CN108587597B - Fluorescent/visible light-heat-induced color-changing material and preparation method and application thereof - Google Patents
Fluorescent/visible light-heat-induced color-changing material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a fluorescent/visible light-heat-induced color-changing material and a preparation method and application thereof, wherein the material is a fluorescent/visible light-heat-induced color-changing material which is prepared by forming a modified rhodamine B compound by rhodamine B and an alkylamine compound under the action of a coupling reagent and an activator and then combining the modified rhodamine B compound with an electron acceptor compound and a synergist.
Description
Technical Field
The invention relates to a fluorescent/visible light-heat-induced color-changing material and a preparation method and application thereof, belonging to the technical field of thermochromic materials.
Background
Thermochromic materials are intelligent materials that measure and represent the temperature and temperature distribution of an object's surface by a change in color. The thermosensitive agents can be classified into inorganic, liquid crystal and organic according to the property of the thermochromic material. The inorganic thermochromic material mainly comprises a transition metal compound, the color change of the inorganic thermochromic material is mainly caused by crystal form change, coordination geometry change or the number of coordination solvent molecules, and the inorganic thermochromic material has bright and bright color and has the defects of poor color recovery, high color change temperature, poor durability and high toxicity. The liquid crystal thermochromic material is an organic compound between liquid and crystal, has the advantages of temperature sensitivity, high response speed and color variability, cannot be directly used due to the structural particularity of the liquid crystal thermochromic material, and must be wrapped in microcapsules to prevent the liquid crystal from being polluted by other compound substances so as to ensure the color generation effect. The organic thermochromic material has various types, different color change mechanisms, various colors, controllable color change temperature, good color recovery and the like, and has wide application in the fields of military, clothing, industry and the like. The defects in the United states are that most organic thermochromic materials only have a thermochromic phenomenon in a visible light area, are single in function, cannot meet the requirements of multiple anti-counterfeiting, encryption and the like in special fields, are difficult to meet the requirements of the fields of medical probes, drug release monitoring and the like, and are limited in application.
Disclosure of Invention
The purpose of the invention is as follows: in view of the above-mentioned problems, an object of the present invention is to provide a fluorescent/visible photothermographic color material, which exhibits a large hysteresis characteristic in a visible light region and an ultraviolet light region and exhibits reversible color change of color development and color fading depending on a temperature change, and which can interconvert and reversibly maintain either a colored or a discolored state even after a medium for external heating or cooling is lost, and a method for preparing the same and use thereof.
The technical scheme is as follows: the invention adopts the following technical scheme:
a fluorescent/visible light-heat-induced color-changing material is prepared by forming a modified rhodamine B compound by rhodamine B and alkylamine compound under the action of a coupling reagent and an activator, and then combining the modified rhodamine B compound with an electron acceptor compound and a synergist.
The color-changing temperature range of the fluorescent/visible light-heat color-changing material is 25-60 ℃.
Preferably, the method comprises the following steps:
the alkylamine compound is any one or a composition of more than two of trialkyl tertiary amine, octadecyl amine, dodecyl primary amine, didodecyl amine, dimethyl tetradecyl amine and diisotridecyl amine.
The coupling reagent comprises any one or a composition of more than two of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, N '-dicyclohexylcarbodiimide, N' -diisopropylcarbodiimide and 1, 3-bis (2, 2-dimethyl-1, 3-dioxolan-4-ylmethyl) carbodiimide.
The activating reagent comprises any one or a composition of more than two of 3-hydroxy-1, 2, 3-benzotriazine-4 (3H) -ketone, N-hydroxysuccinimide, 1-hydroxybenzotriazole and 1-hydroxy-7-azobenzotriazol.
The electron acceptor compound comprises any one or a combination of more than two of boric acid, bisphenol A, magnesium chloride, aromatic sulfone, poly-beta-hydroxybutyric acid and stearic acid.
The synergist comprises any one or a composition of more than two of graphene, fumed silica and titanium dioxide.
The preparation method of the fluorescent/visible light thermochromatic material comprises the following steps:
(1) mixing rhodamine B, an alkylamine compound and a solvent to form a mixture, heating the mixture to 50-90 ℃, adding a coupling reagent and an activating agent under full stirring, carrying out full reaction, cooling, filtering, and evaporating the solvent to obtain an orange product;
(2) dissolving the orange product obtained in the step (1) in a solvent again and purifying by a chromatographic separation method to obtain a modified rhodamine B compound;
(3) and mixing the modified rhodamine B compound with an electron acceptor compound, a synergist and a solvent, heating, dissolving, reacting, and cooling after the reaction is finished to obtain the fluorescent/visible light-thermal photochromic material.
Preferably, the method comprises the following steps:
in the step (1), the weight ratio of rhodamine B, the alkylamine compound and the solvent is 1 (1-5) to 10-20, and the weight ratio of the rhodamine B, the coupling reagent and the activating agent is 1: (0.2-0.8) and (0.3-1.2);
in the step (3), the weight ratio of the modified rhodamine B compound to the electron acceptor compound, the synergist and the solvent is 1 (10-50): (0.001-0.1): 80-120);
the solvent comprises one or more of deionized water, acetone, ethanol, dimethylformamide, isopropanol, tetradecanol, dodecanol, hexadecanol and octadecanol.
The modified rhodamine B compound prepared by the steps (1) and (2) has no fluorescence/visible light and thermal discoloration property, but the acidified aqueous solution of the modified rhodamine B compound has fluorescence/visible light and thermal discoloration property.
Preferably, the preparation method further may comprise:
(1) mixing rhodamine B, an alkylamine compound and a solvent to form a mixture, heating the mixture, premixing for 5-20 min at the speed of 80-1300 rpm, adding a coupling reagent and an activating agent for reacting for 10-150 h, cooling, filtering, and evaporating the solvent to obtain an orange product;
(2) dissolving the orange product obtained in the step (1) in a solvent again and purifying by a chromatographic separation method to obtain a modified rhodamine B compound;
(3) heating the purified product modified rhodamine B compound, the electron acceptor compound, the solvent and the synergist to 60-90 ℃, mixing at the rotating speed of 100-1500 rpm, and cooling to obtain the fluorescent/visible light photochromic material.
More specifically, in one embodiment, the preparation method may include:
(A) adding 1 part by weight of rhodamine B and 1-5 parts by weight of alkylamine compound into 10-20 parts by weight of solvent, heating the mixture to 50-90 ℃, premixing for 5-20 min at the speed of 80-1300 rpm, adding 0.2-0.8 part by weight of coupling reagent and 0.3-1.2 part by weight of activating agent, reacting for 10-150 h, cooling, filtering and evaporating the solvent to obtain an orange product;
(B) dissolving the orange product prepared in the step into a solvent again and purifying the orange product by a chromatographic separation method to obtain a modified rhodamine B compound;
(C) mixing 1 weight part of the purified product with 10-50 weight parts of an electron acceptor compound, 80-120 weight parts of a solvent and 0.001-0.1 weight part of a synergist at a rotating speed of 100-1500 rpm, heating to 60-90 ℃, reacting for 0.5-3 h, and cooling to obtain a final product.
The fluorescent/visible light-heat-induced color-changing material is applied to the fields of anti-counterfeiting, encryption, clothing and medical treatment.
For example, one application scheme may be:
a preparation method of a textile anti-counterfeiting trademark comprises the following steps: and (3) coating or printing the specific position of the textile by using the fluorescent/visible light-thermal photochromic material.
The technical effects are as follows: compared with the prior art, the invention has the advantages that:
the modified rhodamine B compound has the color development performance of opening and closing of a lactone ring by firmly grafting the alkylamine compound on the rhodamine B molecule through a grafting reaction, and the reaction can reach higher grafting rate due to the matched use of the activating agent and the coupling agent, so that the yield of the fluorescent/visible light thermal discoloration material is greatly improved. The addition of the synergist improves the thermal conductivity and the sensitivity of the fluorescent/visible light-heat-induced color-changing material. In addition, the product has the dual functions of thermochromism and thermochromism, has the advantages of high temperature-sensitive response speed, reversible color change, cyclic and repeated color change, stable property and the like, can be used as a multifunctional novel intelligent material to be applied to the fields of anti-counterfeiting, encryption, clothing, medicine and the like, and overcomes the defects of the existing simple thermochromism material in the aspect. In addition, through tests, the aqueous solution of the material also has the functions of pH response visible light color change and pH response fluorescence change, and the property has great application value in certain probe indication fields.
Drawings
FIG. 1 shows modified rhodamine B obtained in examples 1 to 51H NMR spectrum;
FIG. 2 is a photograph showing the effects of the fluorescent/visible photothermographic material obtained in examples 1-5 before and after heating under ultraviolet light and visible light.
Detailed Description
The technical solutions of the present invention are further described in detail by the following specific examples, but it should be noted that the following examples are only used for describing the content of the present invention and should not be construed as limiting the scope of the present invention.
Example 1:
adding 1g of rhodamine B and 2g of octadecylamine into a mixed solvent of 15g of acetone and 5g of deionized water, heating the mixture to 70 ℃ and premixing for 7min at the speed of 300rpm, adding 0.2g of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 0.3g of 3-hydroxy-1, 2, 3-benzotriazin-4 (3H) -one for reaction for 12H, filtering after cooling, and evaporating the solvent to obtain an orange product;
1g of the synthesized orange product was dissolved in isopropanol and purified by chromatographic separation to give a modified rhodamine B compound, which was purified1H NMR test results are shown in the following figure 1, and the figure shows that the absorption peaks at chemical shifts of 1.18-1.34 and 3.05-3.15 are significant, and are characteristic peaks of hydrogen on an octadecyl amine carbon chain, the absorption peaks at chemical shifts of 6.3-6.5, 7.19, 7.28, 7.4-7.5 and 7.8-8.0 are characteristic peaks of hydrogen on a rhodamine B carbon chain, and the octadecyl amine on the surface is successfully grafted to rhodamine;
mixing 0.5g of the purified product with 10g of aromatic sulfone, 40g of tetradecanol and 0.025g of graphene at the rotating speed of 460rpm, heating to 65 ℃, continuously stirring for 0.5h, and cooling to obtain a fluorescent/visible light-heat-induced color-changing material, wherein the effects of the fluorescent/visible light-heat-induced color-changing material before and after heating under ultraviolet light and visible light are shown in figure 2, wherein under an ultraviolet lamp, the material is light pink before heating, and is light blue after heating; under visible light, the material appeared dark pink before heating and yellow after heating.
Example 2:
adding 1g of rhodamine B and 1g of trialkyl tertiary amine into a mixed solution of 10g of ethanol and 5g of deionized water, heating the mixture to 80 ℃, premixing for 5min at the speed of 560rpm, adding 0.3g of N, N' -dicyclohexylcarbodiimide and 0.5g of N-hydroxysuccinimide, reacting for 36h, cooling, filtering and evaporating the solvent to obtain an orange product;
dissolving 1g of the synthesized orange product in ethanol and purifying by chromatography to obtain a modified rhodamine B compound, which1The H NMR measurement results were substantially the same as in example 1;
0.8g of the purified product was mixed with 20g of stearic acid, 70g of cetyl alcohol and 0.04g of fumed silica at 540rpm, heated to 70 ℃ and stirred for 3 hours, cooled to obtain a fluorescent/visible photothermochromic material, the effect of which before and after heating under ultraviolet light and visible light was substantially the same as in example 1.
Example 3:
adding 1g of rhodamine B and 5g of dodecyl primary amine into a mixed solution of 10g of methanol and 10g of deionized water, heating the mixture to 50 ℃, premixing for 7min at the speed of 80rpm, then adding 0.8g of N, N' -diisopropylcarbodiimide and 1.2g of 1-hydroxy-7-azobenzotriazol for reacting for 50h, cooling, filtering and evaporating the solvent to obtain an orange product;
dissolving 1g of the synthesized orange product in acetone and purifying by chromatography to obtain a modified rhodamine B compound, which1The H NMR measurement results were substantially the same as in example 1;
0.5g of the purified product was mixed with 25g of boric acid, 50g of tetradecanol and 0.05g of titanium dioxide at 730rpm, heated to 90 ℃ and continuously stirred for 2 hours, and cooled to obtain a fluorescent/visible photothermochromic material, which had substantially the same effects as those of example 1 before and after heating under ultraviolet light and visible light.
Example 4:
adding 1g of rhodamine B and 1g of didodecylamine into a mixed solvent of 5g of methanol and 5g of ethanol, heating the mixture to 50 ℃ and premixing for 20min at the speed of 200rpm, then adding 0.2g of 1, 3-bis (2, 2-dimethyl-1, 3-dioxolan-4-ylmethyl) carbodiimide and 0.3g of 1-hydroxybenzotriazole to react for 100h, filtering after cooling and evaporating the solvent to obtain an orange product;
dissolving 1g of the synthesized orange product in acetone and purifying by chromatography to obtain a modified rhodamine B compound, which1The H NMR measurement results were substantially the same as in example 1;
0.5g of the purified product was mixed with 5g of poly- β -hydroxybutyric acid, 40g of tetradecanol and 0.0005g of titanium dioxide at a rotation speed of 1000rpm, heated to 80 ℃ and continuously stirred for 1.5 hours, and cooled to obtain a fluorescent/visible photothermochromic material, which had substantially the same effects as in example 1 before and after heating under ultraviolet light and visible light.
Example 5:
adding 1g of rhodamine B and 2.5g of dimethyltetradecylamine into a mixed solvent of 5g of methanol and 10g of acetone, heating the mixture to 60 ℃ and premixing at 450rpm for 15min, subsequently adding 0.6g of N, N' -diisopropylcarbodiimide amine and 0.8g of 3-hydroxy-1, 2, 3-benzotriazin-4 (3H) -one for reaction for 150H, filtering after cooling, and evaporating the solvent to obtain an orange product;
dissolving 1g of the synthesized orange product in dimethylformamide and purifying by chromatographic separation to obtain a modified rhodamine B compound1The H NMR measurement results were substantially the same as in example 1;
0.5g of the purified product was mixed with 15g of bisphenol a, 50g of octadecanol and 0.0005g of graphene at a rotation speed of 600rpm, heated to 70 ℃, and continuously stirred for 2.5h, and cooled to obtain a fluorescent/visible photothermal allochroic material, the effects before and after heating under ultraviolet light and visible light were substantially the same as those of example 1.
It should be understood that the above-mentioned embodiments are merely illustrative of the technical concepts and features of the present invention, which are intended to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and therefore, the protection scope of the present invention is not limited thereby. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (8)
1. The fluorescent/visible light-heat-induced color-changing material is characterized in that the material is a fluorescent/visible light-heat-induced color-changing material which is obtained by forming a modified rhodamine B compound by rhodamine B and an alkylamine compound under the action of a coupling reagent and an activator, and then combining the modified rhodamine B compound with an electron acceptor compound and a synergist; the electron acceptor compound is selected from one or a combination of more than two of boric acid, bisphenol A, magnesium chloride, aromatic sulfone, poly-beta-hydroxybutyric acid and stearic acid; the synergist is selected from any one or a composition of more than two of graphene, fumed silica and titanium dioxide.
2. The fluorescent/visible photothermochromic material of claim 1, wherein said fluorescent/visible photothermochromic material has a color temperature in the range of 25 ℃ to 60 ℃.
3. The fluorescent/visible photothermochromic material according to claim 1, wherein said alkylamine compound is any one or a combination of two or more of trialkylamine, octadecylamine, dodecylamine, didodecylamine, dimethyltetradecylamine, diisotridecylamine.
4. The fluorescent/visible photothermochromic material of claim 1, wherein said coupling agent is selected from the group consisting of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, N '-dicyclohexylcarbodiimide, N' -diisopropylcarbodiimide, 1, 3-bis (2, 2-dimethyl-1, 3-dioxolan-4-ylmethyl) carbodiimide, and combinations of two or more thereof.
5. The fluorescent/visible photothermochromic material according to claim 1, wherein said activating agent is any one or a combination of two or more selected from the group consisting of 3-hydroxy-1, 2, 3-benzotriazin-4 (3H) -one, N-hydroxysuccinimide, 1-hydroxybenzotriazole, and 1-hydroxy-7-azobenzotriazol.
6. The method for preparing the fluorescent/visible photothermochromic material according to any one of claims 1 to 5, comprising the steps of:
(1) mixing rhodamine B, an alkylamine compound and a solvent to form a mixture, heating the mixture to 50-90 ℃, adding a coupling reagent and an activating agent under full stirring, carrying out full reaction, cooling, filtering, and evaporating the solvent to obtain an orange product;
(2) dissolving the orange product obtained in the step (1) in a solvent again and purifying by a chromatographic separation method to obtain a modified rhodamine B compound;
(3) and mixing the modified rhodamine B compound with an electron acceptor compound, a synergist and a solvent, heating, dissolving, reacting, and cooling after the reaction is finished to obtain the fluorescent/visible light-thermal photochromic material.
7. The method for preparing a fluorescent/visible photothermochromic material according to claim 6, wherein:
in the step (1), the weight ratio of rhodamine B, the alkylamine compound and the solvent is 1 (1-5) to 10-20, and the weight ratio of the rhodamine B, the coupling reagent and the activating agent is 1: (0.2-0.8) and (0.3-1.2);
in the step (3), the weight ratio of the modified rhodamine B compound to the electron acceptor compound, the synergist and the solvent is 1 (10-50): (0.001-0.1): 80-120);
the solvent is selected from one or a combination of more than two of deionized water, acetone, ethanol, dimethylformamide, isopropanol, tetradecanol, dodecanol, hexadecanol and octadecanol.
8. Use of the fluorescent/visible photothermochromic material according to any of claims 1 to 5 as anti-counterfeiting, security, clothing or medical material.
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