CN109776534B - Proportional sensing type zinc ion fluorescent probe and preparation method and application thereof - Google Patents
Proportional sensing type zinc ion fluorescent probe and preparation method and application thereof Download PDFInfo
- Publication number
- CN109776534B CN109776534B CN201910102618.1A CN201910102618A CN109776534B CN 109776534 B CN109776534 B CN 109776534B CN 201910102618 A CN201910102618 A CN 201910102618A CN 109776534 B CN109776534 B CN 109776534B
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- zinc ion
- pyridine
- sensing type
- type zinc
- 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.)
- Active
Links
Images
Abstract
The invention belongs to the technical field of ion identification, and particularly relates to a proportion sensing type zinc ion fluorescent probe and a preparation method and application thereof. The structural formula is as follows:
the concentration of zinc ions can be quantitatively detected, the selectivity is good, the sensitivity is high, and the detection limit of the zinc ions is low; the invention also provides a preparation method thereof, which comprises the steps of taking palladium tetrakis (triphenylphosphine) as a catalyst, adding 3, 5-dibromobenzaldehyde, pyridine-4-boric acid and potassium carbonate into a mixed solvent of toluene, ethanol and water, and carrying out heating reflux reaction to obtain 3, 5-bis (4-pyridine) benzaldehyde; dissolving 1, 10-phenanthroline-5, 6-diketone, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline and ammonium acetate in acetic acid, and heating and refluxing for reaction to obtain 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4, 5-f)][1,10]Phenanthroline; the invention also provides the application of the compound.
Description
Technical Field
The invention belongs to the technical field of ion identification, and particularly relates to a proportion sensing type zinc ion fluorescent probe and a preparation method and application thereof.
Background
Alzheimer's Disease (AD) is a common chronic progressive neurological decline disease mainly occurring in the elderly, and typical pathological features of the disease include β -amyloid protein (A β) deposition to form senile plaques, as well as intraneuronal fiber tangles, cerebral amyloid angiopathy, neuronal apoptosis and the like2+) Plays a key role in the deposition process of the brain A β and participates in the pathogenesis process of AD, so the detection of the concentration of zinc ions has important significance.
The zinc ion itself is of full shell electron configuration (3 d)104s0) There is no d-d electron transition, so the zinc ion is colorless. The zinc ions in the zinc complex are also extremely stable, with no electron transfer between the metal and the ligand. And the zinc ions are diamagnetic with a zero nuclear spin. Therefore, signals of common spectrums such as UV spectrum, EPR spectrum and NMR do not exist, and the conventional spectral analysis means does not have direct response to zinc ions. On the other hand, as the zinc ions do not quench fluorescence, the contrast analysis of the zinc ions in cells or tissues can be realized by using the dyeing of a chemical fluorescent probe, and the time-space distribution information of the zinc ions is obtained.
There are two main types of zinc ion probes reported at present: (1) enhanced probes that result in fluorescence enhancement upon zinc ion binding; (2) the zinc ion binds to the proportional sensing fluorescent probe which causes a significant shift in the excitation (or emission) wavelength.
The fluorescence of the enhanced probe is susceptible to intracellular or tissue environments, and the concentration of probe molecules entering cells and tissues is unknown, thus it is difficult to provide quantitative information on the dynamic changes of zinc ions. The proportional sensing type fluorescent probe can realize quantitative detection of zinc ions by utilizing the proportion change of respective emission (or excitation) bands of free probe molecules and zinc ion binding state probe molecules, and is free from the influence of the internal environment of a receptor and the influence of the concentration of the probe molecules. Therefore, the synthetic proportional sensing type zinc ion fluorescent probe has better application prospect.
Chinese patent CN201711073438 discloses a phenanthroline derivative, a zinc ion fluorescent probe and applications thereof, wherein a conjugated fluorophore is introduced into the phenanthroline mother ring by a single bond, and the prepared proportional sensing fluorescent probe also shows movement of fluorescence emission wavelength for other metal ions except zinc ions, especially for cadmium ions of the same main group, and thus is not a probe for specifically recognizing zinc ions.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a proportional sensing type zinc ion fluorescent probe which can quantitatively detect the concentration of zinc ions, has good selectivity, high sensitivity and low detection limit of the zinc ions; the invention also provides a preparation method of the compound, a synthesis process is simple and easy to realize, and the invention also provides application of the compound.
The proportion sensing type zinc ion fluorescent probe has the following structural formula:
the Chinese name is 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline.
The preparation method of the proportional sensing type zinc ion fluorescent probe comprises the following steps: adding 3, 5-dibromobenzaldehyde, pyridine-4-boric acid and potassium carbonate into a mixed solvent of toluene, ethanol and water by taking tetrakis (triphenylphosphine) palladium as a catalyst, and heating and refluxing to react to obtain a product, namely 3, 5-bis (4-pyridine) benzaldehyde; dissolving 1, 10-phenanthroline-5, 6-dione, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline and ammonium acetate in acetic acid, and carrying out heating reflux reaction to obtain the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline.
The reaction equation of the present invention is as follows:
wherein:
the dosage ratio of the tetrakis (triphenylphosphine) palladium, the 3, 5-dibromobenzaldehyde, the pyridine-4-boric acid, the potassium carbonate, the toluene, the ethanol and the water is 1: 9-11: 22-28: 120-128: 45-55: 45-55: 45-55, wherein the four (triphenylphosphine) palladium, the 3, 5-dibromobenzaldehyde, the pyridine-4-boric acid and the potassium carbonate are counted in millimole, and the toluene, the ethanol and the water are counted in milliliter.
The dosage ratio of 1, 10-phenanthroline-5, 6-diketone, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline, ammonium acetate and acetic acid is 1: 1: 1.3-1.6: 4-6: 3.5-4.5, wherein the amount of the 1, 10-phenanthroline-5, 6-diketone, the 3, 5-di (4-pyridine) benzaldehyde, the amount of p-methylaniline and the amount of ammonium acetate are millimoles, and the amount of the acetic acid is milliliter.
As a preferable technical scheme, the preparation method of the proportional sensing type zinc ion fluorescent probe comprises the following steps:
(1) under the protection of nitrogen, adding 3, 5-dibromobenzaldehyde, pyridine-4-boric acid and potassium carbonate into a mixed solvent of toluene, ethanol and water by using tetrakis (triphenylphosphine) palladium as a catalyst, heating and refluxing for reaction, extracting a reaction solution by using dichloromethane after the reaction is finished, performing rotary evaporation and concentration on an extract to obtain a crude product, and performing column chromatography purification to obtain a product of 3, 5-bis (4-pyridine) benzaldehyde;
(2) dissolving 1, 10-phenanthroline-5, 6-dione, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline and ammonium acetate in acetic acid, heating and refluxing for reaction, adding deionized water after the reaction is finished, filtering, precipitating and washing with water, and performing column chromatography purification to obtain the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline.
The heating reflux reaction time in the step (1) is 30-40 hours.
The dosage ratio of the tetrakis (triphenylphosphine) palladium to the dichloromethane in the step (1) is 1: 150-180 where tetrakis (triphenylphosphine) palladium is in millimoles and dichloromethane is in milliliters.
The column chromatography in the step (1) adopts 200-300-mesh column chromatography silica gel, the eluent adopts a mixed solution of dichloromethane and methanol, and the volume ratio of the dichloromethane to the methanol is 79-81:1, preferably 80: 1.
In the step (1), toluene, ethanol and water are used as mixed solvents, so that the yield and the purity of the product are high.
The heating reflux reaction time in the step (2) is 18-24 hours.
In the step (2), the dosage ratio of the 1, 10-phenanthroline-5, 6-diketone to the deionized water is 1: 2.5-4.0, wherein the 1, 10-phenanthroline-5, 6-diketone is calculated by millimole number, and the deionized water is calculated by milliliter.
Column chromatography in step (2) adopts 200-300 mesh column chromatography silica gel, and the eluent adopts a mixed solution of dichloromethane and methanol, and the volume ratio of dichloromethane to methanol is 19-21:1, preferably 20: 1.
The application of the proportional sensing type zinc ion fluorescent probe is applied to the detection of the concentration of zinc ions.
In summary, the invention has the following advantages:
(1) the invention takes the aryl imidazole as a fluorophore and the phenanthroline as a zinc ion recognition group, realizes the proportional sensing of zinc ions through the intramolecular charge transfer effect, and has good selectivity and high sensitivity; the probe is a proportional sensing type zinc ion fluorescent probe and can be used for quantitatively detecting the concentration of zinc ions.
(2) According to the invention, 5 and 6 positions of phenanthroline parent nucleus are modified with imidazole rings with conjugated fluorophores through a Debus-Radziszewski reaction, so that the rigid planar structure of phenanthroline is increased, the concentration of zinc ions can be quantitatively detected, and compared with the prior art, the probe only shows the movement of emission wavelength aiming at the zinc ions, the selectivity is good, the sensitivity is high, and the detection limit of the zinc ions is low.
(3) The preparation method provided by the invention has the advantages of simple synthesis process, easiness in realization, higher yield of the proportional sensing type zinc ion fluorescent probe and good stability in air; the preparation method is simple and feasible, and is suitable for industrial production.
(4) The proportional sensing type zinc ion fluorescent probe is applied to detection of zinc ion concentration, and has the advantages of good selectivity, high sensitivity and low detection limit, wherein the detection limit of zinc ions is 0.716 mu M.
Drawings
FIG. 1 is a graph of the selective fluorescence of metal ions for a proportional sensing type zinc ion fluorescent probe according to the present invention;
FIG. 2 is a zinc ion fluorescence titration curve of the proportional sensing type zinc ion fluorescence probe of the present invention.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
A proportion sensing type zinc ion fluorescent probe is prepared by the following steps:
(1)N2under protection, dissolving 1mmol of tetrakis (triphenylphosphine) palladium, 10mmol of 3, 5-dibromobenzaldehyde, 25mmol of pyridine-4-boric acid and 125mmol of potassium carbonate in a mixed solvent of 50mL of toluene, 50mL of ethanol and 50mL of water, heating and refluxing for 36h, standing and cooling after reaction, extracting 160mL of dichloromethane, decompressing and distilling to remove the solvent, and purifying by column chromatography (the dichloromethane and the methanol are mixed according to a volume ratio of 80: 1) to obtain 3, 5-bis (4-pyridine) benzaldehyde with a yield of 90%;
(2) dissolving 10mmol of 1, 10-phenanthroline-5, 6-diketone, 10mmol of 3, 5-di (4-pyridine) benzaldehyde, 15mmol of p-methylaniline and 50mmol of ammonium acetate in 40mL of acetic acid, and heating and refluxing for reaction. Adding 30mL of deionized water, filtering, precipitating and washing with water, and purifying by column chromatography (dichloromethane and methanol are mixed according to a volume ratio of 20: 1) to obtain the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline. The product was a grey green powdery solid with a yield of 60%.
The compound is verified by nuclear magnetism, mass spectrum and element analysis, and the result shows that the compound has a correct structure, and the structural formula is as follows:
the data are as follows:
nuclear magnetism1H NMR(400MHz,CDCl3)：2.63(s,3H)，7.33(q,1H)，7.37(d,4H)，7.51-7.61(m,5H)，7.73(q,1H)，7.81(s,1H)，7.92(d,2H)，8.67(d,4H)，9.05(d,1H)，9.13(d,1H)，9.18(d,1H)。
Mass spectrum ESI-MS: 541.2([ M ]]+)。
Elemental analysis anal.calcd for C36H24N6：C,79.98；H,4.47；N,15.55.Found：C,80.14；H,4.46；N,15.61％。
And detecting the proportional sensing type zinc ion fluorescent probe prepared in the example.
Respectively preparing 6mM metal ion solutions, wherein the metal ions used are as follows: na (Na)+，K+，Ca2+，Ni2+，Cu2+，Zn2+，Cd2 +The solvent is secondary distilled water, and the preparation is 5.0 × 10-5M2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f][1,10]Phenanthroline solution, wherein the solvent is ethanol and HEPES (pH 7.2) buffer solution which are mixed according to the volume ratio of 1: 1.
1. And (3) detecting the selective effect of the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline on metal ions.
Measurement of 2- (3, 5-bis (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5 ] using a fluorometer]1,10 selectivity of phenanthroline to metal ions: taking 3mL of the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5 ]]1,10 phenanthroline solutions are respectively added with different metal ion solutions with the equivalent weight of 1 and the volume of 25 mu L, the different metal ion solutions are uniformly mixed, fluorescence spectrum scanning is carried out, and the excitation wavelength is 350 nm. As shown in FIG. 1, only Zn was present after addition of 1 equivalent of metal ion2+Red shift occurs, the maximum absorption peak is obtained by adding Zn2+The former 412nm is changed to 456nm, red-shifted by 44nm, and other ions such as Na+、K+、Ca2+、Ni2+、Cu2+、Cd2+The maximum absorption peak of (2) was still 412nm, and no red shift occurred. Illustrative of 2- (3, 5-bis (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f][1,10]Phenanthroline has good selectivity on zinc ions, and is a proportional sensing type fluorescent probe.
2. And detecting the recognition effect of the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline on zinc ions.
Taking 3mL of the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4, 5-f)][1,10]And (3) adding 0.1-1 equivalent of zinc ion solution into the phenanthroline solution respectively, uniformly mixing, and performing fluorescence spectrum scanning to excite the wavelength to 350 nm. To add Zn into the system2+The ratio of the concentration of the probe to the concentration of the probe is an abscissa, and the ratio of the fluorescence intensity at 456nm to 412nm is an ordinate, and the research result is shown in FIG. 2. after 0.5 equivalent of zinc ions are added, the fluorescence intensity ratio is basically unchanged and well accords with a linear relationship within the range of 0-0.5 equivalent. The detection limit of zinc ions was 0.716. mu.M.
Claims (9)
1. A proportion sensing type zinc ion fluorescent probe is characterized in that: the structural formula is as follows:
2. the preparation method of the proportional sensing type zinc ion fluorescent probe of claim 1, which is characterized by comprising the following steps: the method comprises the following steps: adding 3, 5-dibromobenzaldehyde, pyridine-4-boric acid and potassium carbonate into a mixed solvent of toluene, ethanol and water by taking tetrakis (triphenylphosphine) palladium as a catalyst, and heating and refluxing to react to obtain a product, namely 3, 5-bis (4-pyridine) benzaldehyde; dissolving 1, 10-phenanthroline-5, 6-diketone, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline and ammonium acetate in acetic acid, and carrying out heating reflux reaction to obtain the proportional sensing type zinc ion fluorescent probe.
3. The method for preparing the proportional sensing type zinc ion fluorescent probe according to claim 2, characterized in that: the dosage ratio of the tetrakis (triphenylphosphine) palladium, the 3, 5-dibromobenzaldehyde, the pyridine-4-boric acid, the potassium carbonate, the toluene, the ethanol and the water is 1: 9-11: 22-28: 120-128: 45-55: 45-55: 45-55, wherein the four (triphenylphosphine) palladium, the 3, 5-dibromobenzaldehyde, the pyridine-4-boric acid and the potassium carbonate are counted in millimole, and the toluene, the ethanol and the water are counted in milliliter.
4. The method for preparing the proportional sensing type zinc ion fluorescent probe according to claim 2, characterized in that: the dosage ratio of 1, 10-phenanthroline-5, 6-diketone, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline, ammonium acetate and acetic acid is 1: 1: 1.3-1.6: 4-6: 3.5-4.5, wherein the amount of the 1, 10-phenanthroline-5, 6-diketone, the 3, 5-di (4-pyridine) benzaldehyde, the amount of p-methylaniline and the amount of ammonium acetate are millimoles, and the amount of the acetic acid is milliliter.
5. The method for preparing the proportional sensing type zinc ion fluorescent probe according to any one of claims 2 to 4, characterized in that: the method comprises the following steps:
(1) under the protection of nitrogen, adding 3, 5-dibromobenzaldehyde, pyridine-4-boric acid and potassium carbonate into a mixed solvent of toluene, ethanol and water by using tetrakis (triphenylphosphine) palladium as a catalyst, heating and refluxing for reaction, extracting a reaction solution by using dichloromethane after the reaction is finished, performing rotary evaporation and concentration on an extract to obtain a crude product, and performing column chromatography purification to obtain a product of 3, 5-bis (4-pyridine) benzaldehyde;
(2) dissolving 1, 10-phenanthroline-5, 6-dione, 3, 5-di (4-pyridine) benzaldehyde, p-methylaniline and ammonium acetate in acetic acid, heating and refluxing for reaction, adding deionized water after the reaction is finished, filtering, precipitating and washing with water, and performing column chromatography purification to obtain the proportional sensing type zinc ion fluorescent probe 2- (3, 5-di (4-pyridyl) phenyl) -1-p-tolyl-1H-imidazo [4,5-f ] [1,10] phenanthroline.
6. The method for preparing the proportional sensing type zinc ion fluorescent probe according to claim 5, characterized in that: the heating reflux reaction time in the step (1) is 30-40 hours; the dosage ratio of the tetrakis (triphenylphosphine) palladium to the dichloromethane in the step (1) is 1: 150-180 where tetrakis (triphenylphosphine) palladium is in millimoles and dichloromethane is in milliliters.
7. The method for preparing the proportional sensing type zinc ion fluorescent probe according to claim 5, characterized in that: column chromatography in the step (1) adopts 200-300-mesh column chromatography silica gel, the eluent adopts mixed solution of dichloromethane and methanol, and the volume ratio of the dichloromethane to the methanol is 79-81: 1.
8. The method for preparing the proportional sensing type zinc ion fluorescent probe according to claim 5, characterized in that: the heating reflux reaction time in the step (2) is 18-24 hours; in the step (2), the dosage ratio of the 1, 10-phenanthroline-5, 6-diketone to the deionized water is 1: 2.5-4.0, wherein the 1, 10-phenanthroline-5, 6-diketone is calculated by millimole number, and the deionized water is calculated by milliliter.
9. The method for preparing the proportional sensing type zinc ion fluorescent probe according to claim 5, characterized in that: column chromatography in the step (2) adopts 200-300-mesh column chromatography silica gel, the eluent adopts mixed solution of dichloromethane and methanol, and the volume ratio of the dichloromethane to the methanol is 19-21: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910102618.1A CN109776534B (en) | 2019-02-01 | 2019-02-01 | Proportional sensing type zinc ion fluorescent probe and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910102618.1A CN109776534B (en) | 2019-02-01 | 2019-02-01 | Proportional sensing type zinc ion fluorescent probe and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109776534A CN109776534A (en) | 2019-05-21 |
| CN109776534B true CN109776534B (en) | 2020-08-28 |
Family
ID=66504150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910102618.1A Active CN109776534B (en) | 2019-02-01 | 2019-02-01 | Proportional sensing type zinc ion fluorescent probe and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109776534B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112300122A (en) * | 2019-07-26 | 2021-02-02 | 南京理工大学 | Triazole heterocyclic compound and synthesis method thereof |
| CN111154481B (en) * | 2020-01-06 | 2023-03-28 | 山东理工大学 | Preparation method of nano fluorescent probe for detecting deubiquitinase |
| CN114409876B (en) * | 2021-12-13 | 2023-11-07 | 武汉工程大学 | Polymer for identifying cadmium and zinc bimetallic ions, and preparation method, application and analysis method thereof |
| CN114349753B (en) * | 2021-12-15 | 2023-10-13 | 武汉工程大学 | Fluorescent probe for detecting zinc ions and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830901A (en) * | 2010-04-30 | 2010-09-15 | 山西大学 | Selenite ion type compound and preparation method and application thereof |
| CN107513063A (en) * | 2017-09-09 | 2017-12-26 | 福建医科大学 | One kind can identify Cu in HL 602+2 Aryimidazoles and phenanthroline probe and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101297158B1 (en) * | 2010-02-22 | 2013-08-21 | 제일모직주식회사 | Compound for organic photoelectric device and organic photoelectric device including the same |
-
2019
- 2019-02-01 CN CN201910102618.1A patent/CN109776534B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830901A (en) * | 2010-04-30 | 2010-09-15 | 山西大学 | Selenite ion type compound and preparation method and application thereof |
| CN107513063A (en) * | 2017-09-09 | 2017-12-26 | 福建医科大学 | One kind can identify Cu in HL 602+2 Aryimidazoles and phenanthroline probe and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Chromogenic and fluorogenic sensing properties toward cations and anions by a terpyridine/phenylimidazo [4,5-f]phenanthroline hybrid;Ze-Bao Zheng et al.;《Sensors and Actuators B》;20120509;第169卷;第312-319页 * |
| 锌离子荧光探针研究进展;卜露露 等;《应用化学》;20171231;第34卷(第12期);第1355-1369页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109776534A (en) | 2019-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109776534B (en) | Proportional sensing type zinc ion fluorescent probe and preparation method and application thereof | |
| Li et al. | Colorimetric and fluorescent chemosensor for citrate based on a rhodamine and Pb2+ complex in aqueous solution | |
| CN103265539A (en) | Fluorescent probe: benzothiazole-terpyridine compound used for distinguishing and detecting zinc ions and cadmium ions, preparation method and application method thereof | |
| Jothi et al. | Highly sensitive naphthalimide based Schiff base for the fluorimetric detection of Fe 3+ | |
| CN108892672B (en) | Preparation method of rhodamine 6G Schiff base derivative for pH fluorescence sensing | |
| CN112812075A (en) | Preparation method and application of benzothiazole Schiff base-based fluorescent probe | |
| CN113087651B (en) | Compound containing indole group and preparation method and application thereof | |
| CN113121385B (en) | Detectable aquatic Fe 3+ 、Al 3+ 、Cu 2+ And Zn 2+ Fluorescent molecular sensor and application | |
| CN113105361B (en) | Molecular sensor with 'off-on-off' fluorescence detection signal for acidic environment and application thereof | |
| CN103937487A (en) | Phosphorescent fluorinion probe, preparation and applications thereof | |
| CN108864159B (en) | Can be used for detecting Fe in acidic environment3+Pyrrole-phenylboron fluorine fluorescent compound and preparation method thereof | |
| CN108997401B (en) | Fluorescent probe for detecting lead ions and preparation method thereof | |
| CN113861067B (en) | But dynamic detection aquatic Fe 3+ Al and Al 3+ Molecular probe and application thereof | |
| CN114539181B (en) | Fluorescent probe for rapidly detecting aluminum ions and zinc ions and preparation method thereof | |
| CN109503565A (en) | A kind of cadmium ion detection reagent and its preparation method and application | |
| Fang et al. | A Europium-based luminescent chemosensor for Zn2+ with quinoxaline as the antenna | |
| CN115403475A (en) | Preparation method and application of diagnostic reagent for specifically detecting copper ion concentration | |
| CN113880867A (en) | Detectable aquatic Cu2+、Zn2+Molecular sensor and application | |
| Hu et al. | Vicinal diaminobenzoacridine used as the fluorescent probe for trace nitric oxide determination by flow injection spectrofluorimetry and macrophage cells imaging | |
| CN111018773A (en) | Malononitrile phorone zinc ion fluorescent probe and preparation method and application thereof | |
| CN108794345B (en) | Aluminum ion receptor compound and synthesis and application thereof | |
| CN110885324A (en) | Imidazole ionic salt with photo-magnetic dual response, preparation method thereof and detection of ferric ions in aqueous solution | |
| CN111116458A (en) | Fluorescent probe for detecting aluminum ions, and preparation method and application thereof | |
| CN110964514A (en) | Novel pyrazine Schiff base fluorescent probe, and synthetic method and application thereof | |
| LU501538B1 (en) | FLUORESCENT DYE CAPABLE OF DYNAMICALLY MONITORING Fe3+ IN WATER 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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |