CN111675645A - Preparation method of pyrrole-cyanine derivative fluorescent probe - Google Patents
Preparation method of pyrrole-cyanine derivative fluorescent probe Download PDFInfo
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- CN111675645A CN111675645A CN202010638536.1A CN202010638536A CN111675645A CN 111675645 A CN111675645 A CN 111675645A CN 202010638536 A CN202010638536 A CN 202010638536A CN 111675645 A CN111675645 A CN 111675645A
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- pyrrole
- fluorescent probe
- cyanine derivative
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- HCYIOKVZAATOEW-UHFFFAOYSA-M 1,2,3,3-tetramethylindol-1-ium;iodide Chemical compound [I-].C1=CC=C2C(C)(C)C(C)=[N+](C)C2=C1 HCYIOKVZAATOEW-UHFFFAOYSA-M 0.000 claims description 6
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000008247 solid mixture Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 3
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 210000004027 cell Anatomy 0.000 abstract description 8
- 210000000170 cell membrane Anatomy 0.000 abstract description 7
- 150000002500 ions Chemical class 0.000 abstract description 5
- 239000012528 membrane Substances 0.000 abstract description 5
- 150000001793 charged compounds Chemical class 0.000 abstract description 2
- 239000000523 sample Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 1
- -1 NaAcNaHSO4 Chemical compound 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- 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
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- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
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- 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"
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a preparation method of a pyrrole-cyanine derivative fluorescent probe, which has the following structural formula:
because the membrane of the cell membrane is positively charged outside the membrane and negatively charged inside the membrane, the positively charged compound can easily enter the cell through the cell membrane, and the pyrrole-cyanine derivative fluorescent probe contains N+Ions have positive charges, so the pyrrole-cyanine derivative fluorescent probe has three properties of electrophilicity, hydrophilicity and membranophilicity, and can easily enter cells through cell membranes in the using processThereby being convenient for the application of the pyrrole-cyanine derivative fluorescent probe in cells.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of a pyrrole-cyanine derivative fluorescent probe.
Background
The fluorescent probe is a fluorescent molecule which has characteristic fluorescence in an ultraviolet-visible-near infrared region, the fluorescent property of which can be sensitively changed along with the change of the properties of the environment, such as polarity, refractive index, viscosity and the like, and a small molecular substance which is subjected to non-covalent interaction with nucleic acid, protein or other macromolecular structures to change one or more fluorescent properties, and can be used for researching the properties and behaviors of macromolecular substances.
In recent years, fluorescent molecular probe technology has become an important means for detecting important metal ions, anions and small molecules, but the existing fluorescent probes are difficult to enter cells through cell membranes during the use process, thereby influencing the use of the fluorescent probes in the cells. Therefore, we improve the above and propose a method for preparing pyrrole-cyanine derivative fluorescent probe.
Disclosure of Invention
In order to solve the technical problems, the invention provides the following technical scheme:
the invention relates to a preparation method of a pyrrole-cyanine derivative fluorescent probe, which has the following structural formula:
as a preferable technical scheme of the invention, the method comprises the following steps:
A. adding N-methyl-2, 3, 3-trimethylindolium iodide, p-hydroxybenzaldehyde and 1-formylpyrrolidine into a 100mL round-bottom flask, and then dissolving by using an organic solvent;
B. stirring the solution obtained in the step for reaction;
C. cooling the solution obtained by the reaction to room temperature and then spin-drying to obtain a solid mixture;
D. recrystallizing the solid mixture with acetonitrile, filtering, drying, and weighing to obtain light yellow powder;
E. d, adding the product obtained in the step D into a 100mL round-bottom flask, dissolving the product by using acetonitrile, dichloromethane and dimethyl sulfoxide, adding potassium borofluoride to react in a dark environment, and then performing spin drying;
F. and dissolving the object obtained in the step by using acetonitrile, filtering to remove inorganic salt, carrying out spin drying to obtain a solid, recrystallizing by using the acetonitrile, filtering, and drying to obtain the pyrrole-cyanine derivative fluorescent probe.
As a preferred embodiment of the present invention, the weights of N-methyl-2, 3, 3-trimethylindolium iodide, p-hydroxybenzaldehyde and 1-formylpyrrolidine in step A are 0.602g, 0.244g, 0.30g and 15mL, respectively.
As a preferable technical scheme of the invention, the organic solvent used in the step A is absolute ethyl alcohol, and the dosage is 15 mL.
As a preferable technical scheme of the invention, the reaction temperature in the step B is 80 ℃, and the reaction time is 72 h.
In a preferred embodiment of the present invention, the amounts of acetonitrile, dichloromethane and dimethyl sulfoxide used in step E are 10mL, 10mL and 5mL, respectively, and the amount of potassium borofluoride used is 1.10 g.
As a preferred technical scheme of the invention, the temperature of the reaction in the step E is 50 ℃, and the actual reaction time is 3 hours.
The invention has the beneficial effects that: according to the preparation method of the pyrrole-cyanine derivative fluorescent probe, as the outer membrane of a cell membrane is positively charged and the inner membrane is negatively charged, a positively charged compound can easily enter cells through the cell membrane, and the pyrrole-cyanine derivative fluorescent probe contains N+Ions have positive charges, so the pyrrole-cyanine derivative fluorescent probe has three properties of electrophilicity, hydrophilicity and membranophilicity, and can easily enter cells through cell membranes in the using process, thereby being convenient for the pyrrole-cyanine derivative fluorescent probe to be used in the cells.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
FIG. 1 is a schematic structural diagram of a method for preparing a pyrrole-cyanine derivative fluorescent probe according to the present invention;
FIG. 2 shows that the pyrrole-cyanine derivative fluorescent probe obtained by the invention has a molecular weight ratio of 1:1, adding and not adding ultraviolet-visible absorption spectra of various ions to be detected with the same times into a solvent system;
FIG. 3 shows UV-VIS absorption spectra of different concentrations of pyrrole-cyanine derivative fluorescent probes obtained according to the present invention;
FIG. 4 is a fluorescence spectrum of the pyrrole-cyanine derivative fluorescent probe obtained by the present invention when various ions to be detected are not added and added with the same magnification;
Detailed Description
The preferred embodiments of the present invention will be described in conjunction with the accompanying drawings, and it will be understood that they are described herein for the purpose of illustration and explanation and not limitation.
Example (b): as shown in fig. 1-4, the pyrrole-cyanine derivative fluorescent probe of the present invention has the following structural formula:
the method comprises the following steps:
A. adding N-methyl-2, 3, 3-trimethylindolium iodide, p-hydroxybenzaldehyde and 1-formylpyrrolidine into a 100mL round-bottom flask, and then dissolving by using an organic solvent;
B. stirring the solution obtained in the step for reaction;
C. cooling the solution obtained by the reaction to room temperature and then spin-drying to obtain a solid mixture;
D. recrystallizing the solid mixture with acetonitrile, filtering, drying, and weighing to obtain light yellow powder;
E. d, adding the product obtained in the step D into a 100mL round-bottom flask, dissolving the product by using acetonitrile, dichloromethane and dimethyl sulfoxide, adding potassium borofluoride to react in a dark environment, and then performing spin drying;
F. and dissolving the object obtained in the step by using acetonitrile, filtering to remove inorganic salt, carrying out spin drying to obtain a solid, recrystallizing by using the acetonitrile, filtering, and drying to obtain the pyrrole-cyanine derivative fluorescent probe.
Wherein the weights of N-methyl-2, 3, 3-trimethylindolium iodide, p-hydroxybenzaldehyde and 1-formylpyrrolidine in step A are 0.602g, 0.244g, 0.30g and 15mL, respectively.
Wherein the organic solvent used in the step A is absolute ethyl alcohol, and the dosage is 15 mL.
Wherein the reaction temperature in the step B is 80 ℃, and the reaction time is 72 h.
Wherein the dosage of the acetonitrile, the dichloromethane and the dimethyl sulfoxide in the step E is respectively 10mL, 10mL and 5mL, and the dosage of the potassium fluoborate is 1.10 g.
Wherein the reaction temperature in the step E is 50 ℃, and the reaction time is actually 3 h.
The probe spectral property is studied in a solvent system of absolute ethyl alcohol and water 1:1, and the specific experimental operation steps are that 3.63mg of the main body is accurately weighed, dissolved by DMF, transferred into a 10mL volumetric flask, finally added with DMF for constant volume, and the probe is prepared into the probe with the concentration of 1.0 × 10-5mol/L, concentration of other ions is 1.0 × 10-4mol/L (NaNO3, Na2SO4, NaCl, NaAcNaHSO4, NaH2PO4, KF, Na2CO3, Na2HPO4, a3PO 4). The results of measuring the UV absorption of the probe at room temperature after shaking were uniform are shown in FIG. 2.
In order to further study the reaction mechanism of the probe molecule and HSO4, different concentrations of L1 ultraviolet-visible absorption spectrum were prepared by mixing 1.0 × 10-3The mol/L probe molecule solution was dissolved in 3ml of a solvent system of ethanol and water at a ratio of 1:1 to prepare solutions of different concentrations (5.0 × 10)-6M to 8.0 × 10-5M) after shaking uniformly, the mixture was left to stand, and the UV-visible spectrum was measured at room temperature as shown in FIG. 3.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A pyrrole-cyanine derivative fluorescent probe is characterized in that the pyrrole-cyanine derivative fluorescent probe has the following structural formula:
2. the method for preparing a pyrrole-cyanine derivative fluorescent probe according to claim 1, characterized by comprising the following steps:
A. adding N-methyl-2, 3, 3-trimethylindolium iodide, p-hydroxybenzaldehyde and 1-formylpyrrolidine into a 100mL round-bottom flask, and then dissolving by using an organic solvent;
B. stirring the solution obtained in the step for reaction;
C. cooling the solution obtained by the reaction to room temperature and then spin-drying to obtain a solid mixture;
D. recrystallizing the solid mixture with acetonitrile, filtering, drying, and weighing to obtain light yellow powder;
E. d, adding the product obtained in the step D into a 100mL round-bottom flask, dissolving the product by using acetonitrile, dichloromethane and dimethyl sulfoxide, adding potassium borofluoride to react in a dark environment, and then performing spin drying;
F. and dissolving the object obtained in the step by using acetonitrile, filtering to remove inorganic salt, carrying out spin drying to obtain a solid, recrystallizing by using the acetonitrile, filtering, and drying to obtain the pyrrole-cyanine derivative fluorescent probe.
3. The method for preparing a pyrrole-cyanine derivative fluorescent probe according to claim 2, wherein the weights of N-methyl-2, 3, 3-trimethylindolium iodide, p-hydroxybenzaldehyde and 1-formylpyrrolidine in step A are 0.602g, 0.244g, 0.30g and 15mL, respectively.
4. The method for preparing a pyrrole-cyanine derivative fluorescent probe according to claim 2, wherein the organic solvent used in step a is absolute ethyl alcohol in an amount of 15 mL.
5. The method for preparing a pyrrole-cyanine derivative fluorescent probe according to claim 2, wherein the reaction temperature in step B is 80 ℃ and the reaction time is 72 h.
6. The method for preparing a pyrrole-cyanine derivative fluorescent probe according to claim 2, wherein the amounts of acetonitrile, dichloromethane and dimethylsulfoxide in step E are 10mL, 10mL and 5mL, respectively, and the amount of potassium borofluoride is 1.10 g.
7. The method for preparing a pyrrole-cyanine derivative fluorescent probe according to claim 2, wherein the temperature of the reaction in step E is 50 ℃ and the reaction time is substantially 3 h.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103436252A (en) * | 2013-08-05 | 2013-12-11 | 天津理工大学 | Anion fluorescent probe for forming aggregate through anion inducing |
| CN110407734A (en) * | 2019-08-20 | 2019-11-05 | 天津理工大学 | A kind of 2,3,3- tri-methyl indole system nonlinear optical crystal and its preparation method and purposes |
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- 2020-07-06 CN CN202010638536.1A patent/CN111675645A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103436252A (en) * | 2013-08-05 | 2013-12-11 | 天津理工大学 | Anion fluorescent probe for forming aggregate through anion inducing |
| CN110407734A (en) * | 2019-08-20 | 2019-11-05 | 天津理工大学 | A kind of 2,3,3- tri-methyl indole system nonlinear optical crystal and its preparation method and purposes |
Non-Patent Citations (2)
| Title |
|---|
| JIAJIA CHANG等: "Efficient fluorescent chemosensors for HSO4- based on a strategy of anion-induced rotation-displaced H-aggregates", 《CHEM.COMMUN.》 * |
| L.V.KHOKHLOVA等: "Synthesis of Polymethine Dyes Possessing Nonlinear Optical Properties and Preparation of Photoconducting Systems Based Thereupon", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》 * |
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Application publication date: 20200918 |