CN116903638A - Preparation and application of benzothiazole-quinoline derivative - Google Patents
Preparation and application of benzothiazole-quinoline derivative Download PDFInfo
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- CN116903638A CN116903638A CN202310643118.5A CN202310643118A CN116903638A CN 116903638 A CN116903638 A CN 116903638A CN 202310643118 A CN202310643118 A CN 202310643118A CN 116903638 A CN116903638 A CN 116903638A
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- quinoline derivative
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- thiazole
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- BZGWZLIKWOCPLN-UHFFFAOYSA-N 1,3-benzothiazole;quinoline Chemical class C1=CC=C2SC=NC2=C1.N1=CC=CC2=CC=CC=C21 BZGWZLIKWOCPLN-UHFFFAOYSA-N 0.000 title abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 9
- HVXLKRWRWNFGBA-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-dithiol;dihydrochloride Chemical compound Cl.Cl.NC1=CC(S)=C(N)C=C1S HVXLKRWRWNFGBA-UHFFFAOYSA-N 0.000 claims abstract description 8
- OAEGRYMCJYIXQT-UHFFFAOYSA-N dithiooxamide Chemical compound NC(=S)C(N)=S OAEGRYMCJYIXQT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003248 quinolines Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 6
- -1 diethylamino, methoxy Chemical group 0.000 claims description 4
- IMXRZJSHQIESSW-UHFFFAOYSA-N 6-(diethylamino)quinoline-2-carbaldehyde Chemical compound C(C)N(C=1C=C2C=CC(=NC2=CC=1)C=O)CC IMXRZJSHQIESSW-UHFFFAOYSA-N 0.000 claims description 3
- AYIIFDAAXPMDAG-UHFFFAOYSA-N 6-methoxyquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC(OC)=CC=C21 AYIIFDAAXPMDAG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 2
- 229920000178 Acrylic resin Polymers 0.000 claims description 2
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 claims description 2
- OHWLHCNSQHIAGK-UHFFFAOYSA-N S1C=NC=C1.N1=CC=CC2=CC=CC=C12.S1C=NC=C1 Chemical class S1C=NC=C1.N1=CC=CC2=CC=CC=C12.S1C=NC=C1 OHWLHCNSQHIAGK-UHFFFAOYSA-N 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000003828 vacuum filtration Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 19
- 239000007850 fluorescent dye Substances 0.000 abstract description 15
- 239000007787 solid Substances 0.000 abstract description 11
- 238000004043 dyeing Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000011088 parchment paper Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003891 environmental analysis Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- 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"
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention discloses a preparation method and application of a benzothiazole-quinoline derivative, and researches on the influence of substituent groups and pi conjugated systems on optical properties. The method comprises the following steps: quinoline derivative and dithiooxamide (2, 5-diamino-1, 4-benzene dithiol dihydrochloride) are dissolved by N, N-dimethylformamide solvent, and are stirred for 12 hours at 120 ℃ and then separated and purified to obtain the fluorescent dye. The product synthesized by the invention has a larger conjugated system, and the solid fluorescence can be correspondingly regulated and controlled along with the change of substituent groups. The preparation method of the fluorescent dye is simple and easy to operate, has the advantages of simple and easily obtained raw materials, low cost and good performance, and can be applied to the fields of luminescent materials, fluorescent ink (printing materials), anti-counterfeiting materials, printing and dyeing industries, sensors and the like.
Description
Technical Field
The invention belongs to the field of dye fine chemical industry, and particularly relates to a novel fluorescent dye which is simple and easy to synthesize, can adjust fluorescence emission wavelength to a certain extent, and can be applied to luminescent materials, fluorescent ink (printing materials), anti-counterfeiting materials, printing and dyeing industry, sensors and the like.
Background
The social science and technology is advanced gradually, various precise imitation counterfeit technologies are layered endlessly, the national and personal losses are serious, the counterfeit phenomenon makes the social integrity problem face a great challenge, and people continuously promote the consciousness of property protection, so that the development of novel anti-counterfeiting materials and the research of novel anti-counterfeiting technologies become necessary.
Currently, a number of substances having specific chemical, physical and electrical properties are used to prevent and detect counterfeiting. The chemical anti-counterfeiting technology is a new technology developed in recent years, and has the advantages of simple preparation, convenient identification, low cost, good confidentiality, high reliability and the like. Chemical security is a method of discriminating authenticity by using chemical reaction and physical change of a substance under conditions such as heat, light, or magnetism. The fluorescent anti-counterfeiting mark technology utilizes the characteristic of fluorescence emission generated by fluorescent materials under ultraviolet irradiation, and compared with common anti-counterfeiting technologies such as watermarks, lasers, color-changing ink and the like, the fluorescent anti-counterfeiting mark is transparent under visible light, does not influence the original appearance of an article, has good privacy, presents characteristic fluorescence under ultraviolet irradiation, and achieves the aim of anti-counterfeiting identification. Therefore, the fluorescent dye is required to have the characteristics of easiness in printing, dip dyeing and high fluorescence intensity, and besides, the fluorescent dye has the advantages of low synthesis cost, simple and efficient preparation method and simplicity in use, and is also a general concern.
The material anti-counterfeiting technology is developed to various forms, but a single anti-counterfeiting means is easily cracked by lawbreakers and counterfeited to a certain extent, so that in order to achieve the anti-counterfeiting effect with complete significance, the application trend in the anti-counterfeiting field is to combine various anti-counterfeiting technologies together to prepare an anti-counterfeiting material with multiple functions, the combination of various material anti-counterfeiting technologies, the combination of the material anti-counterfeiting technology and the laser holographic anti-counterfeiting technology and the like, so that the fluorescent anti-counterfeiting material is required to have high resistance and is easy to combine with the various anti-counterfeiting technologies.
Disclosure of Invention
The invention aims to synthesize a luminescent adjustable benzothiazole-quinoline derivative fluorescent dye, and the fluorescence wavelength of the series of compounds can be adjusted by different substituents. The synthesized fluorescent dye can be applied to the fields of luminescent materials, fluorescent ink (printing materials), anti-counterfeiting materials, printing and dyeing industry, sensors and the like.
The aim of the invention is achieved by the following technical scheme: the solid fluorescent dye has the following structural formula:
R＝-H,-CHO,N(CH2CH3)2
the substituent R comprises diethylamino, methoxy and hydrogen.
The preparation method of the fluorescent dye compound comprises the following steps: quinoline derivative and dithiooxamide (2, 5-diamino-1, 4-benzene dithiol dihydrochloride) are dissolved by N, N-dimethylformamide solvent, and the fluorescent dye is obtained after separation and purification after stirring reaction for 12 hours at 120 ℃.
The specific synthetic route of the fluorescent dye is as follows:
the substituent R comprises diethylamino, methoxy and hydrogen.
The molar ratio of the quinoline derivative to dithiooxamide (2, 5-diamino-1, 4-benzenedithiol dihydrochloride) is 2: (1-1.5).
Because the traditional organic molecular chromophore has the problem of fluorescence quenching under the aggregation state forms of high concentration, solid state or film and the like, the invention overcomes or slows down the influence of the quenching phenomenon and enables the wavelength to be red shifted by changing a conjugated system and an electron donating group, and a final product can be obtained only by adopting reduced pressure suction filtration without column chromatography purification, thereby having simple and convenient operation. According to the invention, through the fact that different quinoline derivatives are respectively combined with dithiooxamide and 2, 5-diamino-1, 4-benzene dithiophenol dihydrochloride, benzothiazole parent nucleus which is generated by a series of solid fluorescent dyes in a plurality of small molecular fluorescent compounds is paid attention to due to the fact that the benzothiazole parent nucleus has high fluorescence quantum yield and the heterocycle of the benzothiazole parent nucleus is easy to synthesize, thiazole and quinoline are relatively common and popular organic luminophores, and are common in the fields of chemistry, life science, medicine, environmental analysis, cell staining, signal tracking and the like. The invention provides application prospects in various fields of organic chromophores, and can greatly change the fluorescence quantum yield of products and the wavelength of compounds by changing the types of benzene ring substituents. Thereby changing the luminescence color of the solid fluorescent dye.
The synthesis method for preparing the fluorescent dye is simple and feasible, and the raw materials are simple and easy to obtain and have low cost. The organic solid fluorescent dye has good performance and can be applied to the fields of luminescent materials, fluorescent ink (printing materials), anti-counterfeiting materials, printing and dyeing industry, sensors and the like.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of ZH-1 dye.
FIG. 2 is a nuclear magnetic hydrogen spectrum of ZH-2 dye.
FIG. 3 is a nuclear magnetic hydrogen spectrum of YH-1 dye.
FIG. 4 is a nuclear magnetic hydrogen spectrum of YH-2 dye.
FIG. 5 is a nuclear magnetic hydrogen spectrum of YH-3 dye.
FIG. 6 is a graph of fluorescence emission spectra of ZH-1, YH-1 in several polar solvents under 365nm ultraviolet light.
Fig. 7 shows the application of dye to a security film.
Detailed Description
EXAMPLE 1 Synthesis of Compound ZH-1
50mg (0.22 mol) of 6- (diethylamino) quinoline-2-carbaldehyde and 13.2mg (0.11 mol) of dithiooxamide were weighed into a 25ml reaction flask, dissolved in 2ml of DMF, stirred in an oil bath at 120℃for 12 hours, and filtered under reduced pressure to give 29.7mg of a red solid. The yield was 25%.
EXAMPLE 2 Synthesis of Compound ZH-2
50mg (0.267 mol) of 6-methoxyquinoline-2-carbaldehyde and 21.2mg (0.34 mol) of dithiooxamide were weighed into a 25ml reaction flask, dissolved in 2ml of DMF, stirred in an oil bath at 120℃for 12 hours, and filtered under reduced pressure to give 42mg of a yellow solid. The yield was 34%.
EXAMPLE 3 Synthesis of Compound YH-1
50mg (0.22 mol) of 6- (diethylamino) quinoline-2-carbaldehyde and 27mg (0.11 mol) of 2, 5-diamino-1, 4-benzenedithiol dihydrochloride were weighed into a 25ml reaction flask, dissolved in 2ml of DMF, stirred in an oil bath at 120℃for 12 hours, and filtered under reduced pressure to give 40.7mg of pale red solid. The yield was 31%.
EXAMPLE 4 Synthesis of Compound YH-2
50mg (0.32 mol) of quinoline-2-carbaldehyde and 39mg (0.16 mol) of 2, 5-diamino-1, 4-benzenedithiol dihydrochloride were weighed into a 25ml reaction flask, 2ml of DMF was added for dissolution, and the mixture was stirred in an oil bath at 120℃for 12 hours, and then filtered under reduced pressure to obtain 37.5mg of green solid. The yield was 26%.
EXAMPLE 5 Synthesis of Compound YH-3
50mg (0.267 mol) of 6-methoxyquinoline-2-carbaldehyde and 32.7mg (0.134 mol) of 2, 5-diamino-1, 4-benzenedithiol dihydrochloride were weighed into a 25ml reaction flask, dissolved in 2ml of DMF, stirred in an oil bath at 120℃for 12 hours, and filtered under reduced pressure to give 38.1mg of a yellow solid. The yield was 28%.
Example 6: effect of dyes in solvents of different polarity
The prepared ZH-1, ZH-2, YH-1, YH-2, YH-3 compounds were dissolved in DCM solution to prepare a 1mM mother solution. DCM, DMSO, ethanol and toluene are added into test tubes, 3mL of each test tube is added, 6 mu L (2 mu M) of the test tube is taken out from mother liquor and added into each test tube, the ultraviolet-visible absorption spectrum and the fluorescence spectrum of the dye in solvents with different polarities are tested by an ultraviolet-visible absorption spectrometer and a fluorescence spectrometer by adopting ZH-1 excitation wavelength of 480nm and YH-1 excitation wavelength of 460 nm. The test results are shown in FIG. 6, and it can be seen that the dye ZH-1 has a wavelength sequentially red shifted (A in FIG. 6) in four polar solvents Tol, DCM, etOH, DMSO, and the fluorescence color of the solution (B in FIG. 6, tol, DCM, etOH, DMSO in sequence from left to right) is from green to yellow to orange; YH-1 in Tol, DCM, etOH, DMSO four polar solvents, the wavelength red shifted (C in fig. 6), the fluorescence color of the solution (D in fig. 6, tol, DCM, etOH, DMSO solvent from left to right) changed from blue to green to yellow orange as the polarity increased.
Example 7: application of dye in anti-counterfeiting
The prepared ZH-1, ZH-2, YH-1, YH-2 and YH-3 compounds are taken and dissolved in an acrylic resin solution to prepare a solution of 1mg/ml, and then the solution is uniformly smeared on a piece of parchment paper (S, D, X, Y, W in figure 7 is the compounds ZH-1, ZH-2, YH-1, YH-2 and YH-3 in sequence), after the film is cooled and formed, the film is irradiated by ultraviolet light and photographed, and as can be seen from figure 7, the formed film on the parchment paper has little color change observed in sunlight, and obvious fluorescence change can be seen in the ultraviolet light, so the dye has application potential in the aspect of anti-counterfeiting.
Claims (10)
1. A bis-thiazole-quinoline derivative dye, characterized by the following structural formula:
the substituent R includes diethylamino, methoxy, or hydrogen.
2. The benzodithiazole-quinoline derivative dye according to claim 1, wherein the structural formula of the compound comprises any one of:
3. process for the preparation of a dye of a bis-thiazole-quinoline derivative according to claim 1 or 2, characterized in that it comprises the following steps:
quinoline derivative and dithiooxamide (2, 5-diamino-1, 4-benzene dithiol dihydrochloride) are dissolved by N, N-dimethylformamide solvent, stirred and reacted for 10 to 12 hours at the temperature of 100 to 120 ℃, and the dye is obtained by vacuum filtration after the reaction is finished.
4. A process for the preparation of a dye of a bis-thiazole-quinoline derivative according to claim 3, wherein the quinoline derivative comprises 6-diethylaminoquinoline-2-carbaldehyde, 6-methoxyquinoline-2-carbaldehyde or quinoline-2-carbaldehyde.
5. A process for the preparation of a dye of a bis-thiazole-quinoline derivative according to claim 3, wherein the molar ratio of quinoline derivative to dithiooxamide (2, 5-diamino-1, 4-benzenedithiol dihydrochloride) is 2: (1-1.5).
6. A process for the preparation of a dye of a bis-thiazole-quinoline derivative according to claim 3, wherein the solvent is N, N-dimethylformamide, nitrobenzene, THF.
7. Use of a dye of a bis-thiazole-quinoline derivative according to claim 1 for fluorescence emission in a polar solvent.
8. The use according to claim 1, wherein the polar solvent is toluene, methylene chloride, ethanol, dimethyl sulfoxide.
9. The use of a dye of a bis-thiazole-quinoline derivative according to claim 1 as a fluorescent reagent for detecting a polar solvent selected from any one of toluene, methylene chloride, ethanol or dimethyl sulfoxide.
10. The use of a dye of a bis-thiazole-quinoline derivative according to claim 1 as a detection solvent for an anti-counterfeit agent, wherein the solvent is an acrylic resin solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310643118.5A CN116903638A (en) | 2023-06-01 | 2023-06-01 | Preparation and application of benzothiazole-quinoline derivative |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310643118.5A CN116903638A (en) | 2023-06-01 | 2023-06-01 | Preparation and application of benzothiazole-quinoline derivative |
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| CN116903638A true CN116903638A (en) | 2023-10-20 |
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| CN202310643118.5A Pending CN116903638A (en) | 2023-06-01 | 2023-06-01 | Preparation and application of benzothiazole-quinoline derivative |
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| Country | Link |
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