CN109574872A - A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion - Google Patents
A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion Download PDFInfo
- Publication number
- CN109574872A CN109574872A CN201910016174.XA CN201910016174A CN109574872A CN 109574872 A CN109574872 A CN 109574872A CN 201910016174 A CN201910016174 A CN 201910016174A CN 109574872 A CN109574872 A CN 109574872A
- Authority
- CN
- China
- Prior art keywords
- copper ion
- compound
- fluorescence
- solution
- hydroxyl
- 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.)
- Withdrawn
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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"
- G01N2021/6432—Quenching
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention relates to a kind of fluorescence probes and the preparation method and application thereof for detecting copper ion.The present invention first prepares compound 3, then successively heating reflux reaction obtains compound 2 in acetic acid with hexamethylenetetramine；Under nitrogen protection, hydrazine hydrate is mixed with compound 2 and EtOH is added, normal-temperature reaction 3~12 hours, obtain yellow solid fluorescent probe compounds 1；After the copper ion solution that concentration in gradient changes is mixed with 1 solution of compound, measure fluorescence intensity, then using the concentration of copper ion as abscissa, the fluorescence intensity of mixed system is ordinate mapping, the variation of copper ion solution concentration gradient and fluorescence probe solution fluorescence Strength Changes value normal line are established, it can be according to fluorescence intensity from the copper ion concentration read in figure in solution to be measured when application.Fluorescence probe detection prepared by the present invention is limited to 1.15*10‑6M can be used for highly selective Sensitive Detection copper ion.
Description
Technical field
The invention belongs to organic syntheses and technical field of analytical chemistry, and in particular to a kind of for detecting the fluorescence of copper ion
Probe and the preparation method and application thereof.
Background technique
Due to the highly selective and sensitivity of fluorescence probe, the detection for being widely used in cation and anion is worked as
In.These fluorescence probes reach highly selective to adapt to different test environment and tester by chemical modification appropriate
With the purpose of high sensitivity.Currently, AIE fluorescence probe is due to good coherent condition luminescent effect, and chemical stability
By force, solid state fluorescence intensity is high, and environment-adapting ability is strong, and excellent application prospect is shown in fluorescence detection field.
Copper ion is used as in many metalloenzyme, mitochondrial respiratory, iron absorption, radicals scavenging and elastin laminin crosslinking and urges
Agent and structure confactor play indispensable role.However, excessive Cu2+The accumulation of ion leads to many neurologicals
Property disease, if Wei Ersenshi disease, Dyslexia, hypoglycemia, Alzheimer disease, Menkes disease, Parkinson's disease, amyotrophia funiculus lateralis
Hardening, baby's hepatic injury stomach function regulating intestines problem.Therefore, Cu in environmental sample is detected2+The concentration of ion is to environmental protection and human body
Health is of great significance.
Summary of the invention
It is an object of the present invention to provide a kind of fluorescence probes that can be used in copper ion detection, by apparent glimmering
Optical quenching can delicately detect the presence of copper ion, the application prospect having had.
1) for detecting the fluorescence probe of copper ion
Of the present invention a kind of for detecting the fluorescence probe of copper ion, which is a kind of four with hydroxyl
Styrene (compound 1), the entitled N of chemistry, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine, tool
Body structure are as follows:
2) it is prepared for detecting the fluorescent probe compounds 1 of copper ion
Another object of the present invention is to provide the fluorescence probe ((2- hydroxyl -4- (1 ', 2 ', the 2 '-triphenyls of N, N '-two
Vinyl)) benzyl Asia hydrazine, compound 1) preparation method, this method first by benzophenone with to dihydroxy benaophenonel in tetrachloro
Change the lower synthesis compound 3 of titanium catalysis, then successively prepare fluorescence probe with hexamethylenetetramine, hydration hydrazine reaction, feature exists
In:
(1) after obtaining compound 3, by compound 3 and hexamethylenetetramine with the ratio of molar ratio 1:1~20, in acetic acid
In be heated to reflux 20~40 hours, reaction product obtains compound 2 after processing, the compound 2 be 2- hydroxyl -5- (1,
2,2- triphenyl vinyls) benzaldehyde, 2 synthetic route of compound is as follows:
(2) under nitrogen protection, hydrazine hydrate and compound 2 are mixed with the ratio of molar ratio 1:2~3 and EtOH, room temperature is added
Reaction 3~12 hours, after reaction, product are recrystallized with ethyl alcohol/distilled water, are filtered, dry, obtain the spy of yellow solid fluorescence
Needle compound 1, the as N, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine.
Fluorescent probe compounds 1N of the present invention, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl
Sub- hydrazine synthetic route is as follows:
Fluorescent probe compounds 1 produced by the present invention, molecular formula C54H40N2O2, infrared spectroscopy (KBr), v/cm-1:
3437 (Ar-OH), 1626 (C=N).Nucleus magnetic hydrogen spectrum (400MHz, CDCl3) δ: 11.27 (s, 2H, N=C-H), 8.38 (s, 2H,
), OH 6.96-7.12 (m, 34H, ArH), 6.74 (d, J=8Hz, 2H, ArH).Nuclear-magnetism carbon composes (100MHz, CDCl3) δ:
164.45,158.36,143.60,143.36,140.84,139.49,136.78,135.39,131.36,131.27,127.95,
127.81,127.68,126.63,126.46,116.70,116.47. mass spectrum (m/s): calculated value C54H40N2O2748.31(M)+,
Measured value 748.38.
Fluorescence probe N prepared by the present invention, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine
Solid is in yellow, has strong fluorescence transmitting at 626nm, fluorescence quantum yield 0.65, good water solubility, the fluorescence probe is in solution
In with copper ion form 1:1 complex compound, and cause fluorescence that obvious quenching occurs, can be used for the Sensitive Detection of copper ion in environment,
The interference of other ions is small, is a kind of ideal copper ion quick-check sensor.
Compound 3 of the present invention, be using have disclosed method (J.Mater.Chem., 2012,22,3323-
3326), benzophenone is prepared under titanium tetrachloride catalysis with to dihydroxy benaophenonel.
3 entitled 4- (1,2, the 2- triphenyl vinyl) phenol of chemistry of compound, structural formula are as follows:
3) fluorescent probe compounds 1 are used to detect the application of copper ion
N prepared by the present invention, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine can to copper from
Son carries out qualitative, quantitative detection, after the copper ion solution that concentration in gradient changes is mixed with aldehyde radical tetraphenyl ethylene solution, surveys
Fixed corresponding fluorescence intensity, then using the concentration of copper ion as abscissa, the fluorescence intensity of mixed system is ordinate mapping, is built
Vertical copper ion solution concentration gradient variation and N, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine solution
Fluorescence intensity change value normal line, can be according to fluorescence intensity from the copper ion concentration read in solution to be measured in figure.
Beneficial achievement of the invention: prepared N, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl
Sub- hydrazine fluorescence in the presence of copper ion significantly changes, and the detection of copper ion is not interfered in the presence of other ions, and detection is limited to
1.15*10-6M can be used for highly selective Sensitive Detection copper ion, this has important show for the detection of copper ion in complex environment
Real application value.
Detailed description of the invention
Fig. 1 is 10 in aqueous tetrahydrofuran solution-5Mol/L compound 1 and 10-5The UV absorption figure of each ion of mol/L
Spectrum.
Fig. 2 is 10 in aqueous tetrahydrofuran solution-5The UV absorption figure of the copper ion of mol/L compound 1 and various concentration
Spectrum.
Fig. 3 is 10 in aqueous tetrahydrofuran solution-5Mol/L compound 1 and 10-4The fluorescent emission figure of each ion of mol/L
Spectrum.
Fig. 4 is 10 in aqueous tetrahydrofuran solution-5The fluorescence pattern of the copper ion of mol/L compound 1 and various concentration.
Fig. 5 is 10 in aqueous tetrahydrofuran solution-5Mol/L compound 1 and 10-5Mol/L copper ion and 10-5Mol/L interference
The fluorescence ratio figure of ion.
Fig. 6 is the infrared spectrogram of compound 1, it is determined that each structure of functional groups of compound 1.
Fig. 7 is the hydrogen nuclear magnetic resonance spectrogram of compound 1, it is determined that the structure of compound 1.
Fig. 8 is the carbon-13 nmr spectra figure of compound 1, it is determined that the structure of compound 1.
Fig. 9 is the mass spectrogram of compound 1, it is determined that the structure of compound 1.
Figure 10 is the mass spectrogram after 1 complex copper ion of compound, and the strong peak at 811.27 has determined the coordination structure of 1:1.
Specific embodiment
In order to further illustrate the present invention, following serial specific embodiment is provided in conjunction with attached drawing, but the present invention is not by this
The limitation of a little specific embodiments, any understanding person skilled in art will can achieve few modifications of the invention similar
As a result, these changes are also contained among the present invention.
In Fig. 1, tetrahydrofuran and water volume ratio are 9:1 in aqueous tetrahydrofuran solution, and abscissa is wavelength, ordinate is suction
Luminosity.Ultraviolet spectra absorbance is the most obvious to the variation of copper ion in figure, shows that compound 1 has stronger fluorescence to copper ion
Identify responding ability.
In Fig. 2, tetrahydrofuran and water volume ratio are 9:1 in aqueous tetrahydrofuran solution, and abscissa is wavelength, ordinate is suction
Luminosity.Copper ion concentration be followed successively by 1 concentration of compound 0,0.1,0.2,0.4,0.5,0.6,0.8,1.0,1.2,1.4,1.5,
1.6,1.8,2.0 times.Fig. 2 shows 1 absorbance of compound with the raising of copper ion concentration, at being decreased obviously trend.
In Fig. 3, tetrahydrofuran and water volume ratio are 9:1 in aqueous tetrahydrofuran solution, and abscissa is wavelength, ordinate is phase
To fluorescence intensity.Fluorescence intensity decline is bigger, and it is higher to indicate that compound 1 responds ion identification.Only to copper in test ion
Ion obvious responses to, and illustrates compound 1 to copper ion energy Selective recognition.
Fig. 4, tetrahydrofuran and water volume ratio are 9:1 in aqueous tetrahydrofuran solution, and abscissa is wavelength, ordinate is opposite
Fluorescence intensity.Copper ion concentration be followed successively by 1 concentration of compound 0,0.1,0.2,0.4,0.5,0.6,0.8,1.0,1.2,1.4,
1.5,1.6,1.8,2.0 times.Compound 1 is indicated with the raising of copper ion concentration, fluorescent emission intensity is gradually reduced.
In Fig. 5, tetrahydrofuran and water volume ratio are 9:1 in aqueous tetrahydrofuran solution, and ordinate is the ratio of fluorescence intensity,
Ratio illustrates that the interference performance of interfering ion is smaller closer to 1.As can be seen from Figure 5, all ratios illustrate other ions close to 1
Substantially highly sensitive detection of the fluorescence probe of the present invention to copper ion is not interfered.
Embodiment 1
1, compound 3 described in the present embodiment invented after using the technical solution method (J.Mater.Chem.,
2012,22,3323-3326) it is prepared.
3 entitled 1- hydroxyl -4- (1 ', 2 ', the 2 '-triphenyl vinyl) phenol of chemistry of compound, structural formula are as follows:
2, the synthesis step of compound 2:
Into the three-necked flask equipped with 20mL acetic acid, 1.0g (2.8mmol) compound 3 is added, after mixing evenly, adds
0.392g (2.8mmol) hexamethylenetetramine.Under the conditions of 100 DEG C, electromagnetic agitation is heated to reflux 40 hours, and TLC is detected to change
It closes object 3 to completely disappear, stops reaction.It is spin-dried for acetic acid, uses NaHCO3Aqueous solution washing 3 times or more, organic layer is separated, magnesium sulfate is dry
Dry, filtrate is concentrated in filtering, and methanol extraction is added and obtains compound 2, yield 38%.
3, the synthesis step of compound 1:
Under nitrogen protection, the compound 2 of 0.2g (0.5mmol) is added into the three-necked flask equipped with 20mL dehydrated alcohol
With 0.01mL (0.25mol) hydrazine hydrate, after mixing evenly, then 4 drop acetic acid is added dropwise, is stirred to react at room temperature 12 hours, TLC detection
It disappears substantially to raw material.Reaction was completed, is cooled to room temperature, filtering, and ethyl alcohol/distilled water recrystallization obtains compound 1, yield is
80%.
Embodiment 2
1, the synthesis step of compound 2:
Into the three-necked flask equipped with 30mL acetic acid, 1.0g (2.8mmol) compound 3 is added, after mixing evenly, adds
2.0g (14mmol) hexamethylenetetramine.Under the conditions of 100 DEG C, electromagnetic agitation is heated to reflux 30 hours, and TLC is detected to chemical combination
Object 3 completely disappears, and stops reaction.It is spin-dried for acetic acid, uses NaHCO3Aqueous solution washing 3 times or more, organic layer is separated, magnesium sulfate is dry
Dry, filtrate is concentrated in filtering, and methanol extraction is added and obtains compound 2, yield 46%.
2, the synthesis step of compound 1:
Under nitrogen protection, the chemical combination of 0.25g (0.64mmol) is added into the three-necked flask equipped with 30mL dehydrated alcohol
Object 2 and 0.01mL (0.25mol) hydrazine hydrate, after mixing evenly, then are added dropwise 3 drop acetic acid, are stirred to react at room temperature 9 hours, TLC inspection
Survey disappears substantially to hydrazine hydrate.Reaction was completed, is cooled to room temperature, and filtering, ethyl alcohol/distilled water recrystallizes 2 times, obtains compound 1,
Yield is 84%.
Embodiment 3
1, the synthesis step of compound 2:
Into the three-necked flask equipped with 50mL acetic acid, 1.0g (2.8mmol) compound 3 is added, after mixing evenly, adds
(7.8g 56mmol) hexamethylenetetramine.Under the conditions of 100 DEG C, electromagnetic agitation is heated to reflux 20 hours, and TLC is detected to chemical combination
Object 3 completely disappears, and stops reaction.It is spin-dried for acetic acid, uses NaHCO3Aqueous solution washing 3 times or more, organic layer is separated, magnesium sulfate is dry
Dry, filtrate is concentrated in filtering, and methanol extraction is added and obtains compound 2, yield 54%.
2, the synthesis step of compound 1:
Under nitrogen protection, the compound of 0.3g (0.75mmol) is added into the three-necked flask equipped with 40mL dehydrated alcohol
2 and 0.01mL (0.25mol) hydrazine hydrate after mixing evenly, then is added dropwise 3 drop acetic acid, is stirred to react at room temperature 3 hours, TLC detection
It disappears substantially to hydrazine hydrate raw material.Reaction was completed, is cooled to room temperature, and filtering, ethyl alcohol/distilled water recrystallizes 3 times, obtains compound
1, yield 86%.
The above description is only an embodiment of the present invention, is not intended to limit protection scope of the present invention, all to utilize this hair
Equivalent process transformation made by bright specification and accompanying drawing content is applied directly or indirectly in other relevant technical fields,
Similarly it is included within the scope of the present invention.
Claims (5)
1. a kind of for detecting the fluorescence probe of copper ion, it is characterised in that the fluorescence probe, chemistry entitled N, N '-two
(2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine, concrete structure formula are as follows:
2. a kind of for detecting the preparation method of the fluorescence probe of copper ion, this method is first by benzophenone and to hydroxyl hexichol
Ketone synthesizes compound 3 under titanium tetrachloride catalysis, then successively prepares fluorescence with hexamethylenetetramine, hydration hydrazine reaction and visit
Needle, it is characterised in that the compound 3 successively prepares fluorescence probe with hexamethylenetetramine, hydration hydrazine reaction, by following
Step is completed:
1) compound 3 is mixed with hexamethylenetetramine, is heated to reflux in acetic acid, and reaction product obtains compound 2 after processing,
Entitled 2- hydroxyl -5- (1,2, the 2- triphenyl vinyl) benzaldehyde of chemistry of the compound 2, synthetic route are as follows:
2) hydrazine hydrate is mixed with compound 2 under nitrogen protection, EtOH is added, normal-temperature reaction 3~12 hours, reaction terminated
Afterwards, product is recrystallized with ethyl alcohol/distilled water, is filtered, dry, obtains yellow solid fluorescent probe compounds 1, the as N,
N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine, the fluorescent probe compounds 1N, (the 2- hydroxyl of N '-two
Base -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine synthetic route is as follows:
3. according to claim 2 a kind of for detecting the preparation method of the fluorescence probe of copper ion, it is characterised in that institute
That states is heated to reflux, and the time is 20~40 hours.
4. according to claim 2 a kind of for detecting the preparation method of the fluorescence probe of copper ion, it is characterised in that anti-
Compound 3 should be produced to mix with hexamethylenetetramine, molar ratio is 1:1~20.
5. a kind of for detecting the fluorescence probe application of copper ion, it is characterised in that the copper ion solution for changing concentration in gradient
It is strong to measure corresponding fluorescence after the mixing of (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) the benzyl Asia hydrazine solution of N '-two with N
Degree, then using the concentration of copper ion as abscissa, the fluorescence intensity of mixed system is ordinate mapping, and it is dense to establish copper ion solution
Spend change of gradient and N, N '-two (2- hydroxyl -4- (1 ', 2 ', 2 '-triphenyl vinyl)) benzyl Asia hydrazine solution fluorescence intensity change value
Normal line, according to fluorescence intensity from the copper ion concentration read in figure in solution to be measured when application.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910016174.XA CN109574872A (en) | 2019-01-08 | 2019-01-08 | A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910016174.XA CN109574872A (en) | 2019-01-08 | 2019-01-08 | A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109574872A true CN109574872A (en) | 2019-04-05 |
Family
ID=65915898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910016174.XA Withdrawn CN109574872A (en) | 2019-01-08 | 2019-01-08 | A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109574872A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110655919A (en) * | 2019-11-20 | 2020-01-07 | 贵州医科大学 | Copper ion fluorescent probe and preparation method and application thereof |
| CN110938096A (en) * | 2019-08-29 | 2020-03-31 | 广东工业大学 | Platinum complex with aggregation-induced emission and preparation method and application thereof |
| CN113045581A (en) * | 2021-03-25 | 2021-06-29 | 常州大学 | AIE fluorescent probe for detecting copper ions and preparation method and application thereof |
| CN113105360A (en) * | 2021-04-15 | 2021-07-13 | 暨南大学附属第一医院（广州华侨医院） | Multi-modal probe FN and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106957243A (en) * | 2017-03-29 | 2017-07-18 | 湖南科技大学 | A kind of copper ion detection probe based on aggregation-induced emission and its preparation method and application |
| CN108659154A (en) * | 2018-04-25 | 2018-10-16 | 西北师范大学 | The synthetic method of pH response type AIE fluorescence nano polymer quantum dots and application |
-
2019
- 2019-01-08 CN CN201910016174.XA patent/CN109574872A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106957243A (en) * | 2017-03-29 | 2017-07-18 | 湖南科技大学 | A kind of copper ion detection probe based on aggregation-induced emission and its preparation method and application |
| CN108659154A (en) * | 2018-04-25 | 2018-10-16 | 西北师范大学 | The synthetic method of pH response type AIE fluorescence nano polymer quantum dots and application |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110938096A (en) * | 2019-08-29 | 2020-03-31 | 广东工业大学 | Platinum complex with aggregation-induced emission and preparation method and application thereof |
| CN110655919A (en) * | 2019-11-20 | 2020-01-07 | 贵州医科大学 | Copper ion fluorescent probe and preparation method and application thereof |
| CN110655919B (en) * | 2019-11-20 | 2020-11-13 | 贵州医科大学 | Copper ion fluorescent probe and preparation method and application thereof |
| CN113045581A (en) * | 2021-03-25 | 2021-06-29 | 常州大学 | AIE fluorescent probe for detecting copper ions and preparation method and application thereof |
| CN113105360A (en) * | 2021-04-15 | 2021-07-13 | 暨南大学附属第一医院（广州华侨医院） | Multi-modal probe FN and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109574872A (en) | A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion | |
| CN110117282B (en) | Zinc ion fluorescent probe compound and preparation method and application thereof | |
| CN108752377B (en) | Fluorescent probe for detecting peroxynitrite anion, synthetic method and application | |
| CN108675990A (en) | A kind of detection Cu2+Fluorescence probe, preparation method and fluorescent test paper strip preparation and application | |
| CN110964515A (en) | double-Schiff base aluminum ion fluorescent probe, and synthesis method and application thereof | |
| CN111393461B (en) | Palladium ion fluorescent probe compound based on BODIPY and synthetic method thereof | |
| CN110746374B (en) | Tetrastyrene Schiff base Zn2+Fluorescent probe and preparation method and application thereof | |
| CN109749737B (en) | Benzylidene hydrazine fluorescent probe for detecting copper ions as well as preparation method and application thereof | |
| CN109206351B (en) | Cyanine structure based near-infrared fluorescent probe for detecting palladium ions, and preparation method and application thereof | |
| CN108276371B (en) | Coumarin thiocarbazone derivative and preparation method and application thereof | |
| CN108997401B (en) | Fluorescent probe for detecting lead ions and preparation method thereof | |
| CN110669505B (en) | Preparation method and application of red fluorescence enhanced probe for detecting mercury ions | |
| CN107652299B (en) | A kind of multichannel fluorescence probe and preparation method and application based on rhodamine B derivative | |
| CN111848671B (en) | Nitrosonoyl peroxide anion ratio far infrared fluorescent probe, preparation method and application | |
| CN107163072B (en) | It is a kind of to be used to detect fluorescence probe of zinc ion and the preparation method and application thereof | |
| CN115651006B (en) | Hydrogen peroxide ratio type near infrared fluorescent probe with large Stokes displacement and preparation method and application thereof | |
| CN113861068B (en) | Molecular probe for related-on-off-on conversion signals of acid and alkali and application thereof | |
| CN110028952A (en) | A kind of iodide ion identification probe and preparation method thereof | |
| CN111635354B (en) | Multi-ion difference detection fluorescent probe with carbazole Schiff base as recognition receptor | |
| CN111138329B (en) | Preparation method and application of AIE fluorescent probe for detecting palladium ions | |
| CN109574875B (en) | Fluorescent probe for detecting iron ions and preparation method and application thereof | |
| CN109608364B (en) | Preparation method and application of fluorescent probe for detecting mercury ions | |
| CN106967025A (en) | A kind of preparation and its application of 6 chlorine 3 [(the diethylin benzylidene of 2 hydroxyl 4) amino] cumarins | |
| CN110746320A (en) | Preparation method and application of fluorescent probe for detecting iron ions | |
| CN107286056B (en) | Polyamide-anthracene-based Schiff base-containing fluorescent probe compound and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20190405 |
|
| WW01 | Invention patent application withdrawn after publication |