CN114436891B - Color-adjustable aggregation-induced emission material and preparation method and application thereof - Google Patents
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Abstract
A color-controllable aggregation-induced emission material, a preparation method and application thereof. The luminescent material is prepared by performing a Kenaokuer condensation reaction on 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde, has Aggregation Induced Emission Enhancement (AIEE) characteristics and optical characteristics which can be adjusted through various photoresponse paths, shows bright yellow fluorescence in a solid state, and shows a solvent-induced discoloration phenomenon. Based on a cyanostyrene skeleton, the color and fluorescence of the luminescent material can be effectively adjusted through a photoisomerization process and an aggregation state photodimerization process in a solution under the illumination of 420 nm. The yellow fluorescence of the luminescent material can be converted into a gathering induction luminescent material with blue fluorescence after the diethylamino group is protonated, and the original state of the luminescent material can be recovered after the diethylamino group is deprotonated. The optical property of the aggregation-induced emission material with blue fluorescence after protonation can be effectively adjusted through photoisomerization and photocyclization processes under the irradiation of ultraviolet light. The invention has simple process, low cost and high yield.
Description
Technical Field
The invention relates to color regulation and control of an organic luminescent material and application in the technical field of photo patterning and anti-counterfeiting, in particular to a color-regulated aggregation-induced luminescent material and a preparation method and application thereof.
Background
High temporal and spatial resolution and accurate operation due to convenient and non-invasive triggering. Light responsive materials have made significant progress in recent years as an important family of functional stimuli responsive materials, exhibiting significant fluorescent color change, different emission intensities, and even "on/off" switching of fluorescence under light irradiation. However, most photoresponsive materials exhibit only one specific photochemical pathway under light irradiation, which simplifies their function and further limits their application. The cyanostyrene derivative is one of the best candidate materials for constructing the light-responsive fluorescent material, and firstly, the cyanostyrene unit is a typical pi conjugated structure and has attractive fluorescent characteristics. Furthermore, recent studies have shown that most cyanostyrene-based fluorophores exhibit tunable fluorescence behavior and aggregation-induced emission characteristics upon aggregate formation. More importantly, the cyanostyryl fluorophore can react to light irradiation through a variety of photochemical pathways. However, it is still a great challenge how to effectively adjust the optical properties of the cyanobenzene-based fluorophore through different light response pathways to promote the development of advanced functional optical materials and explore the application potential thereof. Therefore, the development of multifunctional aggregation-inducing luminescent materials with controllable optical properties is necessary.
Disclosure of Invention
In view of the above, the present invention provides a color-controllable aggregation-induced emission material, a preparation method and an application thereof, which can undergo a photo-isomerization process in a solution under the irradiation of 420nm light, and undergo a photo-dimerization process in an aggregation state, accompanied by corresponding changes in color and fluorescence; and the protonated aggregation induces the luminescent material to change fluorescence from yellow to blue after the action of acid, and the luminescent material undergoes the processes of photo-isomerization and photo-cyclization under 365nm light irradiation in a solution state and an aggregation state, and is accompanied by the change of fluorescence. The aggregation-induced emission material can be used in the fields of information display, photo-patterning and anti-counterfeiting.
A preparation method of a color-controllable aggregation-induced emission material is characterized by comprising the following preparation steps:
preparing a color-controllable aggregation-induced emission material: adding 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde into an ethanol solution, stirring, and then adding alkali for catalytic reaction; and after the reaction is finished, obtaining a mixed system, centrifuging the mixed system to precipitate a product, separating and drying to obtain the aggregation-induced emission material with adjustable color.
Further, the molar ratio of the 4-biphenylacetonitrile to the 4-diethylaminobenzaldehyde is 1:1, the ethanol solution is absolute ethanol, the reaction temperature is 80-90 ℃, and the reaction time is 6-8 hours; the separation is centrifugal precipitation separation, and ethanol is selected for washing; the reaction is a Kenavenuer condensation reaction and needs to be carried out under the condition of base catalysis. The base is tetrabutylammonium hydroxide.
Further, by introducing a 4-diethylaminobenzaldehyde donor structure and a 4-biphenylacetonitrile acceptor structure, based on a distorted intramolecular charge transfer and intramolecular motion limitation mechanism, the prepared solid powder has bright yellow fluorescence, namely shows excellent aggregation-induced luminescence properties.
Further, the color-controllable aggregation-inducing luminescent material undergoes a photodimerization process under 420nm light irradiation in a poor solvent environment under high water content under the poor solvent environment, accompanied by gradual blue shift and enhancement of yellow fluorescence of an aggregated state under high water content.
Further, the fluorescence of the deprotonated aggregation inducing luminescent material generated by the color controllable aggregation inducing luminescent material after the action of acid changes to blue, and the yellow fluorescence of the deprotonated aggregation inducing luminescent material is recovered under the action of alkali.
Further, the deprotonated aggregation-inducing luminescent material undergoes photoisomerization and photocyclization processes under 365nm light irradiation in solution and aggregation state, accompanied by an enhancement and blue-shift of blue fluorescence.
The application of the aggregation-induced emission material with controllable color prepared by the method is characterized in that: the aggregation-induced emission material with controllable optical properties can be applied to information display, photo patterning and anti-counterfeiting materials.
The aggregation-induced emission material can be applied to information display, and a two-dimensional fluorescent pattern for information display based on the aggregation-induced emission material with adjustable and controllable color is constructed by taking a 96-well plate as a template. The information based on the aggregation-induced emission material with adjustable color is displayed as bright yellow fluorescence under high water content, and after the pH value of the information is adjusted to 1 by using HCl solution, the yellow information is changed into white and emits strong cyan emission. Further, information exposed to 420nm light and information exposed to 365nm ultraviolet light change yellow fluorescence information to green fluorescence and cyan fluorescence information to blue fluorescence due to the occurrence of photodimerization and photocyclization processes, respectively.
The aggregation-induced emission material can be applied to photo patterning, and is dissolved in dichloromethane after being mixed with the aggregation-induced emission material with adjustable color and polyvinyl butyral, and a solvent is volatilized to prepare a film. The film is yellow green under sunlight, green fluorescence is emitted under an ultraviolet lamp, after the film is irradiated by light of 420nm, the color of an irradiation area under the sunlight becomes light, and the green fluorescence under the ultraviolet lamp is blue-shifted. The area covered by the mask is not changed by illumination.
The aggregation-induced emission material can be applied to the field of anti-counterfeiting, and because the aggregation-induced emission material with adjustable color contains a diethylamino group which can realize protonation-deprotonation through acid-base action, the fluorescence color can realize multiple reversible switching between yellow light and blue light through HCl and NaOH solutions; the application of the aggregation-induced emission material with adjustable color in the anti-counterfeiting field can be realized through acid-base regulation.
The preparation method of the aggregation-induced emission material with adjustable color, which is prepared by the method, comprises the following specific preparation steps:
1. adding 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde into ethanol, adding a proper amount of tetrabutylammonium hydroxide for catalytic reaction, and carrying out condensation reflux at 80-90 ℃ for 6-8h; and after the reaction is finished, obtaining a mixed system, centrifuging the mixed system to precipitate a product, separating, washing with ethanol, and drying to obtain the aggregation-induced yellow light emitting material with adjustable color.
2. Preparing a mixed system of tetrahydrofuran and water with water content of 90%, respectively measuring fluorescence spectrograms of the aggregation-induced emission material in different water content systems under the irradiation of 420nm light by using an ultraviolet-visible spectrophotometer and a fluorescence spectrometer, and drawing spectrograms.
3. Fumigating the aggregation-induced emission material powder with hydrochloric acid to obtain acid-fumigated protonated powder, and observing the color and fluorescence changes of the acid-fumigated protonated powder.
4. Preparing a mixed system of the protonated aggregation-induced emission material fumigated by the hydrochloric acid in tetrahydrofuran and water with the water content of 90%, respectively measuring a fluorescence spectrum of the protonated aggregation-induced emission material fumigated by the hydrochloric acid in an aggregation state under 365nm light irradiation by using an ultraviolet-visible spectrophotometer and a fluorescence spectrometer, drawing the spectrum, and observing color change.
The color-controllable aggregation-induced emission material is applied to information display, light patterning, anti-counterfeiting and systems.
The key points of the technology of the invention are as follows:
the color-controllable aggregation-induced emission material of the present invention can obtain an aggregation-induced emission material having bright yellow fluorescence in a solid state with high yield by a simple one-step reaction, has adjustable acid-base response and photochemical response, and further exhibits a variety of color-controllable fluorescence. The current photoreaction system is difficult to realize the multi-mode regulation of fluorescence through a simple way. The material disclosed by the invention is simple in reaction and high in yield, and shows various fluorescence changes regulated and controlled by adjusting acid-base and illumination conditions. The aggregation-induced emission material can be used in the fields of information display, light patterning and anti-counterfeiting.
The invention has the advantages that: the aggregation-induced emission material with adjustable color is generated by performing a Kenaokuer condensation reaction on 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde, and the aggregation-induced emission material is simple in preparation process, low in preparation cost and high in yield. The color and the optical performance of the aggregation-induced emission material can be adjusted through multiple modes, and the aggregation-induced emission material has good application prospects in the fields of information display, light patterning and anti-counterfeiting.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
Fig. 1 is a schematic step diagram of a method for preparing a color-controllable aggregation-induced emission material according to an embodiment of the present invention.
FIG. 2 is a fluorescence spectrum of a color-controllable aggregation-induced emission material in a tetrahydrofuran/water mixed system with a water content of 90% under 420nm light irradiation, with the abscissa representing the wavelength and the ordinate representing the emission intensity, whose emission at 508nm is continuously enhanced and blue-shifted under 420nm light irradiation.
FIG. 3 is a photograph of powder of color controllable aggregation inducing luminescent material before and after fumigation with hydrochloric acid in sunlight and under an ultraviolet lamp.
FIG. 4 shows fluorescence spectra of protonated aggregation-induced emission materials after hydrochloric acid fumigation in a tetrahydrofuran/water mixed system with water content of 90% under 365nm light irradiation. As the irradiation time was prolonged, the emission peak at about 455nm almost disappeared, and the emission peak at 395nm gradually increased.
Fig. 5 is an information display pattern prepared based on the color-controllable aggregation-induced emission material according to an embodiment of the present invention.
Fig. 6 is a photo-patterning photo prepared based on the color-controllable aggregation-inducing luminescent material according to an embodiment of the present invention.
Fig. 7 is a photograph of an anti-counterfeit application prepared based on the color-controllable aggregation-induced emission material according to an embodiment of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be obtained by a person skilled in the art without inventive step based on the embodiments of the present invention, are within the scope of protection of the present invention.
Example 1
1. Fig. 1 is a schematic step diagram of a method for preparing a color-controllable aggregation-induced emission material according to an embodiment of the present invention. The preparation method of the aggregation-induced emission material with adjustable color comprises the following steps:
adding 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde into ethanol, adding a proper amount of tetrabutylammonium hydroxide for catalytic reaction, and carrying out condensation reflux at 80-90 ℃ for 6-8h; and after the reaction is finished, obtaining a mixed system, centrifuging the mixed system to precipitate a product, separating, washing with ethanol, and drying to obtain the aggregation-induced emission material with adjustable color. The yield was 89%.
2. Preparing a mixed system of tetrahydrofuran and water with the water content of 90% in the aggregation-induced emission material, measuring an absorption spectrum and a fluorescence spectrum of the aggregation-induced emission material under the irradiation of 420nm light respectively by using an ultraviolet-visible spectrophotometer and a fluorescence spectrometer, and drawing the spectrum (see figure 2). In a mixed system of tetrahydrofuran and water with water content of 90%, after 420nm light irradiation, the emission at 508nm is continuously enhanced and blue shift occurs.
3. The aggregation inducing luminescent material powder was fumigated with hydrochloric acid to obtain an acid fumigated protonated powder (fig. 3). The aggregation-induced emission material powder changes from yellow fluorescence to blue fluorescence after being fumigated by hydrochloric acid.
4. Preparing a mixed system of tetrahydrofuran and water with water content of 90% of the protonated aggregation-induced emission material after the acid action, respectively measuring an absorption spectrum and a fluorescence spectrum of the protonated aggregation-induced emission material under 365nm light irradiation by using an ultraviolet-visible spectrophotometer and a fluorescence spectrometer, and drawing a spectrum (see fig. 4). At a water content of 90%, the emission peak at 455nm almost disappeared and the emission peak at 395nm gradually increased with the increase of the irradiation time.
5. The information display application of the aggregation-induced emission material with adjustable color provided by the invention comprises the following steps:
fig. 5 shows a pattern for information display based on color-controllable aggregation-inducing luminescent material constructed using a 96-well plate as a template. The yellow pattern "FL" with bright yellow fluorescence was formed by filling the pore with a color-controllable aggregation-inducing luminescent material of a mixed system of tetrahydrofuran and water at 90% water content. After the pH of "L" was adjusted to 1 with HCl solution, the yellow letter "L" turned white, emitting intense cyan fluorescence, and the fluorescent pattern showed "F" with yellow fluorescence and "L" with cyan fluorescence. Further, after exposure to "F" under irradiation of 420nm light and exposure to "L" under 365nm ultraviolet light for 10 minutes, the letter "F" of yellow fluorescence becomes blue fluorescence due to photodimerization reaction of the aggregation inducing luminescent material in an aggregated state. The letter "L" with cyan fluorescence changes to blue fluorescence due to the protonated aggregation inducing a photocyclization reaction of the luminescent material. Thus, two-dimensional fluorescence patterns with multi-modal modulation and high contrast were constructed for information presentation.
6. The light patterning application of the aggregation-induced emission material with adjustable color provided by the invention comprises the following steps:
the color-controllable aggregation-induced emission material is doped with polyvinyl butyral to prepare a film, and the film is yellow in the sun and emits bright green fluorescence under ultraviolet light. By using the crab mask, crab patterns were successfully printed after 10 minutes of light irradiation at 420 nm. Due to the color-controllable aggregation-induced photodimerization of the luminescent material, the color of the illuminated area changes from yellow to yellowish and the fluorescence changes to dark green (fig. 6).
7, the anti-counterfeiting application of the color-controllable aggregation-induced emission material provided by the invention comprises the following steps:
FIG. 7 is a photograph of an anti-counterfeit model prepared using a color-controllable aggregation inducing luminescent material, wherein the letter "AIE" is written using an ink prepared using the aggregation inducing luminescent materialYellow and fluoresces yellow. Becomes colorless after treatment with an acid pen containing 1M HCl and exhibits bright blue fluorescence. In addition, when using 10 -3 When the MNaOH alkali pen is rewritten, the characters can be restored to the original state, and yellow fluorescence is restored. The figure shows that the aggregation-induced emission material has a huge application prospect in the anti-counterfeiting field.
Claims (10)
1. A preparation method of aggregation-induced emission material with adjustable color is characterized in that,
adding 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde into an ethanol solution, stirring, and adding a base catalyst for catalytic reaction; obtaining a mixed system after the reaction is finished, separating and drying the mixed system to obtain the aggregation-induced emission material with adjustable color;
the alkali catalyst is tetrabutyl ammonium hydroxide;
the structural formula of the aggregation-induced emission material is shown in the specification
2. The method of claim 1, wherein the color controllable aggregation-induced emission material comprises: the molar ratio of the 4-biphenylacetonitrile to the 4-diethylaminobenzaldehyde is 1:1, the ethanol solution is absolute ethanol, the reaction temperature is 60-100 ℃, and the reaction time is 6-18h; the separation is centrifugal precipitation separation, and ethanol is selected for washing; the reaction is a Kenavenuer condensation reaction and needs to be carried out in an alkali catalysis environment.
3. The method of producing a color-controllable aggregation-inducing luminescent material according to claim 1 or 2, wherein: through the introduction of a 4-diethylamine benzaldehyde donor structure and a 4-biphenyl acetonitrile acceptor structure, the prepared material has bright fluorescence in an aggregation state based on a twisted intramolecular charge transfer and intramolecular motion restriction mechanism, namely, the material shows excellent aggregation-induced emission properties.
4. The method of producing a color-controllable aggregation-inducing luminescent material according to claim 1 or 2, wherein: the aggregation-induced emission material undergoes a photodimerization process in an aggregated state under irradiation of light of 380-440nm, accompanied by a gradual blue shift and enhancement of its yellow fluorescence.
5. The method of producing a color-controllable aggregation-inducing luminescent material according to claim 1 or 2, wherein: the fluorescence of the deprotonated aggregation-induced emission material generated by the color-controllable aggregation-induced emission material after the action of acid is changed into blue, and the yellow fluorescence of the deprotonated aggregation-induced emission material is recovered after the deprotonation of the color-controllable aggregation-induced emission material under the action of alkali.
6. The method of claim 1 or 2, wherein the color-controllable aggregation-inducing luminescent material comprises: the deprotonated aggregation-inducing luminescent material undergoes a photo-isomerisation and photo-cyclisation process under 365nm light irradiation in solution and in the aggregated state, with an increase in blue fluorescence and a blue shift.
7. A method for preparing the color-controllable aggregation-inducing luminescent material according to claim 1 or 2, comprising the following steps:
1) Adding 4-biphenylacetonitrile and 4-diethylaminobenzaldehyde into ethanol, adding tetrabutylammonium hydroxide for catalytic reaction, and performing condensation reflux at 60-100 ℃ for 6-18h; after the reaction is finished, obtaining a mixed system, centrifuging the mixed system to precipitate a product, separating, washing with ethanol for three times, and drying to obtain the aggregation-induced emission material with adjustable color;
2) Preparing a mixed system of tetrahydrofuran and water with water content of 90%, respectively measuring the fluorescence spectrogram of the aggregation-induced emission material under the irradiation of light of 380-440nm by using a fluorescence spectrometer, and drawing a spectrogram;
3) Fumigating the aggregation-induced emission material powder with hydrochloric acid to obtain acid-fumigated protonated powder, and observing the color and fluorescence changes of the acid-fumigated protonated powder;
4) Preparing a mixed system of tetrahydrofuran and water with the water content of 90% of the protonated aggregation-induced emission material fumigated by the hydrochloric acid, measuring the fluorescence spectrogram of the protonated aggregation-induced emission material fumigated by the hydrochloric acid under the irradiation of light of 320-370nm by using a fluorescence spectrometer, and drawing the spectrogram.
8. The color-controllable aggregation-inducing luminescent material prepared by the method of claim 1, wherein: the color-controllable aggregation-induced emission material can be used for a two-dimensional fluorescent pattern for information display; information of the aggregation-induced emission material with adjustable and controllable color is displayed as bright yellow fluorescence under high water content, and after the pH value of the information is adjusted to 1 by using HCl solution, the yellow information is changed into white and strong cyan emission is emitted; further, information exposed to light of 380 to 440nm and information exposed to ultraviolet light of 320 to 370nm change yellow fluorescence information to green fluorescence and cyan fluorescence information to blue fluorescence due to the occurrence of light dimerization and photocyclization processes, respectively.
9. The color-controllable aggregation-inducing luminescent material prepared by the method of claim 1, wherein: the aggregation-induced emission material can be applied to photo-patterning, and is dissolved in dichloromethane after being mixed with the aggregation-induced emission material with adjustable color and polyvinyl butyral, and a film is prepared after a solvent is volatilized; the film is yellow green under sunlight and emits green fluorescence, and after irradiation of light of 380-440nm, the color of an irradiation area becomes light under the sunlight, and the green fluorescence is blue-shifted; the area covered by the mask is not changed by illumination.
10. The color-controllable aggregation-inducing luminescent material prepared by the method of claim 1, wherein: the aggregation-induced emission material can be applied to the field of anti-counterfeiting, and because the aggregation-induced emission material with adjustable color contains a diethylamino group which can realize protonation-deprotonation through acid-base action, the fluorescence color can realize multiple reversible switching between yellow light and blue light through HCl and NaOH solutions; the application of the aggregation-induced emission material with adjustable color in the anti-counterfeiting field can be realized through acid-base regulation.
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