CN110372880B - Organic supermolecule photochromic compound for two-dimensional code anti-counterfeiting and preparation method thereof - Google Patents
Organic supermolecule photochromic compound for two-dimensional code anti-counterfeiting and preparation method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 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
- YSMNDHXIFHOLRY-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=C(C=1)C(=O)O)C(C1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)O)OC(C1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)O)C1=CC(=CC(=C1)C(=O)O)C(=O)O Chemical compound C(=O)(O)C=1C=C(C=C(C=1)C(=O)O)C(C1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)O)OC(C1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)O)C1=CC(=CC(=C1)C(=O)O)C(=O)O YSMNDHXIFHOLRY-UHFFFAOYSA-N 0.000 claims abstract 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
- 238000010438 heat treatment Methods 0.000 claims description 2
- -1 polytetrafluoroethylene Polymers 0.000 claims description 2
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- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
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- 238000010189 synthetic method Methods 0.000 abstract description 2
- TUFWUFIJANGGQI-UHFFFAOYSA-N CCN(C=C1)C=CC1=C1C=CN(CC)C=C1.Br.Br Chemical compound CCN(C=C1)C=CC1=C1C=CN(CC)C=C1.Br.Br TUFWUFIJANGGQI-UHFFFAOYSA-N 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
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- 238000011160 research Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001845 vibrational spectrum Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
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- 230000007246 mechanism Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 1
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- 150000001988 diarylethenes Chemical class 0.000 description 1
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- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
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Abstract
An organic supermolecule photochromic compound for two-dimensional code anti-counterfeiting and a preparation method thereof belong to the technical field of chemistry, and the compound has the following chemical formula: [ (DEBPY)0.5(H2L)]·1.25H2And O. Mixing Mn (CH)3COO)23, 5-dicarboxy-phenyl-4- (2' -carboxyphenyl) -benzyl ether (H)3L), 1,1 '-diethyl-4, 4' -bipyridine dibromide (DEBPY & Br)2) The mixture with deionized water was heated in a 20mL reaction vessel with a Teflon liner at 130 ℃ for 3 days under sealed conditions, and the reaction vessel was allowed to stand at room temperature for 2 days. This compound was obtained as pale yellow crystals after natural cooling to room temperature. The invention discloses the application of the compound in the aspect of two-dimensional code anti-counterfeiting for the first time. The synthetic method has the characteristics of simple operation, strong repeatability, environmental protection (no need of any toxic organic solvent) and the like. The organic supermolecule compound can be changed from light yellow to green within 1 minute under the irradiation of sunlight, and the application of the organic supermolecule compound to two-dimensional code anti-counterfeiting has high sensitivity and simple and convenient operation.
Description
Technical Field
The invention belongs to the technical field of chemistry, relates to an organic supramolecular compound, and particularly relates to an organic supramolecular photochromic compound for two-dimensional code anti-counterfeiting and a preparation method thereof.
Background
The photochromic material is a substance capable of changing its color under irradiation of light. If the discolored substance can restore the original color by irradiating light with other wavelengths, placing in the dark or heating treatment, the substance is called reversible photochromic material, otherwise, the substance is irreversible photochromic material. In recent years, photochromic materials have been used in information storage elements, decorative and protective packaging materials, self-developing holographic recording photography, national defense and other fields, and are a class of materials with wide application prospects. Photochromic compounds are mainly classified into organic photochromic compounds, inorganic photochromic compounds and organic-inorganic hybrid photochromic compounds. Currently, the research on organic photochromic compounds is mainly focused on Schiff bases, fulgides, azo compounds, diarylethenes, viologens and other compounds and derivatives thereof. However, the application research of organic supramolecular photochromic compounds in the prior art is rarely reported.
As is well known, in recent years, counterfeit and shoddy products are increasing at home and abroad, and counterfeit-making activities are rampant increasingly. In order to better protect enterprise brands and markets and protect consumers' rights, research and development of simple and easy anti-counterfeiting technology is imperative. At present, various anti-counterfeiting technologies have been developed at home and abroad, and the technology of anti-counterfeiting by using a color-changing material is also reported, but many anti-counterfeiting technologies are complicated to operate and limit the application of the anti-counterfeiting technologies. For example, patent CN201721026142.0 discloses a two-dimensional code identification which can be hidden. Under certain bias, the color of the controllable device is similar to that of the substrate, so that the two-dimensional code cannot be identified, and stealth is realized. When the bias voltage is converted to another state, the color of the device can be changed, so that the two-dimensional code can be identified, and the anti-counterfeiting purpose is achieved. However, this method requires a control of the bias voltage, and is complicated to operate and generally requires a professional to operate.
In a word, the existing technology for two-dimensional code anti-counterfeiting by using color-changing materials has some defects, and a new method which is simple and convenient to operate and high in sensitivity needs to be further developed. The invention provides an organic supermolecule photochromic compound which can be used for two-dimensional code anti-counterfeiting. The anti-counterfeiting method is simple and convenient to operate, high in sensitivity and good in application prospect.
Disclosure of Invention
The invention aims to solve the technical problem of disclosing an organic supermolecule photochromic compound. The invention also discloses a preparation method of the organic supermolecule photochromic compound and application of the compound in the aspect of two-dimensional code anti-counterfeiting. The powder of the compound is coated on certain parts of the two-dimensional code, and the color of the compound is similar to that of the substrate when no light is irradiated, so that the two-dimensional code cannot be identified. When the compound is irradiated under the sunlight for less than 1 minute, the light yellow of the compound is changed into green, and the two-dimensional code can be identified.
The organic supermolecule photochromic compound for two-dimensional code anti-counterfeiting has the following chemical formula: [ (DEBPY)0.5(H2L)]·1.25H2O, where DEBPY is 1,1' -diethyl-4, 4' -bipyridine and L is 3, 5-dicarboxy-phenyl-4- (2' -carboxyphenyl) -benzyl ether with one carboxyl group deprotonated.
The compound crystal belongs to a monoclinic system, the space group is C2/C, the unit cell parameter is
β＝100.091(5)°，
The preparation method of the organic supramolecular photochromic compound for two-dimensional code anti-counterfeiting comprises the following steps:
adding a certain amount of Mn (CH)3COO)2、H3L、DEBPY·Br2The mixture with a certain amount of deionized water is sealed and heated for a period of time at a certain temperature in a reaction kettle with a polytetrafluoroethylene lining. And naturally cooling to room temperature after the reaction is finished, and then placing the reaction kettle at room temperature for a period of time to obtain colorless crystals, namely the organic supramolecular photochromic compound capable of being used for two-dimensional code anti-counterfeiting. The invention discloses the application of the compound in the aspect of two-dimensional code anti-counterfeiting for the first time.
The synthetic method has the characteristics of simple operation, strong repeatability, environmental protection (no need of any organic solvent) and the like. The organic supermolecule compound can be changed from light yellow to green within 1 minute under the irradiation of sunlight, and the application of the organic supermolecule compound to two-dimensional code anti-counterfeiting has high sensitivity and simple and convenient operation.
Drawings
FIG. 1 is a diagram of the asymmetric unit structure of the compound;
FIG. 2 shows H in the compound2A 3D supramolecular structure diagram formed by the L anion and the DEBPY cation through hydrogen bonds;
FIG. 3 is a photo of the compound under solar radiation;
FIG. 4 is electron paramagnetic vibration spectra of the compound before and after illumination;
FIG. 5 is the UV-VIS absorption spectrum of the compound before and after illumination;
fig. 6 is a schematic diagram of the compound used for two-dimensional code anti-counterfeiting.
Detailed Description
34.6mg (0.2mmol) of Mn (CH)3COO)239.2mg (0.1mmol) of H3L, 37.4mg (0.1mmol) of DEBPY & Br2The mixture with 15mL of deionized water was heated in a sealed condition at 130 ℃ for 3 days in a 20mL reaction vessel with a Teflon liner. And after the reaction is finished, naturally cooling to room temperature, and then placing the reaction kettle at room temperature for 2 days to obtain light yellow crystals, namely the organic supramolecular photochromic compound for two-dimensional code anti-counterfeiting, wherein the yield is 21%.
The main infrared absorption peaks are: 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).
Related characterization of Compounds
(1) Crystal structure determination of Compounds
Diffraction data for the compounds were collected on a Bruker SMART APEX II diffractometer using Mo KαRay of radiation
The temperature was 293K. The correction is performed using a technical scan. The crystal structure was solved by the direct method using the SHELXS-97 program and refined using the SHELEXL-97 program using the full matrix least squares method. The temperature factor of the non-hydrogen atoms is corrected with anisotropy. Detailed crystallographic data are shown in table 1; the hydrogen bond data are shown in the table2; the crystal structure is shown in figures 1 and 2.
The compound of the invention is characterized in that the crystal of the compound belongs to a monoclinic system, the space group is C2/C, and the unit cell parameter is
β＝100.091(5)°，
The asymmetric unit of the compound comprises half DEBPY cation and one H2L anions and one and a few twenty-five lattice water molecules (fig. 1). The components are connected into a 3D supermolecular structure through intramolecular and intermolecular hydrogen bonding interaction of O-H … O and C-H … O (figure 2).
(2) Photochromic Properties of the Compounds
The compound can change from light yellow to green after being irradiated for 1 minute under ultraviolet light, visible light or sunlight at room temperature. The illuminated compound was heated at 130 ℃ for 5 minutes to return to the original yellow color (FIG. 3). The color change-decoloration process can be repeated for a plurality of rounds. The mechanism of discoloration is the production of viologen radicals by photoinduced electron transfer. The mechanism can be proved by electron paramagnetic vibration spectrum and ultraviolet visible absorption spectrum. The electronic paramagnetic vibration spectrum of the compound after illumination shows the signal of the viologen free radical, while the compound before illumination does not (figure 4). An absorption peak appears at 630nm on the ultraviolet-visible absorption spectrum of the compound after illumination, but does not appear on the ultraviolet-visible absorption spectrum of the compound before illumination (FIG. 5).
(3) Research on two-dimensional code anti-counterfeiting by using compound
And downloading software capable of generating the two-dimensional code by using the mobile phone, and then generating the two-dimensional code with the representative content of 'HYNU'. After the two-dimensional code is printed, two areas are randomly selected and coated with the ethanol suspension of the fully ground organic supramolecular compound powder. The powder is attached to the two-dimensional code paper after the ethanol is evaporated. The color of the compound before illumination is similar to the color of the two-dimensional code substrate, and the two-dimensional code cannot be identified by 'scanning with WeChat'. When the two-dimensional code is taken to be irradiated under the sunlight for within 1 minute, the compound can be changed from light yellow to green, at the moment, the two-dimensional code can be identified, and the display content on the mobile phone is 'HYNU' (fig. 6). The two-dimensional code anti-counterfeiting purpose can be achieved through the mode.
TABLE 1 Main crystallographic data of the Compounds
R1＝Σ||Fo|-|Fc||/Σ|Fo|.wR2＝|Σw(|Fo|2-|Fc|2)|/Σ|w(Fo 2)2|1/2.
TABLE 2 Hydrogen bonding of Compounds
Symmetric code:#1 –x+2,y,-z+1/2；#3 –x+2,-y,-z；#4 x,y-1,z；#5 x-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. an organic supermolecule photochromic compound for two-dimensional code anti-counterfeiting is characterized in that: the chemical formula of the compound is [ (DEBPY)0.5(H2L)]·1.25H2O, wherein DEBPY is 1,1 '-diethyl-4, 4' -bipyridine, H2L is 3, 5-dicarboxy-phenyl-4- (2' -carboxyphenyl) -benzyl ether with one carboxyl group deprotonated; its crystal belongs to monoclinic system, space group is C2/C, unit cell parameter is
β＝100.091(5)°，
2. The preparation method of the organic supramolecular photochromic compound for two-dimensional code anti-counterfeiting according to claim 1 is characterized by comprising the following steps: 34.6mg,0.2mmol of Mn (CH)3COO)239.2mg,0.1mmol of H3L, 37.4mg,0.1mmol of DEBPY & Br2And sealing and heating the mixture with 15mL of deionized water in a 20mL reaction kettle with a polytetrafluoroethylene lining at 130 ℃ for 3 days, naturally cooling to room temperature after the reaction is finished, and standing the reaction kettle at room temperature for 2 days to obtain light yellow crystals, namely the organic supramolecular photochromic compound capable of being used for two-dimensional code anti-counterfeiting.
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Citations (4)
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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 |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030030040A1 (en) * | 2001-08-08 | 2003-02-13 | Luthern John Joseph | Reversibly variable photochromic color composition for articles composed of synthetic resin |
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Patent Citations (4)
| 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 |
| 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 |
|---|
| Photochromism of three supramolecular assemblies derived from benzenecarboxylate donors and viologen acceptors;Liu J. et al.;《Polyhedron》;20190114;第161卷;第237-242页 * |
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