CN110423608A - Double luminescent materials of a kind of solid-liquid with solvent color transition property and preparation method thereof and purposes - Google Patents
Double luminescent materials of a kind of solid-liquid with solvent color transition property and preparation method thereof and purposes Download PDFInfo
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Abstract
A kind of double luminescent materials of solid-liquid with solvent color transition property provided by the invention, which is hexichol amido benzoyl class compound.The present invention also provides the methods for preparing the luminescent material; pass through friedel-crafts acylation by parent of triphenylamine; synthesis obtains hexichol amido benzoyl class compound, and the invention also discloses the purposes of this luminescent material, which can be used for multi-enciphering and anti-fake.The advantage of the invention is that, obtain a kind of material for showing the luminosity of different colours by spraying different solvents, compared with traditional encryption antiforgery method, multi-enciphering can be achieved, make to produce using material of the present invention has encryption and anti-fraud functional pattern, number etc. perfect, to serious blow criminal, the utmostly imitated generation copied of containment.
Description
Technical field
The invention belongs to compound encryption anti-counterfeiting technical field, specially a kind of solid-state-liquid with solvent color transition property
Double luminescent materials of state and preparation method thereof and purposes.
Background technique
With the fast development of national economy, living standards of the people are continuously improved, and encryption becomes in real life with anti-fake
Must be more important, it effectively hits counterfeit and shoddy goods and has become urgent problem in the modern life.Traditional encryption anti-counterfeiting
Often technology content is lower, will be counterfeit by people after a period of time.The digital anti-counterfeitings such as bar code, two dimensional code usually require and data
Serial No. in library compares, and causes workload excessive, cannot judge in time when something goes wrong.Due to anti-fake level
Single, the shortcomings that taking time and effort, encryption anti-counterfeiting technology still faces huge challenge at present.
Luminous organic material is mainly by traditional dissolution induced luminescence dyestuff (DIE) and aggregation-induced emission molecule at present
(AIE) it forms, the former shines in the solution but state of aggregation or when solid-state do not shine, and the latter does not shine in the solution and assembling
Shine bright fluorescence when state.The dye molecule of traditional depolymerization induced luminescence can issue bright fluorescence in the solution, different
Dye molecule by functionalized design appropriate be used in biomolecule and organism selective chemical sensing and biology at
Picture, but since their peculiar aggregation inducings quench (ACQ) behavior, their applications in the solid state are faced with huge challenge.With
Conventional dyes (DIE) molecule is compared, and aggregation-induced emission (AIE) molecule issues strong fluorescence in state of aggregation or solid-state,
Unique AIE characteristic be greatly promoted based on AIE material bio-sensing, organic photoelectric system and in terms of application
Development.However, traditional solution light emitting dye molecules and aggregation-induced emission molecule can only be in a single state (solution or solid-states)
Under show bright fluorescence, and luminescent color is single, is unsuitable for multi-enciphering anti-fake.
Summary of the invention
For solve in the prior art luminous organic material can only a single state shine, luminescent color it is single, be unsuitable for more
The anti-fake problem of re-encryption, the present invention provides a kind of double luminescent materials of solid-liquid with solvent color transition property and its systems
The purpose of Preparation Method and purposes, realization is to obtain a kind of fluorescent molecule with the bifurcation characteristics of luminescence, different molten by spraying
Agent shows the luminosity of different colours, it can be achieved that multi-enciphering, makes to forge and fake compared with traditional encryption antiforgery method
It is equal that criminals are seamless bores.
To achieve the goals above, technical solution provided by the invention is that one kind provided by the invention has solvent color transition
The double luminescent materials of the solid-liquid of property, which is hexichol amido benzoyl class compound, possessed chemical structure
General formula are as follows:
Further, the hexichol amido benzoyl class compound is 4- (N, N- hexichol amido) benzaldehyde or 4- (N, N-
Diphenylamino) phenyl) ethyl ketone or (4- (N, N- diphenylamino) phenyl) phenyl) ketone.
The present invention also provides the methods for preparing above-mentioned luminescent material, including pass through friedel-crafts acylation by parent of triphenylamine
Reaction, synthesis obtain hexichol amido benzoyl class compound.
Further, the hexichol amido benzoyl class compound is 4- (N, N- hexichol amido) benzaldehyde, preparation side
Method are as follows: triphenylamine (4.9g, 0.02mol), phosphorus oxychloride (30.0g, 0.2mol) are dissolved in 50ml DMF, stirred 1 hour
Afterwards, it is poured into ice water, and the sodium hydroxide solution for being 20% with mass concentration neutralizes, filtering；Crude product is with petroleum ether:
Chloroform (1:3) carries out column chromatography as solvent and purifies to obtain pale yellow powder, as 4- (N, N- hexichol amido) benzaldehyde.
Further, the hexichol amido benzoyl class compound is 4- (N, N- diphenylamino) phenyl) ethyl ketone, preparation
Method are as follows: weigh triphenylamine (0.9813g, 4mmol) in 100ml round-bottomed flask, dissolved with methylene chloride (36ml), violent
Anhydrous zinc chloride (0.5452g, 4mmol) is rapidly added under stirring；Under conditions of ice bath, chloroacetic chloride (0.2844ml) is added
Enter and form solution into methylene chloride (4ml), this solution is slowly added into flask；Reaction mixture is stirred at room temperature
After five minutes, return stirring 20 hours at 45 DEG C；After after end of reaction and being cooled to room temperature, 50ml 2M hydrochloric acid is added, is used in combination
Methylene chloride (3 × 30ml) extraction；Anhydrous sodium sulfate is dry after organic phase is washed with water to pH equal to 7, and revolving removes solvent
Methylene chloride；Use ethyl acetate: petroleum ether=1:20 obtains target product as eluant, eluent, by chromatogram column technique.
Further, the hexichol amido benzoyl class compound is (4- (N, N- diphenylamino) phenyl) phenyl) ketone,
Preparation method are as follows:
By triphenylamine (2.45g, 0.01mol), aluminium chloride (1.33g, 0.01mol) and methylene chloride (35mL) are slowly added to
Into methylene chloride (5mL) solution of chlorobenzoyl chloride (1.41g, 0.01mol)；5min is stirred at room temperature and is heated to 45 DEG C later, returns
20h is flowed, 150mL 2mol/L hydrochloric acid solution is added after being cooled to room temperature, separate organic layer and is washed with water to pH=7；Anhydrous sulphur
After sour sodium is dry, vacuum rotary steam removes methylene chloride, and crude product is through chromatographic column using petroleum ether: ethyl acetate=40:1 is eluant, eluent
Isolated yellow solid, as (4- (N, N- diphenylamino) phenyl) phenyl) ketone.
The invention also discloses the purposes of the double luminescent materials of the solid-liquid with solvent color transition property, utilize this
Material can all generate fluorescence color reaction under the conditions of solid-liquid bifurcation, and solvent occurs to generate change when mushy stage variation
The property of color change is applied in production multi-enciphering and anti-fake article.
By adopting the above technical scheme, possessed effect includes: to obtain a kind of solvent table different by sprinkling to the present invention
The material for revealing the luminosity of different colours, it can be achieved that multi-enciphering, makes using this compared with traditional encryption antiforgery method
What invention material was produced has encryption and anti-fraud functional pattern, number etc. perfect, thus serious blow criminal,
The utmostly imitated generation copied of containment.Its detection is sensitive, rapid, practical, and is the exploitation of encryption and Application in Anti-counterfeiting
More efficient, convenient and fast method is provided, saves a large amount of manpower and material resources especially for large batch of detection judgement.Total comes
It says, the double unique bifurcation color developments of luminescent material of this solid-liquid with solvent color transition property of the present invention and solvent color transition are special
Property have laid a good foundation for encryption and anti-fake further develop.
Detailed description of the invention
Fig. 1 is 1H NMR, the 13C NMR and mass spectrogram of DPAB；
Fig. 2 is DPPE's1H NMR,13C NMR and mass spectrogram；
Fig. 3 is DPPM's1H NMR,13C NMR and mass spectrogram.
Specific embodiment
The present invention is further illustrated below in conjunction with specific embodiment, the method and item that do not mentioned in embodiment
Part can all be handled according to the prior art.
Embodiment one: a kind of double luminescent materials of the solid-liquid with solvent color transition property provided by the invention, this shines
Material is hexichol amido benzoyl class compound, possessed general formula of the chemical structure are as follows:
For example, the hexichol amido benzoyl class compound is 4- (N, N- hexichol amido) benzaldehyde, 4- (N, N- diphenylamines
Base) benzaldehyde can be denoted as DPAB.
Method the present invention also provides the luminescent material includes passing through friedel-crafts acylation by parent of triphenylamine,
Synthesis obtains hexichol amido benzoyl class compound.
Specifically: triphenylamine (4.9g, 0.02mol), phosphorus oxychloride (30.0g, 0.2mol) are dissolved in 50ml DMF,
It after stirring 1 hour, is poured into ice water, and the sodium hydroxide solution for being 20% with mass concentration neutralizes, filtering；Crude product
Using petroleum ether: chloroform (1:3) carries out column chromatography as solvent and purifies to obtain pale yellow powder, as 4- (N, N- hexichol amido)
Benzaldehyde.Synthetic route is as follows:
The DPAB that the present invention obtains is characterized using 1H NMR, 13C NMR and mass spectrum, as shown in Figure 1, the compound is solid
Body shows blue emission under the excitation of ultraviolet light.With the increase of solvent polarity red shift can occur for its solution luminescent color,
Corresponding time resolution decay of luminescene curve determines that its solid service life is 1.2-2.0ns, and the service life in THF is respectively 5.8,
5.6 and 5.4ns, so that it is determined that it is fluorescent material.The luminous feature of strong solid luminescence and solution shows that DPAB has bifurcation
(DSE) behavior of shining, unique DSE behavior and solvent color transition characteristic can be used for encrypting and anti-fake.
It is anti-fake that the compound of the present invention is used in digital encryption: firstly, constructing digital " 8 " with TPE solution on rice paper.It is dry
After dry, with a small amount of (about 0.1ml or so), the ethanol solution that mass concentration is 10 mMs of DPAB smears digital " 6 " on its surface.
When solvent volatilizees completely, due to TPE and DPAB be displayed in blue in the solid state it is luminous, observed under ultraviolet lamp blue
Digital " 8 ".Then, using nano-spray instrument sprinkling toluene, tetrahydrofuran or acetonitrile, (amount of sprinkling is can soak pattern i.e. respectively
Can, such as 0.01-0.1ml), unique solvent color transition property makes us observe the number with different luminescent colors respectively
Word " 6 " continues to spray another solvent, can observe the luminescence phenomenon of different colours after a kind of volatilization of solvent, thus using
In the multi-enciphering of number.Certainly, the compound of the present invention can develop the color in toluene, tetrahydrofuran or acetonitrile solution
It shines, or commonly cooperates also to be able to carry out to develop the color in colour-developing solvent in the prior art and shine, therefore, can also use
Other solvents replace TPE solution to construct number.
The compound of the present invention is used in pattern encryption anti-counterfeiting: drawing school badge and school on paper with the ethanol solution of DPAB
Instruction is in the UV lamp after evaporation of the solvent cyan, and after being sprayed with THF solution, pattern and Chinese character is bright under ultraviolet light
Bright cyan can rapidly go to yellow green, this to be sent out in the UV lamp by solid state transformed at liquid by spraying different solvents
Out the light of different colours and be used for anti-counterfeiting design.
The discovery when present invention carries out colour test to DPAB using the prior art, in deep under ultraviolet lamp when DPAB solid
Blue-green is presented in blue in THF solution, presents in Toluene solution light blue, and dark blue-green is presented in EA solution,
Dark yellow-green is presented in DMF solution, buff is presented in Acetonitrile, yellow is presented in DMSO, thus may be used
To illustrate that the compound of the present invention has the double luminous characteristics of solvent color transition, solid-liquid.
Embodiment two: a kind of double luminescent materials of the solid-liquid with solvent color transition property provided by the invention, this shines
Material is hexichol amido benzoyl class compound, possessed general formula of the chemical structure are as follows:
For example, the hexichol amido benzoyl class compound is 4- (N, N- diphenylamino) phenyl) ethyl ketone, 4- (N, N- bis-
Phenylamino) phenyl) ethyl ketone can be denoted as DPPE.
Method the present invention also provides the luminescent material includes passing through friedel-crafts acylation by parent of triphenylamine,
Synthesis obtains hexichol amido benzoyl class compound.
Specifically: it takes triphenylamine (0.9813g, 4mmol) in 100ml round-bottomed flask, is dissolved with methylene chloride (36ml),
Anhydrous zinc chloride (0.5452g, 4mmol) rapidly is added with vigorous stirring；Under conditions of ice bath, by chloroacetic chloride
(0.2844ml), which is added in methylene chloride (4ml), forms solution, this solution is slowly added into flask；By reaction mixture
After being stirred at room temperature five minutes, return stirring 20 hours at 45 DEG C；After after end of reaction and being cooled to room temperature, it is added
50ml2M hydrochloric acid, and extracted with methylene chloride (3 × 30ml)；Anhydrous sodium sulfate is done after organic phase is washed with water to pH equal to 7
Dry, revolving removes methylene chloride；Use ethyl acetate: petroleum ether=1:20 obtains mesh as eluant, eluent, by chromatogram column technique
Mark product.Its synthetic route are as follows:
The DPPE that the present invention obtains is characterized using 1H NMR, 13C NMR and mass spectrum, as shown in Fig. 2, the compound is solid
Body shows blue emission under the excitation of ultraviolet light.With the increase of solvent polarity red shift can occur for its solution luminescent color,
Corresponding time resolution decay of luminescene curve determines that its solid service life is 1.2-2.0ns, and the service life in THF is respectively 5.8,
5.6 and 5.4ns, so that it is determined that it is fluorescent material.The luminous feature of strong solid luminescence and solution shows that DPPE has bifurcation
(DSE) behavior of shining, unique DSE behavior and solvent color transition characteristic can be used for encrypting and anti-fake.
It is anti-fake that the compound of the present invention is used in digital encryption: firstly, constructing digital " 8 " with TPE solution on rice paper.It is dry
After dry, with a small amount of (about 0.1ml or so), the ethanol solution that mass concentration is 10 mMs of DPPE smears digital " 6 " on its surface.
When solvent volatilizees completely, since TPE and DPPE shows that navy blue shines in the solid state, blue is observed under ultraviolet lamp
Number " 8 ".Then, toluene is sprayed using nano-spray instrument respectively, (amount of sprinkling is can soak pattern for tetrahydrofuran or acetonitrile
, such as 0.1-1ml), unique solvent color transition property makes us observe the number with different luminescent colors respectively
" 6 " continue to spray another solvent, can observe the luminescence phenomenon of different colours, to be applied to after a kind of volatilization of solvent
The multi-enciphering of number.Certainly, the compound of the present invention can carry out colour developing hair in toluene, tetrahydrofuran or acetonitrile solution
Light, or commonly cooperate also to be able to carry out to develop the color in colour-developing solvent in the prior art and shine, therefore, it can also use it
He replaces TPE solution to construct number by solvent.
The compound of the present invention is used in pattern encryption anti-counterfeiting: drawing school badge and school on paper with the ethanol solution of DPPE
Instruction is in the UV lamp after evaporation of the solvent navy blue, after being sprayed with THF solution, pattern and Chinese character under ultraviolet light
Bright cyan can rapidly go to dark blue-green, it is this by spray different solvents by it is solid state transformed at liquid in the UV lamp
The light of different colours can be issued and be used for anti-counterfeiting design.
The discovery when present invention carries out colour test to DPPE using the prior art, in deep under ultraviolet lamp when DPPE solid
Dark blue-green is presented in blue in THF solution, presented in Toluene solution it is light blue, presented in EA solution it is light blue,
Bottle green is presented in DMF solution, dark yellow-green is presented in Acetonitrile, yellow green is presented in DMSO, thus
It can illustrate that the compound of the present invention has the double luminous characteristics of solvent color transition, solid-liquid.
Embodiment three: a kind of double luminescent materials of the solid-liquid with solvent color transition property provided by the invention, this shines
Material is hexichol amido benzoyl class compound, possessed general formula of the chemical structure are as follows:
For example, the hexichol amido benzoyl class compound is (4- (N, N- diphenylamino) phenyl) phenyl) ketone, (4-
(N, N- diphenylamino) phenyl) phenyl) ketone can be denoted as DPPM.
Method the present invention also provides the luminescent material includes passing through friedel-crafts acylation by parent of triphenylamine,
Synthesis obtains hexichol amido benzoyl class compound.
Specifically: by triphenylamine (2.45g, 0.01mol), aluminium chloride (1.33g, 0.01mol) and methylene chloride (35mL)
It is slowly added into methylene chloride (5mL) solution of chlorobenzoyl chloride (1.41g, 0.01mol)；5min is stirred at room temperature to be heated to later
45 DEG C, flow back 20h, and 150mL 2mol/L hydrochloric acid solution is added after being cooled to room temperature, and separates organic layer and is washed with water to pH=
7；After anhydrous sodium sulfate is dry, vacuum rotary steam removes methylene chloride, and crude product is through chromatographic column with petroleum ether: ethyl acetate=40:1
For the isolated yellow solid of eluant, eluent, as (4- (N, N- diphenylamino) phenyl) phenyl) ketone.Its synthetic route are as follows:
The DPPM that the present invention obtains is characterized using 1H NMR, 13C NMR and mass spectrum, as shown in figure 3, the compound is solid
Body shows navy blue transmitting under the excitation of ultraviolet light.Its solution luminescent color can occur red with the increase of solvent polarity
It moves, corresponding time resolution decay of luminescene curve determines that its solid service life is 1.2-2.0ns, and the service life in THF is respectively
5.8,5.6 and 5.4ns, so that it is determined that it is fluorescent material.The luminous feature of strong solid luminescence and solution shows that DPPM has
Bifurcation shines (DSE) behavior, unique DSE behavior and solvent color transition characteristic, can be used for encrypting and anti-fake.
It is anti-fake that the compound of the present invention is used in digital encryption: firstly, constructing digital " 8 " with TPE solution on rice paper.It is dry
After dry, with a small amount of (about 0.1ml or so), the ethanol solution that mass concentration is 10 mMs of DPPM smears digital " 6 " on its surface.
When solvent volatilizees completely, since TPE and DPPM shows that navy blue shines in the solid state, observed under ultraviolet lamp dark blue
The number " 8 " of color.Then, using nano-spray instrument sprinkling toluene, tetrahydrofuran or acetonitrile, (amount of sprinkling is can soak figure respectively
Case, such as 0.1-1ml), unique solvent color transition property makes us observe the number with different luminescent colors respectively
Word " 6 " continues to spray another solvent, can observe the luminescence phenomenon of different colours after a kind of volatilization of solvent, thus using
In the multi-enciphering of number.Certainly, the compound of the present invention can develop the color in toluene, tetrahydrofuran or acetonitrile solution
It shines, or commonly cooperates also to be able to carry out to develop the color in colour-developing solvent in the prior art and shine, therefore, can also use
Other solvents replace TPE solution to construct number.
The compound of the present invention is used in pattern encryption anti-counterfeiting: drawing school badge and school on paper with the ethanol solution of DPPM
Instruction is in the UV lamp after evaporation of the solvent navy blue, after being sprayed with THF solution, pattern and Chinese character under ultraviolet light
Bright cyan can rapidly go to pale bluish green, it is this by spray different solvents by it is solid state transformed at liquid in the UV lamp
The light of different colours can be issued and be used for anti-counterfeiting design.
The discovery when present invention carries out colour test to DPPM using the prior art, in deep under ultraviolet lamp when DPPM solid
Pale bluish green is presented in blue in THF solution, presents in Toluene solution light blue, presents in EA solution pacific
Dark yellow-green is presented in color in DMF solution, presents in Acetonitrile light yellow, buff is presented in DMSO, thus
Alternatively bright the compound of the present invention has the double luminous characteristics of solvent color transition, solid-liquid.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made any to repair
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (7)
1. a kind of double luminescent materials of solid-liquid with solvent color transition property, which is characterized in that the luminescent material is diphenylamines
Base benzoyl class compound, possessed general formula of the chemical structure are as follows:
2. the double luminescent materials of the solid-liquid according to claim 1 with solvent color transition property, which is characterized in that institute
Stating hexichol amido benzoyl class compound is 4- (N, N- hexichol amido) benzaldehyde or 4- (N, N- diphenylamino) phenyl) ethyl ketone or
(4- (N, N- diphenylamino) phenyl) phenyl) ketone.
3. a kind of method for preparing any one of the claim 1-2 luminescent materials, which is characterized in that this method includes with three
Aniline is that parent passes through friedel-crafts acylation, and synthesis obtains hexichol amido benzoyl class compound.
4. the method that preparation according to claim 3 has the double luminescent materials of the solid-liquid of solvent color transition property, special
Sign is that the hexichol amido benzoyl class compound is 4- (N, N- hexichol amido) benzaldehyde, preparation method are as follows: by triphen
Amine (4.9g, 0.02mol), phosphorus oxychloride (30.0g, 0.2mol) are dissolved in 50ml DMF, after stirring 1 hour, are poured into
Into ice water, and the sodium hydroxide solution for being 20% with mass concentration neutralizes, filtering；Crude product is with petroleum ether: chloroform (1:3) is made
Column chromatography, which is carried out, for solvent purifies to obtain pale yellow powder, as 4- (N, N- hexichol amido) benzaldehyde.
5. the method that preparation according to claim 3 has the double luminescent materials of the solid-liquid of solvent color transition property, special
Sign is that the hexichol amido benzoyl class compound is 4- (N, N- diphenylamino) phenyl) ethyl ketone, preparation method are as follows: claim
It takes triphenylamine (0.9813g, 4mmol) in 100ml round-bottomed flask, is dissolved with methylene chloride (36ml), with vigorous stirring fastly
Anhydrous zinc chloride (0.5452g, 4mmol) is added fastly；Under conditions of ice bath, chloroacetic chloride (0.2844ml) is added to dichloro
Solution is formed in methane (4ml), this solution is slowly added into flask；Reaction mixture is stirred at room temperature five minutes
Afterwards, return stirring 20 hours at 45 DEG C；After after end of reaction and being cooled to room temperature, 50ml 2M hydrochloric acid is added, and use dichloromethane
Alkane (3 × 30ml) extraction；Anhydrous sodium sulfate is dry after organic phase is washed with water to pH equal to 7, and revolving removes solvent dichloromethane
Alkane；Use ethyl acetate: petroleum ether=1:20 obtains target product as eluant, eluent, by chromatogram column technique.
6. the method that preparation according to claim 3 has the double luminescent materials of the solid-liquid of solvent color transition property, special
Sign is that the hexichol amido benzoyl class compound is (4- (N, N- diphenylamino) phenyl) phenyl) ketone, preparation method
Are as follows:
By triphenylamine (2.45g, 0.01mol), aluminium chloride (1.33g, 0.01mol) and methylene chloride (35mL) are slowly added into benzene
In methylene chloride (5mL) solution of formyl chloride (1.41g, 0.01mol)；5min is stirred at room temperature and is heated to 45 DEG C later, reflux
150mL2mol/L hydrochloric acid solution is added in 20h after being cooled to room temperature, separate organic layer and be washed with water to pH=7；Anhydrous slufuric acid
After sodium is dry, vacuum rotary steam removes methylene chloride, and crude product is through chromatographic column using petroleum ether: ethyl acetate=40:1 is eluant, eluent point
From yellow solid is obtained, as (4- (N, N- diphenylamino) phenyl) phenyl) ketone.
7. the purposes of the double luminescent materials of solid-liquid described in a kind of claim 1 with solvent color transition property, by the material that shines
Material is used for multi-enciphering and anti-fake application.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910590104.5A CN110423608A (en) | 2019-07-02 | 2019-07-02 | Double luminescent materials of a kind of solid-liquid with solvent color transition property and preparation method thereof and purposes |
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| CN111337465A (en) * | 2020-03-06 | 2020-06-26 | 齐鲁工业大学 | Solid-state fluorescence anti-counterfeiting method based on reversible response of amine steam |
| CN113444068A (en) * | 2021-06-25 | 2021-09-28 | 国家纳米科学中心 | Organic luminescent material and preparation method and application thereof |
| CN113943570A (en) * | 2021-10-26 | 2022-01-18 | 江苏大学 | Carbon nanodot/boric acid composite phosphorescent material and preparation method and application thereof |
| CN114716333A (en) * | 2022-03-31 | 2022-07-08 | 西北工业大学 | Sensing type organic intelligent luminescent material and preparation and use method thereof |
| CN115043743A (en) * | 2022-07-22 | 2022-09-13 | 西北师范大学 | Substituted triphenylamine aldehyde, preparation method and application |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111337465A (en) * | 2020-03-06 | 2020-06-26 | 齐鲁工业大学 | Solid-state fluorescence anti-counterfeiting method based on reversible response of amine steam |
| CN113444068A (en) * | 2021-06-25 | 2021-09-28 | 国家纳米科学中心 | Organic luminescent material and preparation method and application thereof |
| CN113943570A (en) * | 2021-10-26 | 2022-01-18 | 江苏大学 | Carbon nanodot/boric acid composite phosphorescent material and preparation method and application thereof |
| CN114716333A (en) * | 2022-03-31 | 2022-07-08 | 西北工业大学 | Sensing type organic intelligent luminescent material and preparation and use method thereof |
| CN114716333B (en) * | 2022-03-31 | 2023-09-08 | 西北工业大学 | Sensing type organic intelligent luminescent material and preparation and use methods thereof |
| CN115043743A (en) * | 2022-07-22 | 2022-09-13 | 西北师范大学 | Substituted triphenylamine aldehyde, preparation method and application |
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