CN108314636B - Polyaryl sulfur oscillation luminescent material and preparation method and application thereof - Google Patents
Polyaryl sulfur oscillation luminescent material and preparation method and application thereof Download PDFInfo
- Publication number
- CN108314636B CN108314636B CN201810203081.3A CN201810203081A CN108314636B CN 108314636 B CN108314636 B CN 108314636B CN 201810203081 A CN201810203081 A CN 201810203081A CN 108314636 B CN108314636 B CN 108314636B
- Authority
- CN
- China
- Prior art keywords
- compound
- polyaryl
- sulfur
- luminescent material
- preparation
- 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.)
- Expired - Fee Related
Links
- 239000000463 material Substances 0.000 title claims abstract description 35
- 230000010355 oscillation Effects 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 6
- 239000011593 sulfur Substances 0.000 title claims abstract description 6
- 238000003384 imaging method Methods 0.000 claims abstract description 15
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 229940125782 compound 2 Drugs 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 150000003464 sulfur compounds Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- -1 aluminum ions Chemical class 0.000 claims description 7
- 229940125904 compound 1 Drugs 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 4
- 229940126214 compound 3 Drugs 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002451 hexacarboxylic acid group Chemical group 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000003534 oscillatory effect Effects 0.000 claims 2
- 229920001230 polyarylate Polymers 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 12
- 238000001514 detection method Methods 0.000 abstract description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005424 photoluminescence Methods 0.000 abstract description 3
- 239000000090 biomarker Substances 0.000 abstract 1
- 238000005286 illumination Methods 0.000 description 10
- 238000000295 emission spectrum Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000012984 biological imaging Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000799 fluorescence microscopy Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- NBBWLOJCZSYDAD-UHFFFAOYSA-N ethyl 4-sulfanylbenzoate Chemical compound CCOC(=O)C1=CC=C(S)C=C1 NBBWLOJCZSYDAD-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- 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
- G01N21/84—Systems specially adapted for particular applications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention belongs to the technical field of organic luminescent materials, and particularly relates to a polyaryl sulfide oscillation luminescent material, and a preparation method and application thereof. The general formula of the molecular structure of the polyaryl sulfur oscillation luminescent material is
The invention relates to a water-soluble photoluminescence material which is obtained by taking a polyaryl sulfur unit as a parent nucleus and deprotonating. The material has the oscillation luminescence characteristic, and can be applied to the aspects of biomarker imaging, metal ion detection and the like.
Description
Technical Field
The invention belongs to the technical field of organic luminescent materials, and particularly relates to a polyaryl sulfide oscillation luminescent material, and a preparation method and application thereof.
Background
Fluorescence imaging techniques have great potential and important research value in the fields of molecular biology and medicine. The conventional molecular probe technology is mostly aimed at imaging research in the visible light region (400-700 nm). However, the further development and application of molecular fluorescence imaging technology are greatly limited by the limited penetration distance of visible light in biological samples and the factors of absorption, scattering and self-luminescence of endogenous substances existing in biological tissues. Although some probe technologies based on near-infrared luminescence and upconversion luminescence have been developed in recent years to overcome some of the disadvantages of visible light luminescence probes, the general low quantum efficiency of the near-infrared luminescence and upconversion luminescence technologies is also a new problem in the development of these technologies. Therefore, the development of new imaging materials and techniques to improve the detection resolution and practicability and the possibility of fully combining with other diagnosis and treatment tasks have important scientific significance for the development of next-generation imaging materials. In combination with the above research backgrounds, it is necessary to find a novel biological imaging material, so that the material can be widely applied in molecular biology and medical fields.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide an oscillating luminescent material and a preparation method thereof, and application in biological imaging and metal ion detection.
The photoluminescence material provided by the invention is a polyaryl sulfur oscillation luminescence material, and the structure of the photoluminescence material is shown as the following formula I:
general formula I
Wherein X is Na+、K+Or NH4 +。
The invention also provides a preparation method of the luminescent material, and the synthetic route is shown as the following formula:
the method comprises the following specific steps:
(1) preparation of Ethyl hexabenzoate-substituted polyaryl Sulfur Compounds
Firstly, adding 4-mercaptoethyl benzoate and hexachlorobenzene into a DMF solvent, and simultaneously adding K2CO3Reacting for 50-60 hours at 55-60 ℃ in nitrogen atmosphere, and stopping the reaction; adding a large amount of distilled water when the mixture is cooled to room temperature to generate yellow precipitate, and purifying by column chromatography after filtration to obtain a polyaryl sulfur compound substituted by ethyl hexabenzoate, which is marked as a compound 1;
(2) preparation of hexacarboxylic acid-substituted polyaryl sulfur compounds
Adding THF into the compound 1 to dissolve the THF, then adding an aqueous solution of sodium hydroxide, and reacting at room temperature for 12-24 hours; after the reaction is finished, hydrochloric acid with the concentration of 1-3M is added to precipitate orange yellow precipitate; filtering, washing and drying to obtain a hexacarboxylic acid substituted polyaryl sulfur compound which is marked as a compound 2;
(3) preparation of hexacarboxylate-substituted polyarylsulfone compounds
And adding the compound 2 into water, and simultaneously adding an alkaline solution of corresponding X to obtain a hexacarboxylate-substituted polyaryl sulfur compound which is marked as a compound 3. Wherein, the compounds 2, X and H2The mol and volume ratio of O is (0.001-0.01 mmol): 0.1-1 mmol): 10-100 ml.
In the invention, the solvent can be plasma water.
The polyaryl sulfide oscillation luminescent material provided by the invention has specific oscillation luminescent characteristics. Namely, when the compound 3 is irradiated by 365nm ultraviolet light in an aqueous solution, the solution is expressed into a green light emitting state from a non-light emitting state; when the illumination is removed, the lamp gradually returns to a non-luminous state; the process is reversible. By repeated introduction and removal of light, an oscillating light emitting characteristic is exhibited.
According to the oscillation luminescence property, the luminescent material can be applied to biological cell imaging. By introducing and removing the illumination, the imaging of the cells is represented by bright field imaging under the illumination and dark field no image after removing the illumination.
The luminescent material can also be used for detecting specific metal ions (zinc ions and aluminum ions). When no metal ion is added, the solution does not emit light, and when zinc ions and aluminum ions are added, strong yellow light is emitted.
The invention utilizes the aggregation-induced emission effect of the polyarylthio parent nucleus to cause the material to aggregate in the solution under illumination, and obtains the biological imaging material and the ion detection material by utilizing the aggregation-induced emission principle.
The material of the invention can be in pure aqueous solution or organic-aqueous mixed solution (e.g. DMF-H)2O、THF-H2O、CH3OH-H2O、C2H5OH-H2O) causes a phenomenon of oscillating light emission.
The oscillation luminescent material of the invention has good biocompatibility and no toxicity because of taking aqueous solution as environment.
The luminescent material is simple in synthesis, cheap and easily available in raw materials, and easy for large-scale commercialization.
Drawings
FIG. 1 shows ultraviolet absorption spectra before and after irradiation of light to cause luminescence of a material.
FIG. 2 is emission spectra at different illumination times in example 1.
Fig. 3 is an oscillating luminescence picture of example 1 with the introduction and removal of illumination.
FIG. 4 is an image of the cells in example 1 with the light introduced and removed.
FIG. 5 is an emission diagram of example 1 with different metal ions added.
FIG. 6 shows the NMR spectrum of the luminescent material 3 synthesized according to the present invention.
FIG. 7 shows the NMR carbon spectrum of the synthesized luminescent material 3 of the present invention.
Detailed Description
The invention will be further elucidated by means of a preferred embodiment, which is only intended for a better understanding of the content of the invention. The examples given therefore do not limit the scope of the invention. The invention is within the scope of protection as long as various improvements made by the method conception and the technical scheme of the invention are adopted or are directly applied to other occasions without improvement.
In the examples, the starting materials and reagents used were all commercially available.
Example 1 (Synthesis of luminescent Material)
The synthesis of the compound 1 comprises the following specific steps:
12 mmol of ethyl 4-mercaptobenzoate and 1mmol of hexachlorobenzene were added to 20 mL of DMF solvent, and 24 mmol of K were added2CO3Reacting for 60 hours at 60 ℃ in a nitrogen atmosphere, and stopping the reaction; cooling to room temperature, adding 100 mL distilled water to generate yellow precipitate, filtering, and purifying by column chromatography to obtain compound 1 from ethyl acetate and petroleum ether (1: 3)The ratio was 72%.
The synthesis of the compound 2 comprises the following specific steps:
after 20 mL of THF was added to 1mmol of Compound 1 and dissolved therein, 20 mL of a 1.5M aqueous solution of sodium hydroxide was added thereto and reacted at room temperature for 24 hours; after the reaction is finished, 30 mL of hydrochloric acid with the concentration of 2M is added to separate out orange-yellow precipitate; after filtration, washing and drying, compound 2 was obtained with a yield of 95%.
The synthesis of the compound 3 comprises the following specific steps:
0.001mmol of compound 2 was weighed, 10ml of distilled water and 0.1 mmol of NaOH were added thereto and stirred for 60 minutes to obtain a sodium salt compound with a concentration of 10%-4M。
0.001mmol of Compound 2 was weighed, 10ml of distilled water and 0.1 mmol of KOH were added thereto, and stirring was carried out for 60 minutes to obtain a potassium salt compound at a concentration of 10-4M。
0.001mmol of Compound 2 was weighed, and 10ml of distilled water and 0.1 mmol of NH were added thereto4OH is stirred for 60 minutes to obtain an ammonium salt compound with the concentration of 10-4M。
Example 2 (phenomenon of light-induced vibration)
And (3) putting 3 mL of the solution with the concentration obtained in the step (3) in a cuvette, detecting an absorption peak with the wavelength range of 250-800 nm, and obtaining an absorption spectrum under different illumination time as shown in an ultraviolet-visible absorption spectrum curve in figure 1. And (3) putting 3 mL of the solution with the concentration obtained in the step (3) in a cuvette, detecting an emission spectrum with the wavelength range of 390 nm-600 nm by taking 365nm as an excitation wavelength to obtain a maximum emission wavelength of 505 nm, and recording the emission spectrum of the solution through different illumination times, wherein the obtained emission spectrum is shown in figure 2. 3 mL of the solution with the concentration obtained in the step 3 is put into a cuvette, a photograph is taken under 365nm light irradiation by using a portable ultraviolet lamp, and greening phosphorescence is emitted at the moment; and then removing the ultraviolet lamp to wait for 10 min to take a picture, and then not emitting light, so as to obtain the oscillation light-emitting picture shown in the figure 3 in a circulating mode.
Example 3 (Bio-imaging)
Adding the solution with the concentration obtained in the step 3 into Hela cells containing 10 mu M for culture, and performing confocal laser imaging. Illuminating and imaging the cultured cells, wherein the cells are green images; after the illumination is removed and imaging is carried out for 10 min, the cells are in a dark state, and the oscillation luminescence imaging chart shown in the figure 4 is obtained by the circulation.
Example 4 (ion detection)
And (3) putting 3 mL of the solution with the concentration obtained in the step (3) in a cuvette, detecting an emission spectrum with the wavelength range of 390 nm-600 nm by taking 365nm as an excitation wavelength, adding different metal ions into the emission spectrum, and recording the emission spectrum, wherein the obtained emission spectrum is shown in figure 5. Wherein when the metal ions are added as zinc and aluminum, the emission intensity is maximized, and intense yellow light is emitted.
Claims (4)
1. A polyaryl sulfur oscillation luminescent material has a structural formula shown as a general formula I:
general formula I
X is Na, K or NH4。
2. The method for preparing the polyarylate-containing oscillatory luminescent material as claimed in claim 1, wherein the synthetic route is represented by the following formula:
the preparation method comprises the following specific steps:
(1) preparation of Ethyl hexabenzoate-substituted polyaryl Sulfur Compounds
Firstly, adding 4-mercaptoethyl benzoate and hexachlorobenzene into a DMF solvent, and simultaneously adding K2CO3Reacting for 50-60 hours at 55-60 ℃ in nitrogen atmosphere, and stopping the reaction; adding a large amount of distilled water when the mixture is cooled to room temperature to generate yellow precipitate, and purifying by column chromatography after filtration to obtain a polyaryl sulfur compound substituted by ethyl hexabenzoate, which is marked as a compound 1;
(2) preparation of a Hexacarboxylic acid-substituted polyaryl Sulfur Compound 2
Adding THF into the compound 1 to dissolve the THF, then adding an aqueous solution of sodium hydroxide, and reacting at room temperature for 12-24 hours; after the reaction is finished, hydrochloric acid with the concentration of 1-3M is added to precipitate orange yellow precipitate; filtering, washing and drying to obtain a hexacarboxylic acid substituted polyaryl sulfur compound which is marked as a compound 2;
(3) preparation of hexacarboxylate-substituted polyarylsulfone compounds
Adding the compound 2 into water, and simultaneously adding an alkaline solution of corresponding X to obtain a hexacarboxylate-substituted polyaryl sulfur compound which is marked as a compound 3; wherein, compound 2, groups X and H2The mol and volume ratio of O is (0.001-0.01 mmol): 0.1-1 mmol): 10-100 ml.
3. The use of the poly-aryl-sulfur oscillatory luminescent material according to claim 1 in biological cell imaging, wherein the introduction and the removal of light are used to realize bright field imaging under light and dark field non-imaging after the removal of light.
4. The use of the polyarylate-oscillation luminescent material of claim 1 for detecting zinc ions and aluminum ions, wherein the solution does not emit light when no metal ions are added, and emits intense yellow light when zinc ions or aluminum ions are added.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810203081.3A CN108314636B (en) | 2018-03-13 | 2018-03-13 | Polyaryl sulfur oscillation luminescent material and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810203081.3A CN108314636B (en) | 2018-03-13 | 2018-03-13 | Polyaryl sulfur oscillation luminescent material and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108314636A CN108314636A (en) | 2018-07-24 |
| CN108314636B true CN108314636B (en) | 2020-05-12 |
Family
ID=62901845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810203081.3A Expired - Fee Related CN108314636B (en) | 2018-03-13 | 2018-03-13 | Polyaryl sulfur oscillation luminescent material and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108314636B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111187205B (en) * | 2020-01-14 | 2021-03-16 | 河南大学 | Fluorescent-multicolor luminescent material with multi-stimulus responsiveness and preparation method and application thereof |
| CN112341379B (en) * | 2020-10-23 | 2022-03-18 | 复旦大学 | Polyaryl thiopyridine cationic salt light-operated cell pyrophoric material and preparation method and application thereof |
| CN115028562B (en) * | 2022-05-30 | 2023-12-22 | 太原理工大学 | Polysulfide aromatic compound, preparation method and application thereof |
-
2018
- 2018-03-13 CN CN201810203081.3A patent/CN108314636B/en not_active Expired - Fee Related
Non-Patent Citations (3)
| Title |
|---|
| Molecular stacking dependent phosphorescence-fluorescence dual emission in a single luminophore for self-recoverable mechanoconversion of multicolor luminescence;Hongwei Wu等;《Chem.Commun.》;20160712;第53卷(第18期);2661-2664 * |
| Persulfurated Aromatic Compounds;Marc Gingras等;《Angew. Chem. Int. Ed.》;20061231;第45卷;1686-1712 * |
| Substitution of Unactivated Aryl Halides by Thiolate Anions in Polyglymes;Stephen D.Pastor等;《J.Org.Chem.》;19851231;第50卷(第24期);4812-4815 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108314636A (en) | 2018-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108314636B (en) | Polyaryl sulfur oscillation luminescent material and preparation method and application thereof | |
| CN103524539B (en) | Luminescent material Zn (phen) (HL) 2and preparation method thereof | |
| CN109438722A (en) | Based on manganese base luminescent metal organic framework material and its preparation method and application | |
| CN111995580A (en) | Fluorescent dye with tetraphenyl ethylene imidazole ring structure and application thereof | |
| CN107311957A (en) | One kind is based on aggregation-induced emission and excited state intramolecular proton transfer compound and its preparation method and application | |
| CN110041351A (en) | A kind of Er (III) luminescent material and preparation method containing phenanthroline, modification imidazolyl carboxylic acid and picolinic acid mixed ligand | |
| CN105542751B (en) | A kind of metal-organic framework material for launching white light and its synthetic method and application | |
| CN102925155B (en) | Near infrared fluorescent probe substrate material of rare earth ion nano alkali metal rare earth fluoride and preparation method of near infrared fluorescent probe substrate material | |
| CN106083841A (en) | A kind of bivalent manganese fluorescent material based on dibromo 1,4 dipropyl 1,4 diazabicylo [2.2.2] octane and its preparation method and application | |
| CN112174941B (en) | Organic compound, scintillator material, and preparation method and application thereof | |
| CN112341379B (en) | Polyaryl thiopyridine cationic salt light-operated cell pyrophoric material and preparation method and application thereof | |
| CN106085412A (en) | The preparation of a kind of bivalent manganese fluorescent material based on dibromo 1,4 dibutyl 1,4 diazabicylo [2.2.2] octane, characterize and apply | |
| CN106146519A (en) | The preparation of a kind of bivalent manganese fluorescent material based on dibromo 1,4 diethyl 1,4 diazabicylo [2.2.2] octane, sign and application | |
| CN102731479B (en) | Organic ligand, rare earth organic fluorescent probe material thereof and preparation method thereof | |
| CN107759504A (en) | A kind of mushy stage has the two-phase organic fluorescence materials and preparation method of strong fluorescence | |
| CN112341462A (en) | Rare earth dysprosium cryptate ether fluorescent complex and preparation method thereof | |
| CN108358972B (en) | Phenanthroline ruthenium complex photosensitive dye and preparation method and application thereof | |
| CN109354586A (en) | Bcl-2 protein process in a kind of preparation of imines acridine fluorescence probe and label Dental clinic | |
| CN108659023A (en) | Rare earth with high fluorescence quantum yield-potassium bimetal complexes | |
| CN111004182A (en) | Small-molecule long-afterglow complex and preparation method thereof | |
| CN114874130B (en) | Organic molecule capable of emitting light by force, preparation method and application thereof | |
| CN111423879B (en) | Multimode-excited single-red-light nano fluorescent material and preparation method thereof | |
| CN110157002A (en) | A kind of rare earth based luminescent material and its preparation method and application of the construction unit of class containing polyacid | |
| CN114957309B (en) | Sulfonyl modified silafluorene and dithiophene sulfonyl silafluorene derivative as well as preparation method and application thereof | |
| CN110804050B (en) | Synthesis of selenazole fluorescent dye compound and performance research 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 | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200512 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |