CN109651416A - Three fluorescence anti-fake material, preparation method and application based on excitation wavelength dependence - Google Patents
Three fluorescence anti-fake material, preparation method and application based on excitation wavelength dependence Download PDFInfo
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- 230000005284 excitation Effects 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims abstract description 30
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000843 powder Substances 0.000 claims abstract description 17
- 239000003086 colorant Substances 0.000 claims abstract description 13
- 241001116389 Aloe Species 0.000 claims abstract description 11
- 235000011399 aloe vera Nutrition 0.000 claims abstract description 11
- 239000002674 ointment Substances 0.000 claims abstract description 11
- 230000008018 melting Effects 0.000 claims abstract description 4
- 238000002844 melting Methods 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 238000004809 thin layer chromatography Methods 0.000 claims description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 7
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000004570 mortar (masonry) Substances 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000007711 solidification Methods 0.000 claims description 3
- 230000008023 solidification Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002114 nanocomposite Substances 0.000 description 2
- 239000002159 nanocrystal Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- -1 Triphenylene boron Chemical compound 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000005539 phosphorimetry Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
- B41M3/14—Security printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Credit Cards Or The Like (AREA)
- Medicinal Preparation (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
A kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, the following steps are included: being coupled Sanya phenyl boric acid and 4- neighbour's carborane bromobenzene to form carborane derivative using Suzuki coupling reaction, by the melting of obtained carborane derivative, it is ground into a powder, it is doped into colourless aloe ointment, pattern is made.It has the characteristics that multiple color fluorescence with pattern made of carborane derivative of the present invention, which is presented three kinds of fluorescence colors, can be used as anti-fake material under three kinds of excitation wavelengths.
Description
Technical field
The invention belongs to technical field of chemistry, and in particular to a kind of anti-fake material of three fluorescence relied on based on excitation wavelength
Material, preparation method and application.
Background technique
Currently, personation has become the worldwide problem got worse, and therefore, the more advanced anti-fake skill of society need
Art means protect important information and things, such as luxury goods, bank note and certificate etc..In in the past few decades, send out
Various anti-counterfeiting technologies have been opened up, including nearest magnetic response technology, plasma safety label and the printing etc. that shines.Wherein because of hair
The characteristics of light printing, which has, is easy design, easy to operate, is easy industrialization, so being most widely applied daily anti-fake
In, it is conventionally used to anti-fake luminescent material and typically exhibits monochrome, it is double-colored, it is dual mode luminous etc..For example, the happy intelligent professor of Lu
(Designing lanthanide-doped nanocrystals with both up-and down-conversion
Luminescence for anti-counterfeiting, Nanoscale.2011,3,4804-4810) it is different by doping
The inorganic nanocrystal of lanthanide series, which is realized, to be converted and lower conversion both of which shines；Song Yanlin teaches (Patterning
Fluorescent Quantum Dot Nanocomposites by Reactive Inkjet Printing,
Small.2015,11,1649-1654) by reactive ink jet printing, the nanocomposite containing fluorescence quantum is carried out figure
Case, to realize anti-fake purpose；Lin Hengwei professor (Triple-Mode Emission of Carbon Dots:
Applications for Advanced Anti-Counterfeiting, Angew.Chem.2016,55,7231-7235) benefit
With a diphenylamines, the polymer of polyvinyl alcohol and the formation of luminous carbon dots realizes luminescence generated by light, upper to convert and three kinds of room temperature phosphorimetry
The anti-fake form of mode.But it is realized using pure small organic molecule and dependable three colors anti-fake material is excited not yet to occur.
Summary of the invention
The object of the present invention is to provide a kind of three fluorescence anti-fake material relied on based on excitation wavelength, preparation method and answer
With it has the characteristics that excitation can rely on polychrome with pattern made of carborane derivative of the present invention, and the material is in three kinds of excitation waves
Under length, three kinds of fluorescence colors are presented, can be used as anti-fake material.
The technical solution adopted by the present invention is that:
A kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, synthetic route are as follows:
It weighs 4- neighbour's carborane bromobenzene (I), Sanya phenyl boric acid (II), tetra-triphenylphosphine palladium and sodium carbonate and is dissolved in tetrahydrofuran
In；Under nitrogen atmosphere protection, 80-100 DEG C is stirred to react 10-15h, meanwhile, determine that raw material reacts in conjunction with thin-layer chromatography (TLC)
After completely, by reaction system water and absolute dichloromethane extracted several times, extraction phase is collected, column chromatographic purifying is used after being spin-dried for again, obtains
To white powder, i.e. target product carborane derivative (III)；Obtained carborane derivative is melted, is ground into mortar
Powder is doped into colourless aloe ointment, and the anti-fake material is made.
Further, 4- carborane bromobenzene (I): Sanya phenyl boric acid (II): tetra-triphenylphosphine palladium: sodium carbonate 1mmol:
1.0-1.2mmol:0.05-0.1mmol:0.5-1.0mmol.
Further, 4- carborane bromobenzene (I): tetrahydrofuran 1mmol:30-40ml.
Further, the leacheate of column chromatography is made of petroleum ether and methylene chloride according to the volume ratio of 10:1.
Further, the mass ratio of carborane derivative and aloe ointment is 1-5%.
Further, different colours are presented in pattern made of the aloe ointment using the doping under three kinds of excitation wavelengths, i.e.,
It is blue under 390nm, white under 365nm, yellow under 254nm, in this, as anti-fake material.
Beneficial effects of the present invention:
It is coupled Sanya phenyl boric acid and 4- carborane bromobenzene to form carborane derivative using Suzuki coupling reaction, through grinding
Study carefully discovery, this derivative is under unformed state, and in different excitation wavelengths, there are three types of different fluorescence colors.To current
Until, realizing the dependable three colors anti-fake material of excitation using pure small organic molecule, there has been no applications, therefore can be used for anti-fake
Aspect.Imagination based on Application in Anti-counterfeiting melts obtained carborane derivative, and solid is doped into colourless aloe ointment after grinding
In ink paste is made, be then printed as required pattern (in two embodiments of the invention, using doggie and two dimension using seal
Code pattern), obtained pattern is irradiated under three kinds of excitation wavelengths, three kinds of fluorescence are presented.This Application in Anti-counterfeiting mode, which has, to be looked into
Proved recipe just and not replaceability the characteristics of.
Detailed description of the invention
Fig. 1 is the molecular structure monocrystalline map of carborane derivative of the present invention；
Fig. 2 is fluorescence spectra of the three fluorescence anti-fake material unformed shape of the present invention under different excitation wavelengths, according to
Fluorescence spectra, under 390nm excitation, peak value is mainly in 420nm, therefore blue is presented in fluorescence, with the reduction of excitation wavelength,
The peak of 560nm gradually increases, become 420 and 560 two it is bimodal, 365nm excitation under, fluorescence present white, excitation wavelength after
It is continuous to reduce, become to account for the peak of 560nm leading, therefore yellow is presented in 254nm excitation；
Fig. 3 is the photograph that different colours are presented in three fluorescence anti-fake material of the present invention (doggie pattern) under three kinds of excitation wavelengths
Piece, blue under 390nm excitation, white under 365nm excitation, lower 254nm excitation is in yellow；
Fig. 4 is that different colours are presented in three fluorescence anti-fake material (pattern in 2 D code) of the present invention under three kinds of excitation wavelengths
Photo, blue under 390nm excitation, white under 365nm excitation, lower 254nm excitation is in yellow.
Specific embodiment
The invention will be further described with reference to embodiments.
It is including following the invention discloses a kind of preparation method of three fluorescence anti-fake material relied on based on excitation wavelength
Step:
Its synthetic route is as follows:
It weighs 4- neighbour's carborane bromobenzene (I), Sanya phenyl boric acid (II), tetra-triphenylphosphine palladium and sodium carbonate and is dissolved in tetrahydrofuran
In；Wherein, 4- carborane bromobenzene (I): Sanya phenyl boric acid (II): tetra-triphenylphosphine palladium: sodium carbonate: tetrahydrofuran 1mmol:1-
1.2mmol:0.05-0.1mmol:0.5-1mmol:30-40ml；Under nitrogen atmosphere protection, 80-100 DEG C of heating stirring reaction,
React 10-15h；Thin-layer chromatography (TLC) determines reaction process, extracts reaction system water and dichloromethane system after terminating reaction
It takes three times, collects extraction phase, do column chromatographic purifying with the leacheate of petroleum ether and methylene chloride 10:1 again after being spin-dried for, obtain white
Powder, i.e. target product carborane derivative (III), wherein 4- carborane bromobenzene (I) molecular weight 299g/mol；Triphenylene boron
Acid (II) 272g/mol；Carborane derivative (III) 446g/mol.
Embodiment 1
A kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, comprising the following steps:
Weigh 4- carborane bromobenzene (I) 0.299g (1mmol), Sanya phenyl boric acid (II) 0.272g (1mmol), four triphenyls
Phosphine palladium 0.057g (0.05mmol) and sodium carbonate 0.0525g (0.5mmol) are dissolved in 30ml tetrahydrofuran；It is protected in nitrogen atmosphere
Under, 80 DEG C of heating stirrings react 10h；Meanwhile reaction process is determined in conjunction with thin-layer chromatography (TLC), it terminates reactant after reacting
System with water and dichloromethane system extraction three times, then with the petroleum ether of 10:1 volume ratio and eluent methylene chloride liquid do column chromatography it is pure
Change, obtain white powder 0.134g, yield 30%, i.e. target product carborane derivative (III), characterize data is as follows:1H
NMR(400MHz,CDCl3) δ 8.81-8.80 (d, J=4Hz, 1H), 8.74-8.66 (m, 5H), 7.86-7.83 (dd, J=8,
4Hz,1H),7.77-7.74(m,2H),7.72-7.67(m,4H),7.65-7.62(m,2H),4.03(s,1H),2.92-2.17
(m,10H),HRMS(MALDI-TOF)m/z:[M]+446.885；
The mono-crystalline structures of molecule are as shown in Figure 1, it can be seen that, carborane derivative prepared by the present invention is brand new object
Matter.
Embodiment 2
A kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, comprising the following steps:
Weigh 4- carborane bromobenzene (I) 0.299g (1mmol), Sanya phenyl boric acid (II) 0.326g (1.2mmol), four triphens
Base phosphine palladium 0.057g (0.05mmol) and sodium carbonate 0.0525g (0.5mmol) are dissolved in 30ml tetrahydrofuran；It is protected in nitrogen atmosphere
Under shield, 80 DEG C of heating stirrings react 12h；Meanwhile reaction process is determined in conjunction with thin-layer chromatography (TLC), it will be reacted after terminating reaction
System water and dichloromethane system extraction three times, then with the leacheate of petroleum ether and methylene chloride 10:1 do column chromatographic purifying,
Obtain white powder 0.147g, yield 33%, i.e. target product carborane derivative (III)；
Embodiment 3
A kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, comprising the following steps:
Weigh 4- carborane bromobenzene (I) 0.299g (1mmol), Sanya phenyl boric acid (II) 0.299g (1.1mmol), four triphens
Base phosphine palladium 0.091g (0.8mmol) and sodium carbonate 0.0525g (0.5mmol) are dissolved in 40ml tetrahydrofuran；It is protected in nitrogen atmosphere
Under shield, 100 DEG C of heating stirrings react 15h；Meanwhile reaction process is determined in conjunction with thin-layer chromatography (TLC), it will be reacted after terminating reaction
System water and dichloromethane system extraction three times, then with the leacheate of petroleum ether and methylene chloride 10:1 do column chromatographic purifying,
Obtain white powder 0.156g, yield 35%, i.e. target product carborane derivative (III)；
Embodiment 4
A kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, comprising the following steps:
Weigh 4- carborane bromobenzene (I) 0.299g (1mmol), Sanya phenyl boric acid (II) 0.326g (1.2mmol), four triphens
Base phosphine palladium 0.114g (0.1mmol) and sodium carbonate 0.0525g (0.5mmol) are dissolved in 40ml tetrahydrofuran；It is protected in nitrogen atmosphere
Under shield, 90 DEG C of heating stirrings react 15h；Meanwhile reaction process is determined in conjunction with thin-layer chromatography (TLC), it will be reacted after terminating reaction
System water and dichloromethane system extraction three times, then with the leacheate of petroleum ether and methylene chloride 10:1 do column chromatographic purifying,
Obtain white powder 0.142g, yield 32%, i.e. target product carborane derivative (III)；Powder, will after melt process
Obtained solid carries out emission spectrum test, and under 390nm excitation, spectrum is mainly in 420nm, with the reduction of excitation wavelength,
There is a peak and gradually increases in 560nm, and formation is bimodal, as shown in Figure 2.
Obtained carborane derivative is melted, is ground into a powder, is doped into colourless aloe ointment, mass ratio in mortar
For 1-5%, the aloe ointment adulterated is patterned with seal, blue is being presented in the case where 390nm is excited for the pattern being prepared,
365nm excitation is lower to be presented white, and yellow is presented under 254nm excitation.
Embodiment 5
A kind of anti-fake form of three colors based on excitation wavelength, comprising the following steps:
It melts, white powder obtained in embodiment 1 by the solid after melting and solidification in mortar under the conditions of 280 DEG C
In be crushed into powder, then powder is doped into colourless aloe ointment, ink paste is made, mass ratio 5% is made small of doggie seal
Dog pattern, obtained doggie pattern are presented different colours under three kinds of excitation wavelengths, blue under 390nm, white under 365nm,
Yellow under 254nm, as shown in Figure 3.
Embodiment 6
A kind of anti-fake form of three colors based on excitation wavelength, comprising the following steps:
It melts, white powder obtained in embodiment 1 by the solid after melting and solidification in mortar under the conditions of 280 DEG C
In be crushed into powder, then powder is doped into colourless aloe ointment, ink paste is made, mass ratio 3% is made of 2 D-code seal
Pattern in 2 D code, obtained pattern in 2 D code are presented different colours under three kinds of excitation wavelengths, blue under 390nm, white under 365nm
Color, yellow under 254nm, as shown in Figure 4.
Above description has shown and described several preferred embodiments of invention, but as previously described, it should be understood that invention is not
It is confined to form disclosed herein, should not be regarded as an exclusion of other examples, and can be used for various other combinations, modification
And environment, and can be carried out within that scope of the inventive concept describe herein by the above teachings or related fields of technology or knowledge
Change.And changes and modifications made by those skilled in the art do not depart from the spirit and scope of invention, then it all should be in the appended power of invention
In the protection scope that benefit requires.
Claims (8)
1. a kind of preparation method of the three fluorescence anti-fake material relied on based on excitation wavelength, which is characterized in that preparation route is such as
Under:
4- neighbour's carborane bromobenzene (I), Sanya phenyl boric acid (II), tetra-triphenylphosphine palladium and sodium carbonate are weighed first is dissolved in tetrahydrofuran
In；Under nitrogen atmosphere protection, 80-100 DEG C is stirred to react 10-15h, meanwhile, raw material fully reacting is determined in conjunction with thin-layer chromatography
Afterwards, by reaction system water and methylene chloride extracted several times, extraction phase is collected, column chromatographic purifying is used after being spin-dried for again, obtains white
Powdered carborane derivative (III)；Finally by after obtained carborane derivative melting and solidification, powder is ground into mortar
End is doped into colourless aloe ointment up to the anti-fake material.
2. the preparation method of the three fluorescence anti-fake material based on excitation wavelength as described in claim 1, which is characterized in that 4-
Adjacent carborane bromobenzene (I): Sanya phenyl boric acid (II): tetra-triphenylphosphine palladium: sodium carbonate 1mmol:1.0-1.2mmol:0.05-
0.1mmol:0.5-1.0mmol.
3. the preparation method of the three fluorescence anti-fake material relied on as described in claim 1 based on excitation wavelength, feature are existed
In 4- neighbour's carborane bromobenzene (I): tetrahydrofuran 1mmol:30-40ml.
4. the preparation method of the three fluorescence anti-fake material relied on as described in claim 1 based on excitation wavelength, feature are existed
In the leacheate of column chromatography is made of petroleum ether and methylene chloride according to the volume ratio of 10:1.
5. the preparation method of the three fluorescence anti-fake material relied on as described in claim 1 based on excitation wavelength, feature are existed
In the mass ratio that carborane derivative accounts for aloe ointment is 1-5%.
6. a kind of three fluorescence anti-fake material relied on based on excitation wavelength, which is characterized in that by any institute of Claims 1 to 5
The method stated is made.
7. a kind of application of the three fluorescence anti-fake material relied on based on excitation wavelength, which is characterized in that by the anti-of claim 6
Seal designs are made in pseudo- material, are then presented different colours under three kinds of excitation wavelengths, i.e. blue under 390nm, white under 365nm
Color, yellow under 254nm.
8. a kind of carborane derivative for three fluorescence anti-fake material, which is characterized in that the structure of the carborane derivative
Structure as described in code name (III) in claim 1.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021058970A1 (en) * | 2019-09-24 | 2021-04-01 | Chromatwist Limited | Polymers |
| CN112898972A (en) * | 2019-12-04 | 2021-06-04 | 中国科学院大连化学物理研究所 | Method for adjusting fluorescence emission wavelength of quantum dot and application |
| CN112940473A (en) * | 2021-02-01 | 2021-06-11 | 浙江播下环保科技有限公司 | Biodegradable material with adjustable fluorescence color and preparation method thereof |
| CN113637028A (en) * | 2021-08-03 | 2021-11-12 | 湖州师范学院 | Hydrostatic pressure fluorescent sensing material based on carborane, and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2021058970A1 (en) * | 2019-09-24 | 2021-04-01 | Chromatwist Limited | Polymers |
| CN112898972A (en) * | 2019-12-04 | 2021-06-04 | 中国科学院大连化学物理研究所 | Method for adjusting fluorescence emission wavelength of quantum dot and application |
| CN112898972B (en) * | 2019-12-04 | 2021-11-30 | 中国科学院大连化学物理研究所 | Method for adjusting fluorescence emission wavelength of quantum dot and application |
| CN112940473A (en) * | 2021-02-01 | 2021-06-11 | 浙江播下环保科技有限公司 | Biodegradable material with adjustable fluorescence color and preparation method thereof |
| CN113637028A (en) * | 2021-08-03 | 2021-11-12 | 湖州师范学院 | Hydrostatic pressure fluorescent sensing material based on carborane, and preparation method and application thereof |
| CN113637028B (en) * | 2021-08-03 | 2024-03-08 | 湖州师范学院 | Hydrostatic pressure fluorescent sensing material based on carborane, and preparation method and application thereof |
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