions have good anti-interference ability,
Detection sensitivity is high, and resolving time is short, can be applied to environment water body example, the bismuth ion detection in living cells, has and answer extensively
Use foreground.
Description of the drawings
Fig. 1 is detection Bi3+Symmetric double rhodamine base fluorescent probe reaction equation；
Fig. 2 is detection Bi3+Symmetric double rhodamine base fluorescent probe to the fluorescence emission spectrogram of compound of metalloform-selective；
Fig. 3 is detection Bi3+Symmetric double rhodamine base fluorescent probe to the Bi of 3eq3+It is glimmering with the other interfering ions of 5eq
Optical emission spectroscopy figure；
Fig. 4 is detection Bi3+Symmetric double rhodamine base fluorescent probe to different Bi3+The fluorescence emission spectrogram of compound of concentration；
Fig. 5 is detection Bi3+Symmetric double rhodamine base fluorescent probe the fluorescence range of linearity；
Fig. 6 is detection Bi3+Symmetric double rhodamine base fluorescent probe reversibility test fluorescence emission spectrogram of compound.
Specific implementation mode
As shown in Figure 1, synthesis detection Bi3+Symmetric double rhodamine base fluorescent probe, concrete scheme is as follows：
Embodiment one
Rhodamine B 1.0g (2.09mmol) is added in the three neck round bottom of 100mL, absolute ethyl alcohol 15mL, stirring is extremely
After rhodamine B is completely dissolved, 0.5mL triethylamines are added, will then be dissolved in the urea 0.0752g (1.25mmol) of 10mL absolute ethyl alcohols
It is slowly dropped to above-mentioned rhodamine B ethanol solution, is heated to 65 DEG C, TLC, which is monitored to raw material point, not to be changed, and room is cooled to
Temperature is spin-dried for, with 5%
Na2CO3Solution is washed, CHCl3Solution extracts, anhydrous MgSO4It is dry, with neutral alumina column chromatography (ethyl alcohol：Two
Chloromethanes=1:200) detection Bi, is obtained3+Symmetric double rhodamine base fluorescent probe.
Embodiment two
As shown in Fig. 2, being separately added into the K of 5 times of equivalents into probe solution+、Na+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、
Fe3+、Cu2+、Pb2+When ion, probe solution is colourless, and fluorescence intensity does not also change at 580nm, it is seen that probe is protected
Original structure is held, can be stable in the presence of in these solution systems.When Bi is added in probe solution3+Afterwards, solution is by no discoloration
For red, fluorescence intensity is remarkably reinforced at 580nm, a strong emission peak occurs.This is because Bi3+With probe reaction so that
The loop coil of rhodamine is opened, and fluorescent emission is generated.
Embodiment three
As shown in figure 3, using the fluorescence intensity of maximum emission peak position as ordinate, metal ion is abscissa, past first
Interfering ion (the K of 5 times of equivalents is separately added into probe solution+、Na+、Fe3+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、Cu2+、Pb2 +), add the Bi of 3 times of equivalents3+, solution immediately becomes red from colorless state, tests its fluorescence intensity, as seen from the figure, at it
In the presence of his interfering ion, probe is to Bi3+Still there is good recognition capability.
Example IV
As shown in Figure 4 and Figure 5,5 μM of probe solutions for preparing 10 parts of 5mL are separately added into 0-50 μM of bismuth ion, carry out glimmering
Light detection (λEx=520nm), fluorescence intensity in each system is calculated, by analyzing fluorescence intensity and Bi at 580nm3+Concentration
Relationship, assessment probe is to Bi3+Response performance.Fig. 4 shows with Bi3+The fluorescence intensity of the increase of concentration, solution gradually increases
By force, until maximum emission intensity is not changing.Fig. 5 shows probe in Bi3+Concentration 4 × 10-6Mol/L~6 × 10-5Mol/L ranges
It is interior in a linear relationship, linearly dependent coefficient R2=0.9858, and probe is to Bi3+Detection be limited to 1.16 × 10-8mol/L。
Embodiment five
As shown in fig. 6, fixed 10 μM of concentration and probe concentration, is added the Bi of 2eq3+Solutions Solution becomes red from colourless, at 580nm
Fluorescence intensity be remarkably reinforced, display probe to Bi3+Response, continuously add the EDTA solution fluorescence remitted its furys of 5eq, this be by
In EDTA and Bi3+Complexing has seized the Bi that part is complexed with probe3+, continuously add the Bi of 2eq3+Afterwards, the fluorescence intensity of system
Enhance again, shows probe and Bi3+Combination be belong to corrdination type identification, and have invertibity.
The preferred embodiment of the present invention is above are only, but the design concept of the present invention is not limited thereto, all profits
The change for carrying out unsubstantiality to the present invention with this design, should all belong to the behavior for invading the scope of the present invention.
Claims (10)
1. a kind of detection Bi3+Symmetric double rhodamine base fluorescent probe, it is characterised in that：The detection Bi3+Symmetric double Luo Dan
Bright base fluorescent probe structural formula is as follows：
2. detecting Bi according to claim 13+Symmetric double rhodamine base fluorescent probe, it is characterised in that：The detection Bi3+
Symmetric double rhodamine base fluorescent probe structural formula in group R1, R2, R3, R4 be that H or group R1, R2, R3 or R4 are selected from
Hydrogen, 1-5 carbon atom alkyl.
3. a kind of detection Bi3+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：Prepare claim 1
The detection Bi3+Symmetric double rhodamine base fluorescent probe, synthetic method is as follows：
1-2mmol rhodamines are weighed, organic solvent is dissolved in, be separately added into acid binding agent and are dissolved in the thiocarbamide of organic solvent
Solution heats, and reflux, TLC, which is monitored to raw material point, not to be changed, cooling, is spin-dried for, and inorganic solution washing, organic extractant solution is done
Drying prescription is dried, and column chromatographic isolation and purification obtains detection Bi3+Symmetric double rhodamine base fluorescent probe.
4. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The organic solvent is absolute methanol, absolute ethyl alcohol, acetonitrile, THF.
5. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The acid binding agent is triethylamine or pyridine.
6. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The rhodamine, thiocarbamide, acid binding agent molar ratio be 1:0.5-0.8:1.0-1.3.
7. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The inorganic solution is 5%Na2CO3Solution.
8. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The extraction organic solution is CHCl3Solution.
9. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The drier is anhydrous MgSO4。
10. detecting Bi according to claim 33+Symmetric double rhodamine base fluorescent probe synthetic method, it is characterised in that：
The column chromatographic isolation and purification solvent is ethyl alcohol and dichloromethane, volume ratio 1：180-230.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112557355A (en) * | 2020-11-12 | 2021-03-26 | 东南大学 | Method for detecting bismuth ions in biological fluid by rare earth fluorescent probe |
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|---|---|---|---|---|
| CN104004514A (en) * | 2014-06-06 | 2014-08-27 | 福建师范大学 | Symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as preparation method and use thereof |
| CN105866085A (en) * | 2016-04-22 | 2016-08-17 | 东华大学 | Method for detecting bismuth ions by utilizing rhodamine-type fluorescent probe |
| CN107417694A (en) * | 2017-05-24 | 2017-12-01 | 延安大学 | A kind of colorimetric and the double response type bismuth ion detection probes of fluorescence and preparation method thereof |
-
2018
- 2018-04-26 CN CN201810388456.8A patent/CN108285462A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004514A (en) * | 2014-06-06 | 2014-08-27 | 福建师范大学 | Symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as preparation method and use thereof |
| CN105866085A (en) * | 2016-04-22 | 2016-08-17 | 东华大学 | Method for detecting bismuth ions by utilizing rhodamine-type fluorescent probe |
| CN107417694A (en) * | 2017-05-24 | 2017-12-01 | 延安大学 | A kind of colorimetric and the double response type bismuth ion detection probes of fluorescence and preparation method thereof |
Non-Patent Citations (1)
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| 申川川: "新型罗丹明Bi(III)荧光探针的合成及性能测试", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112557355A (en) * | 2020-11-12 | 2021-03-26 | 东南大学 | Method for detecting bismuth ions in biological fluid by rare earth fluorescent probe |
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