Reversible thermochromic material based on anthracene derivatives and application thereof
By combining anthracene derivatives with higher fatty acid matrix, a new reversible thermochromic material is formed, which solves the problems of insufficient heat resistance and chemical inertia of existing materials, and achieves high-efficiency temperature detection and good stability of the materials. Application effect.
Patent Information
- Application Number
- CN202411570351.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-11-06
- Publication Date
- 2025-02-14
AI Technical Summary
The existing organic reversible thermochromic materials have problems with insufficient heat resistance and chemical inertia, and are susceptible to the influence of the external environment and lose their ability to reversible color discoloration.
Using reversible thermochromic materials based on anthracene derivatives, materials with good fluorescence properties and thermal stability are formed by combining the compounds of formula I with higher fatty acid matrix such as lauric acid or orthocapric acid.
It realizes easy preparation, good stability and low cost of materials, and can be used to indicate the surface temperature of the object, which is easy to operate and has strong circulation durability.
Smart Images
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Abstract
Description
[Technical field]
[0001] The invention relates to a reversible thermochromic material and application thereof, in particular to a reversible thermochromic material based on anthracene derivatives and application thereof, belonging to the field of organic functional materials. [Background technology]
[0002] Thermochromic materials can change color after heating or cooling, and are widely used in color-changing coatings, textiles and clothing, and anti-counterfeiting. Among them, reversible thermochromic materials can change color after heating to a specific temperature and return to the original color after cooling. They can be used to indicate the temperature of food and beverages and have broad application prospects in food packaging and other fields.
[0003] Reversible thermochromic materials can be divided into inorganic, organic and liquid crystal types according to their composition. Among them, organic thermochromic materials have the advantages of large color change temperature selectivity, narrow color change range, sensitive color change, rich and bright colors, etc., and have been widely used in textiles, printing inks, color-changing coatings and anti-counterfeiting fields. However, existing organic reversible thermochromic materials have disadvantages such as insufficient heat resistance and chemical inertness, and are easily affected by the external environment and lose the ability to reversibly change color. Therefore, it is necessary to develop new organic reversible thermochromic materials with stable performance. [Summary of the invention]
[0004] The purpose of the present invention is to provide a reversible thermochromic material based on anthracene derivatives and its application in view of the above technical analysis and existing problems. The fluorescent compound described in the present invention has a simple structure, is easy to synthesize, has a larger fluorescence emission wavelength and stronger solid fluorescence. The reversible thermochromic material described in the present invention has the advantages of easy preparation, good stability, low cost, etc., and can be used to indicate the surface temperature of an object.
[0005] The present invention discloses the following technical solutions:
[0006] 1. A reversible thermochromic material based on anthracene derivatives, characterized in that the reversible thermochromic material comprises a compound of formula I and a higher fatty acid matrix containing ten to fourteen carbon atoms; the higher fatty acid matrix is selected from at least one of lauric acid or n-decanoic acid; the compound of formula I has the following structural formula:
[0007]
[0008] 2. An application of the above-mentioned reversible thermochromic material based on anthracene derivatives in temperature detection, the application comprising the following steps:
[0009] (1) encapsulating the reversible thermochromic material and attaching it to the surface of an object to be measured;
[0010] (2) Observe the color change of the reversible thermochromic material under ultraviolet light or visible light to determine the temperature range of the surface of the object to be measured.
[0011] Preferably, the wavelength range of the ultraviolet light source is 250-400 nm.
[0012] The present invention has the following advantages:
[0013] (1) The preparation method of the reversible thermochromic material provided by the present invention is simple and has good fluorescence properties and thermal stability.
[0014] (2) The reversible thermochromic material provided by the present invention can be applied to temperature detection, is easy to operate, and has strong cycle durability.
Brief Description of the Drawings
[0015] Figure 1 is the fluorescence spectrum of the compound represented by formula I in DMSO solution;
[0016] Figure 2 It is the fluorescence spectrum of the solid powder of the compound shown in Formula I. [Specific implementation method]
[0017] The present invention is described in detail below in conjunction with the accompanying drawings and specific embodiments. It should be understood by those skilled in the art that the following embodiments are only used to illustrate the present invention and should not be used to limit the scope of protection of the present invention.
[0018] Embodiment 1:
[0019] Synthesis of the compound shown in formula I:
[0020]
[0021] Sodium methoxide (27 mg, 0.05 mmol) was added to a solution of 9,10-anthracene dialdehyde (117 mg, 0.1 mol) in methanol (10 ml). The reaction mixture was stirred at room temperature for 10 hours. The solid was filtered and washed with ethanol. The solid was dissolved in chloroform and 20% NaOH aqueous solution (25 ml: 20 ml), and [[4-(diethylamino)phenyl]methyl]triphenylphosphonium bromide (257 mg, 0.05 mmol) and 15 mg of tetrabutylammonium bromide were added. The solution was heated to reflux and reacted for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature and the organic solvent was removed. The crude product was purified by silica gel to obtain 73 mg of a yellow solid with a yield of 29%.
[0022] The product structure was characterized by H-NMR spectroscopy.
[0023] 1H NMR(500MHz,DMSO-d6)δ8.95(s,1H),8.47(dd,J=7.5,1.9Hz,2H),8.15–8.09( m,2H),8.06(dd,J=8.8,5.2Hz,2H),7.85(d,J=16.5Hz,1H),7.63(s,1H),7.62( s,2H),7.60(s,2H),7.58(d,J=5.1Hz,1H),7.47(t,J=8.8Hz,2H),6.85(d,J=16 .5Hz,1H),6.75(d,J=8.8Hz,2H),3.42(q,J=6.9Hz,4H),1.14(t,J=7.0Hz,6H).
[0024] Embodiment 2:
[0025] The optical properties of the compound of formula I prepared in Example 1, such as ultraviolet absorption and fluorescence emission, were studied.
[0026] The compound of formula I was dissolved in DMSO solution to prepare a concentration of 10 -5 M solution to be tested. Through ultraviolet absorption and fluorescence tests, it was found that the maximum absorption wavelength of the compound of formula I in DMSO solution was 450nm, the maximum fluorescence emission wavelength was about 500nm, and the Stokes shift could reach 50nm. In solution, the compound of formula I can emit a weak yellow fluorescence after being excited. In solid state, the compound of formula I can emit a bright red fluorescence after being excited, and its fluorescence emission wavelength is about 610nm.
[0027] Embodiment 3:
[0028] Preparation of reversible thermochromic materials based on compounds of formula I and lauric acid.
[0029] The compound of formula I is placed in a round-bottom flask, and then lauric acid is added. The mass ratio of the compound of formula I to lauric acid is 1:1000. The lauric acid is melted by heating to 50°C. Under ultrasonic conditions, the compound of formula I is uniformly dispersed in the lauric acid. After cooling, a solid mixture is obtained. The obtained solid mixture is ground into powder to obtain a reversible thermochromic material based on the compound of formula I and lauric acid.
[0030] Embodiment 4:
[0031] Preparation of reversible thermochromic materials based on compounds of formula I and n-decanoic acid.
[0032] The compound of formula I is placed in a round-bottom flask, and then n-decanoic acid is added. The mass ratio of the compound of formula I to lauric acid is 1:1000. The n-decanoic acid is melted by heating to 50°C. Under ultrasonic conditions, the compound of formula I is uniformly dispersed in the n-decanoic acid. After cooling, a solid mixture is obtained. The obtained solid mixture is ground into powder to obtain a reversible thermochromic material based on the compound of formula I and n-decanoic acid.
[0033] Embodiment 5:
[0034] Application of reversible thermochromic materials based on compound of formula I and lauric acid in temperature detection.
[0035] A small amount of reversible thermochromic material based on compound of formula I and lauric acid was encapsulated in a plastic sheet and attached to the surface of a 100ml beaker. 90ml of water was poured into the beaker. When the water temperature was lower than 35°C, the reversible thermochromic material was yellow. Under 365nm ultraviolet light, the reversible thermochromic material emitted red fluorescence. When the water temperature was heated to 40°C, the reversible thermochromic material turned orange. Under 365nm ultraviolet light, the red fluorescence of the reversible thermochromic material disappeared. After turning off the heating, as the water temperature gradually decreased from 40°C to 35°C, the red fluorescence of the reversible thermochromic material gradually recovered. The above results show that this reversible thermochromic material can be used to indicate whether the surface temperature of the beaker is higher than 40°C.
[0036] Embodiment 6:
[0037] Application of reversible thermochromic materials based on compound of formula I and n-decanoic acid in temperature detection.
[0038] A small amount of reversible thermochromic material based on compound of formula I and n-decanoic acid was encapsulated in a plastic sheet and attached to the surface of a 100ml beaker. 90ml of water was poured into the beaker. When the water temperature was below 25°C, the reversible thermochromic material was yellow. Under 365nm ultraviolet light, the reversible thermochromic material emitted red fluorescence. When the water temperature was heated to 30°C, the reversible thermochromic material turned orange. Under 365nm ultraviolet light, the red fluorescence of the reversible thermochromic material disappeared. After turning off the heating, as the water temperature gradually decreased from 30°C to 25°C, the red fluorescence of the reversible thermochromic material gradually recovered. The above results show that this reversible thermochromic material can be used to indicate whether the surface temperature of the beaker is higher than 30°C.
[0039] The above description is only a preferred embodiment of the present invention, which is merely illustrative and not restrictive of the present invention. It is understood by those skilled in the art that many changes, modifications, and even equivalent changes may be made thereto within the scope defined by the patent claims of the present invention, but all of them will fall within the protection scope of the present invention.
Claims
1. A reversible thermochromic material based on anthracene derivatives, characterized in that: The reversible thermochromic material comprises a compound of formula I and a higher fatty acid matrix containing ten to fourteen carbon atoms; the higher fatty acid matrix is selected from at least one of lauric acid or n-decanoic acid; the compound of formula I has the following structural formula:
2. The use of the reversible thermochromic material according to claim 1 in temperature detection, characterized in that: The application steps are as follows: (1) encapsulating the reversible thermochromic material and attaching it to the surface of an object to be measured; (2) Observe the color change of the reversible thermochromic material under ultraviolet light or visible light to determine the temperature range of the surface of the object to be measured.
3. The use of the reversible thermochromic material in temperature detection according to claim 2, characterized in that: The wavelength range of the ultraviolet light source is 250-400nm.