CN111848465A - Difunctional fluorescent probe molecule, preparation and application - Google Patents
Difunctional fluorescent probe molecule, preparation and application Download PDFInfo
- Publication number
- CN111848465A CN111848465A CN202010835219.9A CN202010835219A CN111848465A CN 111848465 A CN111848465 A CN 111848465A CN 202010835219 A CN202010835219 A CN 202010835219A CN 111848465 A CN111848465 A CN 111848465A
- Authority
- CN
- China
- Prior art keywords
- solution
- fluorescent
- mixed solution
- probe
- fluorescent probe
- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention relates to a preparation method of a fluorine ion and cyanide detection probe, belonging to the technical field of fluorescent probes. The invention reacts 1, 3, 5-trioxane with glacial acetic acid, and uses DMSO/H2Recrystallizing with oxygen; reacting 4,4' -diamino diphenyl sulfone with the compound obtained before to prepare the difunctional fluorescent molecular probe; and filtering, washing, drying and weighing the product to obtain the final product. The probe realizes F pair on two channels of ultraviolet and fluorescence‑And CN‑Simultaneous rapid selective recognition, especially in the fluorescent channel, by addition of F‑And CN‑Later on not onlyDifferent degrees of quenching of the fluorescence intensity of the probe molecules and red-shifting of the emission peak occur, which is a distinctive measure of F‑And CN‑Is very effective.
Description
Technical Field
The invention relates to a dual-function fluorescent probeA preparation method and an application thereof, in particular to a method for detecting F-And CN-Belonging to the technical field of fluorescent probes.
Background
Single molecule optical sensors selectively detect a variety of anions through changes in solution color and spectral response, the design and synthesis of which have been extensively studied due to their important roles in biological and chemical processes and academic challenges. Among all anions, especially cyanide and fluoride, play an important role in everyday life, biochemical activities and a wide range of industrial products. Cyanide is mainly released to the environment through the gold and silver exploitation process, but is an anion with extremely strong toxicity in biology and environment, and can cause poisoning. Meanwhile, fluoride is a biologically crucial anion because it plays an established role in the treatment of osteoporosis and dental health, but the presence of excess fluoride causes dental plaque, fluorosis, bone disease, liver, thyroid gland and other organs to be damaged. Therefore, there is a strong need for an effective sensing method for detecting cyanide and fluoride.
Over the past decades, a large number of chemical sensors based on various mechanisms have been reported for detecting cyanides and fluorides, such as the formation of anionic complexes with transition metals, Excited State Intramolecular Proton Transfer (ESIPT), deprotonation, nucleophilic addition reactions, excimer-monomer switching, and hydrogen bonding interactions. However, most cannot be identified either in the same measurement method or with the use of masking agents. In this regard, the multifunctional chemical sensor can perform multi-analyte detection through different recognition mechanisms or different binding sites, and has the advantages of low cost, dynamic response, real-time detection and the like. In addition, the single-molecule chemical sensor can realize simultaneous detection of multiple analytes, and has potential application prospect in the development of molecular logic gates.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: provide a method capable of detecting F simultaneously-And CN-The fluorescent probe of (1).
The purpose of the invention is realized by the following technical scheme:
a bifunctional fluorescent probe molecule has the following structural formula:
the preparation method of the difunctional fluorescent probe molecule comprises the following specific steps:
the method comprises the following steps: dissolving about 1g of 1, 3, 5-trioxane in 50ml of glacial acetic acid, and dropwise adding 3-6ml of salicylaldehyde while stirring after complete dissolution; obtaining a mixed solution A;
step two: dripping 3-5 drops of catalyst concentrated sulfuric acid into the mixed solution A; obtaining solution B after the reaction is completed;
step three: cooling the solution B, pouring the solution B into a beaker filled with crushed ice in a thin stream shape, washing solid substances with alcohol, and then drying to obtain solid;
step four: dissolving about 1g of the solid obtained in step three with about 20g of 4,4' -diaminodiphenyl sulfone in 50ml of DMF solution; dripping 3-5 drops of catalyst concentrated hydrochloric acid at the temperature of 20-40 ℃; after the reaction is finished, cooling to room temperature; with DMSO/H2Filtering, drying and recrystallizing the product by using an O or DMF solution. Obtaining the fluorescent probe.
Qualitative detection of F Using a Dual-function fluorescent Probe-And CN-The method comprises the following specific steps:
step one, rough measurement: adding the solution to be detected into the probe solution, and observing the color of the mixed solution, wherein the mixed solution contains F-The solution of (A) is orange yellow and contains CN-The solution of (a) was unchanged.
Step two, fine measurement: putting the mixed solution obtained in the step one into a fluorescence spectrometer, wherein the peak value has obvious selective response;
quantitative detection of F Using fluorescent probes-And CN-The method comprises the following specific steps:
step one, preparing a light sensing material into a fluorescent sensing material dispersion liquid with the concentration of C1 multiplied by 10 < -5 > mol/L by using an organic solvent;
step two, other negative ions are mixed with F-And CN-Respectively preparing the ions into solutions with the molar ratio of 50 to the fluorescent sensing material; respectively mixing the dispersion liquid prepared in the step one with the solution to obtain mixed solution; measuring the fluorescence intensity value of the mixed solution;
step three, preparing F-And CN-Solutions A and B with a molar ratio to the fluorescent sensing material of 0.5, 1, 2, 5, 10, 20, 30,40 and 50; respectively mixing the dispersion liquid prepared in the step one with the solution A and the solution B to obtain mixed solution C and mixed solution D; measuring the change in the fluorescence intensity values of the mixed solutions C and D and F-And CN-Correspondence of concentration (unit: 10)-5M)。
Further, F is detected-The detection limit of (2) was 0.53. mu.M.
Further, detecting CN-The detection limit of (2) was 0.63. mu.M.
Has the advantages that:
a fluorescent probe of the invention, respectively identified as F-And CN-The reaction is carried out to form new substances, so that the corresponding ultraviolet spectrogram and the fluorescence spectrogram are respectively influenced, and the sensitivity and the specificity are high.
Drawings
FIG. 1 shows that the fluorescent probe of the present invention can distinguish F from naked eyes-And CN-
FIG. 2 shows fluorescence emission spectra with F of the fluorescent probe according to the present invention-A trend graph of increasing content;
FIG. 3 shows fluorescence emission spectra of the fluorescent probe according to the present invention with CN-Trend graph of content increase.
Detailed Description
The invention is further explained by combining the attached drawings and the embodiment and the attached drawings.
Example 1
A fluorescent probe has the following structural formula:
a preparation method of a fluorescent probe comprises the following specific steps:
the method comprises the following steps: dissolving 0.62g of 1, 3, 5-trioxane in 50ml of glacial acetic acid, and dropwise adding 3ml of salicylaldehyde while stirring after complete dissolution; obtaining a mixed solution A;
step two: dripping 3 drops of catalyst concentrated sulfuric acid into the mixed solution A; obtaining solution B after the reaction is completed;
step three: cooling the solution B, pouring the solution B into a beaker filled with crushed ice in a thin stream shape, washing solid substances with alcohol, and then drying to obtain solid;
step four: dissolving 0.50g of the solid obtained in step three and 21.82g of 4,4' -diaminodiphenyl sulfone in 20ml of DMF solution; dripping 3 drops of catalyst concentrated hydrochloric acid at the temperature of 24 ℃; after the reaction is finished, cooling to room temperature; with DMSO/H2And filtering, drying and recrystallizing the product by using the O solution. Obtaining the fluorescent probe.
The fluorescent probe is used for the probe F-And CN-The fluorescence detection of (2):
the method comprises the following steps:
preparing probe molecule solution by accurately weighing 2.5mg probe compound with an analytical balance, adding the probe compound into a 10mL volumetric flask, adding prepared aqueous DMF or DMSO solution into the volumetric flask, and after the compound is completely dissolved, fixing the volume to prepare the probe compound with the concentration of 5 × 10-4Accurately transferring 0.1mL of original mother solution into a 10mL volumetric flask by using a 100-one 1000-microliter transfer gun, and adding DMF or DMSO solution to a constant volume to prepare the solution with a concentration of 5 × 10-6mol/L of the solution to be tested.
Accurate weighing F by a balance for detecting target compound allocation-And CN-Adding the tetrabutylammonium salt into a 10mL volumetric flask, adding DMF or DMSO solution into the volumetric flask, and after the compound is completely dissolved, fixing the volume to prepare the tetrabutylammonium salt with the concentration of 1 × 10-4Original mother liquor of mol/L, other ionic solution (Cl)-、Br-、I-、OAc-、PF6 -、HSO4 -、SO42-、ClO4 -) Are also prepared into 1 × 10 respectively according to the same method-4mol/L of original mother liquor.
Fluorescence intensity of the fluorescent probe is dependent on F-The content increasing change comprises the following specific steps:
a series of probe solutions (total acidity controlled by DMSO buffer solution with pH 7.3) were prepared in a concentration range of 20 samples, and F was added to the solutions in sequence at different equivalent concentrations-The concentration of the solution is 0-40 mu M. After the addition is completed, the reaction is kept still for a period of time, and the fluorescence response of the reaction is tested, and the result shows that the fluorescence intensity of the probe gradually increases and then keeps basically unchanged along with the increase of the concentration, so that the result shown in the figure 1 is obtained. As can be seen in the figure, with F-The fluorescence intensity at 390nm and 600nm peaks, as measured by the fluorescence emission intensity at 340nm and F added-The equivalent concentrations of (a) were fitted with a non-linear correlation, resulting in a fitted correlation constant R2 of up to 0.9927.
Fluorescence emission spectra of fluorescent probes with CN-The content increasing change comprises the following specific steps:
preparing a series of probe solutions (pH 7.3 DMSO buffer solution to control overall acidity) for 20 samples, and sequentially adding CN with different equivalent concentrations to the solutions-The concentration of the solution is 0-40 mu M. After the addition is completed, the reaction is kept still for a period of time, and the fluorescence response of the reaction is tested, and the result shows that the fluorescence intensity of the probe gradually increases and then keeps basically unchanged along with the increase of the concentration, so that the result shown in figure 2 is obtained. As the concentration of CN-increased, the fluorescence intensity at 510nm peaked. By the intensity of fluorescence emission of the probe at 340nm and the added CN-The equivalent concentrations of (a) were fitted with a non-linear correlation, resulting in a fitted correlation constant R2 of up to 0.9931.
Other anion pairs F-And CN-Influence of detection
From fig. 3 we can clearly see the fluorescence emission spectra of the probe molecules and their presence in DMSO buffer (pH 7.3) in the presence of other anions. As can be seen from the test results, other anions (Cl) were added-、Br-、I-、OAc-、PF6 -、HSO4 -、SO42-、ClO4 -) Thereafter, F-And CN-The peak values of the probe are at 390nm and 510nm respectively, and the addition of other anions hardly causes any quenching of the fluorescence intensity of the probe, so that the method has the advantages of sensitivity, low cost and one-probe multi-purpose, and is widely applied to trace F in environment and production-And CN-Detection of (3).
Example 2
A fluorescent probe has the following structural formula:
a preparation method of a fluorescent probe comprises the following specific steps:
the method comprises the following steps: 0.90g of 1, 3, 5-trioxane is dissolved in 50ml of glacial acetic acid, and 5ml of salicylaldehyde is dropwise added while stirring after complete dissolution; obtaining a mixed solution A;
step two: dripping 5 drops of catalyst concentrated sulfuric acid into the mixed solution A; obtaining solution B after the reaction is completed;
step three: cooling the solution B, pouring the solution B into a beaker filled with crushed ice in a thin stream shape, washing solid substances with alcohol, and then drying to obtain solid;
step four: dissolving the solid obtained in step three, 0.75, and 22.32g of 4,4' -diaminodiphenyl sulfone in 20ml of DMF solution; dripping 5 drops of catalyst concentrated hydrochloric acid at 35 ℃; after the reaction is finished, cooling to room temperature; the product was filtered, dried and recrystallized from DMF solution. Obtaining the fluorescent probe.
The fluorescent probe is used for the probe F-And CN-The fluorescence detection in (3) was the same as in example 1.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. The present invention is not limited to the above-described embodiments, which are described in the specification and illustrated only for illustrating the principle of the present invention, but various changes and modifications may be made within the scope of the present invention as claimed without departing from the spirit and scope of the present invention. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (3)
1. A bifunctional fluorescent probe molecule characterized by: the structural formula is as follows:
2. a method of making a bifunctional fluorescent probe molecule according to claim 1, characterized in that: the method comprises the following specific steps:
the method comprises the following steps: dissolving about 1g of 1, 3, 5-trioxane in 50ml of glacial acetic acid, and dropwise adding 3-6ml of salicylaldehyde while stirring after complete dissolution; obtaining a mixed solution A;
step two: dripping 3-5 drops of catalyst concentrated sulfuric acid into the mixed solution A; obtaining solution B after the reaction is completed;
step three: cooling the solution B, pouring the solution B into a beaker filled with crushed ice in a thin stream shape, washing solid substances with alcohol, and then drying to obtain solid;
step four: dissolving about 1g of the solid obtained in step three with about 20g of 4,4' -diaminodiphenyl sulfone in 50ml of DMF solution; dripping 3-5 drops of catalyst concentrated hydrochloric acid at the temperature of 20-40 ℃; after the reaction is finished, cooling to room temperature; with DMSO/H2Filtering, drying and recrystallizing the product by using an O or DMF solution; obtaining the fluorescent probe.
3. Qualitative detection of F using bifunctional fluorescent probe molecules according to claim 1 in solution-And CN-The method of (2), characterized by: the method comprises the following specific steps:
step one, rough measurement: adding the solution to be detected into the probe solution, and observing the color of the mixed solution, wherein the mixed solution contains F-The solution of (A) is orange yellow and contains CN-The solution of (a) is unchanged;
step two, fine measurement: putting the mixed solution obtained in the step one into a fluorescence spectrometer, wherein the peak value has obvious selective response;
quantitative detection of F Using fluorescent probes-And CN-The method comprises the following specific steps:
step one, preparing a light sensing material into a fluorescent sensing material dispersion liquid with the concentration of C1 multiplied by 10 < -5 > mol/L by using an organic solvent;
step two, other negative ions are mixed with F-And CN-Respectively preparing the ions into solutions with the molar ratio of 50 to the fluorescent sensing material; respectively mixing the dispersion liquid prepared in the step one with the solution to obtain mixed solution; measuring the fluorescence intensity value of the mixed solution;
step three, preparing F-And CN-Solutions A and B with a molar ratio to the fluorescent sensing material of 0.5, 1, 2, 5, 10, 20, 30,40 and 50; respectively mixing the dispersion liquid prepared in the step one with the solution A and the solution B to obtain mixed solution C and mixed solution D; measuring the change in the fluorescence intensity values of the mixed solutions C and D and F-And CN-Correspondence of concentration (unit: 10)-5M)；
Further, F is detected-The detection limit of (2) is 0.53. mu.M;
further, detecting CN-The detection limit of (2) was 0.63. mu.M.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010835219.9A CN111848465B (en) | 2020-08-19 | 2020-08-19 | Difunctional fluorescent probe molecule, preparation and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010835219.9A CN111848465B (en) | 2020-08-19 | 2020-08-19 | Difunctional fluorescent probe molecule, preparation and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111848465A true CN111848465A (en) | 2020-10-30 |
| CN111848465B CN111848465B (en) | 2021-10-15 |
Family
ID=72970309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010835219.9A Active CN111848465B (en) | 2020-08-19 | 2020-08-19 | Difunctional fluorescent probe molecule, preparation and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111848465B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864155A (en) * | 2018-08-14 | 2018-11-23 | 江西科技师范大学 | A kind of preparation method of novel bissiropyran power color group |
| CN109734684A (en) * | 2018-12-20 | 2019-05-10 | 中国科学院宁波材料技术与工程研究所 | A kind of biology base fire retarding epoxide resin presoma and its preparation method and application based on natural phenolic monomer |
-
2020
- 2020-08-19 CN CN202010835219.9A patent/CN111848465B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864155A (en) * | 2018-08-14 | 2018-11-23 | 江西科技师范大学 | A kind of preparation method of novel bissiropyran power color group |
| CN109734684A (en) * | 2018-12-20 | 2019-05-10 | 中国科学院宁波材料技术与工程研究所 | A kind of biology base fire retarding epoxide resin presoma and its preparation method and application based on natural phenolic monomer |
Non-Patent Citations (2)
| Title |
|---|
| C. S. MARVEL 等: "Heat Stability Studies on Chelates from Schiff Bases of Salicylaldehyde Derivatives", 《J.AMER.CHEM.SOC.》 * |
| EL-SAYED M. E. MANSOUR 等: "Synthesis and Properties of Some Schiff-Base Polymers Containing Sulfur", 《MACROMOLECULAR REPORTS》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111848465B (en) | 2021-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhou et al. | Design principles of spectroscopic probes for biological applications | |
| Chao et al. | A ratiometric fluorescence probe for monitoring cyanide ion in live cells | |
| Lvova et al. | Recent advances in magnesium assessment: From single selective sensors to multisensory approach | |
| Tavallali et al. | A novel development of dithizone as a dual-analyte colorimetric chemosensor: detection and determination of cyanide and cobalt (II) ions in dimethyl sulfoxide/water media with biological applications | |
| Duong et al. | Development of novel optical pH sensors based on coumarin 6 and nile blue A encapsulated in resin particles and specific support materials | |
| Shamsipur et al. | A new chelation induced enhanced fluorescence-type optical sensor based on parared immobilized in a plasticized PVC membrane for selective determination of Zn (II) ions | |
| CN104877672A (en) | Two-photon fluorescent probe for identifying palladium (0) and preparation method and application of two-photon fluorescent probe | |
| Aziz et al. | Design of a highly sensitive and selective bulk optode based on fluorescence enhancement of N, N′-bis-(1-hydroxyphenylimine) 2, 2′-pyridil Schiff base: Monitoring of zinc (II) ion in real samples and DFT calculation | |
| CN103666451A (en) | Carbazole-thiophene schiff base fluorescent probe compound for detecting and recognizing Fe<3+> and Cr<3+> | |
| Wang et al. | In situ synthesis of fluorescent copper nanoclusters for rapid detection of ascorbic acid in biological samples | |
| CN105548174B (en) | A kind of photoswitch type measures the detecting probe method of pH value of solution | |
| Zhou et al. | Au@ Ag@ ZIF-8 multifunction probe with internally o-phenylenediamine encoding for the colorimetric, fluorescence, and SERS multi-mode optical detection of reactive sulfur species | |
| CN104830312A (en) | Fluorescence-enhanced probe compound preparation method and trivalent chromium ion detection method | |
| CN112945925B (en) | Method for detecting permanganate acid radicals by coumarin-based probe | |
| CN110672576B (en) | Method for measuring isoniazid by quantum dot fluorescence quenching method | |
| CN111848465B (en) | Difunctional fluorescent probe molecule, preparation and application | |
| CN110669503B (en) | Preparation and application of carbon monoxide near-infrared fluorescent probe | |
| CN108440547A (en) | A kind of rhodamine 6G Schiff bases fluorescence probe and its preparation and application | |
| Hu et al. | A selective optical sensor for picric acid assay based on photopolymerization of 3-(N-methacryloyl) amino-9-ethylcarbazole | |
| CN104181137A (en) | Method for detecting content of lead ions in water sample | |
| CN115181068B (en) | TPI derivative fluorescent probe and application thereof in preparation of copper ion detection reagent | |
| CN102519884A (en) | Method for easily and quickly measuring hydrogen peroxide | |
| CN111662279B (en) | Naphthalene-substituted carbazole-benzothiazolyl hydrazone compound and preparation method and application thereof | |
| CN105647516B (en) | A kind of pH value is luminous to indicate material and its preparation method and application | |
| Tang et al. | Ruthenium bipyridine complexes as electrochemiluminescent transducers for ionophore-based ion-selective detection |
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 |