CN105732721A - Light-emitting off-color material with information security storage function and preparation method and application of light-emitting off-color material - Google Patents
Light-emitting off-color material with information security storage function and preparation method and application of light-emitting off-color material Download PDFInfo
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- CN105732721A CN105732721A CN201610038228.9A CN201610038228A CN105732721A CN 105732721 A CN105732721 A CN 105732721A CN 201610038228 A CN201610038228 A CN 201610038228A CN 105732721 A CN105732721 A CN 105732721A
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- color
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The invention belongs to the field of synchronization and application of light-emitting off-color materials, discloses a preparation method and application of a light-emitting off-color material with an information security storage function, and belongs to the field of application of visible light emitting off-color materials. The light-emitting off-color material is a complex prepared from platinum (II), 5,5'-di(trimethyl acetenyl)-2,2'-dipyridyl ligand and 3-bromo-phenylacetylene auxiliary ligand. According to different responses of color and light emission of the light-emitting off-color material to tetrahydrofuran steam, the material can be used in security storage of information. In addition, the material not only has advantages of high sensitivity, high security, high stability, visibility, low cost, good plasticity, easiness in operation, recyclable use and the like, but also has wide application prospects and relatively high commercial values in the field of information security materials.
Description
Technical field
The invention belongs to synthesis and the application of color-changing materials, be specifically related to one and there is information security
The preparation method and applications of the color-changing materials of storage function.
Background technology
Society, information security has vital meaning, especially in daily life and production
It is in fields such as economy and military affairs, and information leakage problem once occurs, and consequence is hardly imaginable.Therefore, seek
Look for safely and effectively information storage means particularly important.At present, information store material relate generally to have to light,
The signals such as electricity, magnetic have the material of specific response.Owing to preparing of traditional information storage material is considerably complicated,
Cost is high, operation sequence is complicated, with high content of technology, and needs specific complex instrument could realize its letter
The reading of breath, significantly limit the promotion and application of this kind of material.Research and development new type of safe storage material has
Important meaning and value.The advantages such as optical material is big due to its memory density, visual phenomenon become and have more
One of information storage material for bright prospects.In recent ten years, information based on color-changing materials storage
Technology increasingly causes the extensive concern of people.This kind of color-changing materials is by specific outside stimulus
After, the structure of material and excited level can change, and macroscopically present material color and (or) luminescence
Notable change, therefore can utilize the variation characteristic of its color and (or) luminescence to store to the safety realizing information.
With traditional information record compared with storage method, this utilize color-changing materials information is carried out storage and
The method of encryption has that higher sensitivity, equipment and operation be simple, low cost and safety coefficient high etc. many
Advantage.Therefore, utilize color-changing materials that information carries out safety and store the method becoming most application prospect
One of.
China Patent Publication No. CN102372748A: disclosed in this patent, the chemical formula of probe molecule is
Pt(TMSC≡CbpyC≡CTMS)(C≡CC6H4F-2)2；Pt(TMSC≡CbpyC≡CTMS)(C≡CC6H4F
-3)2With Pt (TMSC ≡ CbpyC ≡ CTMS) (C ≡ CC6H4F-4)2.And the complex molecule related in the present invention
Chemical combination formula be Pt (TMSC ≡ CbpyC ≡ CTMS) (C ≡ CC6H4Br-3)2.Although the two structure have similar it
Place, but the character of compound but differs widely:
(1) response condition of the luminous coloration character of compound is different.Patent CN102372748A relates to
Compound halogenated hydrocarbon steam and mechanical friction are had luminous coloration response, and the change related in the present invention
Compound has the response of the luminous coloration to oxolane steam.
(2) process of luminous coloration is different.The compound related in patent CN102372748A is to chlorohydrocarbon
The luminous coloration response of vapour molecule or mechanism is that a step completes, after compound completes response, its
Luminous and color no longer changes, and the compound related in the present invention has and sends out oxolane steam
Phototropic response substep is carried out, and coordination compound color and luminescence after touching oxolane steam first become
Redness, if being further continued for contacting oxolane steam, then color and luminescence can become again orange.
(3) condition of luminous coloration response is different, and the compound related in patent CN102372748A is to chlorine
Luminous coloration response for hydrocarbon vapour molecule is not have any condition to limit, and the change related in the present invention
Compound has condition limit for luminous coloration response and the process thereof of oxolane steam.
Complex molecule in conjunction with dichloromethane or chloroform has the two step luminous colorations sound to oxolane steam
Should, and the complex molecule of other solvent molecule to respond the luminous coloration of oxolane be that a step completes.
These differences finally make the complex molecule related in the present invention have the information security storage function of uniqueness.
Summary of the invention
Object of the present invention is to provide a kind of information security based on bivalence platinum complex storage material；This
The another object of invention there is provided a kind of luminescence that can be used for information security storage based on bivalence platinum complex
The preparation method and applications of off-color material.
Technical scheme:
A kind of color-changing materials with information security storage function, this color-changing materials be with 5,5 '-
Two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl be part, 3-bromobenzene acetylene be platinum (II) compound of assistant ligand,
Its chemical formula is Pt (TMSC ≡ CbpyC ≡ CTMS) (C ≡ CC6H4Br-3)2, wherein
TMSC ≡ CbpyC ≡ CTMS is 5,5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl；C≡CC6H4Br-3
For 3-bromobenzene acetenyl, its structural formula is as follows:
The preparation method of described color-changing materials, step is as follows:
(1) being the 5 of 1:0.8-1.5,5 '-two (trimethylsilyl acetylene bases)-2 by mol ratio, 2 '-bipyridyl is sub-with diformazan
Sulfone platinum chloride joins in dry acetonitrile solution, and 5,5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl exists
Concentration in solution is 0.03-0.3mol/L, under the conditions of anhydrous and oxygen-free stir 8-48 hour, generate 5,5 '-
Two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl platinum chloride intermediate；
(2) by mol ratio be the Hydro-Giene (Water Science). of 1-100:1-120:10-200:20-700, diisopropylamine, in
Mesosome Pt (TMSC ≡ CbpyC ≡ CTMS) Cl2Join in dichloromethane solution with 3-bromobenzene acetylene,
Pt(TMSC≡CbpyC≡CTMS)Cl2Concentration in dichloromethane solution is 0.01-0.5mol/L, carries out anti-
Should, obtain color-changing materials Pt (TMSC ≡ CbpyC ≡ CTMS) (C ≡ CC6H4Br-3)2。
The application of described color-changing materials, this color-changing materials is applied to the storage of the safety to information,
Make the secret writing paper containing its component or thin film, for anti-fake material, for the detection of oxolane steam,
Or it is fabricated to the reagent paper containing its component, detection box and related reagent.
Described color-changing materials is through dichloroethanes, toluene, methanol, acetone, acetonitrile, methanol, second
After alcohol or ethyl acetate etc. process, it is respectively provided with identical color and luminescence.But steam when it touches oxolane
After gas, their color and luminescence can occur bigger difference.Utilize the sample that dichloromethane or chloroform processed
Product its color and luminescence after touching oxolane steam can first become redness and become orange the most again；And use
The sample that other solvent processed directly is become orange from orange-yellow after touching oxolane steam.Just
Based on such optical characteristics, this color-changing materials can be applicable to the paper with information security storage function
, the making of the material such as thin film.
Research shows, through solvent process orange-yellow sample, its emission maximum peak position 561nm (609nm,
Acromion), this luminosity belongs to the metal of mixing and jumps to the electric charge of part to the charge transtion of part and part
Move.After the sample that dichloromethane or chloroform processed is placed in oxolane steam by we, coordination compound
Color and luminescence all can be become red from orange-yellow, the red shift of emission maximum peak position has been arrived at 713nm, this
Time coordination compound luminosity belong to the metal-metal charge transtion to part；If continuing to be placed on tetrahydrochysene
In furan steam ambient, the luminescence of coordination compound and color can become again orange, emission maximum peak position move to
619nm (574nm, acromion), luminosity belongs to the metal of mixing and arrives to charge transtion and the part of part
The charge transtion of part.On the other hand, at methanol, acetone, acetonitrile, methanol, ethyl acetate equal solvent
The coordination compound sample managed touches the orange luminescence sample after oxolane steam, and emission spectrum is at 617nm
(578nm, shoulder seam), belongs to the metal of mixing equally to the charge transtion of part and part to the electric charge of part
Transition, is continued to contact oxolane steam, and its color and luminescence no longer occur any change.
The invention has the beneficial effects as follows:
(1) present invention utilizes and has the selectivity knowledge that different packed structures platinum (II) coordination compound stimulates for signal specific
Other character, by the regulation and control to coordination compound packed structures thus realize coordination compound for information security store
Function.
(2) this information storage material has information input and encryption, information deciphering and the merit such as reading and information destroying
Can, and also have with low cost, safety is high, response is quick, visualize, equipment is small and exquisite is prone to
Operate and without advantages such as Professional knowledges.
(3) this information storage material has good application, can make various information storage and anti-forge paper, thin
Film etc..
(4) this information storage material has good reusing, can repeatedly use, and is prone to preserve.
Accompanying drawing explanation
Fig. 1 is color-changing materials emission spectrum under different conditions.
In figure: a adsorbs chloroform；Oxolane is inhaled again to red after b absorption chloroform；C absorption oxolane is to red
Continue after color to inhale oxolane to orange；D adsorbs methanol；Oxolane is inhaled again to orange after e absorption methanol.
Fig. 2 is to cooperate with thing as information storage material in information write and encryption, information deciphering and reading, information
Destroy and the schematic diagram of material recovery process.
Detailed description of the invention
The detailed description of the invention of the present invention is further illustrated below in conjunction with accompanying drawing and technical scheme.
Step 1:[5,5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl] preparation of platinous chloride.Take
The 5 of equivalent, 5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl and dimethyl sulfoxide platinum chloride are in anhydrous acetonitrile
Stirred under nitrogen atmosphere 8 hours.Recycle silicon glue post isolated product, productivity 70-75%.Elementary analysis is tied
Really: by C20H24Cl2N2PtSi2Value of calculation (%) C39.09, H3.94, N4.56；Measured value (%) C39.12,
H3.93,N4.54。1H NMR(CDCl3): 0.313 (s, 18H), 7.875 (d, J (H, H)=4.8Hz, 2H),
8.154 (d, J (H, H)=4.8Hz, 2H), 9.861 (s, 2H).
The preparation of step 2:Pt (II) coordination compound color-changing materials.Under nitrogen protection, take step 1 gained and produce
Bromobenzene acetylene between thing and 2.5 equivalents, the Hydro-Giene (Water Science). of 0.05 equivalent, at diisopropylamine and dichloromethane (body
Long-pending than 1:10) stirring reaction 24h under room temperature in solution.Recycle silicon glue post isolated product, productivity 75-80%.
Elementary analysis result: by C36H32Br2N2PtSi2Value of calculation (%) C47.85, H3.57, N3.10；Measured value (%)
C47.83,H3.59,N3.12。1H NMR(CDCl3): 0.297 (s, 18H), 7.109 (t, J (H, H)=7.6Hz,
2H), 7.294 (d, J (H, H)=8.4Hz, 2H), 7.476 (d, J (H, H)=7.6Hz, 2H), 7.692 (s, 2H),
7.959 (d, J (H, H)=8.4Hz, 2H), 8.117 (d, J (H, H)=8.4Hz, 2H), 9.720 (s, 2H).
Step 3: combine accompanying drawing 1, illustrates color-changing materials emission spectrum under different conditions.
Color-changing materials after touching the steams such as dichloromethane, chloroform, methanol, acetone, its color and
Luminescence is orange-yellow, and the position of emission spectrum is at 561nm (609nm, acromion).When dichloromethane and chlorine
After imitative coordination compound touches oxolane steam, originally its color and luminescence can become red, emission spectrum
Position be 713nm, continue contact oxolane steam after, its color and luminescence can become again orange, send out
Optical position is at 619nm (574nm, acromion).And the sample combining other vapour molecules such as methanol, acetone exists
After touching oxolane steam, its color and luminescence then can become orange, and emission spectrum is at 617nm
(578nm, shoulder seam).When we will become orange sample adsorption dichloromethane, chloroform, methanol, acetone etc.
After steam, its color and luminous all can become initial orange-yellow.
Step 4: combine accompanying drawing 2, descriptive information stores safely the actually used operation of material.
(1) sample that methanol processed it is uniformly adhered on paper or makes thin-film material, then with dichloro
Methane or chloroform write information as ink on paper.After solvent volatilization is dry, no matter daylight or in ultraviolet
All cannot be identified the information of write under lamp, this process achieves write and the encryption of information.
(2) being exposed in oxolane steam ambient by the paper of write information, on paper, the information of write will
Show, thus realize deciphering and the reading of information.
(3) continue to be exposed in oxolane steam after a period of time by step (2) has been read information, that
The information of write will be wholly absent, thus realizes the destruction of information.
(4) paper after information destroying is re-exposed in the steams such as methanol, it is possible to before changing back to information write
State, thus realize the recycling of material.It is reused several times the character to material and will not produce any
Impact.
Claims (4)
1. a color-changing materials with information security storage function, it is characterised in that this color-changing materials is
With 5,5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl be part, 3-bromobenzene acetylene be the platinum of assistant ligand
(II) compound, its chemical formula is Pt (TMSC ≡ CbpyC ≡ CTMS) (C ≡ CC6H4Br-3)2, wherein
TMSC ≡ CbpyC ≡ CTMS is 5,5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl；C≡CC6H4Br-3
For 3-bromobenzene acetenyl, its structural formula is as follows:
2. the preparation method of the color-changing materials described in claim 1, it is characterised in that step is as follows:
(1) it is the 5 of 1:0.8-1.5,5 '-two (trimethylsilyl acetylene bases)-2 by mol ratio, 2 '-bipyridyl and dimethyl sulfoxide chlorine
Changing platinum and join in dry acetonitrile solution, 5,5 '-two (trimethylsilyl acetylene bases)-2,2 '-bipyridyl is at solution
In concentration be 0.03-0.3mol/L, under the conditions of anhydrous and oxygen-free stir 8-48 hour, generate 5,5 '-two (three
Methyl silico acetylene base)-2,2 '-bipyridyl platinum chloride intermediate；
(2) it is the Hydro-Giene (Water Science). of 1-100:1-120:10-200:20-700, diisopropylamine, intermediate by mol ratio
Pt(TMSC≡CbpyC≡CTMS)Cl2Join in dichloromethane solution with 3-bromobenzene acetylene,
Pt(TMSC≡CbpyC≡CTMS)Cl2Concentration in dichloromethane solution is 0.01-0.5mol/L, carries out anti-
Should, obtain color-changing materials Pt (TMSC ≡ CbpyC ≡ CTMS) (C ≡ CC6H4Br-3)2。
3. the application of the color-changing materials described in claim 1, it is characterised in that utilize at dichloromethane or chloroform
The color-changing materials managed, then its color and luminescence first become redness the most again after contacting oxolane steam
Become orange；And the color-changing materials processed with other solvents, then touch after oxolane steam straight
Connect and become orange from orange-yellow；This color-changing materials is applied to the storage of the safety to information, makes containing it
The secret writing paper of component or thin film, for anti-fake material, for the detection of oxolane steam, or be fabricated to
Reagent paper, detection box and related reagent containing its component.
Application the most according to claim 3, it is characterised in that other described solvents be dichloroethanes, toluene,
Methanol, acetone, acetonitrile, methanol, ethanol or ethyl acetate.
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Cited By (4)
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| CN108250224A (en) * | 2018-03-09 | 2018-07-06 | 南京邮电大学 | A kind of longevity regulation method and its application of Cu (I) complex |
| CN109337670A (en) * | 2018-10-09 | 2019-02-15 | 大连理工大学 | A kind of steam color-changing materials with information encrypt-decrypt function, preparation method and applications |
| CN112028945A (en) * | 2020-09-29 | 2020-12-04 | 大连理工大学 | Intelligent light-emitting switch material with self-encryption function, preparation method and application thereof |
| CN112047981A (en) * | 2020-09-29 | 2020-12-08 | 大连理工大学 | Temperature-controlled intelligent vapor luminescent switch material, preparation method and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108250224A (en) * | 2018-03-09 | 2018-07-06 | 南京邮电大学 | A kind of longevity regulation method and its application of Cu (I) complex |
| CN108250224B (en) * | 2018-03-09 | 2020-04-21 | 南京邮电大学 | Method for regulating and controlling service life of Cu (I) complex and application thereof |
| CN109337670A (en) * | 2018-10-09 | 2019-02-15 | 大连理工大学 | A kind of steam color-changing materials with information encrypt-decrypt function, preparation method and applications |
| CN109337670B (en) * | 2018-10-09 | 2021-06-18 | 大连理工大学 | Vapor luminescent color-changing material with information encryption-decryption function, preparation method and application thereof |
| CN112028945A (en) * | 2020-09-29 | 2020-12-04 | 大连理工大学 | Intelligent light-emitting switch material with self-encryption function, preparation method and application thereof |
| CN112047981A (en) * | 2020-09-29 | 2020-12-08 | 大连理工大学 | Temperature-controlled intelligent vapor luminescent switch material, preparation method and application thereof |
| CN112028945B (en) * | 2020-09-29 | 2021-04-20 | 大连理工大学 | Intelligent light-emitting switch material with self-encryption function, preparation method and application thereof |
| CN112047981B (en) * | 2020-09-29 | 2021-05-11 | 大连理工大学 | Temperature-controlled intelligent vapor luminescent switch material, preparation method and application thereof |
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