CN112778178A - Fluorescent material with piezochromism and lyotropic chromotropic effect and preparation method thereof - Google Patents
Fluorescent material with piezochromism and lyotropic chromotropic effect and preparation method thereof Download PDFInfo
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- 230000002535 lyotropic effect Effects 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 230000000694 effects Effects 0.000 title abstract description 4
- -1 cyano-substituted p-phenylene ethylene compound Chemical class 0.000 claims abstract description 86
- 238000002845 discoloration Methods 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims description 64
- 239000007787 solid Substances 0.000 claims description 52
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- 238000001914 filtration Methods 0.000 claims description 25
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- 230000002194 synthesizing effect Effects 0.000 claims description 21
- 238000005406 washing Methods 0.000 claims description 21
- MDAIEMJGQUSUIW-UHFFFAOYSA-N CCCCOC(C=O)(C=C1)C=CC1(C=O)OCCCC Chemical compound CCCCOC(C=O)(C=C1)C=CC1(C=O)OCCCC MDAIEMJGQUSUIW-UHFFFAOYSA-N 0.000 claims description 20
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- 238000004440 column chromatography Methods 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- BBPATOFBGJZMJM-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)acetonitrile Chemical compound CSC1=CC=C(CC#N)C=C1 BBPATOFBGJZMJM-UHFFFAOYSA-N 0.000 claims description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003208 petroleum Substances 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 239000011259 mixed solution Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 7
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 7
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 238000000227 grinding Methods 0.000 claims description 7
- 229920002866 paraformaldehyde Polymers 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 4
- LQLQDKBJAIILIQ-UHFFFAOYSA-N Dibutyl terephthalate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 LQLQDKBJAIILIQ-UHFFFAOYSA-N 0.000 claims description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims description 2
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
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- 238000000634 powder X-ray diffraction Methods 0.000 description 4
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
The invention relates to a fluorescent material with piezochromism and lyotropic chromotropic color and a preparation method thereof. Belongs to the technical field of fluorescent materials. The fluorescent material with piezochromism and lyotropic chromotropic effect comprises a cyano-substituted p-phenylene ethylene compound, wherein the cyano-substituted p-phenylene ethylene compound has the following structural formula:
the invention also discloses a preparation method of the fluorescent material with piezochromism and lyotropic chromotropic color. The fluorescent material has both the lyotropic discoloration performance and the piezochromic performance, has wider application range compared with the prior fluorescent material, and is beneficial to popularization.
Description
Technical Field
The invention belongs to the technical field of fluorescent materials, and particularly relates to a fluorescent material with piezochromism and lyotropic chromotropic color and a preparation method thereof.
Background
Generally, organic color-changing materials are realized by changing the chemical structure of compounds, but solid-state chemical reactions make the synthesis of such piezochromic materials difficult due to incompleteness and irreversibility. Therefore, it is becoming more and more important to make molecules exhibit the fluorescent piezochromic behavior by adjusting the molecular stacking mode of small organic molecules.
The pressure-induced fluorescence color-changing material is a novel force-stimulated response intelligent material, and changes the luminous color and luminous intensity of molecules by changing the physical accumulation mode of the molecules. The material has potential application in the fields of micro-stress sensing, information storage, trademark anti-counterfeiting, luminescent devices and the like.
In addition, the lyotropic color-changing material controls the fluorescence emission spectrum of the compound through the polarity of the solvent, thereby showing different fluorescence capabilities, being widely used in the fields of color developing agents and molecular recognition and having potential application value.
However, at present, there are still few fluorescent materials having both lyotropic discoloration and color-press discoloration, and therefore, it is of great significance to design and synthesize novel fluorescent materials having both lyotropic discoloration and color-press discoloration properties.
Disclosure of Invention
The invention provides a fluorescent material with piezochromism and lyotropic chromotropic effect and a preparation method thereof for solving the technical problems.
In order to solve the above problems, the present invention provides a fluorescent material having piezochromic and lyotropic discoloration.
The technical scheme for solving the technical problems is as follows: a fluorescent material with piezochromic and lyotropic discoloration comprises a cyano-substituted p-phenylene ethylene compound, wherein the cyano-substituted p-phenylene ethylene compound has the following structural formula:
the fluorescent material with piezochromism and lyotropic chromotropic color has the advantages that:
1. with the increase of the polarity of the solvent, the fluorescence maximum emission peak of the fluorescent material gradually redshifts, and the fluorescent material has the property of lyotropic discoloration; the fluorescent material of the invention has red shift of the maximum fluorescence emission peak by grinding, and the maximum fluorescence emission peak recovers the initial state after being heated and melted at high temperature, thus having piezochromic property.
2. The fluorescent material of the invention has both the lyotropic discoloration and the piezochromic discoloration, has wider application range compared with the prior fluorescent material, and is beneficial to popularization.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the fluorescent material shows orange solid fluorescence in an initial state, shows red solid fluorescence after being ground, red-shifts the solid fluorescence emission wavelength from 612nm to 632nm, and reaches 20nm after being heated and melted at high temperature, and then recovers the orange solid fluorescence in the initial state.
The beneficial effect of adopting the further scheme is that: has excellent piezochromic performance.
Further, the fluorescence maximum peak gradually red-shifts with the increase of the polarity of the solvent.
The beneficial effect of adopting the further scheme is that: has excellent lyotropic discoloration performance.
Secondly, the present invention provides a method for preparing the above fluorescent material having piezochromism and lyotropic chromotropic color to solve the above technical problems.
The technical scheme for solving the technical problems is as follows: a method for preparing the fluorescent material with piezochromism and lyotropic discoloration comprises the following steps:
step 1, synthesizing intermediate butyl p-phenylene ether
Adding 8-10mmol of hydroquinone and 25-30mmol of potassium carbonate into 40-50ml of ethanol for dissolving, uniformly stirring, heating for reflux reaction, dropwise adding 25-30mmol of 1-bromobutane, cooling to room temperature after the reaction is finished, filtering to obtain filter residue, washing with ethanol, and drying to obtain white powdery solid, namely the dibutyl terephthalate;
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
Taking 8-10mmol of the dibutyl p-phenylene ether obtained in the step 1 and 25-30mmol of paraformaldehyde, adding acetic acid to dissolve, uniformly stirring, heating and stirring for reaction, simultaneously dropwise adding 15-25ml of a 30% wt hydrobromic acid solution, filtering to obtain filter residues, washing with ethanol, and drying to obtain a white scaly solid, namely the 1, 4-dibutoxy p-phenylbenzyl bromide;
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Taking 3-5mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2, adding 10-15mmol of sodium bicarbonate, dissolving by using dimethyl sulfoxide, heating for reflux reaction, filtering to obtain filter residue, drying in vacuum to obtain orange solid, and performing column chromatography to obtain orange powder, namely 1, 4-dibutoxy p-phthalaldehyde;
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Taking 1-3mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3, adding 2-4mmol of p-methylthio phenylacetonitrile and 15-25ml of tert-butyl alcohol, heating and stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, quickly adding 3-5mmol of potassium tert-butoxide to form a bright yellow solution, heating and stirring for reaction, filtering, washing with methanol, drying to obtain a yellow precipitate, and performing column chromatography to obtain orange red powder which is a cyano-substituted p-phenylene ethylene compound to obtain the fluorescent material with piezochromism and lyochromic.
The preparation method of the fluorescent material with piezochromism and lyotropic chromotropic color has the advantages that:
1. the preparation method has reasonable and feasible synthetic route, simple steps and mild conditions and has higher yield.
2. The cyano-substituted p-phenylene vinylene compound prepared by the method has piezochromic and lyotropic discoloration properties, and has potential application value in the fields of micro-stress sensing, information storage, trademark anti-counterfeiting, luminescent devices and the like.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, in the step 1, the temperature of the heating reflux reaction is 40-50 ℃ and the time is 4-5 h.
The beneficial effect of adopting the further scheme is that: the intermediate butyl p-phenylene ether is prepared.
Further, in the step 1, the time for dropwise adding the 1-bromobutane is 20-30 min.
The beneficial effect of adopting the further scheme is that: is beneficial to substitution reaction, improves the yield and is beneficial to preparing the p-phenylene dibutyl ether.
Further, in the step 2, the temperature of the heating stirring reaction is 65-75 ℃, and the time is 6-8 h.
The beneficial effect of adopting the further scheme is that: is beneficial to the preparation of the intermediate 1, 4-dibutoxy-p-phenylbenzyl bromide.
Further, in step 3, the temperature of the heating reflux reaction is 105-115 ℃, and the time is 1-2 h.
The beneficial effect of adopting the further scheme is that: is beneficial to the preparation of the intermediate 1, 4-dibutyloxy terephthalaldehyde.
Further, in the step 4, the heating and stirring temperature is 50-60 ℃, the heating and stirring reaction temperature is 50-60 ℃, and the time is 0.5-1 h.
The beneficial effect of adopting the further scheme is that: is beneficial to the preparation of cyano-substituted p-phenylene ethylene compounds.
Further, in the step 3, the liquid carrier for column chromatography is a mixed solution of petroleum ether and dichloromethane in a volume ratio of (2-3) to 1;
in the step 4, the liquid carrier for column chromatography is a mixed solution of petroleum ether and dichloromethane in a volume ratio of (1-1.5): 1.
The beneficial effect of adopting the further scheme is that: the purity is improved.
Drawings
FIG. 1 is a piezochromic fluorescence emission spectrum of a cyano-substituted p-phenylene ethylene fluorescent material prepared in example 1 of the present invention;
FIG. 2 is a X-ray diffraction pattern of piezochromic powder of cyano-substituted p-phenylethene fluorescent material prepared in example 1 of the present invention;
FIG. 3 is a fluorescence emission spectrum of a cyano-substituted p-phenylene vinylene fluorescent material prepared in example 1 of the present invention in different polar solvents.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
Example 1
This example provides a fluorescent material with piezochromic and lyotropic discoloration, which includes a cyano-substituted p-phenylene vinylene compound, and the structural formula of the cyano-substituted p-phenylene vinylene compound is as follows:
the fluorescent material shows orange solid fluorescence in an initial state, shows red solid fluorescence after being ground, and then recovers the orange solid fluorescence in the initial state after being heated and melted at high temperature. The fluorescent material gradually red-shifts the maximum peak of fluorescence with the increase of the polarity of the solvent.
In addition, the present embodiment also provides a method for preparing the fluorescent material with piezochromism and lyotropic chromotropic color, which includes the following steps:
step 1, synthesizing an intermediate p-phenylene dibutyl ether
Putting 10mmol of hydroquinone and 30mmol of potassium carbonate into a two-mouth bottle, adding 50ml of ethanol for dissolving, uniformly stirring, heating to 50 ℃, maintaining the reflux reaction at 50 ℃ for 5 hours, dropwise adding 30mmol of 1-bromobutane within 30min, generating a white precipitate after the reaction is finished, cooling to room temperature, filtering by adopting suction filtration, taking out filter residue, washing the filter residue with ethanol, and drying to constant weight to obtain a white powdery solid, namely the dibutyl phthalate.
The reaction formula of step 1 is as follows:
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
And (3) putting 10mmol of the dibutyl p-phenylene ether obtained in the step (1) and 30mmol of paraformaldehyde into a two-neck bottle, adding a proper amount of acetic acid to dissolve and uniformly stir, heating to 75 ℃, stirring to react for 8 hours, simultaneously dropwise adding 25ml of 30% wt hydrobromic acid solution into the two-neck bottle, generating a white scale-shaped precipitate after the reaction is finished, filtering by suction, taking filter residue, washing the filter residue by ethanol, and drying to constant weight to obtain a white scale-shaped solid, namely the 1, 4-dibutoxy p-phenylbenzyl bromide.
The reaction formula of step 2 is as follows:
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Putting 5mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2 into a round-bottom flask, adding 15mmol of sodium bicarbonate, adding a proper amount of dimethyl sulfoxide to dissolve, heating to 115 ℃, maintaining the reflux at 115 ℃ to react for 1h, generating orange yellow precipitate after the reaction is finished, filtering by suction to obtain filter residue, drying in vacuum to obtain orange yellow solid, and performing column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 2:1 as a carrier to obtain orange powder, namely 1, 4-dibutoxy terephthalaldehyde.
The reaction formula of step 3 is as follows:
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Putting 2mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3 into a two-neck bottle, adding 4mmol of p-methylthio phenylacetonitrile and 25ml of tert-butyl alcohol, heating to 60 ℃, stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, then quickly adding 5mmol of potassium tert-butoxide to form a bright yellow solution, heating to 60 ℃, maintaining the stirring at 60 ℃ for reaction for 1h to generate yellow precipitate, carrying out suction filtration, washing with methanol, drying to obtain yellow precipitate, and carrying out column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 1:1 as a carrier to obtain orange red powder, namely the cyano-substituted p-phenylene ethylene compound.
The reaction formula of step 4 is as follows:
example 2
This example provides a fluorescent material with piezochromic and lyotropic discoloration, which includes a cyano-substituted p-phenylene vinylene compound, and the structural formula of the cyano-substituted p-phenylene vinylene compound is as follows:
the fluorescent material shows orange solid fluorescence in an initial state, shows red solid fluorescence after being ground, and then recovers the orange solid fluorescence in the initial state after being heated and melted at high temperature. The fluorescent material gradually red-shifts the maximum peak of fluorescence with the increase of the polarity of the solvent.
In addition, the present embodiment also provides a method for preparing the fluorescent material with piezochromism and lyotropic chromotropic color, which includes the following steps:
step 1, synthesizing intermediate butyl p-phenylene ether
Putting 8mmol of hydroquinone and 30mmol of potassium carbonate into a two-mouth bottle, adding 45ml of ethanol for dissolving, uniformly stirring, heating to 45 ℃, maintaining the reflux reaction at 45 ℃ for 5 hours, dropwise adding 30mmol of 1-bromobutane within 25min, generating a white precipitate after the reaction is finished, cooling to room temperature, filtering by adopting suction filtration, taking out filter residue, washing the filter residue with ethanol, and drying to constant weight to obtain a white powdery solid, namely the dibutyl phthalate.
The reaction formula of step 1 is as follows:
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
Putting 8mmol of the dibutyl p-phenylene ether obtained in the step 1 and 25mmol of paraformaldehyde into a two-neck bottle, adding a proper amount of acetic acid to dissolve and uniformly stir, heating to 75 ℃, stirring to react for 6 hours, simultaneously dropwise adding 20ml of 30% wt hydrobromic acid solution into the two-neck bottle, generating white scale-shaped precipitate after the reaction is finished, filtering by suction, taking filter residue, washing the filter residue by ethanol, and drying to constant weight to obtain white scale-shaped solid, namely 1, 4-dibutoxy p-phenylbenzoylbromide.
The reaction formula of step 2 is as follows:
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Putting 3mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2 into a round-bottom flask, adding 10mmol of sodium bicarbonate, adding a proper amount of dimethyl sulfoxide to dissolve, heating to 115 ℃, maintaining the reflux at 115 ℃ to react for 1h, generating orange yellow precipitate after the reaction is finished, filtering by suction to obtain filter residue, drying in vacuum to obtain orange yellow solid, and performing column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 2:1 as a carrier to obtain orange powder, namely 1, 4-dibutoxy terephthalaldehyde.
The reaction formula of step 3 is as follows:
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Putting 3mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3 into a two-neck bottle, adding 4mmol of p-methylthio phenylacetonitrile and 25ml of tert-butyl alcohol, heating to 60 ℃, stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, then quickly adding 5mmol of potassium tert-butoxide to form a bright yellow solution, heating to 60 ℃, maintaining the stirring at 60 ℃ for reaction for 1h to generate yellow precipitate, carrying out suction filtration, washing with methanol, drying to obtain yellow precipitate, and carrying out column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 1:1 as a carrier to obtain orange red powder, namely the cyano-substituted p-phenylene ethylene compound.
The reaction formula of step 4 is as follows:
example 3
This example provides a fluorescent material with piezochromic and lyotropic discoloration, which includes a cyano-substituted p-phenylene vinylene compound, and the structural formula of the cyano-substituted p-phenylene vinylene compound is as follows:
the fluorescent material shows orange solid fluorescence in an initial state, shows red solid fluorescence after being ground, and then recovers the orange solid fluorescence in the initial state after being heated and melted at high temperature. The fluorescent material gradually red-shifts the maximum peak of fluorescence with the increase of the polarity of the solvent.
In addition, the present embodiment also provides a method for preparing the fluorescent material with piezochromism and lyotropic chromotropic color, which includes the following steps:
step 1, synthesizing intermediate butyl p-phenylene ether
Putting 10mmol of hydroquinone and 25mmol of potassium carbonate into a two-mouth bottle, adding 40ml of ethanol for dissolving, uniformly stirring, heating to 50 ℃, maintaining the reflux reaction at 50 ℃ for 4 hours, dropwise adding 25mmol of 1-bromobutane within 20min, generating a white precipitate after the reaction is finished, cooling to room temperature, filtering by adopting suction filtration, taking out filter residue, washing the filter residue with ethanol, and drying to constant weight to obtain a white powdery solid, namely the dibutyl phthalate.
The reaction formula of step 1 is as follows:
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
And (3) putting 10mmol of the dibutyl p-phenylene ether obtained in the step (1) and 30mmol of paraformaldehyde into a two-neck bottle, adding a proper amount of acetic acid to dissolve and uniformly stir, heating to 65 ℃, stirring to react for 7 hours, simultaneously dropwise adding 15ml of 30% wt hydrobromic acid solution into the two-neck bottle, generating a white scale-shaped precipitate after the reaction is finished, filtering by suction, taking filter residue, washing the filter residue by ethanol, and drying to constant weight to obtain a white scale-shaped solid, namely the 1, 4-dibutoxy p-phenylbenzyl bromide.
The reaction formula of step 2 is as follows:
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Putting 4mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2 into a round-bottom flask, adding 12mmol of sodium bicarbonate, adding a proper amount of dimethyl sulfoxide to dissolve, heating to 105 ℃, maintaining the temperature of 105 ℃ for reflux reaction for 2 hours, generating orange yellow precipitate after the reaction is finished, filtering by suction filtration to obtain filter residue, drying in vacuum to obtain orange yellow solid, and performing column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 2:1 as a carrier to obtain orange powder, namely 1, 4-dibutoxy terephthalaldehyde.
The reaction formula of step 3 is as follows:
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Putting 2mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3 into a two-neck bottle, adding 3mmol of p-methylthio phenylacetonitrile and 17ml of tert-butyl alcohol, heating to 55 ℃, stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, then quickly adding 4mmol of potassium tert-butoxide to form a bright yellow solution, heating to 55 ℃, maintaining the stirring at 55 ℃, reacting for 0.5h to generate yellow precipitate, filtering by suction, washing with methanol, drying to obtain yellow precipitate, and then carrying out column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 1:1 as a carrier to obtain orange red powder, namely the cyano-substituted p-phenylene ethylene compound.
The reaction formula of step 4 is as follows:
example 4
This example provides a fluorescent material with piezochromic and lyotropic discoloration, which includes a cyano-substituted p-phenylene vinylene compound, and the structural formula of the cyano-substituted p-phenylene vinylene compound is as follows:
the fluorescent material shows orange solid fluorescence in an initial state, shows red solid fluorescence after being ground, and then recovers the orange solid fluorescence in the initial state after being heated and melted at high temperature. The fluorescent material gradually red-shifts the maximum peak of fluorescence with the increase of the polarity of the solvent.
In addition, the present embodiment also provides a method for preparing the fluorescent material with piezochromism and lyotropic chromotropic color, which includes the following steps:
step 1, synthesizing intermediate butyl p-phenylene ether
Putting 9mmol of hydroquinone and 27mmol of potassium carbonate into a two-mouth bottle, adding 45ml of ethanol for dissolving, uniformly stirring, heating to 40 ℃, maintaining the reflux reaction at 40 ℃ for 4 hours, dropwise adding 25mmol of 1-bromobutane within 30min, generating a white precipitate after the reaction is finished, cooling to room temperature, filtering by adopting suction filtration, taking out filter residue, washing the filter residue with ethanol, and drying to constant weight to obtain a white powdery solid, namely the dibutyl phthalate.
The reaction formula of step 1 is as follows:
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
Placing 10mmol of the dibutyl p-phenylene ether obtained in the step 1 and 27mmol of paraformaldehyde into a two-neck bottle, adding a proper amount of acetic acid to dissolve and uniformly stir, heating to 70 ℃, stirring to react for 8 hours, simultaneously dropwise adding 25ml of 30% wt hydrobromic acid solution into the two-neck bottle, generating white scale-shaped precipitate after the reaction is finished, filtering by suction, taking filter residue, washing the filter residue by ethanol, and drying to constant weight to obtain white scale-shaped solid, namely 1, 4-dibutoxy p-phenylbenzoylbromide.
The reaction formula of step 2 is as follows:
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Putting 5mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2 into a round-bottom flask, adding 10mmol of sodium bicarbonate, adding a proper amount of dimethyl sulfoxide to dissolve, heating to 110 ℃, maintaining the temperature at 110 ℃ for reflux reaction for 2 hours, generating orange yellow precipitate after the reaction is finished, filtering by suction filtration to obtain filter residue, drying in vacuum to obtain orange yellow solid, and performing column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 3:1 as a carrier to obtain orange powder, namely 1, 4-dibutoxy terephthalaldehyde.
The reaction formula of step 3 is as follows:
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Putting 1mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3 into a two-neck bottle, adding 2mmol of p-methylthio phenylacetonitrile and 15ml of tert-butyl alcohol, heating to 50 ℃, stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, then quickly adding 3mmol of potassium tert-butoxide to form a bright yellow solution, heating to 50 ℃, maintaining the temperature at 50 ℃, stirring and reacting for 1h to generate yellow precipitate, carrying out suction filtration, washing with methanol, drying to obtain yellow precipitate, and carrying out column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 1.5:1 as a carrier to obtain orange red powder, namely the cyano-substituted p-phenylene ethylene compound.
The reaction formula of step 4 is as follows:
example 5
This example provides a fluorescent material with piezochromic and lyotropic discoloration, which includes a cyano-substituted p-phenylene vinylene compound, and the structural formula of the cyano-substituted p-phenylene vinylene compound is as follows:
the fluorescent material shows orange solid fluorescence in an initial state, shows red solid fluorescence after being ground, and then recovers the orange solid fluorescence in the initial state after being heated and melted at high temperature. The fluorescent material gradually red-shifts the maximum peak of fluorescence with the increase of the polarity of the solvent.
In addition, the present embodiment also provides a method for preparing the fluorescent material with piezochromism and lyotropic chromotropic color, which includes the following steps:
step 1, synthesizing intermediate butyl p-phenylene ether
Putting 10mmol of hydroquinone and 25mmol of potassium carbonate into a two-mouth bottle, adding 50ml of ethanol for dissolving, uniformly stirring, heating to 50 ℃, maintaining the reflux reaction at 50 ℃ for 4 hours, dropwise adding 30mmol of 1-bromobutane within 30min, generating a white precipitate after the reaction is finished, cooling to room temperature, filtering by adopting suction filtration, taking out filter residue, washing the filter residue with ethanol, and drying to constant weight to obtain a white powdery solid, namely the dibutyl phthalate.
The reaction formula of step 1 is as follows:
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
And (3) putting 10mmol of the dibutyl p-phenylene ether obtained in the step (1) and 30mmol of paraformaldehyde into a two-neck bottle, adding a proper amount of acetic acid to dissolve and uniformly stir, heating to 65 ℃, stirring to react for 7 hours, simultaneously dropwise adding 20ml of 30% wt hydrobromic acid solution into the two-neck bottle, generating a white scale-shaped precipitate after the reaction is finished, filtering by suction, taking filter residue, washing the filter residue by ethanol, and drying to constant weight to obtain a white scale-shaped solid, namely the 1, 4-dibutoxy p-phenylbenzyl bromide.
The reaction formula of step 2 is as follows:
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Putting 4mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2 into a round-bottom flask, adding 15mmol of sodium bicarbonate, adding a proper amount of dimethyl sulfoxide to dissolve, heating to 105 ℃, maintaining the temperature of 105 ℃ to carry out reflux reaction for 1h, generating orange yellow precipitate after the reaction is finished, filtering by suction filtration to obtain filter residue, drying in vacuum to obtain orange yellow solid, and carrying out column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 2:1 as a carrier to obtain orange powder, namely 1, 4-dibutoxy terephthalaldehyde.
The reaction formula of step 3 is as follows:
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Putting 3mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3 into a two-neck bottle, adding 3mmol of p-methylthio phenylacetonitrile and 20ml of tert-butyl alcohol, heating to 60 ℃, stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, then quickly adding 4mmol of potassium tert-butoxide to form a bright yellow solution, heating to 60 ℃, maintaining the stirring at 60 ℃, reacting for 0.5h to generate yellow precipitate, filtering by suction, washing with methanol, drying to obtain yellow precipitate, and then carrying out column chromatography by using a mixed solution of petroleum ether and dichloromethane in a volume ratio of 1.5:1 as a carrier to obtain orange red powder, namely the cyano-substituted p-phenylene ethylene compound.
The reaction formula of step 4 is as follows:
experimental example 1
In this experimental example, the cyano-substituted p-phenylene vinylene compound prepared in example 1 is subjected to structural characterization, including nuclear magnetic hydrogen spectrum and carbon spectrum, as follows:
1H NMR(400MHz,CDCl3)δ7.99(s,2H),7.87(s,2H),7.61(d,J＝8.6Hz,4H),7.30(d,J＝8.6Hz,4H),4.11(t,J＝6.3Hz,4H),2.53(s,6H),1.89-1.78(m,4H),1.50-1.46(m,4H),0.90(t,J＝12.5Hz,6H)；13C NMR(100HMz,CDCl3):δ＝147.5,145.9,138.6,130.7,126.7,126.6,118.8,116.0,114.8,99.5,68.8,31.8,19.2,13.9,13.8。
experimental example 2
In this experimental example, the piezochromic properties of the fluorescent material comprising cyano-substituted p-phenylene vinylene compound prepared in example 1 were measured, specifically, a fluorescence emission spectrogram and a powder X-ray diffraction spectrogram were measured, as shown in fig. 1 and 2.
As can be seen from FIG. 1, the piezochromic properties of the cyano-substituted p-phenylene vinylene compound were that the cyano-substituted p-phenylene vinylene compound exhibited orange solid fluorescence in the initial state and red solid fluorescence after grinding with a mortar. FIG. 1 clearly shows that the solid state fluorescence emission wavelength of cyano-substituted p-phenylethene compounds red-shifted from 612nm to 632nm before and after grinding, and the solid state fluorescence wavelength red-shifted to 20 nm. The ground sample is melted by high temperature, and the solid state fluorescence of the ground sample is restored to the initial state, namely the emission wavelength is 612 nm. The cyano-substituted p-phenylene ethylene compounds are proved to have typical piezochromic properties.
As can be seen from fig. 2, the cyano-substituted p-phenylene vinylene compound exhibited orange solid fluorescence in the initial state and red solid fluorescence after being ground with a mortar. Fig. 2 clearly shows that the crystal form of cyano-substituted p-phenylene vinylene compound is changed before and after grinding, the main peak positions of powder X-ray diffraction of cyano-substituted p-phenylene vinylene compound before grinding are 5.49, 17.62, 25.95 and 30.95 degrees, and the main peak positions of powder X-ray diffraction of cyano-substituted p-phenylene vinylene compound after grinding are 4.42, 7.65, 15.45, 17.62 and 24.76 degrees. The ground sample is melted at high temperature, and the main peak position of the powder X-ray diffraction of the sample is basically restored to the initial state. The cyano-substituted p-phenylene ethylene compounds are proved to have typical piezochromic properties.
Experimental example 3
In this experimental example, the lyotropic color change property of the fluorescent material made of the cyano-substituted p-phenylene vinylene compound prepared in example 1 is detected, and specifically, a fluorescence emission spectrum is detected, as shown in fig. 3.
As can be seen from FIG. 3, cyano-substituted p-phenylethenes were formulated into 10 with solvents of different polarity, Dichloromethane (DCM), Toluene (Toluene), Tetrahydrofuran (THF), Acetonitrile (Acetonitrile) and dimethyl sulfoxide (DMSO)-5And (3) testing the fluorescence properties of the solutions to be tested with mol/L concentration under the excitation wavelength of 400 nm. As shown in FIG. 3, the cyano-substituted p-phenylene vinylenes have a maximum fluorescence emission wavelength of 506nm in methylene chloride, 520nm in toluene, 532nm in acetonitrile, 516nm in tetrahydrofuran, and 536nm in dimethyl sulfoxide. The data show that the wavelength of the maximum fluorescence emission peak of the cyano-substituted p-phenylene ethylene compound gradually red shifts with the increase of the polarity of the solvent. This indicates that cyano-substituted p-phenylene vinylenes have typical lyotropic color properties.
In the description of the present invention, it is to be understood that the terms "central," "longitudinal," "lateral," "upper," "lower," "front," "rear," "left," "right," "vertical," "horizontal," "top," "bottom," "inner," "outer," and the like are used in the orientation or positional relationship indicated in the drawings, which are merely for convenience in describing the invention and to simplify the description, and are not intended to indicate or imply that the referenced device or element must have a particular orientation, be constructed and operated in a particular orientation, and are therefore not to be construed as limiting the invention. Furthermore, the terms "first", "second", etc. are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first," "second," etc. may explicitly or implicitly include one or more of that feature. In the description of the invention, the meaning of "a plurality" is two or more unless otherwise specified.
In the description of the invention, it is to be noted that, unless otherwise explicitly specified or limited, the terms "mounted", "connected" and "connected" are to be construed broadly, e.g. as being fixed or detachable or integrally connected; can be mechanically or electrically connected; they may be connected directly or indirectly through intervening media, or they may be interconnected between two elements. The specific meaning of the above terms in the creation of the present invention can be understood by those of ordinary skill in the art through specific situations.
It is to be noted that "comprising" in the present invention means that it may include other components in addition to the components described, and the "comprising" may be replaced with "being" or "consisting of … …" in a closed manner.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A fluorescent material with piezochromic and lyotropic discoloration is characterized by comprising a cyano-substituted p-phenylene ethylene compound, wherein the cyano-substituted p-phenylene ethylene compound has the following structural formula:
2. the fluorescent material having piezochromic and lyotropic discoloration according to claim 1, wherein said fluorescent material exhibits orange solid fluorescence in the initial state, red solid fluorescence after grinding, red shift of solid fluorescence emission wavelength from 612nm to 632nm, red shift of solid fluorescence wavelength to 20nm, and then returns to orange solid fluorescence in the initial state after melting by heating at high temperature.
3. The fluorescent material having both piezochromic and lyochromic characteristics according to claim 1, wherein the fluorescent material gradually red-shifts the fluorescence maximum peak with increasing polarity of the solvent.
4. A method for the preparation of a fluorescent material with piezochromic and lyochromic properties according to any one of claims 1 to 3, characterized in that it comprises the following steps:
step 1, synthesizing intermediate butyl p-phenylene ether
Adding 8-10mmol of hydroquinone and 25-30mmol of potassium carbonate into 40-50ml of ethanol for dissolving, uniformly stirring, heating for reflux reaction, dropwise adding 25-30mmol of 1-bromobutane, cooling to room temperature after the reaction is finished, filtering to obtain filter residue, washing with ethanol, and drying to obtain white powdery solid, namely the dibutyl terephthalate;
step 2, synthesis of intermediate 1, 4-dibutoxy p-phenylbenzyl bromide
Taking 8-10mmol of the p-xylylene dibutyl ether obtained in the step 1 and 25-30mmol of paraformaldehyde, adding acetic acid to dissolve and uniformly stir, heating and stirring for reaction, simultaneously dropwise adding 15-25ml of 30% wt hydrobromic acid solution, filtering to obtain filter residue, washing with ethanol, and drying to obtain a white scaly solid, namely 1, 4-dibutoxy p-xylylene bromide;
step 3, synthesizing an intermediate 1, 4-dibutyloxy terephthalaldehyde
Taking 3-5mmol of 1, 4-dibutoxy p-phenylbenzoyl bromide obtained in the step 2, adding 10-15mmol of sodium bicarbonate, dissolving by using dimethyl sulfoxide, heating for reflux reaction, filtering to obtain filter residue, drying in vacuum to obtain orange solid, and performing column chromatography to obtain orange powder, namely 1, 4-dibutoxy p-phthalaldehyde;
step 4, synthesizing cyano-substituted p-phenylene ethylene compounds
Taking 1-3mmol of 1, 4-dibutyloxy terephthalaldehyde obtained in the step 3, adding 2-4mmol of p-methylthio phenylacetonitrile and 15-25ml of tert-butyl alcohol, heating and stirring until the p-methylthio phenylacetonitrile and the tert-butyl alcohol are completely dissolved, quickly adding 3-5mmol of potassium tert-butoxide to form a bright yellow solution, heating and stirring for reaction, filtering, washing with methanol, drying to obtain a yellow precipitate, and performing column chromatography to obtain orange red powder which is a cyano-substituted p-phenylene ethylene compound to obtain the fluorescent material with piezochromism and lyochromic.
5. The method for preparing a fluorescent material having piezochromic and lyochromic characteristics according to claim 4, wherein in step 1, the temperature of the heating reflux reaction is 40 to 50 ℃ and the time is 4 to 5 hours.
6. The method for preparing a fluorescent material having piezochromic and lyochromic characteristics according to claim 4, wherein in step 1, the time for dropwise addition of 1-bromobutane is 20-30 min.
7. The method for preparing a fluorescent material having piezochromic and lyochromic characteristics according to claim 4, wherein in step 2, the temperature of the heating stirring reaction is 65-75 ℃ and the time is 6-8 h.
8. The method for preparing a fluorescent material with piezochromic and lyochromic characteristics as claimed in claim 4, wherein in step 3, the temperature of the heating reflux reaction is 105 ℃ and 115 ℃ for 1-2 h.
9. The method for preparing a fluorescent material having piezochromic and lyochromic characteristics according to claim 4, wherein in step 4, the temperature of the heating and stirring is 50 to 60 ℃, the temperature of the heating and stirring reaction is 50 to 60 ℃, and the time is 0.5 to 1 hour.
10. The method for preparing a fluorescent material having piezochromic and lyochromic characteristics according to any one of claims 3 to 9, wherein in step 3, the liquid carrier used for the column chromatography is a mixture of petroleum ether and dichloromethane in a volume ratio of (2-3): 1;
in the step 4, the liquid carrier adopted by the column chromatography is a mixed solution of petroleum ether and dichloromethane in a volume ratio of (1-1.5): 1.
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