CN106188102A - A kind of water solublity dendroid list imide compound fluorescent probe and its preparation method and application - Google Patents
A kind of water solublity dendroid list imide compound fluorescent probe and its preparation method and application Download PDFInfo
- Publication number
- CN106188102A CN106188102A CN201610504575.6A CN201610504575A CN106188102A CN 106188102 A CN106188102 A CN 106188102A CN 201610504575 A CN201610504575 A CN 201610504575A CN 106188102 A CN106188102 A CN 106188102A
- Authority
- CN
- China
- Prior art keywords
- dendroid
- pae
- detection
- imide compound
- water solublity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 0 CCCCC**(CC1*(C)C1C*N=C)=C1CC1 Chemical compound CCCCC**(CC1*(C)C1C*N=C)=C1CC1 0.000 description 2
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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 discloses a kind of water solublity dendroid list imide compound fluorescent probe and its preparation method and application.The amido functional group of dendrimer end group is incorporated in single acid anhydride system by the present invention, drastically increase its water solublity, and be combined with the light stability of analog derivative, obtain a kind of water solublity dendroid list imide compound, as metal ion and the application of hydrion fluorescent probe, it is used for detecting Fe3+、Cr3+And H+.Present invention achieves a probe in detecting different kinds of ions, specific dendroid list imide compound is used for multiple cation detection, extend the imido range of application of dendroid list, it is thus achieved that probe have selectivity, sensitivity and the strongest capacity of resisting disturbance well.
Description
Technical field
The present invention relates to a kind of polyion spectral probe, be specifically related to a kind of for water solublity dendroid list imidizate
Compound is as the application in detection metal ion and hydrionic fluorescent probe.
Background technology
Imide analog compounds has light, heat, chemical stability and the excellent dyeability of excellence, and fluorescent quantum produces
Rate is high, and fluorescence emission peak is narrow, it is possible to separate with cellular context fluorescence, has at biological fields such as protein, nucleic acid, cell detection
Wide application prospect, therefore, is widely used in the fields such as organic semiconducting materials, laser dye and biological fluorescent labeling.
Dendritic macromole is the functional polymer that a class formation can change and design, the design of peripheral high concentration end group
The dendritic macromole of difference in functionality can be constructed, be widely used in optics, electricity, medical science, catalyst, nanometer green wood
The aspects such as material, liquid crystal.Meanwhile, dendritic macromole has stable, and non-immunogenicity is high to the transport efficacy of bioactivator
Advantage, has become a kind of widest pharmaceutical carrier the most.The dendritic macromole of fluorescent compound label is that scientists is ground
One of focus studied carefully.Dendroid fluorescent material have light capture, Photo-induced electron transfer (PET), fluorescent switch, energy storage and
The specific functions such as conversion, have potential using value in fields such as chemical sensor, biological detection and medicine transmission.
Analog derivative poorly water-soluble, limits its application in living things system, and scientists has attempted a lot of method
Improve the water solublity of analog derivative.But the imide analog compounds of prior art water miscible is substantially reduced improving simultaneously
The fluorescence quantum yield of analog derivative, does not the most nearly all have fluorescence.How to improve acid imide
The while that compound being water miscible, do not reduce its fluorescence quantum yield, and can apply to polyion probe, be that the application wishes to solve
Problem.
Summary of the invention
It is an object of the invention to the water solublity dendroid list acid imide being to provide a kind of light, heat, chemical stability good
Compound, and use it for fluorescent probe；And by select specific condition, limit testing conditions, it is achieved to multiple sun from
The detection of son.
For reaching above goal of the invention, the concrete technical scheme of a first aspect of the present invention is: provide a kind of water solublity tree
Dendritic single imide compound, I is as follows for its formula:
First synthesis end group is the dendritic macromole of amido, and then with 3,4,9,10-tetracarboxylic anhydrides are sent out as fluorescence
The group of penetrating, utilizes amido and anhydride reaction to prepare dendroid list imide compound Formulas I, is used for detecting Fe3+、Cr3+And H+。
A second aspect of the present invention provides the preparation method of a kind of water solublity dendroid list imide compound, and it includes
Following steps:
(1) intermediate end group be 8 acrylate dendritic macromole PAE (=)8Synthesis: by trimethylolpropane
Triacrylate, ethylenediamine, absolute methanol mix, and heating is reacted, and react the washing of complete absolute methanol, obtain colourless
Bright thick liquid, reaction equation is as follows；
(2) intermediate end group is the dendritic macromole PAE (NH of 8 primary amine groups2)8Synthesis: by PAE (=)8With second two
Amine mixes, and heating is reacted, decompression distillation, washs by ethyl acetate, obtains pale yellow transparent thick liquid, and reaction equation is such as
Under；
(3) synthesis of intermediate 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium: by 3,4,9,10-
Tetracarboxylic anhydride is hydrolyzed to tetrabasic carboxylic acid potassium salt in KOH aqueous solution, between salt acid for adjusting pH value to 4-6, generates 3,4,9,
10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium, reaction equation is as follows；
(4) synthesis of water solublity dendroid list imide compound: by PAE (NH2)8It is mixed in isopropanol-water in advance to mix
Close in solution, in mixed solution, add 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium, react under room temperature
4-6 hour, react after then heating to 80 DEG C-95 DEG C, be subsequently adding dilute hydrochloric acid acidifying, last filtration washing, use aqueous slkali room
Temperature adds standing separation after KCl saturated solution after processing, and filters, and washing obtains brown-red solid Formulas I product water solublity dendroid
Single imide compound, reaction equation is as follows；
One optimal technical scheme of the present invention, is heated to 25 DEG C-35 DEG C in described step (1), step (2) and reacts.
One optimal technical scheme of the present invention, in described step (3), pH scope is 4-6.
One optimal technical scheme of the present invention provides the preparation method of a kind of water solublity dendroid list imide compound,
It comprises the steps:
(1) intermediate end group be 8 acrylate dendritic macromole PAE (=)8Synthesis: by trimethylolpropane
Triacrylate, ethylenediamine, absolute methanol mix, and are heated to 30 DEG C, react 6 hours, wash with absolute methanol, obtain colourless
Bright thick liquid；
(2) intermediate end group is the dendritic macromole PAE (NH of 8 primary amine groups2)8Synthesis: by PAE (=)8With second two
Amine mixes, and is heated to 30 DEG C, reacts 24 hours, decompression distillation, washs by ethyl acetate, obtains pale yellow transparent thick liquid；
(3) synthesis of intermediate 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium: by 3,4,9,10-
Tetracarboxylic anhydride is hydrolyzed to tetrabasic carboxylic acid potassium salt in KOH aqueous solution, regulation pH value to 4-6, generate 3,4,9,10-tetracarboxylic acids-
3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium；
(4) synthesis of water solublity dendroid list imide compound: by PAE (NH2)8It is mixed in isopropanol-water in advance to mix
Close in solution, in mixed solution, add 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium, react under room temperature
4 hours, after then heating to 90 DEG C react 2 hours, be subsequently adding 20% dilute hydrochloric acid be acidified 1-2 hour, filter, washing, use
5%KOH aqueous solution room temperature treatment adds standing separation after KCl saturated solution after two hours, filter, and washing obtains brownish red solid
Body Formulas I product water solublity dendroid list imide compound.
The use of the water solublity dendroid list imide compound that a third aspect of the present invention provides a kind of structural formula to be Formulas I
On the way, it is for as detection Fe3+Or Cr3+Or H+Fluorescent probe.
The detection Fe of described fluorescent probe3+Method be to detect fluorescence spectrum in aqueous, by detection 547nm at
Fluorescence intensity obtain Fe3+Concentration；The concentration of described water solublity dendroid list imide compound is 100 μMs；Fluorescence swashs
Sending out wavelength is 497nm.
The detection Cr of described fluorescent probe3+Method be to detect fluorescence spectrum in aqueous, glimmering at detection 547nm
Light intensity obtains Cr3+Concentration；The concentration of described water solublity dendroid list imide compound is 100 μMs；Fluorescence excitation ripple
A length of 497nm.
Described fluorescent probe detection H+Method be to detect fluorescence spectrum in aqueous, by detection 547nm at glimmering
Light intensity obtains the concentration of different pH value water solublity dendroid list imide compound；Described water solublity dendroid list acyl is sub-
The concentration of amines is 100 μMs；Fluorescence exciting wavelength is 497nm.
The water solublity dendroid list imide compound with Formulas I structure claimed in the present invention, the most also
Can represent with PAE-PM, there is equal implication.
Owing to technique scheme is used, the present invention compared with prior art has the advantage that
1. present invention achieves the imido synthesis of water-soluble mono, improve the water solublity of analog derivative.
2. present invention achieves a probe in detecting many kinds of metal ions and hydrion.
3. the probe of the present invention has good selectivity, sensitivity and the strongest capacity of resisting disturbance.
4. water miscible make fluorescent quenching compared to the imide analog compounds of prior art improving simultaneously,
The present invention detects Fe3+And Cr3+Making Fluorescence Increasing, detection sensitivity improves.
Accompanying drawing explanation
Fig. 1 is the fluorescence emission spectrum of the PAE-PM solution in the embodiment of the present invention 2 containing different metal ion；
Fig. 2 A is containing variable concentrations Fe in the embodiment of the present invention 33+The fluorescence emission spectrum of PAE-PM solution；Fig. 2 B is
The fluorescence emission spectrum of PAE-PM solution and Fe3+The graph of a relation of concentration.
Fig. 3 A is containing variable concentrations Cr in the embodiment of the present invention 43+The fluorescence emission spectrum of PAE-PM solution；Fig. 3 B is
The fluorescence emission spectrum of PAE-PM solution and Cr3+The graph of a relation of concentration.
Fig. 4 be in the embodiment of the present invention 5 coexistent metallic ion to containing Fe3+The shadow of PAE-PM solution maximum fluorescence intensity
Ring；
Fig. 5 be in the embodiment of the present invention 6 coexistent metallic ion to containing Cr3+The shadow of PAE-PM solution maximum fluorescence intensity
Ring；
Fig. 6 A is the fluorescence emission spectrum of the PAE-PM solution of different pH value in the embodiment of the present invention 7, and Fig. 6 B is PAE-PM
The fluorescence emission spectrum of solution and the graph of a relation of pH.
Detailed description of the invention
The following examples are that the present invention is expanded on further, but present disclosure is not limited to this.Present invention explanation
Embodiment in book is only used for that the present invention will be described, and protection scope of the present invention is not played restriction effect by it.This
The protection domain of invention is only defined by the claims, and those skilled in the art are institute on the basis of embodiment disclosed by the invention
Any omission of making, replace or revise and fall within protection scope of the present invention.
Embodiment 1
The preparation of fluorescent probe
Intermediate end group is the dendritic macromole (PAE (=) of 8 acrylate8) synthesis:
By 60g trimethylolpropane trimethacrylate, 2.4g ethylenediamine, the mixing of 30mL absolute methanol, it is heated to 30 DEG C, instead
Answer 6 hours, wash with absolute methanol, obtain water white thick liquid.
Intermediate end group is the dendritic macromole (PAE (NH of 8 primary amine groups2)8) synthesis:
By the PAE of 4.665 weight portions (=)8With 108 weight portion ethylenediamine mixing, being heated to 30-50 DEG C, reaction 24 is little
Time, decompression distillation, wash by ethyl acetate, obtain pale yellow transparent thick liquid.
The synthesis of intermediate 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium:
By 3g 3,4,9,10-tetracarboxylic anhydrides add in the KOH aqueous solution of 35mL 5%, are heated to 90 DEG C, and reaction 4 is little
Time.Being cooled to room temperature, add 12.5mL 10% phosphoric acid solution, continue to react 1 hour at 90 DEG C, filter, washing final vacuum dries
Dry.
The synthesis of water solublity dendroid list imide compound (PAE-PM):
By 1g PAE (NH2)8It is mixed in advance in 50mL isopropanol-water (7:3) mixed solution.Add in mixed solution
4.16g 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium, reacts 4 hours under room temperature, then heats to 90
React 2 hours after DEG C.The dilute hydrochloric acid adding 40mL 20% is acidified 1-2 hour, filters, and washing, with 60mL 5%KOH aqueous solution
Room temperature treatment adds standing separation after 20mL KCl saturated solution after 2 hours, filter, and washing obtains brown-red solid 2.14g,
Productivity: 78.21%.
FT-IR (KBr, cm-1): ν=3442,1687,1646,1594,1472,1243,812,752,611.1H-NMR
(CHCl3-d6, 400MHz, δ/ppm) and each peak is corresponding with the proton peak in PAE-PM structure in nuclear magnetic spectrogram: δ 8.56 (d, 32H),
8.18 (d, 32H), 4.68 (t, 16H), 4.234 (m, 16H), 4.171 (m, 16H), 3.509 (m, 8H), 2.963 (d, 24H),
2.862 (t, 8H), 2.601 (t, 4H), 2.269 (t, 16H), 1.798 (m, 8H), 1.264 (t, 12H).
Embodiment 2
The PAE-PM fluorescence spectrum selectivity to metal ion
In aqueous, determine PAE-PM and add metal ion Cr3+、Fe2+、Fe3+、Co2+、Ni2+、Cu2+、Zn2+、
Hg2+、Pb2+Fluorescence spectrum front and back, finds that PAE-PM is to Fe3+And Cr3+Having good response, result is as shown in Figure 1.
Fig. 1 is the fluorescence emission spectrum of the PAE-PM solution containing different metal ion.Solvent is water, concentration: PAE-PM
(40 μMs), metal ion (100 μMs), excitation wavelength lambda ex:497nm, slit width: 10/10nm, voltage: 650V.Figure has Fe3 +、Cr3+Make fluorescence intensity be greatly enhanced, illustrate PAE-PM in water to Fe3+、Cr3+There are good selectivity and sensitivity.
Embodiment 3
PAE-PM fluoroscopic examination Fe3+: PAE-PM fluorescence spectrum and Fe3+The relation of concentration
With water as solvent, test concentrations is respectively the Fe of 0,2.5,10,20,50,100,150,180,200,250 μMs3+Right
The impact of the fluorescence spectrum of the aqueous solution of the PAE-PM of 10 μMs, result such as Fig. 2.
Wherein, λ ex=497nm, λ em=547nm, slit width: 10/10nm, voltage: 650V.Maximum fluorescence intensity F with
Fe3+The relation of concentration.
From Fig. 2 A, 2B it can be seen that in 0～180 μM of concentration range, along with Fe3+The increase of concentration, the fluorescence of PAE-PM
Intensity gradually strengthens, and fluorescence intensity and Fe3+Concentration is certain linear relationship, and linear equation is F=312120 [Fe3+]+
1240, correlation coefficient is R=0.9385.Visible, PAE-PM can be with detection by quantitative Fe3+。
Embodiment 4
PAE-PM fluoroscopic examination Cr3+: PAE-PM fluorescence spectrum and Cr3+The relation of concentration
With water as solvent, the Cr of test concentrations difference 0,2.5,10,20,50,100,150,180,200,250 μMs3+To 10 μ
The impact of the fluorescence spectrum of the aqueous solution of the PAE-PM of M, result such as Fig. 3.
Wherein, λ ex=497nm, λ em=547nm, slit width: 10/10nm, voltage: 650V.Maximum fluorescence intensity F with
Cr3+The relation of concentration.
From Fig. 3 A, 3B it can be seen that in 0～150 μM of concentration range, along with Cr3+The increase of concentration, the fluorescence of PAE-PM
Intensity gradually strengthens, and fluorescence intensity and Cr3+Concentration is certain linear relationship, and linear equation is F=8573000 [Cr3+]
+ 1771, correlation coefficient is R=0.9734.Visible, PAE-PM can be with detection by quantitative Cr3+。
Embodiment 5
PAE-PM fluoroscopic examination Fe3+: PAE-PM detects Fe3+Time anti-interference
Fig. 4 is that environment coexisting ion relevant with biology is to PAE-PM/Fe3+The impact of aqueous solution fluorescence intensity.
Wherein, solvent is water, concentration: PAE-PM (40 μMs), metal ion (100 μMs), and excitation wavelength lambda ex:497nm is narrow
Seam width: 10/10nm, voltage: 650V.
As can be seen from Figure 4, Zn2+、Cr3+、Co2+、Pb2+、Ni2+、K+、Cu2+、Na+、Hg2+And Fe2+To Fe3+/ PAE-PM fluorescence is strong
Degree impact is little.Therefore, in water, PAE-PM is reliable high selectivity and high sensitivity Fe3+Fluorescent probe.
Embodiment 6
PAE-PM fluoroscopic examination Cr3+: PAE-PM detects Cr3+Time anti-interference
Fig. 5 is that environment coexisting ion relevant with biology is to PAE-PM/Cr3+The impact of aqueous solution fluorescence intensity.
Wherein, solvent is water, concentration: PAE-PM (40 μMs), metal ion (100 μMs), and excitation wavelength lambda ex:497nm is narrow
Seam width: 10/10nm, voltage: 650V.
As can be seen from Figure 5, Zn2+、Co2+、Pb2+、Ni2+、K+、Cu2+、Na+、Hg2+、Fe2+And Fe3+To Cr3+/ PAE-PM fluorescence is strong
Degree impact is little.Therefore, in water, PAE-PM is reliable high selectivity and high sensitivity Cr3+Fluorescent probe.
Embodiment 7
PAE-PM fluoroscopic examination H+: PAE-PM fluorescence spectrum and H+The relation of concentration
With water as solvent, test concentrations pH respectively is 2.07,3.10,3.98,4.94,6.21,7.08,8.05,8.95,
9.99,10.94,12.02 impact on the fluorescence spectrum of the PAE-PM aqueous solution of 10 μMs, result such as Fig. 6.
Wherein, λ ex=497nm, λ em=547nm, slit width: 10/10nm, voltage: 650V.Maximum fluorescence intensity F with
The relation of pH concentration.
As can be seen from Figure 6B, under different pH value, the aqueous solution fluorescence intensity change of PAE-PM is obvious, and except system
Fluorescence intensity change outside, waveform and wavelength of fluorescence all create change.When pH value is acid i.e. 2.07～4.94
In the range of time, the fluorescence intensity of PAE-PM reduces with the increase of pH value；When pH value by acidity to alkali transition that is 6.21～
Time in the range of 8.05, the fluorescence intensity of PAE-PM reaches minimum the most weak；When pH value is that alkalescence is i.e. 8.95～12.02
In the range of time, the fluorescence intensity of PAE-PM steeply rises and with the change of waveform, and transmitted wave length occurs obvious red shift, by
About 547nm red shift is to about 585nm.Therefore, in water, PAE-PM is reliable high selectivity and high sensitivity H+Fluorescence is visited
Pin.
Examples detailed above, only for technology design and the feature of the explanation present invention, its object is to allow the person skilled in the art be
Will appreciate that present disclosure and implement according to this, can not limit the scope of the invention with this.All according to present invention essence
God's equivalent transformation of being done of essence or modification, all should contain within protection scope of the present invention.
Claims (8)
1. a water solublity dendroid list imide compound, I is as follows for its formula:
2. a preparation method for water solublity dendroid list imide compound, it comprises the steps:
(1) intermediate end group be 8 acrylate dendritic macromole PAE (=)8Synthesis: by trimethylolpropane tris third
Olefin(e) acid ester, ethylenediamine, absolute methanol mix, and heating is reacted, and react the washing of complete absolute methanol, obtain water white
Thick liquid, reaction equation is as follows；
(2) intermediate end group is the dendritic macromole PAE (NH of 8 primary amine groups2)8Synthesis: by PAE (=)8Mix with ethylenediamine
Closing, heating is reacted, distillation of then reducing pressure, and washs by ethyl acetate, obtains pale yellow transparent thick liquid, and reaction equation is such as
Under；
(3) synthesis of intermediate 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium: by 3,4,9,10-tetra-
Carboxylic acid anhydrides is hydrolyzed to tetrabasic carboxylic acid potassium salt in KOH aqueous solution, and regulation pH value is acid, generates 3,4,9,10-tetracarboxylic acid-3,4-
Anhydride-9-carboxylic acid-10-carboxylic acid potassium, reaction equation is as follows；
(4) synthesis of water solublity dendroid list imide compound: by PAE (NH2)8It is mixed in isopropanol-water mixing in advance molten
In liquid, in mixed solution, add 3,4,9,10-tetracarboxylic acid-3,4-anhydride-9-carboxylic acid-10-carboxylic acid potassium, under room temperature, react 4-6
Hour, react after then heating to 80 DEG C-95 DEG C, add dilute hydrochloric acid acidifying, last filtration washing, use aqueous slkali room temperature treatment
Standing separation after rear addition KCl saturated solution, filters, and washing obtains brown-red solid Formulas I product, i.e. water solublity dendroid
Single imide compound, reaction equation is as follows；
Preparation method the most according to claim 2, it is characterised in that described step (1), step (2) are heated to 25 DEG C-
35 DEG C are reacted.
Preparation method the most according to claim 2, it is characterised in that in described step (3), pH scope is 4-6.
5. the purposes of water solublity dendroid list imide compound as claimed in claim 1, it is for as detection Fe3+Or
Cr3+Or H+Fluorescent probe.
Purposes the most according to claim 5, it is characterised in that described fluorescent probe detection Fe3+Method be, at aqueous solution
Middle detection fluorescence spectrum, obtains Fe by the fluorescence intensity at detection 547nm3+Concentration.
Purposes the most according to claim 5, it is characterised in that described fluorescent probe detection Cr3+Method be, at aqueous solution
Middle detection fluorescence spectrum, obtains Cr by the fluorescence intensity at detection 547nm3+Concentration.
Purposes the most according to claim 5, it is characterised in that described fluorescent probe detection H+Method be, in aqueous
Detection fluorescence spectrum, obtains different pH value by the fluorescence intensity at detection 547nm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610504575.6A CN106188102B (en) | 2016-06-30 | 2016-06-30 | A kind of water-soluble dendroid list imide compound fluorescence probe and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610504575.6A CN106188102B (en) | 2016-06-30 | 2016-06-30 | A kind of water-soluble dendroid list imide compound fluorescence probe and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106188102A true CN106188102A (en) | 2016-12-07 |
| CN106188102B CN106188102B (en) | 2017-12-26 |
Family
ID=57462733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610504575.6A Active CN106188102B (en) | 2016-06-30 | 2016-06-30 | A kind of water-soluble dendroid list imide compound fluorescence probe and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106188102B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558640A (en) * | 2018-05-08 | 2018-09-21 | 青岛科技大学 | A kind of Cu2+Tetrabasic carboxylic acid potassium assembly and the preparation method and application thereof |
| CN110308120A (en) * | 2018-06-19 | 2019-10-08 | 常熟理工学院 | For detecting aniline and hydrionic fluorescence probe |
| CN110305328A (en) * | 2018-06-19 | 2019-10-08 | 常熟理工学院 | Dendroid visible light initiator and its preparation method and application |
| CN110317346A (en) * | 2018-06-19 | 2019-10-11 | 常熟理工学院 | Dendroid fluorescein sodium-salt compounded of iodine visible light initiator and its preparation method and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0966468B1 (en) * | 1997-03-05 | 2004-09-22 | Ciba SC Holding AG | Crown ether-derivatised perylenes |
| CN103045230A (en) * | 2012-10-16 | 2013-04-17 | 福州大学 | Polyethylene terephthalate (PET) type Fe<3+> fluorescent probe and preparation method and application thereof |
-
2016
- 2016-06-30 CN CN201610504575.6A patent/CN106188102B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0966468B1 (en) * | 1997-03-05 | 2004-09-22 | Ciba SC Holding AG | Crown ether-derivatised perylenes |
| CN103045230A (en) * | 2012-10-16 | 2013-04-17 | 福州大学 | Polyethylene terephthalate (PET) type Fe<3+> fluorescent probe and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| DONG-MEI XU ET AL.: "Synthesis and Characterization of Stearyl-Group-Terminated Dendrimers and Thermosensitivity of Their Toluene Solutions", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
| 宁春花等: "萘酰亚胺树枝状聚( 胺-酯) 荧光材料的合成及性能", 《精细化工》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558640A (en) * | 2018-05-08 | 2018-09-21 | 青岛科技大学 | A kind of Cu2+Tetrabasic carboxylic acid potassium assembly and the preparation method and application thereof |
| CN108558640B (en) * | 2018-05-08 | 2021-02-23 | 青岛科技大学 | Cu2+-perylene potassium tetracarboxylate assembly and preparation method and application thereof |
| CN110308120A (en) * | 2018-06-19 | 2019-10-08 | 常熟理工学院 | For detecting aniline and hydrionic fluorescence probe |
| CN110305328A (en) * | 2018-06-19 | 2019-10-08 | 常熟理工学院 | Dendroid visible light initiator and its preparation method and application |
| CN110317346A (en) * | 2018-06-19 | 2019-10-11 | 常熟理工学院 | Dendroid fluorescein sodium-salt compounded of iodine visible light initiator and its preparation method and application |
| CN110308120B (en) * | 2018-06-19 | 2021-09-03 | 常熟理工学院 | Fluorescent probe for detecting aniline and hydrogen ions |
| CN110305328B (en) * | 2018-06-19 | 2022-03-04 | 常熟理工学院 | Dendritic visible light initiator and preparation method and application thereof |
| CN110317346B (en) * | 2018-06-19 | 2022-04-15 | 常熟理工学院 | Dendritic fluorescein sodium-iodonium salt visible light initiator and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106188102B (en) | 2017-12-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Cheng et al. | “Reactive” probe for hydrogen sulfite: good ratiometric response and bioimaging application | |
| Li et al. | Highly selective colorimetric/fluorometric dual-channel sensor for cyanide based on ICT off in aqueous solution | |
| Zhu et al. | A highly sensitive ratiometric fluorescent probe with a large emission shift for imaging endogenous cysteine in living cells | |
| Dolai et al. | A triazole linked C-glycosyl pyrene fluorescent sensor for selective detection of Au3+ in aqueous solution and its application in bioimaging | |
| CN111423423B (en) | Application of ratiometric fluorescent probe in detecting peroxynitrite anion | |
| CN108070092B (en) | Supermolecular gel based on functionalized column [5] arene and application thereof in identifying iron ions and L-Cys | |
| Li et al. | A tetraphenylethylene-based “turn on” fluorescent sensor for the rapid detection of Ag+ ions with high selectivity | |
| Jiao et al. | A schiff-base dual emission ratiometric fluorescent chemosensor for Hg2+ ions and its application in cellular imaging | |
| Fan et al. | A fluorescent probe for the dual-channel detection of Hg2+/Ag+ and its Hg2+-based complex for detection of mercapto biomolecules with a tunable measuring range | |
| CN106188102A (en) | A kind of water solublity dendroid list imide compound fluorescent probe and its preparation method and application | |
| Dong et al. | A novel ferrocenyl-based multichannel probe for colorimetric detection of Cu (II) and reversible fluorescent “turn-on” recognition of Hg (II) in aqueous environment and living cells | |
| Liao et al. | Nitrogen-doped carbon quantum dots as a fluorescent probe to detect copper ions, glutathione, and intracellular pH | |
| Wang et al. | A visual and fluorometric probe for Al (III) and Fe (III) using diketopyrrolopyrrole-based Schiff base | |
| Sahana et al. | Naphthalene based highly selective OFF–ON–OFF type fluorescent probe for Al3+ and NO2− ions for living cell imaging at physiological pH | |
| CN107602600B (en) | Amino-substituted aza-BODIPY near-infrared pH fluorescent probe and preparation method and application thereof | |
| CN107814808B (en) | A kind of near-infrared response type two-photon fluorescence probe and its preparation method and application | |
| Yuan et al. | New switch on fluorescent probe with AIE characteristics for selective and reversible detection of mercury ion in aqueous solution | |
| Gan et al. | A conveniently prepared and hypersensitized small molecular fluorescent probe: rapidly detecting free zinc ion in HepG2 cells and Arabidopsis | |
| CN106008343A (en) | Naphthalimide based mercury-ion fluorescence probe as well as preparation method and application thereof | |
| Li et al. | Colorimetric and fluorometric dual-modal probes for cyanide detection based on the doubly activated Michael acceptor and their bioimaging applications | |
| Yu et al. | A diethylamino pyridine formyl Schiff base as selective recognition chemosensor for biological thiols | |
| Cen et al. | Synthesis and characterization of a sensitive and selective Fe3+ fluorescent sensor based on novel sulfonated calix [4] arene‐based host‐guest complex | |
| Petdum et al. | [5] Helicene-rhodamine 6 G hybrid-based sensor for ultrasensitive Hg2+ detection and its biological applications | |
| Kataria et al. | Pyrazine-based hollow spherical self-assemblies: A portable tool for detection of volatile organic amines | |
| Bai et al. | Easily available aggregation-induced enhanced emission fluorescent material for detecting 1, 3-diaminopropane in gas-liquid-solid three-phase and bioimaging application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220321 Address after: 215500 5th floor, building 4, 68 Lianfeng Road, Changfu street, Changshu City, Suzhou City, Jiangsu Province Patentee after: Changshu intellectual property operation center Co.,Ltd. Address before: 215500 Changshou City South Three Ring Road No. 99, Suzhou, Jiangsu Patentee before: CHANGSHU INSTITUTE OF TECHNOLOGY |
|
| TR01 | Transfer of patent right |