CN116693488A - Coumarin dye capable of being used for latent fingerprint development and technical field of preparation method of fingerprint powder - Google Patents
Coumarin dye capable of being used for latent fingerprint development and technical field of preparation method of fingerprint powder Download PDFInfo
- Publication number
- CN116693488A CN116693488A CN202310663801.5A CN202310663801A CN116693488A CN 116693488 A CN116693488 A CN 116693488A CN 202310663801 A CN202310663801 A CN 202310663801A CN 116693488 A CN116693488 A CN 116693488A
- Authority
- CN
- China
- Prior art keywords
- fingerprint
- fluorescent dye
- powder
- color
- fluorescent
- 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.)
- Pending
Links
- 239000000843 powder Substances 0.000 title claims abstract description 69
- 238000011161 development Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 12
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title description 5
- 229960000956 coumarin Drugs 0.000 title description 3
- 235000001671 coumarin Nutrition 0.000 title description 3
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 43
- 239000004519 grease Substances 0.000 claims abstract description 16
- NSYSSMYQPLSPOD-UHFFFAOYSA-N triacetate lactone Chemical compound CC1=CC(O)=CC(=O)O1 NSYSSMYQPLSPOD-UHFFFAOYSA-N 0.000 claims abstract description 12
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 claims abstract description 10
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 15
- 238000007664 blowing Methods 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 239000004579 marble Substances 0.000 claims description 6
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229960002429 proline Drugs 0.000 claims description 4
- 229930182821 L-proline Natural products 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000003760 magnetic stirring Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 3
- 239000012498 ultrapure water Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000799 fluorescence microscopy Methods 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000012822 chemical development Methods 0.000 description 3
- 238000011840 criminal investigation Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- ZHBYCCVSWKWSMR-UHFFFAOYSA-N 2-hydroperoxybenzoic acid Chemical compound OOC1=CC=CC=C1C(O)=O ZHBYCCVSWKWSMR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- -1 halogen alkyne Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/117—Identification of persons
- A61B5/1171—Identification of persons based on the shapes or appearances of their bodies or parts thereof
- A61B5/1172—Identification of persons based on the shapes or appearances of their bodies or parts thereof using fingerprinting
-
- 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
- C09B57/02—Coumarine dyes
-
- 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
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pathology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medical Informatics (AREA)
- Physics & Mathematics (AREA)
- Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Measurement Of The Respiration, Hearing Ability, Form, And Blood Characteristics Of Living Organisms (AREA)
Abstract
The application provides a novel color-changing fluorescent dye capable of responding to grease, which is synthesized by taking 2, 4-dihydroxybenzaldehyde, 4-hydroxy-6-methyl-2-pyrone and 3-bromopropyne as raw materials, has a structure different from that of the existing fluorescent dye, is a novel grease-responding fluorescent dye, and can be used for developing fingerprints, responding to potential fingerprints and causing color change, and fluorescent fingerprint powder is changed from the original orange fluorescent color to the yellow fluorescent color after response.
Description
The application belongs to the technical field of color-changing fluorescent dyes, and particularly relates to a response-type color-changing fluorescent dye, and a preparation method and application thereof.
Background
The existing fingerprint developing technology can be divided into a physical developing method and a chemical developing method, wherein the physical developing method is mainly metal deposition or powder spraying, and is realized through electrostatic adsorption between fluorescent powder or magnetic powder and biological residues in fingerprints, such as amino acid, biological grease or other chemical substances. The chemical development method comprises ninhydrin method, cyanoacrylate fuming method, silver nitrate method and other methods, mainly depends on the reaction of the used chemical substances and the organic matters remained in the fingerprint, and has the defects of stable development, high development delay, high toxicity, low contrast and the like. Therefore, the above-mentioned physical development method and chemical development have a need for solving the problems.
Fluorescent fingerprint powder development stands out in a plurality of methods, and becomes a popular latent fingerprint development means in criminal investigation at present. However, the color change of the fluorescent fingerprint powder sold on the market at present cannot be realized, and all places adhered with the fingerprint powder can show fluorescence, so that the fingerprints remained on the substrate with static electricity or uneven are difficult to realize high-resolution development, and the requirements of criminal investigation on fingerprint extraction cannot be met.
Disclosure of Invention
The application provides a novel color-changing fluorescent dye capable of responding to grease, a preparation method and application thereof, wherein the structure of the novel color-changing fluorescent dye is different from that of the conventional fluorescent dye, the novel color-changing fluorescent dye is a novel grease-responding fluorescent dye, the novel color-changing fluorescent dye is prepared by a simple preparation method, a product with high stability and low toxicity is obtained in a high yield, the obtained compound is applied to fingerprint development, and can respond to potential fingerprints to cause color change, and fluorescent fingerprint powder is changed from original orange fluorescent color to yellow fluorescent color after response, so that the novel grease-responding fluorescent dye has high anti-interference performance and high biocompatibility, can be developed and imaged in a high-resolution, high-contrast and strong anti-interference manner in real time, and can be applied to various materials and complex criminal investigation environments.
The technical scheme of the application is as follows:
in a first aspect, the present application provides an oil-responsive color-shifting fluorescent dye having the structure of formula I:
in a second aspect, the application also provides a preparation method of the novel response type color-changing fluorescent dye, which specifically comprises the following steps:
step 1, adding 2, 4-dihydroxybenzaldehyde and 4-hydroxy-6-methyl-2-pyrone into a flask according to a certain molar ratio, then adding ultrapure water, starting magnetic stirring to fully dissolve raw materials, adding L-prolyl as a catalyst at a constant temperature, refluxing and stirring for 2 hours, and carrying out suction filtration to obtain intermediate powder with yellow reaction, wherein yellow granular substances can be observed to precipitate out of reaction liquid along with the progress of the reaction;
adding acetone to dissolve the intermediate prepared in the step 2 and the step 1, adding anhydrous potassium carbonate and 3-bromopropyne, stirring at room temperature for 4 hours, adding water, extracting with a small amount of dichloromethane for multiple times, evaporating and drying to obtain the target compound (yellow-green solid)
The reaction process is shown in a formula II:
specifically, the molar ratio of aldehyde to ketone to proline is 10:15:1, a step of; the molar ratio of the intermediate to the anhydrous potassium carbonate to the 3-bromopropyne is 1:2:1.
in a second aspect, the application also provides application of the novel grease response type color-changing fluorescent dye, and the novel grease response type color-changing fluorescent dye is prepared into fluorescent fingerprint powder and applied to the identification of latent fingerprints.
Specifically, the preparation of the fluorescent fingerprint powder comprises the following steps:
weighing a certain amount of response type color-changing fluorescent dye, dissolving in an organic solvent, adding montmorillonite as a carrier, uniformly mixing the fluorescent dye and the carrier in the organic solvent by utilizing an ultrasonic technology, evaporating the solvent by a rotary evaporator, and grinding and drying to obtain the required fluorescent fingerprint powder.
Specifically, the mass ratio of the response type color-changing fluorescent dye to montmorillonite in the preparation of the fluorescent fingerprint powder is 20 mg/3 g. .
Specifically, the carrier is montmorillonite.
Specifically, the application in the latent fingerprint identification specifically comprises the following steps:
step 1, dipping the prepared novel fluorescent fingerprint powder on a substrate where the latent fingerprints are located by using a clean fluff rod, enabling the fingerprint powder to fall on the surface of the substrate uniformly, enabling the fingerprint powder to be attached to the positions where the fingerprints are left to display orange, and then blowing off the fingerprints outside the fingerprint area by using a dust blowing ball.
And step 2, irradiating under an ultraviolet lamp, and responding yellow fluorescence by the novel fluorescent fingerprint powder with clear fingerprint lines to obtain a response type color-changing fluorescence imaging of the latent fingerprint. Specifically, the ultraviolet light source irradiation is performed under the illumination condition with the wavelength of 350-430 nm.
Specifically, the substrate is at least one of tinfoil, glass, marble and optical disk
The hydroxyl salicylic acid is used as an initial raw material, the hydroxyl salicylic acid is reacted with 4-hydroxy-6-methyl-2-pyrone to obtain a hydroxyl substituted coumarin-beta-diketone structure, then the halogen alkyne is utilized to react with phenolic hydroxyl to convert an electron donor group on the carbon of the 7 th position of the coumarin from hydroxyl to alkynyloxy, so that a novel dye is obtained, the novel dye is prepared into fluorescent fingerprint powder, and has photochromic property, and the color change response principle is that the prepared fluorescent dye interacts with biological grease in fingerprints such as oleic acid, cholesterol and the like to cause color change, namely orange carried by the fluorescent dye turns yellow. The fluorescent dye has the advantages of simple chemical molecular crystal structure, better light stability, stronger light sensitivity, higher fluorescence efficiency, better biocompatibility and lower toxicity. Because the fat-soluble oil is good, the oil can be combined with trace oil remained in the fingerprint, and fluorescent color change is caused by the change of the dissolution environment, so that the fingerprint development can be realized, and the fingerprint identification efficiency and the result effectiveness are improved.
Compared with the prior art, the application has the beneficial effects that:
(1) The structure of the prepared response type color-changing fluorescent dye is different from that of the existing fluorescent dye, the novel response type color-changing fluorescent dye is novel, the raw material cost required by preparation is low, the preparation flow is simple, the target product can be obtained only by two steps, the yield is high, the stability of the produced dye is good, the biotoxicity is low, and meanwhile, the fluorescent dye has color-changing performance and can be applied to the identification of latent fingerprints;
(2) The fluorescent fingerprint powder prepared by the application is applied to the latent fingerprint display, changes the fluorescent color after responding to the fingerprint, combines the advantages of the existing physical development method and the existing chemical development method, has stronger anti-interference performance, higher resolution and contrast, higher fingerprint display precision, can develop in real time and does not damage DNA information in the fingerprint;
(3) The fluorescent fingerprint powder prepared by the application is not limited by a substrate material in the process of latent fingerprint identification, has excellent latent fingerprint developing effect in the areas of residual fingerprints on various common substrates such as tinfoil, glass, marble, optical discs and the like, reduces the application limitation of the fingerprint powder, and reduces the interference caused by signals of the fluorescent fingerprint powder.
Drawings
For a clearer description of the technical solutions of the embodiments of the present application, the drawings that are needed in the embodiments of the present application will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present application, and therefore should not be considered as limiting the scope, and other related drawings can be obtained according to these drawings without inventive effort for a person of ordinary skill in the art.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the fluorescent fingerprint powder prepared in example 1;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of the fluorescent fingerprint powder prepared in example 1;
FIG. 3 is a high resolution mass spectrum of the fluorescent fingerprint powder prepared in example 1;
FIGS. 4a and 4b are images of fluorescent fingerprint powder prepared in example 1 after the fluorescent fingerprint powder is in contact with the latent fingerprint on the optical disc, and the fluorescent fingerprint powder is developed and imaged under sunlight and ultraviolet irradiation;
FIGS. 5a and 5b are views showing the development and imaging of the fluorescent fingerprint powder prepared in example 1 and the fingerprint on the optical disc under ultraviolet irradiation after the fluorescent fingerprint powder and the latent fingerprint are sounded, and comparing the detail;
FIGS. 6a and 6b are images of the fluorescent fingerprint powder prepared in example 1 after the fluorescent fingerprint powder is made to sound with the glass latent fingerprint, and the fluorescent fingerprint powder is developed and imaged under sunlight and ultraviolet irradiation;
FIGS. 7a and 7b are images of fluorescent fingerprint powder prepared in example 1 after the fluorescent fingerprint powder is made to sound with the latent fingerprint on tinfoil, and the fluorescent fingerprint powder is developed and imaged under sunlight and ultraviolet irradiation;
FIGS. 8a and 8b are images of the fluorescent fingerprint powder prepared in example 1 after the fluorescent fingerprint powder is made to sound with the latent fingerprint on marble, and the fluorescent fingerprint powder is developed and imaged under sunlight and ultraviolet irradiation;
Detailed Description
The following description of the embodiments of the present application will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present application, but not all embodiments. All other embodiments, which are derived by a person skilled in the art based on the embodiments of the application, fall within the scope of protection of the application.
Example 1
Preparing grease response type color-changing fluorescent dye:
a dried 100mL round bottom flask was taken, 10 mmoles of 2, 4-dihydroxybenzaldehyde 15 mmoles of 4-hydroxy-6-methyl-2-pyrone was added thereto, then 30mL of ultrapure water was added thereto and magnetic stirring was started to dissolve the raw material sufficiently, 1 mmoles of L-proline was added as a catalyst at a constant temperature of 85℃and stirred under reflux for 2 hours. As the reaction proceeded, it was observed that yellow particulate matter precipitated out of the reaction liquid. The end point of the reaction was determined by TLC detection, after the end of the reaction, the flask was naturally cooled to room temperature, and then suction filtration was performed to obtain 2.13g of an intermediate powder of reaction yellow.
Another 50mL single neck round bottom flask was taken, 4.1mmol of intermediate was added thereto and 10mL of acetone was added thereto for dissolution, and 8mmol of anhydrous carbonic acid and 4.5mmol of 3-bromopropyne were further added and kept stirring at room temperature for 4 hours. Yellow-green insolubles were observed in the solution. After the completion of the reaction, as determined by TLC detection, 10mL of water was added, and the reaction mixture was extracted a small amount of a plurality of times with methylene chloride and dried by evaporation, to finally obtain 1.06g of a yellowish green solid as the target compound, the yield was 90.6%.
The structure of the grease response color-changing fluorescent dye is shown in formula Ia:
nuclear magnetic detection results:
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the grease-responsive color-changing fluorescent dye prepared in example 1.
The nuclear magnetic information is: 1 H NMR(500MHz,CDCl 3 )δ＝15.89(s,1H),8.54(s,1H),7.50(d,J＝8.8Hz,1H),6.92(s,1H),6.90(s,2H),4.73(s,2H),2.53(s,1H),2.18(s,3H).13C NMR(125MHz,CDCl 3 )δ＝193.56,167.94,157.27,153.04,151.15,140.22,125.56,112.23,108.87,107.72,96.26,95.81,51.14,24.44,22.00.HRMS:m/z[M+Na] + calculation C 16 H 12 NaO 5 + Theoretical value: 307.0577, actual value: 307.0587.
FIG. 2 is a nuclear magnetic resonance carbon spectrum of the grease-responsive color-changing fluorescent dye prepared in example 1.
FIG. 3 is a high resolution mass spectrum of the grease-responsive color-changing fluorescent dye prepared in example 1.
The results show that the compound prepared in this example has the structure shown in formula Ia.
Example 2
The fluorescent fingerprint powder prepared in example 1 is applied to the latent fingerprint appearance of the surface of an optical disc.
A clean fluff bar is dipped in fingerprint powder, the fluff bar is gently shaken above the surface of a material with fingerprints printed in advance, so that the fingerprint powder uniformly falls on the surface of the material, and then a dust blowing ball is used for blowing the fingerprint powder outside the fingerprint area to take a photo under sunlight, as shown in fig. 4a, and the photo is taken under UV 365nm, as shown in fig. 4 b.
And after the fluorescent fingerprint is developed on the surface of the optical disk and the fingerprint, shooting by using a camera to obtain clear fingerprint imaging. The various feature information contained in the fingerprint can be derived on the fingerprint image as in fig. 5a and 5b, including level 2 and level 3 features. Fig. 5b shows the characteristics of identifiable grain bifurcation point (No. 1 position), termination point (No. 2 position), isolated point (No. 3 position), short grain (No. 6 and No. 9 position) and other secondary nodes and tertiary node sweat gland holes (No. 4, 5, no. 7 and No. 8 positions). Considering that the highest recognition level of the application scene of the current fingerprint recognition is three-level node recognition, the fingerprint powder capable of achieving three-level recognition can meet the condition of realizing the application of latent fingerprints under specific scenes, namely the fingerprint powder based on montmorillonite carriers, which is tested by the section, can meet the use requirements of the application in the fields of government, law enforcement and the like
Example 3
The fluorescent fingerprint powder prepared in example 1 is applied to the latent fingerprint visualization of the glass surface. A clean fluff bar is dipped in fingerprint powder, the fluff bar is gently shaken above the surface of a material with fingerprints printed in advance, so that the fingerprint powder uniformly falls on the surface of the material, and then a dust blowing ball is used for blowing the fingerprint powder outside the fingerprint area to take a photo under sunlight, as shown in fig. 6a, and the photo is taken under UV 365nm, as shown in fig. 6 b.
And after the fluorescent fingerprint is developed on the surface of the glass and the fingerprint, shooting by using a camera to obtain clear fingerprint imaging.
Example 4
The fluorescent fingerprint powder prepared in the example 1 is applied to the latent fingerprint appearance of the surface of the tinfoil. A clean fluff bar is dipped in fingerprint powder, the fluff bar is gently shaken above the surface of a material with fingerprints printed in advance, the fingerprint powder is uniformly dropped on the surface of the material, and then a dust blowing ball is used for blowing the fingerprint powder outside the fingerprint area to take a photo under sunlight, as shown in fig. 7a, and the photo is taken under UV 365nm, as shown in fig. 7 b.
And after the fluorescent fingerprint is developed on the surface of the tinfoil and the fingerprint, shooting by using a camera to obtain clear fingerprint imaging.
Example 5
The fluorescent fingerprint powder prepared in example 1 was applied to latent fingerprint development on the marble surface. A clean fluff bar is dipped in fingerprint powder, the fluff bar is gently shaken above the surface of a material with fingerprints printed in advance, so that the fingerprint powder uniformly falls on the surface of the material, and then a dust blowing ball is used for blowing the fingerprint powder outside the fingerprint area to take a photo under sunlight, as shown in fig. 8a, and the photo is taken under UV 365nm, as shown in fig. 8 b.
And after the fluorescent fingerprint is developed on the marble surface and the fingerprint, shooting by using a camera to obtain clear fingerprint imaging.
The above-described embodiments are merely preferred embodiments of the present application, which are intended to be illustrative, not limiting; it will be understood by those skilled in the art that many changes may be made and equivalents may be substituted for elements thereof without departing from the scope of the application as defined in the claims below.
Claims (9)
1. An oil-responsive color-changing fluorescent dye, characterized by having the structure of formula I:
2. a method for preparing the grease response type color-changing fluorescent dye according to claim 1, which is characterized by comprising the following steps:
step 1, adding 4-hydroxy-6-methyl-2-pyrone and 2, 4-dihydroxybenzaldehyde into a flask according to a certain molar ratio, then adding ultrapure water, starting magnetic stirring to fully dissolve raw materials, adding L-proline as a catalyst at a constant temperature, refluxing and stirring for 2 hours, separating out yellow particulate matters, and obtaining yellow powder as an intermediate through suction filtration;
and 2, adding acetone into the yellow powder obtained in the step 1 for dissolution, adding anhydrous potassium carbonate and 3-bromopropyne, stirring for 4 hours at room temperature, adding water, extracting for a plurality of times with a small amount of dichloromethane, evaporating and drying to obtain the target compound yellow-green solid.
3. The method for preparing the grease-responsive color-changing fluorescent dye according to claim 2, wherein the molar ratio of 2, 4-dihydroxybenzaldehyde, 4-hydroxy-6-methyl-2-pyrone and L-proline is 10:15:1.
4. the preparation method of the grease response type color-changing fluorescent dye according to claim 2, which is characterized in that the mole ratio of the intermediate, anhydrous potassium carbonate and 3-bromopropyne is 1:2:1.
5. the use of the grease-responsive color-changing fluorescent dye according to claim 1, further prepared into responsive fluorescent fingerprint powder, and applied to fingerprint development technology.
6. The use of the grease-responsive color-changing fluorescent dye according to claim 5, wherein the preparation of the fluorescent fingerprint powder specifically comprises the following steps:
weighing a certain amount of response type color-changing fluorescent dye, dissolving in an organic solvent, adding montmorillonite as a carrier, mixing the fluorescent dye and the carrier uniformly in the organic solvent by utilizing an ultrasonic technology, evaporating the solvent by a rotary evaporator, grinding and drying to obtain the required fluorescent fingerprint powder, wherein the mass ratio of montmorillonite to the fluorescent dye is 20:3.
7. The use of a responsive color-changing fluorescent dye as claimed in claim 6, wherein the use in latent fingerprint development comprises the steps of:
step 1, scattering the prepared novel fluorescent fingerprint powder on a substrate where the latent fingerprints are located, enabling the fingerprint powder to fall on the surface of the substrate uniformly, enabling the fingerprint powder to be attached to the positions where the fingerprints remain to display orange color, and then blowing off the fingerprint powder outside the fingerprint area;
and step 2, irradiating under an ultraviolet lamp, and responding yellow fluorescence by the novel fluorescent fingerprint powder with clear fingerprint lines to obtain a response type color-changing fluorescence imaging of the latent fingerprint.
8. The use of a responsive color-changing fluorescent dye as claimed in claim 7, wherein the irradiation with ultraviolet light source is carried out under light conditions of 365nm wavelength.
9. The use of a responsive color-changing fluorescent dye as claimed in claim 8, wherein the substrate is at least one of tinfoil, marble, glass.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310663801.5A CN116693488A (en) | 2023-06-06 | 2023-06-06 | Coumarin dye capable of being used for latent fingerprint development and technical field of preparation method of fingerprint powder |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310663801.5A CN116693488A (en) | 2023-06-06 | 2023-06-06 | Coumarin dye capable of being used for latent fingerprint development and technical field of preparation method of fingerprint powder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116693488A true CN116693488A (en) | 2023-09-05 |
Family
ID=87844515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310663801.5A Pending CN116693488A (en) | 2023-06-06 | 2023-06-06 | Coumarin dye capable of being used for latent fingerprint development and technical field of preparation method of fingerprint powder |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116693488A (en) |
-
2023
- 2023-06-06 CN CN202310663801.5A patent/CN116693488A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105061775B (en) | It is a kind of that the method for preparing new fluorescent organic solid material is assembled by Cucurbituril anion | |
| CN111303867B (en) | Application of diarylethene compounds in fingerprint fluorescence color development | |
| Wang et al. | Carbon dot powders with cross-linking-based long-wavelength emission for multicolor imaging of latent fingerprints | |
| CA2622283A1 (en) | Method for obtaining highly luminescent lanthanide complexes | |
| CN107311957A (en) | One kind is based on aggregation-induced emission and excited state intramolecular proton transfer compound and its preparation method and application | |
| CN113582931A (en) | Fluorescent dye probe for latent fingerprint detection and preparation method and application thereof | |
| Di Pietro et al. | New Coumarin Dipicolinate Europium Complexes with a Rich Chemical Speciation and Tunable Luminescence | |
| CN116693488A (en) | Coumarin dye capable of being used for latent fingerprint development and technical field of preparation method of fingerprint powder | |
| CN114573622A (en) | Linear type boron-dipyrromethene electron donor with 180-degree coordination angle, supramolecular metallare, synthesis process and application | |
| CN115160253B (en) | Fluorescent dye probe for detecting latent fingerprints based on NBD fluorophores and preparation method and application thereof | |
| CN108314636A (en) | A kind of polyaryl sulphur oscillation luminescent material and its preparation method and application | |
| CN102660254B (en) | Iridium complex-containing phosphorescent material, preparation method and application in mercury ion detection | |
| CN114805130A (en) | Fluorescent powder material for displaying latent fingerprints and application thereof | |
| CN116855100B (en) | Triphenylamine dye capable of being directly used for latent fingerprint development and preparation method and application thereof | |
| CN113087878B (en) | Fluorescent conjugated polymer, preparation method and application in oil fingerprint and blood fingerprint display | |
| CA2411414C (en) | A novel expanded porphyrin and a method for synthesis thereof | |
| CN111303141B (en) | 2- (2-hydroxyphenyl) benzothiazole derivative, preparation method thereof and application thereof in fluorescence anti-counterfeiting | |
| EP3788118A1 (en) | Powder formed from "core-envelope"-type particles, comprising coordination polymers containing rare earths, method for the production thereof, material and use derived there-from | |
| CN116400068B (en) | Reagent for revealing potential biological trace containing DNA and revealing method | |
| Durgi et al. | Solid‐State Organic Fluorophore for Latent Fingerprint Detection and Anti‐Counterfeiting Applications | |
| Mostafa et al. | Synthesis and photophysical properties of fluorescein esters as potential organic semiconductor materials | |
| CN116655480A (en) | Responsive color-changing fluorescent dye and preparation method and application thereof | |
| CN113121798B (en) | Water-soluble cationic fluorescent conjugated polymer, preparation method and application in fingerprint appearance | |
| Lianglu et al. | Synthesis of a Tetrahedral Metal–Organic Supramolecular Cage with Dendritic Carbazole Arms | |
| CN116769467A (en) | Supermolecule light capturing system based on column [5] arene, preparation method thereof and application thereof in latent fingerprint imaging |
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 |