CN116655480A - Responsive color-changing fluorescent dye and preparation method and application thereof - Google Patents
Responsive color-changing fluorescent dye and preparation method and application thereof Download PDFInfo
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 103
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 112
- 230000004044 response Effects 0.000 claims abstract description 31
- SNWQUNCRDLUDEX-UHFFFAOYSA-N inden-1-one Chemical class C1=CC=C2C(=O)C=CC2=C1 SNWQUNCRDLUDEX-UHFFFAOYSA-N 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011521 glass Substances 0.000 claims description 16
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 238000000227 grinding Methods 0.000 claims description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 238000001291 vacuum drying Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 239000010985 leather Substances 0.000 claims description 8
- 230000001105 regulatory effect Effects 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- -1 nitro, amino, methoxy Chemical group 0.000 claims description 5
- 238000012632 fluorescent imaging Methods 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000011161 development Methods 0.000 abstract description 13
- 230000008859 change Effects 0.000 abstract description 11
- 238000003384 imaging method Methods 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 10
- 239000004519 grease Substances 0.000 abstract description 5
- 238000011840 criminal investigation Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 16
- 238000001228 spectrum Methods 0.000 description 16
- 108020004414 DNA Proteins 0.000 description 14
- 238000001514 detection method Methods 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 239000002390 adhesive tape Substances 0.000 description 9
- 241000220225 Malus Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000002604 ultrasonography Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000012634 fragment Substances 0.000 description 5
- 239000006247 magnetic powder Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 235000021016 apples Nutrition 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012800 visualization Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 102000053602 DNA Human genes 0.000 description 3
- 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 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052901 montmorillonite Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- 238000012822 chemical development Methods 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
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000001502 gel electrophoresis Methods 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- UUNZJPCKMDLQPO-UHFFFAOYSA-N 4-nitro-inden-1-one Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=CC2=O UUNZJPCKMDLQPO-UHFFFAOYSA-N 0.000 description 1
- GDISUFGKUMDDGG-UHFFFAOYSA-N 5-bromoinden-1-one Chemical compound BrC1=CC=C2C(=O)C=CC2=C1 GDISUFGKUMDDGG-UHFFFAOYSA-N 0.000 description 1
- GOYSNRKWKPRHEA-UHFFFAOYSA-N 5-hydroxyinden-1-one Chemical compound OC1=CC=C2C(=O)C=CC2=C1 GOYSNRKWKPRHEA-UHFFFAOYSA-N 0.000 description 1
- RUBAXSSGWHONDJ-UHFFFAOYSA-N 5-methoxyinden-1-one Chemical compound COC1=CC=C2C(=O)C=CC2=C1 RUBAXSSGWHONDJ-UHFFFAOYSA-N 0.000 description 1
- KMKOJHXZHZFMSQ-UHFFFAOYSA-N 6-nitroinden-1-one Chemical compound [O-][N+](=O)C1=CC=C2C=CC(=O)C2=C1 KMKOJHXZHZFMSQ-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
- 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
- 108020004682 Single-Stranded DNA Proteins 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 238000011897 real-time detection Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
Abstract
The application provides a grease response type color-changing fluorescent dye, which is synthesized by taking 4-formyltrianiline and indenone compounds as raw materials, has a structure different from the existing fluorescent dye, is a novel grease response type fluorescent dye, has the advantages of simple preparation method, high product yield, good stability and low biotoxicity, can respond to potential fingerprints to cause color change when being applied to fluorescent fingerprint powder, and has higher contrast ratio, anti-interference performance and biocompatibility compared with other fluorescent dyes, can realize imaging effects of high resolution, high contrast ratio, strong anti-interference performance and real-time development, and has wide application prospect in the identification of the potential fingerprints in complex criminal investigation environment.
Description
Technical Field
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 latent fingerprint developing technology can be divided into a chemical developing method and a physical developing method, wherein the chemical developing method comprises a cyanoacrylate fuming method, a silver nitrate method, an ninhydrin method and the like, and mainly depends on the reaction of a developer and organic matters remained in fingerprints, and the method is classical and stable, but has the defects of incapability of real-time detection, low contrast, high toxicity and the like. The physical development method is mainly powder spraying or metal deposition, and is realized through electrostatic adsorption between fluorescent powder or magnetic powder and finger secretions such as skin grease, amino acid or other chemical substances. Therefore, the physical development method and the chemical development method have respective advantages and disadvantages.
Fluorescent fingerprint powder development stands out in a plurality of methods, and becomes a common latent fingerprint development means in criminal investigation at present. However, the fluorescent fingerprint powder sold in the market at present has no color-changing property, and all places adhered with the fingerprint powder can show fluorescence, so that fingerprints remained on uneven or electrostatic materials are difficult to develop with high resolution, and the requirements of criminal investigation on fingerprint extraction are not met.
Disclosure of Invention
The embodiment of the application provides a response type color-changing fluorescent dye, a preparation method and application thereof, wherein the structure of the response type color-changing fluorescent dye is different from that of the existing fluorescent dye, and the response type color-changing fluorescent dye is novel.
The technical scheme of the application is as follows:
in a first aspect, the present application provides a responsive color-changing fluorescent dye having the structure of formula I:
wherein R is at least one of hydrogen, bromine, fluorine, hydroxyl, nitro, amino, methoxy or methyl.
In a second aspect, the application also provides a preparation method of the response type color-changing fluorescent dye, which specifically comprises the following steps:
step 1, weighing 4-formyltrianiline, indenone compounds and NaOH according to a certain molar ratio, placing the materials into a flask, adding a certain amount of absolute ethyl alcohol, heating and stirring for reaction, and cooling to room temperature after TLC monitoring reaction is completed;
and 2, regulating the pH value to 6-7 by using a saturated potassium carbonate solution, extracting by using ethyl acetate, then vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, namely the response type color-changing fluorescent dye.
The reaction process is shown in a formula II:
specifically, the molar ratio of the 4-formyltrianiline, the indenone compound and NaOH is 1:1:1.5.
Specifically, the heating temperature is 40-50 ℃, and the stirring time is 10-14 h.
In a second aspect, the application also provides application of the response type color-changing fluorescent dye, which is prepared into fluorescent fingerprint powder and applied to the latent fingerprint identification.
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 a carrier, uniformly mixing by ultrasonic, evaporating the solvent by a rotary evaporator, and grinding and drying to obtain fluorescent fingerprint powder.
Specifically, the mass ratio of the response type color-changing fluorescent dye to the carrier in the preparation of the fluorescent fingerprint powder is 0.001:1-0.02:1.
Specifically, the carrier is at least one selected from montmorillonite, silicon dioxide or magnetic powder.
Specifically, the application in the latent fingerprint identification specifically comprises the following steps:
step 1, coating prepared fluorescent fingerprint powder on the surface area where the latent fingerprints are located, and removing the fluorescent fingerprint powder which is not adsorbed;
and 2, irradiating the surface area of the latent fingerprint by using an ultraviolet light source, wherein the fluorescent fingerprint powder presents orange red of the fluorescent fingerprint powder in the fingerprint-free area, and presents bright yellow at the fingerprint-containing part to obtain the response type color-changing fluorescent 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 glass, tinfoil, apple, leather and coin.
The 4-formyltrianiline and indenone compounds are used as raw materials, and the response type color-changing fluorescent dye is obtained through condensation reaction, and has photochromic fluorescence color-changing performance after being prepared into fluorescent fingerprint powder, wherein the color-changing response principle is that the prepared fluorescent dye interacts with grease secretion of fingers, such as oleic acid, cholesterol and the like to cause color change, namely orange red carried by the fluorescent dye changes into bright yellow. The fluorescent dye has the chemical molecular structure of containing triphenylamine structural unit and indenone unit as fluorophores, and the triphenylamine structural unit and the indenone unit are connected through carbon-carbon double bonds, so that the fluorescent dye has the advantages of simple crystal structure, good light stability, enhanced light sensitivity, high fluorescence efficiency, good biocompatibility and low toxicity. Because of good fat solubility, the fingerprint identification device can be combined with trace grease in finger secretion, and fluorescent color change is caused by change of dissolution environment, so that the latent fingerprint can be displayed, and fingerprint identification efficiency and 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 fluorescent dye is prepared by the steps of easily obtaining raw materials required by preparation, simple preparation process and low production cost, a target product can be obtained by only two steps, the yield is high, the product stability 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 identification of the latent fingerprints, and after the fluorescent fingerprint powder responds to the fingerprints, the color change occurs, and the fluorescent fingerprint powder combines the advantages of a physical development method and a chemical development method, and has the excellent imaging effects of strong interference resistance, high resolution, high contrast, high fingerprint appearance precision, no damage to DNA information in the fingerprints, real-time development and the like;
(3) The fluorescent fingerprint powder prepared by the application is not limited by the material of the substrate in the latent fingerprint identification, and can show the latent fingerprint developing effect in the areas of residual fingerprints on various substrates such as leather, coins, apples, and the like, so that the applicability of the fingerprint powder is widened, and the interference caused by signals of the fluorescent fingerprint powder is reduced. A step of
Drawings
In order to more clearly illustrate 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 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 skilled in the art.
FIG. 1 shows the fluorescence spectrum and photo changes of the a-fluorescent fingerprint powder prepared in example 1 under ultraviolet light before and after the response of the a-fluorescent fingerprint powder and the latent fingerprint;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the a-responsive color-changing fluorescent dye prepared in example 1;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the b-responsive color-changing fluorescent dye prepared in example 2;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the c-responsive color-changing fluorescent dye prepared in example 3;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the d-responsive color-changing fluorescent dye prepared in example 4;
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the e-responsive color-changing fluorescent dye prepared in example 5;
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum of the f-responsive color-changing fluorescent dye prepared in example 6;
FIG. 8 is a nuclear magnetic resonance hydrogen spectrum of the g-responsive color-changing fluorescent dye prepared in example 7;
FIG. 9 is a nuclear magnetic resonance hydrogen spectrum of the h-responsive color-changing fluorescent dye prepared in example 8;
FIG. 10a shows the effect of the a-fluorescent fingerprint powder prepared in example 1 after development of latent fingerprints on glass and 15 days of storage;
FIG. 10b is a graph showing the latent fingerprint imaging on glass 15 days ago with the a-fluorescent fingerprint powder prepared in example 1;
FIG. 10c is a detailed analysis of latent fingerprint imaging on glass using the a-fluorescent fingerprint powder prepared in example 1;
FIG. 10d is a graph showing the effect of developing the latent fingerprints on glass with black tape after developing the latent fingerprints on glass with the a-fluorescent fingerprint powder prepared in example 1, and comparing gray values;
FIG. 11a is a graph showing the effect of rubbing with transparent adhesive tape after developing the latent fingerprint on tinfoil with the a-fluorescent fingerprint powder prepared in example 1, and comparing gray values;
FIG. 11b is a graph showing the comparison of the fingerprint information before and after rubbing with transparent adhesive tape after developing the latent fingerprint on tinfoil with the fluorescent fingerprint powder of the a-fluorescent fingerprint powder prepared in example 1;
FIG. 11c is an electron microscope image of the prepared a-fluorescent fingerprint powder of example 1 for latent fingerprint imaging on tinfoil;
FIG. 12 is a graph of latent fingerprint images and gray scale contrast analysis of the a-fluorescent fingerprint powder prepared in example 1 for apples;
FIG. 13 is a graph of latent fingerprint images and gray scale contrast analysis of the a-fluorescent fingerprint powder prepared in example 1 for leather;
FIG. 14 is a graph of latent fingerprint images and gray scale contrast analysis of the a-fluorescent fingerprint powder prepared in example 1 for use on coins;
FIG. 15 is a graph showing the change of DNA fragments of d-responsive color-changing fluorescent dye at different molar ratios;
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 an a-responsive color-changing fluorescent dye:
placing 2mmol of 4-formyltrianiline, 2mmol of 1-indenone and 3mmol of NaOH in a 50ml flask, adding 20ml of ethanol, heating to 50 ℃ and stirring for 12h, detecting the reaction to be complete by TLC, and cooling to room temperature;
adjusting pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, namely the a-responsive color-changing fluorescent dye, with a yield of 88.43%.
The structure of the a-responsive color-changing fluorescent dye is shown in formula Ia, namely (E) -2- (4- (diphenylamino) benzyl) -1-indenone:
the synthetic route for the a-responsive metameric fluorescent dye prepared in example 1 is shown in formula IIa:
preparing a-fluorescent fingerprint powder:
20mg of the a-fluorescent dye prepared in example 1 is taken and dissolved in ethanol solution, 3g of montmorillonite is added, after being mixed uniformly by ultrasound, the solvent is evaporated by a rotary evaporator, and then the a-fluorescent fingerprint powder is obtained by grinding and drying.
Color change response:
FIG. 1 shows the fluorescence spectrum and photo changes of the a-fluorescent fingerprint powder prepared in example 1 under ultraviolet light before and after the response of the a-fluorescent fingerprint powder and the latent fingerprint. The fluorescent fingerprint powder is orange powder, emits orange-red fluorescence, presents bright yellow in the place with the fingerprint after fingerprint development, has a maximum emission wavelength of 605nm before response, has a maximum emission wavelength of 560nm after response with CIE coordinates of (0.519,0.468) and has CIE coordinates of (0.376,0.442) as shown in figure 1, and can observe obvious fluorescent color change.
Nuclear magnetic detection results:
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the a-responsive color-changing fluorescent dye prepared in example 1.
The nuclear magnetic information is:
1 H NMR(500MHz,Chloroform-d)δ7.94(d,J＝7.6Hz,1H),7.69-7.59(m,2H),7.60-7.54(m,3H),7.45(t,J＝7.4Hz,1H),7.38-7.27(m,3H),7.22–7.08(m,9H),4.06-4.01(m,2H)。
the results show that the compound prepared in this example has the structure shown in formula Ia.
Example 2
Preparation of b-responsive color-changing fluorescent dye:
placing 4mmol of 4-formyltrianiline, 4mmol of 5-bromo-1-indenone and 6mmol of NaOH in a 90ml flask, adding 40ml of ethanol, heating to 50 ℃ and stirring for 14h, detecting the reaction to be complete by TLC, and cooling to room temperature;
regulating pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, which is the b-responsive color-changing fluorescent dye with a yield of 87.81%.
The structure of the b-responsive color-changing fluorescent dye, namely (E) -2- (4- (diphenylamino) benzyl) -5-bromo-1-indenone is shown as a formula Ib:
the synthetic route of the b-responsive color-changing fluorescent dye is shown in a formula IIb:
b-fluorescent fingerprint powder is prepared:
20mg of the b-fluorescent dye prepared in the example 2 is taken and dissolved in ethanol solution, 3g of silicon dioxide is added, after being uniformly mixed by ultrasound, the solvent is evaporated by a rotary evaporator, and then the b-fluorescent fingerprint powder is obtained by grinding and drying.
Nuclear magnetic detection results:
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the b-responsive color-changing fluorescent dye prepared in example 2.
The nuclear magnetic information is:
1 H NMR(500MHz,Chloroform-d)δ7.79(d,J＝8.1Hz,1H),7.73(s,1H),7.67(s,1H),7.59(d,J＝8.0Hz,1H),7.55(d,J＝8.8Hz,2H),7.35(t,J＝7.9Hz,4H),7.20(d,J＝7.9Hz,4H),7.16(t,J＝7.4Hz,2H),7.10(d,J＝8.8Hz,2H),4.01(s,2H)。
the results show that the compound prepared in this example has the structure shown in formula Ib.
Example 3
Preparation of c-responsive color-changing fluorescent dye:
1.5mmol of 4-formyltrianiline, 1.5mmol of 5-fluoro-1-hydroxy indenone and 2.25mmol of NaOH are placed in a 35ml flask, 15ml of ethanol is added, the mixture is heated to 45 ℃ and stirred for 10 hours, TLC detection reaction is completed, and the mixture is cooled to room temperature;
regulating pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, which is the c-responsive color-changing fluorescent dye with a yield of 84.98%.
The structure of the c-responsive color-changing fluorescent dye, namely (E) -2- (4- (diphenylamino) benzyl) -5-fluoro-1-indenone is shown as a formula Ic:
the synthetic route of the c-responsive color-changing fluorescent dye is shown in a formula IIc:
c-optical fingerprint powder is prepared:
15mg of the c-fluorescent dye prepared in example 3 is taken and dissolved in ethanol solution, 2g of magnetic powder is added, after being uniformly mixed by ultrasound, the solvent is evaporated by a rotary evaporator, and then the c-fluorescent fingerprint powder is obtained by grinding and drying.
Nuclear magnetic detection results:
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the c-responsive color-changing fluorescent dye prepared in example 3.
The nuclear magnetic information is:
1 H NMR(500MHz,Chloroform-d)δ7.94(dd,J＝8.5,5.3Hz,1H),7.63(d,J＝2.2Hz,1H),7.55(d,J＝8.7Hz,2H),7.35(d,J＝15.7Hz,2H),7.29(s,1H),7.26-7.07(m,11H),4.02(s,2H)。
the results show that the compound prepared in this example has the structure shown in formula Ic.
Example 4
Preparing d-responsive color-changing fluorescent dye:
1.5mmol of 4-formyltrianiline, 1.5mmol of 5-hydroxy-1-indenone and 2.25mmol of NaOH are placed in a 35ml flask, 15ml of ethanol is added, the mixture is heated to 45 ℃ and stirred for 10 hours, TLC detection reaction is carried out until the reaction is complete, and the mixture is cooled to room temperature;
regulating pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, which is the d-responsive color-changing fluorescent dye with a yield of 84.98%.
The structure of the d-responsive color-changing fluorescent dye, namely-2- (4- (diphenylamino) benzyl) -5-hydroxy-1-indenone, is shown as a formula Id:
the synthetic route of the d-responsive color-changing fluorescent dye is shown as a formula IId:
preparing d-optical fingerprint powder:
dissolving 15mg of the d-fluorescent dye prepared in the example 4 in ethanol solution, adding 2g of magnetic powder, uniformly mixing by ultrasonic, evaporating the solvent by a rotary evaporator, grinding and drying to obtain the d-fluorescent fingerprint powder.
Nuclear magnetic detection results:
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the d-responsive color-changing fluorescent dye prepared in example 4.
The nuclear magnetic information is:
1 H NMR(500MHz,DMSO-d 6 )δ10.55(s,1H),7.64(t,J＝8.4Hz,3H),7.38(q,J＝9.3,8.5Hz,5H),7.15(dd,J＝20.2,7.7Hz,6H),7.00–6.93(m,3H),6.86(dd,J＝8.4,2.0Hz,1H),3.97(s,2H). 13 C NMR(126MHz,DMSO-d 6 )δ191.68,164.79,153.17,148.81,146.80,134.06,132.38,131.04,130.22,129.68,128.70,126.01,125.62,124.68,121.48,32.31.HRMS:m/z[M+H] + calcd for C 28 H 22 NO 2 + 。
the results show that the compound prepared in this example has the structure shown in formula Id.
Example 5
Preparation of an e-responsive color-changing fluorescent dye:
1.5mmol of 4-formyltrianiline, 1.5mmol of 5-methoxy-1-indenone and 2.25mmol of NaOH are placed in a 35ml flask, 15ml of ethanol is added, the mixture is heated to 40 ℃ and stirred for 12 hours, TLC detection reaction is completed, and the mixture is cooled to room temperature;
regulating pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, which is the e-responsive color-changing fluorescent dye with a yield of 81.28%.
The structure of the E-responsive color-changing fluorescent dye, namely (E) -2- (4- (diphenylamino) benzyl) -5-methoxy-1-indenone is shown as a formula Ie:
the synthetic route of the e-responsive color-changing fluorescent dye is shown in a formula IIe:
preparing e-optical fingerprint powder:
15mg of the e-fluorescent dye prepared in example 5 is taken and dissolved in ethanol solution, 2g of magnetic powder is added, after being mixed uniformly by ultrasound, the solvent is evaporated by a rotary evaporator, and then the e-fluorescent fingerprint powder is obtained by grinding and drying.
Nuclear magnetic detection results:
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the e-responsive color-changing fluorescent dye prepared in example 5.
The nuclear magnetic information is:
1 H NMR(500MHz,Chloroform-d)δ7.88(d,J＝8.5Hz,1H),7.69–7.48(m,2H),7.39–7.32(m,4H),7.19(d,J＝7.5Hz,4H),7.16–7.07(m,3H),7.02–6.98(m,1H),3.99(s,2H),3.94(s,3H).13C NMR(126MHz,Chloroform-d)δ192.81,164.98,152.25,149.05,146.88,132.66(d,J＝27.8Hz),131.84,129.49,128.61,125.98,125.44,124.05,121.64,115.05,109.74,55.66,32.65.HRMS:m/z[M+H] + calcd for C 29 H 24 NO 2 + ,Theory:418.1807,Found:418.1802。
the results show that the compound prepared in this example has the structure shown in formula Ie.
Example 6
Preparing f-response color-changing fluorescent dye:
placing 4mmol of 4-formyltrianiline, 4mmol of 6-nitro-1-indenone and 6mmol of NaOH into a 90ml flask, adding 40ml of ethanol, heating to 50 ℃ and stirring for 14h, detecting the reaction to be complete by TLC, and cooling to room temperature;
regulating pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, which is the f-responsive color-changing fluorescent dye with a yield of 87.81%.
The f-responsive color-changing fluorescent dye, namely (E) -2- (4- (diphenylamino) benzyl) -6-nitro-1-indenone has a structure shown in a formula If:
the synthetic route of the f-responsive color-changing fluorescent dye is shown as a formula IIf:
preparing f-fluorescent fingerprint powder:
20mg of the f-fluorescent dye prepared in example 6 is taken and dissolved in ethanol solution, 3g of silicon dioxide is added, after being mixed uniformly by ultrasound, the solvent is evaporated by a rotary evaporator, and then the f-fluorescent fingerprint powder is obtained by grinding and drying.
Nuclear magnetic detection results:
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum of the f-responsive color-changing fluorescent dye prepared in example 6.
The nuclear magnetic information is:
1 H NMR(500MHz,DMSO-d 6 )δ8.53(dd,J＝8.4,2.3Hz,1H),8.43(d,J＝2.3Hz,1H),7.93(d,J＝8.4Hz,1H),7.72(d,J＝8.7Hz,2H),7.58(s,1H),7.41(t,J＝7.8Hz,4H),7.19(dd,J＝20.6,7.6Hz,6H),6.97(d,J＝8.7Hz,2H),4.24(d,J＝2.1Hz,2H).13C NMR(126MHz,Chloroform-d)δ192.01,154.95,150.05,148.04,146.46,139.61,136.09,132.44,130.52,129.62,128.28,127.11(d,J＝21.1Hz),125.84,124.61,120.87,119.43,32.86,29.70.HRMS:m/z[M+H] + calcd for C 29 H 24 NO 2 + ,Theory:433.1547,Found:433.1555。
the results show that the compound prepared in this example has the structure shown in formula If.
Example 7
Preparation of g-responsive color-changing fluorescent dye:
placing 2mmol of 4-formyl triphenylamine, 2mmol of 4-nitro-1-indenone and 3mmol of NaOH into a 50ml flask, adding 20ml of ethanol, heating to 50 ℃ and stirring for 12h, detecting the reaction to be complete by TLC, and cooling to room temperature;
adjusting pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, namely g-responsive color-changing fluorescent dye, with a yield of 84.15%.
The structure of the g-responsive color-changing fluorescent dye is shown in formula Ia, namely (E) -2- (4- (diphenylamino) benzyl) -4-nitro-1-indenone:
the synthetic route for the g-responsive metameric fluorescent dye prepared in example 7 is shown in formula IIg:
preparing g-fluorescent fingerprint powder:
20mg of the g-fluorescent dye prepared in example 7 is taken and dissolved in ethanol solution, 3g of montmorillonite is added, after being mixed uniformly by ultrasound, the solvent is evaporated by a rotary evaporator, and then the g-fluorescent fingerprint powder is obtained by grinding and drying.
Nuclear magnetic detection results:
FIG. 8 is a nuclear magnetic resonance hydrogen spectrum of the g-responsive color-changing fluorescent dye prepared in example 7.
The nuclear magnetic information is:
1 H NMR(500MHz,DMSO-d 6 )δ8.50(d,J＝8.0Hz,1H),8.26(d,J＝7.5Hz,1H),7.74(s,1H),7.69(t,J＝7.8Hz,1H),7.64(d,J＝8.8Hz,1H),7.37(t,J＝7.9Hz,4H),7.29(s,1H),7.26–7.15(m,6H),7.13(d,J＝8.8Hz,2H),4.50(s,2H).13C NMR(126MHz,Chloroform-d)δ191.79,150.11,146.48,145.79,144.14,141.57,136.17,132.63,130.00,129.79,129.63,129.19,128.86,127.18,125.88,124.61,120.88,33.66.HRMS:m/z[M+H] + calcd for C 29 H 24 NO 2 + ,Theory:433.1547,Found:433.1561。
the results show that the compound prepared in this example has the structure shown in formula Ig.
Example 8
Preparing an h-responsive color-changing fluorescent dye:
placing 4mmol of 4-formyltrianiline, 4mmol of 6-amino-1-indenone and 6mmol of NaOH into a 90ml flask, adding 40ml of ethanol, heating to 50 ℃ and stirring for 14h, detecting the reaction by TLC until the reaction is complete, and cooling to room temperature;
regulating pH to 7 with saturated potassium carbonate solution, extracting with ethyl acetate, vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, which is the h-responsive color-changing fluorescent dye with a yield of 87.81%.
The structure of the h-responsive color-changing fluorescent dye, namely (E) -2- (4- (diphenylamino) benzyl) -6-amino-1-indenone is shown as a formula Ih:
the synthetic route of the h-responsive color-changing fluorescent dye is shown in a formula IIh:
preparing h-fluorescent fingerprint powder:
20mg of the h-fluorescent dye prepared in example 8 is taken and dissolved in ethanol solution, 3g of silicon dioxide is added, after being uniformly mixed by ultrasound, the h-fluorescent fingerprint powder is obtained after grinding and drying after solvent evaporation by a rotary evaporator.
Nuclear magnetic detection results:
FIG. 9 is a nuclear magnetic resonance hydrogen spectrum of the h-responsive color-changing fluorescent dye prepared in example 8.
The nuclear magnetic information is:
1 H NMR(500MHz,Chloroform-d)δ7.60(d,J＝2.1Hz,1H),7.58–7.51(m,2H),7.38–7.31(m,5H),7.22–7.16(m,5H),7.14(td,J＝7.3,1.4Hz,2H),7.09(dd,J＝9.0,2.1Hz,2H),6.98(dd,J＝8.0,2.4Hz,1H),3.92(d,J＝2.0Hz,2H),3.84(s,2H).13C NMR(126MHz,Chloroform-d)δ193.57,148.27,145.96,145.27,139.08,138.57,132.49,132.41,131.09,128.61,127.68,125.71,124.59,123.20,121.48,120.66,107.77,31.00,28.81.HRMS:m/z[M+H] + calcd for C 29 H 24 NO 2 + ,Theory:403.1805,Found:403.1809。
the results show that the compound prepared in this example has the structure shown in formula Ih.
Example 9
Latent fingerprint visualization by applying the a-fluorescent fingerprint powder prepared in example 1 to glass surface
Dipping a small amount of prepared fluorescent fingerprint powder by using a brush, coating the fluorescent fingerprint powder on the surface area of the glass where the latent fingerprint is located, removing the fluorescent fingerprint powder which is not adsorbed by using an ear cleaning ball, standing for 1min, irradiating by using a 365m ultraviolet lamp, and shooting by using a camera to obtain a fingerprint image.
Obtaining a latent fingerprint copy:
and (3) flatly covering the developed fingerprint surface with a black adhesive tape, and taking down the adhesive tape after pressing and attaching to obtain a copy.
The fluorescent fingerprint powder is orange powder, emits orange-red fluorescence, presents bright yellow color at the position with the fingerprint after the development of the fingerprint, can observe the bright yellow color change at the position with the fingerprint after the irradiation of an ultraviolet lamp, and is photographed by a camera to obtain clear fingerprint imaging. The fingerprint image can obtain various characteristic information contained in the fingerprint, including level 2 and level 3 characteristics.
FIG. 10a shows the effect of the a-fluorescent fingerprint powder prepared in example 1 after development of latent fingerprints on glass and 15 days of storage; as can be seen from fig. 10a, the fingerprint appearance information is complete, the glass after fingerprint development has no change after 15 days of storage, and the fingerprint detail information is still clearly visible.
FIG. 10b is a graph showing the latent fingerprint imaging on glass 15 days ago with the a-fluorescent fingerprint powder prepared in example 1; from fig. 10b, it can be seen that the a-fluorescent fingerprint powder was used for the latent fingerprint image on the glass 15 days ago, and the fingerprint information was still clearly visible;
FIG. 10c is a detailed analysis of latent fingerprint imaging on glass using the a-fluorescent fingerprint powder prepared in example 1; as can be seen from fig. 10c, the fingerprint appears with high accuracy, and the 3-level features including sweat pores are also fully visible.
FIG. 10d is a graph showing the effect of developing the latent fingerprints on glass with black tape after developing the latent fingerprints on glass with the a-fluorescent fingerprint powder prepared in example 1, and comparing gray values; it can be seen from fig. 10d that the developed fingerprint is imprinted with a black tape, the copy information is complete, and it is proved that the developed fingerprint has a high contrast to highlight the potential fingerprint by a high gray scale contrast value.
Example 10
Latent fingerprint development by applying the a-fluorescent fingerprint powder prepared in example 1 to the surface of tinfoil
A small amount of prepared fluorescent fingerprint powder is dipped by a brush, coated on the surface area of the tinfoil where the latent fingerprint is located, the fluorescent fingerprint powder which is not adsorbed is removed by an ear washing ball, after the fluorescent fingerprint powder stays for 30 seconds, the fluorescent fingerprint powder is irradiated by a 365nm ultraviolet lamp, the part with the fingerprint is bright yellow, and a clear fingerprint image is obtained by shooting by a camera.
Obtaining a latent fingerprint copy:
and flatly covering the developed fingerprint surface by using a transparent adhesive tape, and taking down the adhesive tape after pressing and attaching to obtain a copy.
FIG. 11a is a graph showing the effect of rubbing with transparent adhesive tape after developing the latent fingerprint on tinfoil with the a-fluorescent fingerprint powder prepared in example 1, and comparing gray values; it can be seen from fig. 11a that the developed fingerprint is subjected to rubbing by using the transparent adhesive tape, the copy information is complete, the developed fingerprint has high contrast through the gray level contrast value, and the potential fingerprint and the information thereof can be obviously observed.
FIG. 11b is a graph showing the comparison of the fingerprint information before and after rubbing with transparent adhesive tape after developing the latent fingerprint on tinfoil with the fluorescent fingerprint powder of the a-fluorescent fingerprint powder prepared in example 1; as can be seen from fig. 11b, the fingerprint appearance accuracy is high, and fine information such as the 3-level characteristic effect (sweat pore distribution) can be visually observed.
FIG. 11c is an electron microscope image of the prepared a-fluorescent fingerprint powder of example 1 for latent fingerprint imaging on tinfoil; as can be seen from FIG. 11c, fine information such as ridge width, gap, sweat pore diameter and the like of the fingerprint can be obtained through a scanning electron microscope means.
Example 11
Latent fingerprint visualization by applying the a-fluorescent fingerprint powder prepared in example 1 to apple surface
A small amount of prepared a-fluorescent fingerprint powder is dipped by a brush and coated on the surface area of the latent fingerprints on apples, the fluorescent fingerprint powder which is not adsorbed is removed by an ear washing ball, after the black fingerprint powder stays for 50 seconds, the black fingerprint powder is irradiated by a 380nm ultraviolet lamp, the portion with the fingerprints is bright yellow, and a clear fingerprint image is obtained by shooting by a camera.
FIG. 12 is a graph of latent fingerprint images and gray scale contrast analysis of the a-fluorescent fingerprint powder prepared in example 1 for apples; as can be seen from fig. 12, on the surface of the apple, the fingerprint has high appearance accuracy and complete fingerprint information, and the potential fingerprint and the information thereof can be obviously observed by proving that the apple has high contrast through gray scale contrast values.
Example 12
Latent fingerprint visualization by applying the a-fluorescent fingerprint powder prepared in example 1 to leather surface
Dipping a small amount of prepared fluorescent fingerprint powder by using a brush, coating the fluorescent fingerprint powder on the surface area of the leather where the latent fingerprint is located, removing the fluorescent fingerprint powder which is not adsorbed by using an ear washing ball, after the fluorescent fingerprint powder stays for 30 seconds, radiating by using a 365nm ultraviolet lamp, and obtaining the response type color-changing fluorescent imaging of the latent fingerprint by using a bright yellow part with the fingerprint. The fluorescent fingerprint powder is orange powder, emits orange-red fluorescence, is bright yellow at the part with the fingerprint, and is photographed by a camera to obtain clear fingerprint imaging.
FIG. 13 is a graph of latent fingerprint images and gray scale contrast analysis of the a-fluorescent fingerprint powder prepared in example 1 for leather; as can be seen from fig. 13, on the leather surface, the fingerprint has high accuracy, the fingerprint information is complete, and the fingerprint has high contrast as proved by the gray scale contrast value, so that the potential fingerprint and the information thereof can be obviously observed.
Example 13
Latent fingerprint visualization by applying the fluorescent fingerprint powder prepared in example 1 to coin surface
Dipping a small amount of prepared fluorescent fingerprint powder by using a brush, coating the fluorescent fingerprint powder on the surface area of the latent fingerprint on the coin, removing the fluorescent fingerprint powder which is not adsorbed by using an ear washing ball, standing for 10 seconds, and then irradiating by using a 410nm ultraviolet lamp, wherein the part with the fingerprint is bright yellow, so as to obtain the response type color-changing fluorescent imaging of the latent fingerprint. The fluorescent fingerprint powder is orange powder, emits orange-red fluorescence, is bright yellow at the part with the fingerprint, and is photographed by a camera to obtain clear fingerprint imaging.
FIG. 14 is a graph of latent fingerprint images and gray scale contrast analysis of the a-fluorescent fingerprint powder prepared in example 1 for use on coins; as can be seen from fig. 14, on the surface of the coin, the fingerprint has high appearance accuracy and complete fingerprint information, and the potential fingerprint and the information thereof can be obviously observed by proving that the coin has high contrast through gray scale contrast values.
DNA gel electrophoresis experiments:
the DNA gel electrophoresis experiment proves that the d-response color-changing fluorescent dye can not induce DNA to hydrolyze or break into smaller fragments, and FIG. 15 is a DNA fragment change chart of the d-response color-changing fluorescent dye in different molar ratios;
channel 1 in FIG. 15 is a marker (for reference to DNA fragment size); channel 2 is pure DNA, channel 3 is pure d-responsive color-changing fluorescent dye, and channels 4-7 are DNA and d-responsive color-changing fluorescent dye in the molar ratio of 1:1,1:10,1:100 and 1:1000 respectively. The experimental process is that the fluorescent dye reacts with double-stranded DNA for 1h at 37 ℃ in advance according to the proportion, and then the d-response color-changing fluorescent dye is subjected to DNA gel experiment. As is clear from fig. 15, double-stranded DNA is not hydrolyzed by dye induction into single-stranded DNA or cut into smaller fragments.
Therefore, in the criminal investigation process, even if the fingerprint comparison fails, the suspected person can be further tracked through extracting the residual DNA in the fingerprint.
The foregoing description of the preferred embodiments of the present application is merely illustrative, and not restrictive, of the application. It will be understood by those skilled in the art that many changes, modifications and even equivalent changes may be made thereto, which fall within the scope of the application as defined by the appended claims.
Claims (10)
1. A responsive color-changing fluorescent dye characterized by having the structure of formula I:
wherein R is at least one of hydrogen, bromine, fluorine, hydroxyl, nitro, amino, methoxy or methyl.
2. A method for preparing a responsive color-changing fluorescent dye as claimed in claim 1, comprising the steps of:
step 1, weighing 4-formyltrianiline, indenone compounds and NaOH according to a certain molar ratio, placing the materials into a flask, adding a certain amount of absolute ethyl alcohol, heating and stirring for reaction, and cooling to room temperature after TLC monitoring reaction is completed;
and 2, regulating the pH value to 6-7 by using a saturated potassium carbonate solution, extracting by using ethyl acetate, then vacuum drying, and separating the product by column chromatography to obtain orange-red solid powder, namely the response type color-changing fluorescent dye.
3. The method for preparing a response type color-changing fluorescent dye according to claim 2, wherein the molar ratio of the 4-formyltrianiline, the indenone compound and the NaOH is 1:1:1.5.
4. The method for preparing a response type color-changing fluorescent dye according to claim 2, wherein the heating temperature is 40-50 ℃ and the stirring time is 10-14 h.
5. The use of the responsive color-changing fluorescent dye according to claim 1, which is prepared into fluorescent fingerprint powder and applied to latent fingerprint identification.
6. The use of a responsive color-changing fluorescent dye as claimed in claim 5, wherein the preparation of the fluorescent fingerprint powder comprises the steps of:
weighing a certain amount of response type color-changing fluorescent dye, dissolving in an organic solvent, adding a carrier, uniformly mixing by ultrasonic, evaporating the solvent by a rotary evaporator, and grinding and drying to obtain fluorescent fingerprint powder.
7. The use of a responsive color-changing fluorescent dye according to claim 6, wherein the mass ratio of the responsive color-changing fluorescent dye to the carrier in the preparation of the fluorescent fingerprint powder is 0.001:1-0.02:1.
8. The application of the responsive color-changing fluorescent dye according to claim 6, which is applied to the identification of latent fingerprints, and specifically comprises the following steps:
step 1, coating prepared fluorescent fingerprint powder on a substrate where the latent fingerprints are positioned, and removing the fluorescent fingerprint powder which is not adsorbed;
and 2, irradiating the substrate on which the latent fingerprint is positioned by using an ultraviolet light source, wherein the fluorescent fingerprint powder is bright yellow at the part with the fingerprint, and obtaining the response type color-changing fluorescent imaging of the latent fingerprint.
9. The use of a responsive color-changing fluorescent dye as claimed in claim 8, wherein the irradiation of the ultraviolet light source is performed under the illumination condition of 350-430 nm wavelength.
10. The use of a responsive color-changing fluorescent dye as claimed in claim 6, wherein the substrate is at least one of glass, tinfoil, apple, leather, coin.
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