CN108774151B - Azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction, preparation method thereof and application of azobenzene derivative as optical switch adhesive - Google Patents
Azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction, preparation method thereof and application of azobenzene derivative as optical switch adhesive Download PDFInfo
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- CN108774151B CN108774151B CN201810475434.5A CN201810475434A CN108774151B CN 108774151 B CN108774151 B CN 108774151B CN 201810475434 A CN201810475434 A CN 201810475434A CN 108774151 B CN108774151 B CN 108774151B
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- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
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Abstract
The invention discloses an azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction, a preparation method thereof and application of the azobenzene derivative as an optical switch adhesive. The invention uses two hydroxyls of dinaphthol to react with carboxyl azobenzene and gallic acid derivative respectively to obtain the final product through two esterification reactions. Based on the properties of low melting point and long absorption waveband of the solid azobenzene compound, absorbed light energy can be converted into heat under the irradiation of green light, and the azobenzene derivative is melted due to the increase of temperature. When the temperature drops below the melting point at room temperature, the azobenzene derivative in the liquid state exists in the solid state again, and has strong adhesive property. After being irradiated again with green light, the adhesive layer melts again, loses adhesive property, and becomes solid again when cooled to room temperature, and adhesive force is displayed. The optical switch adhesive is very easy to dissolve in common organic solvents, easy to clean and recycle, and reusable, and is an adhesive which is green, environment-friendly and resource-saving.
Description
Technical Field
The invention belongs to the technical field of bonding materials, and particularly relates to an azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction, a preparation method thereof and application of the azobenzene derivative as an optical switch bonding agent.
Background
Adhesives play a very important role in both production and life as bridges for joining two materials. The adhesive is an indispensable material in the national economic field, has wide application and multiple varieties compared with other high polymer materials, is also called as an industrial monosodium glutamate, and becomes an indispensable material in many modern industries. Adhesives are also ubiquitous in life, such as you must have done: the adhesive tape or the hook is used for adhering objects, so that the use is convenient and simple, but if the adhesive tape or the hook is improperly used, the adhesive tape or the hook is easy to fall off, and the objects cannot be adhered after falling off; the all-purpose adhesive is dropped on hands or clothes carelessly, becomes solid quickly and is difficult to wash, and cannot be recycled. Adhesive materials face difficult recycling, non-reusable challenges, which also present significant environmental and resource challenges. Therefore, the development of green recyclable adhesives has important academic value and practical application significance for chemical science, material science, resource saving and environmental protection.
The azobenzene compound is an organic micromolecular dye with simple structure and relatively low melting point, has very obvious J aggregation phenomenon in a solid state, and can enable the azobenzene compound to absorb light with longer wavelength in the solid state. According to the principle of photothermal effect, light can be converted into heat, the temperature gradually rises along with continuous illumination to reach a melting point, the phase state is changed, illumination is stopped, and the solid state is recovered. Two adhesion states corresponding to the adhesive: the adhesive force is strong in a solid state; losing adhesion in the liquid state. The phase state transformation process is highly reversible and can be used repeatedly. In view of the above, the development of the optical switch adhesive for inducing the solid-liquid conversion of the azobenzene derivative based on the photothermal effect has a good application prospect in the fields of environmental protection and resource conservation.
Disclosure of Invention
In order to solve the technical problems, the invention provides an azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction, a preparation method thereof and application of the azobenzene derivative as an optical switch adhesive, and the technical scheme is as follows:
an azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction is characterized in that the molecular structural formula is as follows:
wherein R is 1 ＝-OC n H 2n+1 N =1-18 and is an integer; r is 2 ＝-C n H 2n+1 N =1-18 and is an integer, -I, -Br, -Cl, -NO 2 or-NH 2 Any one of them.
The preparation method of the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction is characterized in that two hydroxyl groups of dinaphthol are respectively reacted with carboxyl azobenzene and gallic acid derivative through two-step esterification reaction to obtain a final product.
Further, the preparation method of the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction comprises the following specific steps:
1) The gallic acid methyl ester and bromopentane are added into a two-port reaction tube according to a molar ratio of 1 2 CO 3 ，K 2 CO 3 The molar ratio of the catalyst to the gallic acid methyl ester is 1-2, the TBAB is equivalent to the catalyst, then the acetone solvent is added, the mixture is uniformly stirred under the nitrogen atmosphere and reacts for 48-72 h at the temperature of 70-90 ℃; cooling to room temperature after complete reaction, rotatably distilling off the acetone solvent, extracting with dichloromethane and water, concentrating the organic phase, and purifying with silica gel column to obtain a product a1-COOCH 3 ；
2) Reacting the product a1-COOCH of step 1) 3 Adding the mixture and potassium hydroxide into a reaction tube according to a molar ratio of 1 to 2, then adding an ethanol solvent, uniformly stirring the mixture under the nitrogen atmosphere, and reacting the mixture for 4 to 6 hours at 70 to 90 ℃; cooling to room temperature after complete reaction, adjusting the pH value of the product to 1 by using dilute hydrochloric acid, filtering, and washing the solid product to be neutral by using deionized water to obtain a product marked as a1-COOH;
3) Adding azobenzene derivatives COOH-AZO and bisnaphthol into a two-port reaction tube according to a molar ratio of 1; pouring the mixture into a beaker after the reaction is completed, adding water and dichloro to extract an organic phase, removing dichloromethane by rotary evaporation, and purifying by a silica gel column to obtain a product a1-OH;
4) Adding the product a1-COOH of the step 2) and the product a1-OH of the step 3) into a two-port reaction tube according to a molar ratio of 1; and pouring the mixture into a beaker after the reaction is completed, adding water and dichloro to extract an organic phase, removing dichloromethane by rotary evaporation, and purifying by a silica gel column to obtain the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction.
Further, the molecular structural formula of the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction is as follows:
further, the structural formulas of the azobenzene derivative COOH-AZO, the double naphthol and the methyl gallate are sequentially as follows from left to right:
the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction is used as a reversible optical switch adhesive.
Further, the solid optical switch adhesive with adhesive property can convert absorbed light energy into heat under the irradiation of green light, and the increase of temperature causes the azobenzene derivative to be melted and has no adhesive property; after the temperature of the azobenzene derivative is reduced to be lower than the melting point at room temperature, the liquid azobenzene derivative exists in a solid state again and has adhesive property.
About 5mg of azobenzene derivative P1 is placed on a glass plate, and is melted by the action of green light or directly heated, and then another glass plate is covered on the liquid, and the liquid is cooled at room temperature until P1 becomes solid again, and the two glass plates are tightly adhered together, and can be used for lifting a heavy object with the mass which is 2200,000 times that of P1 per se. When green light is irradiated on P1 bonding two glass sheets, P1 melts, the adhesive loses its adhesive property, and when it is cooled down to room temperature again, P1 becomes solid and exhibits a very strong adhesive property. Green light acts as a switch to determine the strength of the bond, and the process is highly reversible. The adhesive combined with the optical switch is very easy to dissolve in common organic solvents such as dichloromethane and the like, is easy to clean and recycle,
the invention has the technical advantages that:
1) The azobenzene derivative-based optical switch adhesive designed and synthesized by the invention has strong absorption in a green light zone in a solid state, P1 can efficiently convert green light into heat, and the photo-thermal effect is very good. The melting point of the azobenzene derivative-based photoswitch adhesive designed and synthesized by the invention is about 44 ℃, the heat converted from green light can melt P1, and the phase state can be changed by simple green light irradiation without heating by a heat source.
2) The two bonding strength states of the azobenzene derivative-based optical switch adhesive designed and synthesized by the invention correspond to the solid state and the liquid state of P1, and can be controlled by green light irradiation, and the phase state transformation is pure physical change, so the invention is highly reversible. The azobenzene derivative-based optical switch adhesive designed and synthesized by the invention can control phase state change highly reversibly through photothermal effect, so that the adhesive can be recycled for many times, and has good application prospect in the fields of environmental protection and resource conservation.
3) The azobenzene derivative-based optical switch adhesive designed and synthesized by the invention has very good solubility in common organic solvents such as dichloromethane and the like, is easy to remove and recycle, can be repeatedly used, and can be applied to the field of green and environment-friendly adhesives with resource saving.
Drawings
FIG. 1 shows structural formulas of azobenzene derivatives and analogues thereof, wherein R1= -OC n H 2n+1 ,n＝1,2,3,…18,R2＝-C n H 2n+1 (n＝1,2,3,…18)、-I、-Br、-Cl、 -NO 2 、-NH 2 。
FIG. 2 is a reaction scheme of P1 in example 1.
FIG. 3 is a graph showing an ultraviolet absorption spectrum of P1 in a solid state in application example 1.
FIG. 4 is a graph showing the phase change of P1 solid powder before and after irradiation of green light in application example 1.
FIG. 5 shows the temperature of the solid powder P1 under irradiation of green light captured by an infrared camera as a function of irradiation time in application example 1.
FIG. 6 is a graph showing the temperature change with time of the P1 solid powder and a blank glass plate in application example 1 under irradiation of green light.
FIG. 7 is a graph showing the cycle curve of the temperature of the P1 solid powder under irradiation with green light as a function of irradiation time in application example 1.
Fig. 8 is a stress-strain curve measured by bonding two aluminum sheets using P1 in example 2.
FIG. 9 is a schematic view of lifting a weight of 11.15kg from two aluminum sheets bonded by P1 in application example 2.
FIG. 10 shows that the green light irradiation of application example 2 melts the adhesive and loses the adhesive effect.
Detailed Description
The following will further illustrate the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction, its preparation method and application with reference to specific examples, but the scope of the present invention is not limited thereto.
Preparation example 1:
1. 3.68g (20 mmol) of methyl gallate and 9.365g (62.0 mmol) of bromopentane are added into a two-port reaction tube, and 5.52g (40.0 mmol) of K is added 2 CO 3 Adding TBAB with catalyst equivalent (20 mg), then adding 100ml of acetone solvent, stirring uniformly under nitrogen atmosphere, and reacting for 48h at 70 ℃; cooling to room temperature after complete reaction, removing acetone solvent by rotary evaporation, extracting with dichloromethane and water, concentrating organic phase, and purifying with silica gel column to obtain product a1-COOCH 3 ；
1 H NMR(400MHz,CDCl 3 )δ7.28(s,2H),4.04(dt,J＝10.4,5.2Hz, 6H),3.90(s,3H),1.81(ddd,J＝19.5,13.9,6.9Hz,6H),1.44(ddt,J＝35.4, 14.5,7.3Hz,12H),0.94(td,J＝7.1,3.3Hz,9H)；
2. 2.96g (7.5 mmol) of a1-COOCH 3 Adding 815mg (15 mmol) of potassium hydroxide into a reaction tube, then adding 50ml of ethanol solvent, stirring uniformly under nitrogen atmosphere, and reacting for 4h at 80 ℃; after the reaction is completed, cooling to room temperature, regulating pH of product to 1 by using dilute hydrochloric acid, filtering and usingWashing the solid product to be neutral by deionized water, and recording the obtained product as a1-COOH with the yield of 96.5%;
1 H NMR(400MHz,CDCl3)δ7.36(s,2H),4.07(dd,J＝14.4,6.8Hz, 6H),1.91–1.75(m,6H),1.53–1.37(m,12H),0.96(dd,J＝11.3,7.1Hz, 9H)；
3. adding 113mg (0.5 mmol) of azobenzene derivatives COOH-AZO and 572mg (2 mmol) of binaphthol into a two-port reaction tube, adding 110mg (0.7 mmol) of EDC and 20 mg (0.16 mmol) of DMAP, adding 20ml of dichloromethane to dissolve all reactants, stirring uniformly under a nitrogen atmosphere, and reacting at room temperature for 48 hours; pouring the mixture into a beaker after the reaction is completed, adding water and dichloro to extract an organic phase, removing dichloromethane by rotary evaporation, purifying the mixture by a silica gel column, and taking dichloromethane as a flushing agent to obtain a product which is marked as a1-OH;
1 H NMR(400MHz,CDCl3)δ8.14(d,J＝8.9Hz,1H),8.02(d,J＝ 8.2Hz,1H),7.95–7.87(m,2H),7.85–7.69(m,6H),7.63–7.47(m,5H), 7.43–7.28(m,4H),7.25(d,J＝4.6Hz,1H),7.22–7.13(m,1H)；
4. adding 50mg (0.13 mmol) of a1-COOH and 50mg (0.1 mmol) of a1-OH into a two-port reaction tube, adding 25mg (0.12 mmol) of EDC and 10mg (0.008 mmol) of DMAP, adding 15ml of dichloromethane to dissolve all reactants, stirring uniformly under a nitrogen atmosphere, and reacting at room temperature for 48 hours; pouring the mixture into a beaker after the reaction is completed, adding water and dichloro to extract an organic phase, removing dichloromethane by rotary evaporation, purifying the mixture by a silica gel column, wherein a flushing agent is dichloromethane solution, and the obtained final product azobenzene derivative with adhesive property is marked as P1;
1 H NMR(400MHz,CDCl3)δ8.04–7.96(m,2H),7.96–7.84(m, 4H),7.74(d,J＝9.2Hz,4H),7.60(dd,J＝8.9,1.9Hz,2H),7.55–7.48(m, 3H),7.48–7.40(m,3H),7.39–7.29(m,3H),6.84(s,2H),3.93(t,J＝6.6 Hz,2H),3.76–3.63(m,4H),1.77–1.66(m,6H),1.39(tdd,J＝14.0,9.8, 6.1Hz,12H),0.91(dt,J＝10.8,7.1Hz,9H)；
the structural formulas of the azobenzene derivatives COOH-AZO, the double naphthol and the methyl gallate are as follows:
from left to right, COOH-AZO, binaphthol and gallic acid methyl ester are sequentially arranged.
Application example 1:
(1) The P1 solid powder has specific absorption to green light, and the absorption spectrum is measured by taking 5mg of P1, so that the absorption is proved to exist in a green light region (figure 3).
(2) Placing solid powder P1 on weighing paper sheet, and weighing with 175mW cm -2 The powder was illuminated by green light at power and the temperature of the powder was gradually increased and gradually melted after reaching the melting point (fig. 4).
(3) Using 175mW cm -2 The powder was illuminated by green light at power and the infrared camera captured data of its temperature rise over time of illumination over 6 minutes as shown in figure 5.
(4) Sample P1 and blank glass plate were each at 175mW cm -2 The power of the green light irradiation and the temperature profile with time of the light irradiation are shown in fig. 6, which shows that the sample P1 indeed has a very good photothermal effect.
(5) Cycling profile of solid powder of sample P1 under green illumination with temperature as a function of illumination time (fig. 7).
Application example 2:
(1) 5mg of azobenzene derivative P1 was placed on an aluminum sheet, and the azobenzene derivative P1 was melted by the action of green light or directly heated and then covered with another aluminum sheet on a liquid, and cooled at room temperature until P1 became solid again, and the two aluminum sheets were closely adhered to each other, and FIG. 8 is a stress-strain curve for testing the adhesion strength.
(2) 5mg of azobenzene derivative P1 was placed on an aluminum sheet, and acted on by green light to melt it or directly heated to melt it, and then another sheet was placed on top of the liquid, cooled at room temperature until P1 became solid again, and the two sheets adhered closely together and could be used to lift a weight 2200,000 times the mass of P1 itself (FIG. 9).
(3) Within 5 minutes, 175mW cm -2 The two glass plates, with the 5mg P1 sample bonded together, were separated by green light illumination (FIG. 10).
Claims (3)
1. An azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction is characterized in that the molecular structural formula is as follows:
2. the azobenzene derivative for realizing solid-liquid transition based on photo-thermal induction according to claim 1 is used as an optical switch adhesive having reversibility.
3. The use of the azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction according to claim 1 as a reversible optical switch adhesive is characterized in that the optical switch adhesive with solid state and adhesive property can convert absorbed light energy into heat under the irradiation of green light, and the increase of temperature causes the azobenzene derivative to melt itself without adhesive property; after the temperature is reduced to below the melting point at room temperature, the azobenzene derivative in the liquid state exists in the solid state again, and has the adhesive property.
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| CN112965627B (en) * | 2021-02-10 | 2023-05-30 | Tcl华星光电技术有限公司 | Preparation method of green light sacrificial layer and touch display panel |
| CN112859417B (en) * | 2021-03-02 | 2022-07-12 | Tcl华星光电技术有限公司 | Retaining wall material and manufacturing method of color film substrate |
| CN114133925B (en) * | 2021-11-26 | 2024-02-02 | 北京京东方技术开发有限公司 | Quantum dot film, display device and preparation method of quantum dot film |
| CN114133547B (en) * | 2022-01-17 | 2022-07-19 | 江南大学 | Light-operated bonding-debonding underwater hyperbranched adhesive and preparation method and application thereof |
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