CN114058045A - Organic room temperature phosphorescent thin film material with hydrothermal stimulus response and excitation dependence, preparation and application - Google Patents
Organic room temperature phosphorescent thin film material with hydrothermal stimulus response and excitation dependence, preparation and application Download PDFInfo
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- C08J2329/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
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Abstract
The invention belongs to the field of room temperature phosphorescence, and particularly relates to an organic room temperature phosphorescence thin film material with hydrothermal stimulus response and excitation dependence characteristics, and preparation and application thereof; the film material comprises a PVA main chain and a phosphorescent chromophore combined with the PVA main chain; the phosphorescent chromophore is a mixture of 3-biphenylboronic acid, 1-naphthoic acid and 1-pyreneboronic acid, wherein the mass ratio of the 3-biphenylboronic acid to the 1-naphthoic acid to the 1-pyreneboronic acid to the PVA main chain is 1-10:1-10: 5-10; the mass ratio of the boric acid mixture to the PVA main chain is 4-32: 480-1500. According to the application, three aromatic boric acids are combined with a PVA main chain, the three aromatic boric acids have good phosphorescence properties at low temperature and different pi-conjugation degrees, and the room-temperature phosphorescence properties can be controlled through external stimulation of heat and water, so that the afterglow color can be adjusted.
Description
Technical Field
The invention belongs to the field of room temperature phosphorescence, and particularly relates to an organic room temperature phosphorescence thin film material with hydrothermal stimulus response and excitation dependence characteristics, and preparation and application thereof.
Background
Organic Room Temperature Phosphorescence (RTP) is a light emission phenomenon that has been widely focused in recent years. The material has the advantages of low toxicity, long emission life, large Stokes shift and the like. Therefore, great attention has been paid in the past few years. In particular, the long-lived room temperature phosphorescent materials observed with the naked eye make them more favorable for monitoring under external stimuli than the short-lived fluorescent materials, which is more favorable for their development as stimuli-responsive materials. Nevertheless, the search for stimuli-responsive room temperature phosphorescent materials is still in the preliminary stage, mainly because room temperature phosphorescent emission tends to be realized in a crystalline state, and the disadvantages of poor reproducibility and poor solution processability of crystals greatly limit the application thereof. For example, some materials such as pure organic room temperature phosphorescent materials reported by Wang Zhang Yuan et al have stimulus response characteristics that depend mainly on the crystal structure (adv. Mater.2015,27, 6195-. Other materials, such as the pure organic room temperature phosphorescent materials reported by ZHENGUO Chi et al, produce efficient phosphorescence by increasing the rate of interstitial hopping through strong spin-orbit coupling of heavy atoms and organic moieties with lone pairs of electrons but have difficulty in simultaneously controlling the sites of stimulus response, so that there is no property of stimulus response (Angew. chem. int. Ed.2016,55, 2181-. To overcome these disadvantages, amorphous room temperature phosphorescent systems have been found which generally provide a rigid environment. In particular, this strategy of doping small organic molecules into rigid polymers is more attractive due to the better film-forming ability of the polymers. How to achieve response to external stimuli and to excite the dependent room temperature phosphorescence remains a great challenge today.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide an organic room temperature phosphorescent thin film material with hydrothermal stimulus response and excitation dependence characteristics, and preparation and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a multiphosphorous photogenic chromophore thin film material comprising a PVA backbone and a phosphorescent chromophore associated with said PVA backbone; the phosphorescent chromophore is a mixture of 3-biphenylboronic acid, 1-naphthoic acid and 1-pyreneboronic acid, wherein the mass ratio of the 3-biphenylboronic acid to the 1-naphthoic acid to the 1-pyreneboronic acid to the PVA main chain is 1-10:1-10: 5-10; the mass ratio of the boric acid mixture to the PVA main chain is 4-32: 480-1500.
The mass ratio of the 3-biphenylboronic acid to the 1-naphthalene boronic acid to the 1-pyreneboronic acid is 1:1: 5.
The mass ratio of the boric acid mixture to the PVA backbone was 7: 480.
The invention also comprises a preparation method of the film material, which comprises the following steps:
s1, putting 3-biphenyl boric acid, 1-naphthalene boric acid and 1-pyrene boric acid into a container filled with water according to a proportion, and ultrasonically dispersing the mixture to enable the final concentration of the mixed liquid of the mixed boric acid to be 1-8 g/L;
s2, putting the PVA into a container filled with water, heating to 65-90 ℃, stirring to completely dissolve the PVA, cooling to room temperature to the concentration of 160-500g/L to obtain a PVA aqueous solution;
s3, mixing the mixed boric acid aqueous solution obtained in the step S1 and the polyvinyl alcohol aqueous solution obtained in the step S2 according to the mass ratio of the mixed boric acid to the polyvinyl alcohol of (4-32): (480-1500), and then adding ammonia water, wherein the volume mass ratio of the ammonia water to the polyvinyl alcohol is as follows: 0.5-5 ML: 0.48-1.5 g; stirring the mixture at 65-90 deg.C for 10-30min for reacting; dripping the reacted water solution on a cover glass; then, the cover glass is heated at 65-90 ℃ until the water is completely evaporated, and the polymer film containing the mixed boric acid is respectively obtained after cooling to room temperature.
Preferably, the mass concentration of the mixed boric acid in the step S1 is 1.75 g/L; the concentration of the polyvinyl alcohol aqueous solution in the step S2 is 160 g/L; in the step S3, the mass ratio of the polyvinyl alcohol to the mixed boric acid is 480: 7; the volume mass ratio of the ammonia water to the polyvinyl alcohol is 1 mL: 0.48 g.
The invention also comprises the application of the film material, which is applied to the fields of color paper and color ink.
Compared with the prior art, the invention has the beneficial effects that:
according to the application, three aromatic boric acids are combined with a PVA main chain, the three aromatic boric acids have good phosphorescence properties and different pi-conjugation degrees at low temperature, and meanwhile, the PVA is used as the main chain because hydroxyl on the PVA can react with hydroxyl in aromatic boric acid molecules to form a B-O covalent bond, so that the thermal motion of the aromatic boric acid molecules can be limited, and then the room-temperature phosphorescence emission is promoted; on the other hand, polyvinyl alcohol exhibits excellent water absorption. In a humid environment, the rigid environment of the polyvinyl alcohol is broken, providing active sites for a stimulatory response. Thus, control of the room temperature phosphorescent properties by external stimuli of heat and water may enable adjustment of the afterglow color. The film prepared by the method can enable the material to emit bright room-temperature phosphorescence after being irradiated by a common ultraviolet lamp through stimulation of water or heat, and the persistence time of macroscopic persistence of the film reaches 7 s.
Drawings
FIG. 1 is a repeated cycle of the heating/water fumigation process of the mixed boronic acid containing polymer film of example 1 under 254nm excitation in accordance with the present invention.
FIG. 2 is a repeated cycle of the heating/water fumigation process of the polymer film containing mixed boric acid under excitation at 312nm in example 1 of the present invention.
FIG. 3 is a repeated cycle of the heating/water fumigation process of the mixed boronic acid containing polymer film of example 1 under 365nm excitation in accordance with the present invention.
FIG. 4 is a phosphorescence emission spectrum at a non-excitation wavelength of the polymer film containing the mixed boric acid in example 1 of the present invention.
FIG. 5 is a graph showing the effects of the application of the color paper and the color ink in example 4 of the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the present invention will be further described in detail with reference to the accompanying drawings and preferred embodiments.
Example 1: the preparation method of the multi-phosphor photoproduction chromophore film material comprises the following steps:
and (3) preparing a polymer film (BNP-BOH-PVA) containing mixed boric acid in the structural formula (V).
Polyvinyl alcohol was chosen as the rigid matrix polymer and 3-biphenylboronic acid, 1-naphthaleneboronic acid and 1-pyreneboronic acid were mixed in a 1:1:5 ratio (the same example below) to be the phosphorescent chromophore. 3mL of a 160g/L aqueous polyvinyl alcohol solution, 4mL of a 1.75g/L mixed aqueous boric acid solution and 1mL of aqueous ammonia were stirred at 80 ℃ for 30 min. 0.7mL of the prepared aqueous solution was dropped on a cover glass. Then, the cover glass is heated at 80 ℃ until the water is completely evaporated, and the polymer film containing the mixed boric acid is obtained after the cover glass is cooled to the room temperature.
Example 2: and (3) preparing a polymer film (BNP-BOH-PVA) containing mixed boric acid in the structural formula (V). Polyvinyl alcohol is selected as a rigid matrix polymer, and 3-biphenyl boric acid, 1-naphthalene boric acid and 1-pyrene boric acid are selected as phosphorescent chromophores. 3mL of a 500g/L polyvinyl alcohol aqueous solution, 4mL of a 1g/L mixed boric acid aqueous solution and 0.5mL of aqueous ammonia were stirred at 65 ℃ for 20 min. 0.7mL of the prepared aqueous solution was dropped on a cover glass. Then, the cover glass is heated at 90 ℃ until the water is completely evaporated, and the polymer film containing the mixed boric acid is obtained after the cover glass is cooled to the room temperature.
Example 3: and (3) preparing a polymer film (BNP-BOH-PVA) containing mixed boric acid in the structural formula (V). Polyvinyl alcohol is selected as a rigid matrix polymer, and 3-biphenyl boric acid, 1-naphthalene boric acid and 1-pyrene boric acid are selected as phosphorescent chromophores. 3mL of a 300g/L aqueous polyvinyl alcohol solution, 4mL of a 8g/L mixed aqueous boric acid solution, and 5mL of aqueous ammonia were stirred at 90 ℃ for 10 min. 0.7mL of the prepared aqueous solution was dropped on a cover glass. Then, the cover glass is heated at 65 ℃ until the water is completely evaporated, and the polymer film containing the mixed boric acid is obtained after cooling to the room temperature.
Example 4: filter paper is soaked in the BNP-BOH-PVA aqueous solution obtained in example 1, and a piece of multicolor paper is obtained after drying. The ultraviolet lamps with the wavelengths of 254nm, 312nm and 365nm are respectively used for excitation, and after the ultraviolet lamps are switched off, the three colors of blue, yellow green and red are respectively presented. The letter "R" is written with water on paper because room temperature phosphorescent emission can be quenched with water. When the UV irradiation is stopped, the non-luminous letter "R" clearly contrasts with the afterglow of the unquenched paper. Then, the letters will be erased after heating the paper. The multicolor paper can be used for repeated writing with water and erasing with heat. Meanwhile, the method can also be used for manufacturing multi-color ink, and the afterglow of the pattern presents different colors under the irradiation of ultraviolet rays with different wavelengths. Similarly, after fumigation with water, no pattern was visible after the UV lamp was turned off.
Secondly, performance verification of phosphorescent material
1. The polymer film containing mixed boric acid obtained in example 1 was taken and tested for photophysical properties after steam fumigation and after heating:
as shown in FIGS. 1 to 3, phosphorescence spectra of BNP-BOH-PVA films with excitation wavelengths of 254nm, 312nm and 365nm, respectively, were tested. We have found that when the film is fumigated with water vapour, it does not exhibit phosphorescent emission. After heating, the phosphorescence of the film is significantly enhanced. At this time, it is considered that the moisture in the film is completely evaporated. In addition, the room temperature phosphorescence properties of the film material can be controlled by means of heating and steam fumigation, and the cycle can be repeated for a plurality of times.
As shown in fig. 4, the room temperature phosphorescent emission red-shifts from blue to green to yellow and then red with increasing excitation wavelength. Therefore, for an amorphous stimulus-responsive material having a very long afterglow, a wide range of color adjustment can be achieved, which is advantageous for expanding its practical application in many fields.
2. The method described in embodiment 4 can be applied to the fields of color paper and color ink, and the effect is shown in fig. 5.
The invention discloses a rapid preparation method and application of an organic room temperature phosphorescent film with stimulus response characteristics and stimulus dependence, wherein the organic room temperature phosphorescent film comprises three aromatic boric acid micromolecules and polyvinyl alcohol. The three organic small molecules and the polymer are subjected to dehydration condensation reaction according to a certain proportion, and the organic room temperature phosphorescent film with excitation wavelength dependence and excitation response characteristics can be obtained. The polymer film prepared by the invention shows ultra-long room temperature phosphorescence, and the afterglow which is visible to the naked eye is about 7 s. Also, the room temperature phosphorescence characteristics of the obtained film are very sensitive to water and thermal stimuli, since water can break the hydrogen bonds between adjacent polyvinyl alcohols, thereby changing the rigidity of the system. Based on the characteristics, the film material can also be used in the application fields of colored paper and colored ink. The invention provides a simple and effective design strategy for developing the room-temperature phosphorescent material which is excitation-dependent and has stimulus response.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. An organic room temperature phosphorescent film material with hydrothermal stimulus response and excitation dependence characteristics is characterized by comprising a PVA main chain and phosphorescent chromophores combined with the PVA main chain; the phosphorescent chromophore is a mixture of 3-biphenylboronic acid, 1-naphthoic acid and 1-pyreneboronic acid, wherein the mass ratio of the 3-biphenylboronic acid to the 1-naphthoic acid to the 1-pyreneboronic acid to the PVA main chain is 1-10:1-10: 5-10; the mass ratio of the boric acid mixture to the PVA main chain is 4-32: 480-1500.
2. The organic room temperature phosphorescent thin film material with hydrothermal stimulus response and excitation dependence characteristics as claimed in claim 1, wherein the mass ratio of 3-biphenylboronic acid, 1-naphthalene boronic acid and 1-pyreneboronic acid is 1:1: 5.
3. The organic room temperature phosphorescent thin film material with hydrothermal stimulus response and excitation dependence of claim 1, wherein the mass ratio of the boric acid mixture to the PVA main chain is 7: 480.
4. A method for preparing a film material according to any one of claims 1 to 3, comprising the steps of:
s1, putting 3-biphenyl boric acid, 1-naphthalene boric acid and 1-pyrene boric acid into a container filled with water according to a proportion, and ultrasonically dispersing the mixture to enable the final concentration of the mixed liquid of the mixed boric acid to be 1-8 g/L;
s2, putting the PVA into a container filled with water, heating to 65-90 ℃, stirring to completely dissolve the PVA, cooling to room temperature to the concentration of 160-500g/L to obtain a PVA aqueous solution;
s3, mixing the mixed boric acid aqueous solution obtained in the step S1 and the polyvinyl alcohol aqueous solution obtained in the step S2 according to the mass ratio of the mixed boric acid to the polyvinyl alcohol of (4-32): (480-1500), and then adding ammonia water, wherein the volume mass ratio of the ammonia water to the polyvinyl alcohol is as follows: 0.5-5 ML: 0.48-1.5 g; stirring the mixture at 65-90 deg.C for 10-30min for reacting; dripping the reacted water solution on a cover glass; then, the cover glass is heated at 65-90 ℃ until the water is completely evaporated, and the polymer film containing the mixed boric acid is respectively obtained after cooling to room temperature.
5. The organic room temperature phosphorescent thin film material having hydrothermal stimulus response and excitation-dependent characteristics as claimed in claim 4, wherein the mass concentration of the mixed boric acid in step S1 is 1.75 g/L; the concentration of the polyvinyl alcohol aqueous solution in the step S2 is 160 g/L; in the step S3, the mass ratio of the polyvinyl alcohol to the mixed boric acid is 480: 7; the volume mass ratio of the ammonia water to the polyvinyl alcohol is 1 mL: 0.48 g.
6. Use of a film material according to any of claims 1-2 in the field of coloured paper and coloured ink.
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