CN110305148A - A kind of Subjective and Objective Cd (II) photochromic coordination polymer and preparation method thereof can be used for two-dimension code anti-counterfeit - Google Patents
A kind of Subjective and Objective Cd (II) photochromic coordination polymer and preparation method thereof can be used for two-dimension code anti-counterfeit Download PDFInfo
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- 239000013256 coordination polymer Substances 0.000 title claims abstract description 53
- 229920001795 coordination polymer Polymers 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000008367 deionised water Substances 0.000 claims abstract description 4
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 229910001868 water Inorganic materials 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 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
- 230000005595 deprotonation Effects 0.000 claims description 2
- 238000010537 deprotonation reaction Methods 0.000 claims description 2
- 238000012718 coordination polymerization Methods 0.000 claims 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 4
- 230000001681 protective effect Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 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
- 238000005286 illumination Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000005298 paramagnetic effect Effects 0.000 description 3
- 238000001845 vibrational spectrum Methods 0.000 description 3
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- -1 purpurine free radical Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- 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
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- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F3/00—Labels, tag tickets, or similar identification or indication means; Seals; Postage or like stamps
- G09F3/02—Forms or constructions
- G09F3/0297—Forms or constructions including a machine-readable marking, e.g. a bar code
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
A kind of Subjective and Objective Cd (II) photochromic coordination polymer and preparation method thereof can be used for two-dimension code anti-counterfeit, belongs to technical field of chemistry, and coordination polymer has following chemical formula: [Cd (DEBPY)0.5(L)]·H2O.By Cd (CH3COO)2·2H2O, 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.The pale yellow crystals of the coordination polymer are obtained after cooled to room temperature.Present invention firstly discloses application of the coordination polymer 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).Subjective and Objective Cd (II) photochromic coordination polymer 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 coordination polymer, and in particular to it is anti-that one kind can be used for two dimensional code
Pseudo- Subjective and Objective Cd (II) photochromic coordination polymer and preparation method thereof.
Background technique
Photochromic material refers to the substance that can change self color under the irradiation of the light of certain wavelength.If after discoloration
Substance by irradiate other wavelength light, it is dark place or the modes such as heat treatment can restore original color, then this object
Matter is known as ability of reverse photochromism material, is otherwise irreversible photochromic material.In recent years, photochromic material is deposited in information
Storage element, decoration and protective packaging material, autography holographic recording are taken a picture and all various aspects such as national defence are applied, and are that one kind has
The material of wide application prospect.Photochromic compound is broadly divided into photochromic compounds, inorganic photochromic chemical combination
Object and hybrid inorganic-organic class photochromic compound.Compared with inorganic and organic photochromic material, coordination polymer (has
One kind of machine inorganic hybridization compound is weak mutually by covalent bond or hydrogen bond etc. by metal ion or metal cluster and organic ligand
Act on be formed by connecting with the compound without limit structure) can be in conjunction with the thermal stability of inorganic compound, high intensity and organic
Compound is easy to the advantages of modifying processing, and can cooperate with and generate some new excellent properties.Therefore, photochromic coordination polymer
As current one of research hotspot.
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 Subjective and Objective Cd (II) photochromic coordination polymer, can be used for
Two-dimension code anti-counterfeit.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 preparation of the photochromic coordination polymer of Subjective and Objective Cd (II)
Method.The present invention also discloses application of this coordination polymer in terms of two-dimension code anti-counterfeit.By the coordination polymer
Certain positions that alcohol suspension is applied to two dimensional code are made in powder after being fully ground, dry rear powder and be attached to two dimensional code paper
On.The coordination polymer is close with base color when no light, thus two dimensional code can not be identified.By two dimensional code under sunlight
Within irradiation 1 minute, coordination polymer becomes green from light yellow, and two dimensional code can be identified at this time.
This Subjective and Objective Cd (II) the photochromic coordination polymer that can be used for two-dimension code anti-counterfeit has following chemical formula,
That is: [Cd (DEBPY)0.5(L)]·H2O, wherein DEBPY is 1,1'- diethyl -4,4'- bipyridyl, and L is carboxyl deprotonation
3,5- dicarboxyls-phenyl -4- (2'- carboxyl phenyl)-benzylic ether.
Coordination polymer crystal belongs to anorthic system, space group P-1, and cell parameter is α=73.808 (5) °, β=68.675 (5) °, γ=80.239 (5) °,
The preparation method of described Subjective and Objective Cd (II) the photochromic coordination polymer that can be used for two-dimension code anti-counterfeit, including
Following steps:
By a certain amount of Cd (CH3COO)2·2H2O、H3L、DEBPY·Br2Exist with the mixture of a certain amount of deionized water
Heated sealed is for a period of time under certain temperature in reaction kettle with polytetrafluoroethyllining lining.Room is naturally cooled to after reaction
Temperature obtains pale yellow crystals after filtration, washing and drying, as can be used for Subjective and Objective Cd (II) light-induced variable of two-dimension code anti-counterfeit
Color coordination polymer.Present invention firstly discloses application of the coordination polymer in terms of two-dimension code anti-counterfeit.
Synthetic method of the invention has easy to operate, repeated strong, environmentally protective (being not necessarily to any toxic organic solvent)
The features such as.Subjective and Objective Cd (II) photochromic coordination polymer can be by pale yellow discoloration within 1 minute under sunlight irradiation
For green, it is used for two-dimension code anti-counterfeit high sensitivity, it is easy to operate.
Detailed description of the invention
Fig. 1 is the coordination context diagram of Cd (II) ion in the coordination polymer;
Fig. 2 is the body, two-dimensional stratiform figure that L anion and Cd (II) ion are formed in the coordination polymer;
Fig. 3 is the topology diagram of body, two-dimensional layer in the coordination polymer;
Fig. 4 is the Magnetic Properties of Three-Dimensional Supramolecular Complex figure that body, two-dimensional layer and DEBPY guest molecule are formed in the coordination polymer;
Fig. 5 is photochromic photo of the coordination polymer under sunlight irradiation;
Fig. 6 is electron paramagnetic vibrational spectrum of the coordination polymer before and after illumination;
Fig. 7 is ultraviolet-visible absorption spectroscopy of the coordination polymer before and after illumination;
Fig. 8 is the schematic diagram that the coordination polymer is used for two-dimension code anti-counterfeit.
Specific embodiment
By the Cd (CH of 53.3mg (0.2mmol)3COO)2·2H2The H of O, 39.2mg (0.1mmol)3L, 37.4mg
The DEBPYBr of (0.1mmol)2Mixture with 15mL deionized water is in the reaction kettle with polytetrafluoroethyllining lining of 20mL
Heated sealed 3 days at 130 DEG C.Cooled to room temperature after reaction obtains light yellow crystalline substance after filtration, washing and drying
Body as can be used for Subjective and Objective Cd (II) photochromic coordination polymer of two-dimension code anti-counterfeit, yield 25%.
Main infrared absorption peak are as follows: 3725 (w), 3428 (m), 3052 (m), 2859 (w), 1615 (s), 1557 (s),
1447 (s), 1376 (s), 1261 (m), 1176 (w), 1119 (w), 1034 (m), 923 (w), 835 (w), 777 (s), 725 (m)
666 (w), 569 (w), 520 (w), 422 (w).
The relevant characterization of coordination polymer
(1) crystal structure determination of coordination polymer
The diffraction data of coordination polymer crystal is collected on Bruker SMART APEX II diffractometer, using Mo
KαRayTemperature is 293K.It is corrected using technology scanning.Crystal structure is to pass through SHELXS-97
Program is solved with direct method, carries out refine using SHELEXL-97 program with complete matrix least square method.The temperature of non-hydrogen atom
The factor is modified with anisotropy.Detailed crystallographic data is shown in Table 1;Representative bond distance, bond angle and hydrogen bond data are shown in Table 2;
Crystal structure is shown in Fig. 1-4.
The coordination polymer of invention is it is characterized in that the coordination polymer crystal belongs to anorthic system, space group P-1,
Cell parameter isα=73.808 (5) °, β
=68.675 (5) °, γ=80.239 (5) °,It include one in the asymmetric unit of coordination polymer
A Cd (II) ion, half of DEBPY cation, a L anion and a lattice hydrone.Cd1 takes the four directions of pentacoordinate
Coordination configuration is bored, from five oxygen atom ligands (Fig. 1) from five different L anion.Two symmetrical relevant Cd (II)
Ion connects into a paddle-wheel like double-core unit by four carboxylic groups.Each double-core unit connects six L anion, each L
Anion and three double-core units are coordinated.In this way, double-core unit is connected into a two-dimensional layer by L anion, is formed
The main structure (Fig. 2) of coordination polymer.It is analyzed from topological angle, each L anion is considered as a 3- connection
Node, each double-core unit can regard a 6- connecting node as, and two-dimensional layer entire in this way, which can simplify into one, has (43)
(46·66·83) symbol (3,6)-connect topological network (Fig. 3).Guest molecule DMBPY cation and hydrone are located at two dimension
Between layer, two-dimensional layer is connected by a Subjective and Objective three by intramolecular and intermolecular O-H ... O and C-H ... O interaction of hydrogen bond
It ties up supramolecular structure (Fig. 4).
(2) the photochromic property research of coordination polymer
The coordination polymer at room temperature, irradiates 1 minute under ultraviolet light, visible light or sunlight, can be by pale yellow
Discoloration is green.After coordination polymer after illumination is placed 6 hours in the dark, and original yellow (Fig. 5) can be reverted to.
The repeatable more wheels of discoloration-decolorization.Discoloration mechanism is to generate purpurine free radical by the electronics transfer of photoinduction.The mechanism can
It is proved by electron paramagnetic vibrational spectra and ultraviolet-visible absorption spectroscopy.Go out on coordination polymer electron paramagnetic vibrational spectra after illumination
Existing purpurine Free Radical Signal, and the coordination polymer before illumination is without this signal (Fig. 6).Coordination polymer UV, visible light after illumination
Occur an absorption peak on absorption spectrum at 630nm, and without this absorption peak (Fig. 7) before illumination.
(3) coordination polymer 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 coordination polymer powder being fully ground is coated
Alcohol suspension.Powder is attached on two dimensional code paper after ethanol evaporation.Coordination polymer color and two dimensional code base before illumination
Bottom 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, coordination polymer can become green from light yellow, and two dimensional code can be identified at this time, show that content is " HYNU " on mobile phone
(Fig. 8).It can achieve the purpose of two-dimension code anti-counterfeit in this way.
The predominant crystal data of 1. coordination polymer of table
R1=Σ | | Fo|-|Fc||/Σ|Fo|.wR2=| Σ w (| Fo|2-|Fc|2)|/Σ|w(Fo 2)2|1/2.
The representative bond distance of 2. coordination polymer of tableBond angle [°] and hydrogen bond
Symmetrical code:#1- x ,-y ,-z+2;#2- x+1 ,-y ,-z+2;#3- x+1 ,-y+1 ,-z+1;#4X, y+1, z -1;#7–x+
1 ,-y ,-z+1;#8X, y+1, z;#9X+1, y, z.
Claims (2)
1. a kind of Subjective and Objective Cd (II) photochromic coordination polymer that can be used for two-dimension code anti-counterfeit, it is characterised in that: chemical formula
For [Cd (DEBPY)0.5(L)]·H2O, wherein DEBPY is 1,1'- diethyl -4,4'- bipyridyl, and L is carboxyl deprotonation
3,5- dicarboxyls-phenyl -4- (2'- carboxyl phenyl)-benzylic ether;Its crystal belongs to anorthic system, space group P-1, structure cell
Parameter is α=73.808 (5) °, β=
68.675 (5) °, γ=80.239 (5) °,
2. a kind of Subjective and Objective Cd (II) photochromic coordination polymer that can be used for two-dimension code anti-counterfeit according to claim 1
Preparation method, it is characterised in that include the following steps: the Cd (CH of 53.4mg (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, is filtered, is washed after reaction
After washing, drying, pale yellow crystals are obtained, as can be used for Subjective and Objective Cd (II) photochromic coordination polymerization of two-dimension code anti-counterfeit
Object.
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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 |
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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 |
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