CN110372880A - A kind of organic supermolecular photochromic compound and preparation method thereof can be used for two-dimension code anti-counterfeit - Google Patents
A kind of organic supermolecular photochromic compound and preparation method thereof can be used for two-dimension code anti-counterfeit Download PDFInfo
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- CN110372880A CN110372880A CN201910705543.6A CN201910705543A CN110372880A CN 110372880 A CN110372880 A CN 110372880A CN 201910705543 A CN201910705543 A CN 201910705543A CN 110372880 A CN110372880 A CN 110372880A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 239000008367 deionised water Substances 0.000 claims abstract description 4
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 7
- -1 3,5- dicarboxyl-phenyl Chemical group 0.000 claims description 6
- IUGBAYSNSMFNGS-UHFFFAOYSA-N 1-ethyl-4-(1-ethylpyridin-4-ylidene)pyridine Chemical group C1=CN(CC)C=CC1=C1C=CN(CC)C=C1 IUGBAYSNSMFNGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 2
- 230000005588 protonation Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 4
- 230000001681 protective effect Effects 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- LCEBDKLPALDQPV-UHFFFAOYSA-L 1-ethyl-4-(1-ethylpyridin-1-ium-4-yl)pyridin-1-ium;dibromide Chemical compound [Br-].[Br-].C1=C[N+](CC)=CC=C1C1=CC=[N+](CC)C=C1 LCEBDKLPALDQPV-UHFFFAOYSA-L 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 238000005286 illumination Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 5
- 238000004847 absorption spectroscopy Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 230000005298 paramagnetic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001845 vibrational spectrum Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001988 diarylethenes Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06K—GRAPHICAL DATA READING; PRESENTATION OF DATA; RECORD CARRIERS; HANDLING RECORD CARRIERS
- G06K17/00—Methods or arrangements for effecting co-operative working between equipments covered by two or more of main groups G06K1/00 - G06K15/00, e.g. automatic card files incorporating conveying and reading operations
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- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06K—GRAPHICAL DATA READING; PRESENTATION OF DATA; RECORD CARRIERS; HANDLING RECORD CARRIERS
- G06K19/00—Record carriers for use with machines and with at least a part designed to carry digital markings
- G06K19/06—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code
- G06K19/06009—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code with optically detectable marking
- G06K19/06037—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code with optically detectable marking multi-dimensional coding
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- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06K—GRAPHICAL DATA READING; PRESENTATION OF DATA; RECORD CARRIERS; HANDLING RECORD CARRIERS
- G06K19/00—Record carriers for use with machines and with at least a part designed to carry digital markings
- G06K19/06—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code
- G06K19/06009—Record carriers for use with machines and with at least a part designed to carry digital markings characterised by the kind of the digital marking, e.g. shape, nature, code with optically detectable marking
- G06K19/06046—Constructional details
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- G06Q30/00—Commerce
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- G06Q30/0185—Product, service or business identity fraud
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
A kind of organic supermolecular photochromic compound and preparation method thereof can be used for two-dimension code anti-counterfeit, belongs to technical field of chemistry, and compound has following chemical formula: [(DEBPY)0.5(H2L)]·1.25H2O.By Mn (CH3COO)2, 3,5- dicarboxyls-phenyl -4- (2'- carboxyl phenyl)-benzylic ether (H3L), 1,1'- diethyl -4,4'- bipyridinium dibromide (DEBPYBr2) with the mixture of deionized water in the reaction kettle with polytetrafluoroethyllining lining of 20mL heated sealed 3 days at 130 DEG C, then reaction kettle is placed at room temperature for 2 days.The pale yellow crystals of the compound are obtained after cooled to room temperature.Present invention firstly discloses application of the compound in terms of two-dimension code anti-counterfeit.Synthetic method of the invention has the characteristics that easy to operate, repeated strong, environmentally protective (without any toxic organic solvent).The organic supermolecular compound can become green from light yellow within 1 minute under sunlight irradiation, be used for two-dimension code anti-counterfeit high sensitivity, easy to operate.
Description
Technical field
The invention belongs to technical field of chemistry, are related to a kind of organic supermolecular compound, and in particular to one kind can be used for two
Tie up the anti-fake organic supermolecular photochromic compound and preparation method thereof of code.
Background technique
Photochromic material refers to the substance that can change self color under the irradiation of light.If the substance after discoloration passes through
Original color can be restored by irradiating the modes such as light, dark placement or the heat treatment of other wavelength, then this substance is referred to as reversible
Otherwise photochromic material is irreversible photochromic material.In recent years, photochromic material is in information storage elements, dress
All various aspects such as decorations and protective packaging material, the photograph of autography holographic recording and national defence are applied, and are that one kind is widely used
The material of prospect.Photochromic compound is broadly divided into photochromic compounds, inorganic photochromic compound and organic-
Inorganic hybridization class photochromic compound.Currently, being concentrated mainly on schiff bases, prisoner's essence to the research of photochromic compounds
On the compounds such as acid anhydrides, azo-compound, diarylethene and purpurine and its derivative.However, in the prior art to organic
The application study of supermolecule photochromic compound is rarely reported.
It is well known that in recent years, counterfeit and shoddy goods both domestic and external are increasing, manufacturing and marketing fake activity is becoming increasingly rampant.For
Brand names and market are preferably protected, consumers' rights and interests is protected, researchs and develops easy-to-use anti-counterfeiting technology imperative.
Currently, having developed a variety of anti-counterfeiting technologies both at home and abroad, anti-fake technology is carried out using off-color material and is also had been reported that, but it is many anti-
Pseudo- technical operation is cumbersome, limits its application.For example, patent CN201721026142.0 discloses a kind of two dimensional code that can be stealthy
Mark.Under certain bias, it can control device close with base color, cause two dimensional code that can not be identified, realize stealthy.When turn
It changes when being biased into another state, device color can be changed, so that two dimensional code is identified, to reach anti-fake purpose.But this
Kind mode needs to control bias, complicated for operation, generally requires professional and operates.
In short, the technology for carrying out two-dimension code anti-counterfeit currently with off-color material needs further to develop there are some disadvantages
Easy to operate, high sensitivity new method.The present invention provides a kind of organic supermolecular photochromic compound, can be used for two dimensional code
It is anti-fake.The method for anti-counterfeit is easy to operate, high sensitivity, there is preferable application prospect.
Summary of the invention
The technical problem to be solved by the present invention is to disclose a kind of organic supermolecular photochromic compound.The present invention is gone back simultaneously
The preparation method for disclosing this organic supermolecular photochromic compound and the application in terms of two-dimension code anti-counterfeit.By the chemical combination
The powder of object is applied to certain positions of two dimensional code, and the compound is close with base color when no light, thus two dimensional code can not be by
Identification.Within irradiating 1 minute under sunlight, compound becomes green from light yellow, and two dimensional code can be identified at this time.
This organic supermolecular photochromic compound that can be used for two-dimension code anti-counterfeit has following chemical formula, it may be assumed that
[(DEBPY)0.5(H2L)]·1.25H2O, wherein DEBPY is 1,1'- diethyl -4,4'- bipyridyl, and L is a carboxyl deprotonation
3,5- dicarboxyl-phenyl -4- (2'- the carboxyl phenyl)-benzylic ether changed.
Compound crystal belongs to monoclinic system, space group C2/c, and cell parameter is β=100.091 (5) °,
The preparation method of the organic supermolecular photochromic compound that can be used for two-dimension code anti-counterfeit, including walk as follows
It is rapid:
By a certain amount of Mn (CH3COO)2、H3L、DEBPY·Br2Mixture with a certain amount of deionized water is with poly- four
Heated sealed is for a period of time under certain temperature in the reaction kettle of vinyl fluoride liner.Cooled to room temperature after reaction, so
Reaction kettle is placed at room temperature for a period of time afterwards, obtains clear crystal, the organic supermolecular that as can be used for two-dimension code anti-counterfeit is photic
Electrochromic compound.Present invention firstly discloses application of the compound in terms of two-dimension code anti-counterfeit.
Synthetic method of the invention has spies such as easy to operate, repeated strong, environmentally protective (being not necessarily to any organic solvent)
Point.The organic supermolecular compound can become green from light yellow within 1 minute under sunlight irradiation, be used for two dimension
The anti-fake high sensitivity of code, it is easy to operate.
Detailed description of the invention
Fig. 1 is the asymmetric cell structure chart of the compound；
Fig. 2 is H in the compound2The supramolecular structured composition of 3D that L anion and DEBPY cation are formed by hydrogen bond；
Fig. 3 is photochromic photo of the compound under sunlight irradiation；
Fig. 4 is electron paramagnetic vibrational spectrum of the compound before and after illumination；
Fig. 5 is ultraviolet-visible absorption spectroscopy of the compound before and after illumination；
Fig. 6 is the schematic diagram that the compound is used for two-dimension code anti-counterfeit.
Specific embodiment
By the Mn (CH of 34.6mg (0.2mmol)3COO)2, the H of 39.2mg (0.1mmol)3L, 37.4mg's (0.1mmol)
DEBPY·Br2It is sealed at 130 DEG C in reaction kettle of the 20mL with polytetrafluoroethyllining lining with the mixture of 15mL deionized water
Heating 3 days.Cooled to room temperature after reaction, then reaction kettle is placed at room temperature for 2 days, pale yellow crystals are obtained, as may be used
For the organic supermolecular photochromic compound of two-dimension code anti-counterfeit, yield 21%.
Main infrared absorption peak are as follows: 3730 (w), 3402 (m), 3060 (m), 2865 (w), 1722 (w), 1540 (s),
1451(s),1404(s),1367(s),1265(m),1127(m),1034(m),933(w),870(w),826(w),769(s),
733(m),666(w),471(w)。
The relevant characterization of compound
(1) crystal structure determination of compound
The diffraction data of compound is collected on Bruker SMART APEX II diffractometer, using Mo KαRayTemperature is 293 K.It is corrected using technology scanning.Crystal structure is by SHELXS-97 program
It is solved with direct method, carries out refine using SHELEXL-97 program with complete matrix least square method.The temperature factor of non-hydrogen atom
It is modified with anisotropy.Detailed crystallographic data is shown in Table 1；Hydrogen bond data are shown in Table 2；Crystal structure is shown in Fig. 1,2.
The compound of invention is it is characterized in that the compound crystal belongs to monoclinic system, space group C2/c, structure cell ginseng
Number isβ=100.091 (5) °,It include half of DEBPY cation, a H in the asymmetric unit of compound2L anion and one
Two or five lattice hydrones (Fig. 1) of point.It is mutual by intramolecular and intermolecular O-H ... O and C-H ... O hydrogen bond between these components
Effect connects into a 3D supramolecular structure (Fig. 2).
(2) the photochromic property research of compound
The compound at room temperature, irradiates 1 minute under ultraviolet light, visible light or sunlight, can be by pale yellow discoloration
For green.Compound after illumination is heated 5 minutes at 130 DEG C, and original yellow (Fig. 3) can be reverted to.Discoloration-decoloration
The repeatable more wheels of process.Discoloration mechanism is to generate purpurine free radical by the electronics transfer of photoinduction.The mechanism can pass through electronics
Paramagnetic vibrational spectra and ultraviolet-visible absorption spectroscopy prove.There is purpurine free radical on compound electron paramagnetic vibrational spectra after illumination
Signal, and the compound before illumination is without this signal (Fig. 4).On compound ultraviolet-visible absorption spectroscopy after illumination at 630nm
There is an absorption peak, and without this absorption peak (Fig. 5) on the compound ultraviolet-visible absorption spectroscopy before illumination.
(3) compound is used for the research of two-dimension code anti-counterfeit
With the software of one producible two dimensional code of mobile phone-downloaded, then generates and represent content as the two dimensional code of " HYNU ".It will
After two dimensional code prints, two regions are arbitrarily selected, the organic supermolecular chemical combination being fully ground is coated
The alcohol suspension of object powder.Powder is attached on two dimensional code paper after ethanol evaporation.Compound colors and two dimensional code before illumination
Base color is close, can not identify two dimensional code with " wechat, which is swept, to be swept " at this time.Two dimensional code is taken irradiated under sunlight 1 minute with
Interior, compound can become green from light yellow, and two dimensional code can be identified at this time, show that content is " HYNU " (figure on mobile phone
6).It can achieve the purpose of two-dimension code anti-counterfeit in this way.
The predominant crystal data of 1. compound of table
R1=Σ | | Fo|-|Fc||/Σ|Fo|.wR2=| Σ w (| Fo|2-|Fc|2)|/Σ|w(Fo 2)2|1/2.
The hydrogen bond of 2. compound of table
Symmetrical code:#1–x+2,y,-z+1/2；#3–x+2,-y,-z；#4x,y-1,z；#5x-1/2,y-1/2,z；#6 –
x+3/2,y-1/2,-z+1/2；#7 x,-y,z+1/2。
Claims (2)
1. a kind of organic supermolecular photochromic compound that can be used for two-dimension code anti-counterfeit, it is characterised in that: the chemistry of compound
Formula is [(DEBPY)0.5(H2L)]·1.25H2O, wherein DEBPY is 1,1'- diethyl -4,4'- bipyridyl, and L is that a carboxyl is gone
3,5- dicarboxyl-phenyl -4- (2'- carboxyl phenyl)-benzylic ether of protonation；Its crystal belongs to monoclinic system, and space group is
C2/c, cell parameter are β=100.091
(5) °,
2. a kind of preparation of organic supermolecular photochromic compound that can be used for two-dimension code anti-counterfeit according to claim 1
Method, it is characterised in that its preparation includes the following steps: the Mn (CH of 34.6mg (0.2mmol)3COO)2, 39.2mg
The H of (0.1mmol)3The DEBPYBr of L, 37.4mg (0.1mmol)2With the mixture of 15mL deionized water in 20mL with poly- four
In the reaction kettle of vinyl fluoride liner at 130 DEG C heated sealed 3 days, cooled to room temperature after reaction, then by reaction kettle
2 days are placed at room temperature for, pale yellow crystals are obtained, as can be used for the organic supermolecular photochromic compound of two-dimension code anti-counterfeit.
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Citations (5)
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|---|---|---|---|---|
| JPS56118063A (en) * | 1980-02-25 | 1981-09-16 | Rikagaku Kenkyusho | Preparation of viologen cation radical using cyclic multidentate ligand metal complex |
| US20030030040A1 (en) * | 2001-08-08 | 2003-02-13 | Luthern John Joseph | Reversibly variable photochromic color composition for articles composed of synthetic resin |
| CN106957270A (en) * | 2017-03-24 | 2017-07-18 | 宁波大学 | A kind of nitrouracil medicine supermolecule eutectic and preparation method thereof |
| CN107522722A (en) * | 2017-08-02 | 2017-12-29 | 淮阴师范学院 | A kind of two-fold penetration Zn (II) complex available for inkless and erasable printing and preparation method thereof |
| CN109942831A (en) * | 2019-04-10 | 2019-06-28 | 山西师范大学 | Two kinds of photochromic purpurine Subjective and Objective MOFs materials and its preparation and application |
-
2019
- 2019-08-01 CN CN201910705543.6A patent/CN110372880B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56118063A (en) * | 1980-02-25 | 1981-09-16 | Rikagaku Kenkyusho | Preparation of viologen cation radical using cyclic multidentate ligand metal complex |
| US20030030040A1 (en) * | 2001-08-08 | 2003-02-13 | Luthern John Joseph | Reversibly variable photochromic color composition for articles composed of synthetic resin |
| CN106957270A (en) * | 2017-03-24 | 2017-07-18 | 宁波大学 | A kind of nitrouracil medicine supermolecule eutectic and preparation method thereof |
| CN107522722A (en) * | 2017-08-02 | 2017-12-29 | 淮阴师范学院 | A kind of two-fold penetration Zn (II) complex available for inkless and erasable printing and preparation method thereof |
| CN109942831A (en) * | 2019-04-10 | 2019-06-28 | 山西师范大学 | Two kinds of photochromic purpurine Subjective and Objective MOFs materials and its preparation and application |
Non-Patent Citations (1)
| Title |
|---|
| LIU J. ET AL.: "Photochromism of three supramolecular assemblies derived from benzenecarboxylate donors and viologen acceptors", 《POLYHEDRON》 * |
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