2-dimethylamino terephthalic acid-tetracyano benzene co-crystal, its preparation method and application

Abstract

The application provides a 2-amino terephthalic acid dimethyl ester-tetracyano benzene eutectic crystal as well as a preparation method and application thereof, the eutectic crystal is of a triclinic system, a space group is a cell parameter is alpha = 95.041 (2) °, beta = 90.337 (2) °, gamma = 97.670 (2) °, and a cell volume is The 2-amino terephthalic acid dimethyl ester-tetracyano benzene eutectic crystal provided by the application increases the solid melting point of the organic compound from 133.39 DEG C to 162.23 DEG C without changing the covalent bond of the compound, enhances the thermal stability, and meanwhile, the fluorescence emission color, the fluorescence lifetime and the quantum yield are obviously changed.

Description

Technical Field

[0001] This invention belongs to the field of organic solid-state luminescent material preparation technology, specifically relating to a eutectic of 2-aminodimethyl terephthalate-tetracyanobenzene, its preparation method, and its application. Background Technology

[0002] Dimethyl 2-aminoterephthalate is an organic luminescent material with excellent luminescent properties. It can also be used as an intermediate in pharmaceuticals, dyes, and color film pigments. Its molecular formula is C2. 10 H 11 NO4, with a molecular weight of 209.2, is named Dimethyl aminoterephthalate (DMAT). According to literature reports, 2-aminoterephthalate (DMAT) currently exists in two crystalline forms, named DMAT-B and DMAT-G. DMAT-B is prepared under environmental conditions by dissolving a solid raw material in dichloromethane and petroleum ether, sealing the test tube with a sealing film, and then using a slow solvent diffusion method to produce colorless, uniform, and clean-surfaced, strip-shaped crystals. Under ultraviolet light irradiation, DMAT-B exhibits strong deep blue luminescence, with a maximum absorption wavelength at 420 nm, a maximum emission wavelength at 449 nm, an absolute fluorescence quantum yield of 0.50, and a fluorescence lifetime of 14.22 ns. DMAT-G is prepared under environmental conditions by dissolving a solid raw material in dichloromethane and ethanol, and then using a slow solvent diffusion method to produce light green, plate-like crystals. Under ultraviolet light irradiation, DMAT-G exhibits green fluorescence, with a maximum emission wavelength at 499 nm, an absolute fluorescence quantum yield of 0.22, and a fluorescence lifetime of 20.55 ns. To date, there have been no reports of eutectic synthesis based on dimethyl 2-aminoterephthalate.

[0003] Cocrystals are single-phase crystalline solid materials formed by two or more different molecular or ionic compounds in a fixed stoichiometric ratio, distinct from both solvates and simple salts. The earliest report on cocrystals dates back to 1844, when the renowned chemist F. Wohler synthesized a p-benzoquinone-hydroquinone cocrystal in an experiment. In 2016, the MJ Zaworotko research group classified cocrystals into two categories based on the properties of the cocrystal formations: molecular cocrystals (MCCs) and ionic cocrystals (ICCs). Building upon this, the Li Hongzhen research group at the China Academy of Engineering Physics proposed classifying cocrystals into five types: atomic cocrystals, molecular cocrystals, ionic cocrystals, metallic cocrystals, and mixed-type cocrystals. In the past decade or so, due to the availability of abundant ligand databases and the greater diversity of crystal structures compared to polymorphs, cocrystals have attracted widespread attention from researchers and have made significant progress in applications such as energetic materials, drug development, and optoelectronic materials.

[0004] Organic light-emitting materials not only have potential applications in fields such as light-emitting diodes, field-effect transistors, photovoltaic devices, sensors, solid-state lasers, optical waveguides, and information storage, but are also extremely important in research fields such as biology, chemistry, materials science, and translational research. For example, in 2020, Professor Yan Dongpeng's research group at Beijing Normal University successfully prepared two organic cocrystals using 4-(1-naphthylene)pyridine as a model compound and selecting structurally similar fluorobenzoic acid analogs as ligands. The cocrystal formed by 4-(1-naphthylene)pyridine and 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid exhibited significant optical waveguide properties, two-photon photoelectric emission, and high-performance polarized fluorescence under ultraviolet light irradiation. After irradiation, the crystal maintained its original morphology without breaking, and the emission wavelength and intensity of the crystal did not change. In contrast, the cocrystal formed by 4-(1-naphthylene)pyridine and 2,3,5,6-tetrafluorobenzoic acid rapidly underwent macroscopic splitting and jumping behavior after ultraviolet light irradiation. With the development of supramolecular chemistry and organic solid-state chemistry, researchers have gradually discovered that the emission performance of organic solids can be modulated by changing the spatial arrangement of organic fluorescent molecules. However, due to the complexity of the spatial structure of molecules when they form solids, the emission color of materials is often unpredictable. Therefore, how to rationally design the interaction modes and stacking methods of organic molecules inside molecular solids, and thus modulate their optical properties, is one of the important problems facing the field of organic light-emitting materials. Summary of the Invention

[0005] This invention provides a eutectic of 2-aminodimethyl terephthalate-tetracyanobenzene, its preparation method, and its application. Without altering the covalent bonds of the compound, this invention prepares an organic eutectic fluorescent material based on 2-aminodimethyl terephthalate by slow solvent evaporation under low-temperature conditions. The process is simple, reproducible, and mild, and the product has high crystallinity, which can provide guidance for the development of organic light-emitting crystal materials.

[0006] One objective of this invention is to provide a 2-aminodimethyl terephthalate-tetracyanobenzene eutectic, wherein the molecular formula of the 2-aminodimethyl terephthalate-tetracyanobenzene eutectic is C2. 20 H 12 N5O4.

[0007] The crystallographic characteristics of the 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic provided by this invention include crystallization in a triclinic crystal system and a space group of Cell parameters are α = 95.041(2)°, β = 90.337(2)°, γ = 97.670(2)°, and the unit cell volume is

[0008] The X-ray powder diffraction pattern of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic provided by this invention has the following 2θ diffraction angles: 12.5±0.2°, 13.7±0.2°, 14.7±0.2°, 16.1±0.2°, 16.3±0.2°, 17.3±0.2°, 17.9±0.2°, 19.1±0.2°, 19.8±0.2°, 21.0±0.2°, 21.2±0.2°, 22.4±0.2°, 22.8±0.2°, 2 Characteristic peaks are found at 4.4±0.2°, 25.2±0.2°, 25.7±0.2°, 25.9±0.2°, 27.0±0.2°, 27.8±0.2°, 28.8±0.2°, 29.3±0.2°, 29.8±0.2°, 30.2±0.2°, 30.5±0.2°, 30.7±0.2°, and 30.9±0.2°, with 12.5±0.2° being the initial peak and the relative intensity of the characteristic peak at 27.8±0.2° being 100%.

[0009] The differential scanning calorimetry (DSC) spectrum of the 2-aminoterephthalate-tetracyanobenzene eutectic provided by this invention shows that the eutectic has a characteristic melting peak at 162.2 ± 1.0 °C.

[0010] A second objective of this invention is to provide a method for preparing the 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic as described in one objective, the method comprising the following steps:

[0011] Dimethyl 2-aminoterephthalate solid raw material and tetracyanobenzene solid raw material are ground in an organic solvent, then dissolved in an organic solvent, and evaporated and crystallized at 5-15℃ to obtain 2-aminoterephthalate-tetracyanobenzene eutectic.

[0012] Preferably, the molar ratio of the 2-aminoterephthalate solid raw material to the tetracyanobenzene solid raw material is 1:(0.8-1.2).

[0013] Preferably, the organic solvent includes any one or any combination of two of ethanol, acetone, butanone, or acetonitrile.

[0014] Preferably, the grinding time is 10-20 minutes.

[0015] Preferably, the amount of organic solvent added for dissolution is 2-5 mL, based on the amount of the solid mixture obtained after grinding being 15-30 mg.

[0016] Preferably, the evaporation and crystallization are carried out under dark conditions, and the evaporation and crystallization time is 7-15 days.

[0017] As a preferred technical method of the present invention, the preparation method includes the following steps:

[0018] Dimethyl 2-aminoterephthalate solid raw material and tetracyanobenzene solid raw material were added to a mortar at a molar ratio of 1:(0.8-1.2), a few drops of organic solvent were added, and the mixture was ground for 10-20 minutes.

[0019] 15-30 mg of the ground product was added to 2-5 mL of organic solvent and dissolved completely. The solution was then evaporated in a dark environment at 5-15℃. After one week, 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic was obtained. The product was a bright yellow blocky crystal.

[0020] The third objective of this invention is to provide the application of the aforementioned 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic in improving thermal stability and regulating fluorescence performance.

[0021] Compared with the prior art, the present invention has the following beneficial effects:

[0022] This invention is the first to synthesize a 2-aminoterephthalate-tetracyanobenzene eutectic. Without changing the covalent bonds, the solid melting point of the eutectic is increased from 133.39℃ for the original 2-aminoterephthalate to 162.2℃ for the 2-aminoterephthalate-tetracyanobenzene eutectic, thus improving the thermal stability of the solid luminescent material.

[0023] The 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic synthesized in this invention exhibits a bright yellow color under ultraviolet light irradiation. The maximum emission wavelength of the 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic shows a significant red shift compared to that of 2-aminoterephthalate dimethyl terephthalate. The average fluorescence lifetime and quantum yield of the 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic are significantly different from those of the original 2-aminoterephthalate dimethyl terephthalate compound.

[0024] This invention uses a low-temperature solvent slow evaporation method to prepare 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic, which is simple, mild, and produces crystal products with high crystallinity. Attached Figure Description

[0025] Figure 1 The asymmetric unit of the 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic synthesized in this invention.

[0026] Figure 2 The packing structure diagram of the 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic synthesized in this invention in the ac plane.

[0027] Figure 3 The packing structure diagram of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic synthesized in this invention in the bc plane.

[0028] Figure 4 X-ray diffraction pattern of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic of this invention.

[0029] Figure 5 Differential scanning calorimetry (DSC) chromatogram of 2-aminoterephthalate dimethyl terephthalate-tetracyanophenyl eutectic.

[0030] Figure 6 Microscopic photograph of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic of this invention.

[0031] Figure 7 The fluorescence spectrum of the 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic of this invention.

[0032] Figure 8 The fluorescence lifetime of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic of the present invention. Detailed Implementation

[0033] It should be noted that the following detailed descriptions are exemplary and intended to provide further explanation of the present invention. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The technical solutions of the present invention are further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as specific limitations thereof.

[0034] Example 1

[0035] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 14.3 mg of tetracyanobenzene solid raw material were added to a mortar, 3 drops of ethanol were added, and the mixture was ground for 10 min. 15 mg of the ground product was added to 2 mL of ethanol and dissolved completely. The mixture was then evaporated in a dark environment at 5 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0036] Example 2

[0037] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 14.3 mg of tetracyanobenzene solid raw material were added to a mortar, 2 drops of acetone were added, and the mixture was ground for 15 min. 15 mg of the ground product was added to 3 mL of acetone and dissolved completely. The mixture was then evaporated in a dark environment at 10 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0038] Example 3

[0039] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 21.4 mg of tetracyanobenzene solid raw material were added to a mortar, 3 drops of acetone were added, and the mixture was ground for 15 min. 25 mg of the ground product was added to 5 mL of acetone and dissolved completely. The mixture was then evaporated in a dark environment at 10 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0040] Example 4

[0041] 20.9 mg of 2-aminoterephthalate solid raw material and 17.8 mg of tetracyanobenzene solid raw material were added to a mortar, 2 drops of butanone were added, and the mixture was ground for 20 min. 20 mg of the ground product was added to 5 mL of butanone and dissolved completely. The mixture was then evaporated in a dark environment at 15 °C. After one week, 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0042] Example 5

[0043] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 17.8 mg of tetracyanobenzene solid raw material were added to a mortar, 2 drops of acetonitrile were added, and the mixture was ground for 20 min. 30 mg of the ground product was added to 5 mL of acetonitrile and dissolved completely. The mixture was then evaporated in a dark environment at 5 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0044] Example 6

[0045] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 21.4 mg of tetracyanobenzene solid raw material were added to a mortar, 3 drops of acetone were added, and the mixture was ground for 15 min. 25 mg of the ground product was added to 2 mL of ethanol and 3 mL of acetone and dissolved completely. The mixture was then evaporated in a dark environment at 10 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0046] Example 7

[0047] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 17.8 mg of tetracyanobenzene solid raw material were added to a mortar, 2 drops of butanone were added, and the mixture was ground for 20 min. 20 mg of the ground product was added to 2 mL of butanone and 3 mL of acetonitrile and dissolved completely. The mixture was then evaporated in a dark environment at 15 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0048] Example 8

[0049] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 14.3 mg of tetracyanobenzene solid raw material were added to a mortar, 3 drops of ethanol were added, and the mixture was ground for 10 min. 15 mg of the ground product was added to 2 mL of ethanol and 3 mL of acetonitrile and dissolved completely. The mixture was then evaporated in a dark environment at 10 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0050] Example 9

[0051] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 21.4 mg of tetracyanobenzene solid raw material were added to a mortar, 3 drops of acetone were added, and the mixture was ground for 15 min. 25 mg of the ground product was added to 2 mL of acetone and 1 mL of acetonitrile and dissolved completely. The mixture was then evaporated in a dark environment at 10 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0052] Example 10

[0053] 20.9 mg of dimethyl 2-aminoterephthalate solid raw material and 17.8 mg of tetracyanobenzene solid raw material were added to a mortar, 3 drops of butanone were added, and the mixture was ground for 15 min. 25 mg of the ground product was added to 2 mL of ethanol and 2 mL of butanone and dissolved completely. The mixture was then evaporated in a dark environment at 10 °C. After one week, 2-dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic was obtained.

[0054] The 2-aminoterephthalate dimethyl terephthalate-tetracyanophenyl eutectic prepared in the embodiments of the present invention was characterized and its properties were determined. The specific methods are as follows:

[0055] 1. Instruments used for SCXRD testing: Single-crystal X-ray diffractometer

[0056] Instrument model: Rigaku Saturn 70 single crystal diffractometer (Japan);

[0057] Test method: CCD detector (graphite monochromator), molybdenum target Mo-Kα rays The sampling temperature was 113.15K.

[0058] The 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic prepared in the embodiments of the present invention belongs to the triclinic crystal system, space group [missing information]. The unit cell parameters are α = 95.041(2)°, β = 90.337(2)°, γ = 97.670(2)°, and the unit cell volume is As attached Figure 1 As shown, the asymmetric unit contains one 2-aminoterephthalate (2-dimethyl terephthalate) molecule and one tetracyanobenzene molecule. The packing structure of the 2-aminoterephthalate-tetracyanobenzene eutectic in the ac plane is shown in the attached figure. Figure 2 As shown in the attached figure, the packing structure of the 2-aminodimethyl terephthalate-tetracyanobenzene eutectic in the bc plane is as follows. Figure 3 As shown in Table 1, the crystallographic parameters of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic are shown in Table 1.

[0059] Table 1

[0060]

[0061] 2. Instruments used for PXRD testing: X-ray powder diffractometer

[0062] Instrument model: Rigaku D / max-2500 (Japan);

[0063] Test method: Copper target Cu-Kα rays Voltage 40kV, current 100mA, test angle 2-40°, step size 8° / min, exposure time 0.2s, test temperature room temperature (25℃), light tube slit width 1mm, detector slit width 2.7mm.

[0064] The powder X-ray diffraction pattern of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic obtained in Example 1 of this invention is attached. Figure 4 As shown. X-ray powder diffraction of the 2-aminoterephthalate-tetracyanobenzene eutectic showed diffraction angles of 12.5±0.2°, 13.7±0.2°, 14.7±0.2°, 16.1±0.2°, 16.3±0.2°, 17.3±0.2°, 17.9±0.2°, 19.1±0.2°, 19.8±0.2°, 21.0±0.2°, 21.2±0.2°, 22.4±0.2°, 22.8±0.2°, and 24.4±0.2° at 2θ angles. Characteristic peaks are found at 0.2°, 25.2±0.2°, 25.7±0.2°, 25.9±0.2°, 27.0±0.2°, 27.8±0.2°, 28.8±0.2°, 29.3±0.2°, 29.8±0.2°, 30.2±0.2°, 30.5±0.2°, 30.7±0.2°, and 30.9±0.2°, with 12.5±0.2° being the initial peak and the relative intensity of the characteristic peak at 27.8±0.2° being 100%.

[0065] 3. DSC testing instrument: Differential calorimeter scanner

[0066] Instrument model: Mettler Toledo DSC1 / 500;

[0067] Test method: Sample amount 5-10mg, heating rate 10℃ / min, protective gas nitrogen flow rate 50mL / min.

[0068] Differential scanning calorimetry analysis was performed on the 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic prepared in the embodiments of the present invention, as shown in the attached figure. Figure 5 As shown, the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic exhibits a sharp endothermic peak at 162.2℃, indicating that its melting point is approximately 162.2℃, further demonstrating that this substance is a single crystalline phase.

[0069] 4. Instruments for crystal morphology testing: Optical microscope

[0070] The crystal morphology of the 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic product obtained in this invention was observed, as shown in the attached figure. Figure 6 As shown (Note: This appendix) Figure 6The color image was bright yellow (it was adjusted to grayscale as required for submission), and the product is a bright yellow blocky crystal.

[0071] 5. Instruments for fluorescence emission spectroscopy and fluorescence lifetime testing: FLS1000, Edinburgh, UK

[0072] The 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic prepared in the embodiments of the present invention exhibits a bright rose-red color under ultraviolet light irradiation, with a maximum emission wavelength of 574 nm (see attached image). Figure 7 Compared to dimethyl 2-aminoterephthalate, the emission wavelength shows a significant red shift, and the average fluorescence lifetime of the dimethyl 2-aminoterephthalate-tetracyanobenzene eutectic is 7.13 ns (see appendix). Figure 8 The quantum yield is 1.33%.

[0073] This invention discloses and proposes a 2-aminoterephthalate dimethyl terephthalate-tetracyanophenyl eutectic, its preparation method, and its applications. The products and methods of this invention have been described through preferred embodiments. Those skilled in the art will readily be able to modify or appropriately alter and combine the methods and products described herein without departing from the content, spirit, and scope of this invention to achieve the technical requirements of this invention. It is particularly important to note that all similar substitutions and modifications are obvious to those skilled in the art and are considered to be included within the spirit, scope, and content of this invention.

Claims

1. A 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic, characterized in that, The molecular formula of the 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic is C 20 H 12 N5O4; The crystallographic characteristics of the 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic include crystallization in a triclinic crystal system with space group P. The unit cell parameters are a = 6.5105(2) Å, b = 7.1449(2) Å, c = 9.9272(2) Å, α = 95.041(2) °, β = 90.337(2) °, γ = 97.670(2) °, and the unit cell volume is 455.81(2) Å. 3 .

2. The 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic according to claim 1, characterized in that, The X-ray powder diffraction pattern of the 2-aminoterephthalate-tetracyanobenzene eutectic shows diffraction angles of 12.5±0.2°, 13.7±0.2°, 14.7±0.2°, 16.1±0.2°, 16.3±0.2°, 17.3±0.2°, 17.9±0.2°, 19.1±0.2°, 19.8±0.2°, 21.0±0.2°, 21.2±0.2°, 22.4±0.2°, 22.8±0.2°, and 24°. Characteristic peaks are found at 0.4±0.2°, 25.2±0.2°, 25.7±0.2°, 25.9±0.2°, 27.0±0.2°, 27.8±0.2°, 28.8±0.2°, 29.3±0.2°, 29.8±0.2°, 30.2±0.2°, 30.5±0.2°, 30.7±0.2°, and 30.9±0.2°, with 12.5±0.2° being the initial peak and the relative intensity of the characteristic peak at 27.8±0.2° being 100%.

3. The 2-aminoterephthalate dimethyl ester-tetracyanobenzene eutectic according to claim 1, characterized in that, The differential scanning calorimetry (DSC) spectrum of the 2-aminoterephthalate-tetracyanobenzene eutectic showed a characteristic melting peak at 162.2 ± 1.0 °C.

4. The method for preparing the 2-aminoterephthalate dimethyl terephthalate-tetracyanobenzene eutectic according to any one of claims 1-3, characterized in that, The preparation method includes the following steps: Dimethyl 2-aminoterephthalate solid raw material and tetracyanobenzene solid raw material are ground in an organic solvent, then dissolved in an organic solvent, and evaporated and crystallized at 5-15℃ to obtain 2-aminoterephthalate-tetracyanobenzene eutectic.

5. The preparation method according to claim 4, characterized in that, The molar ratio of the 2-aminoterephthalate solid raw material to the tetracyanobenzene solid raw material is 1:(0.8-1.2).

6. The preparation method according to claim 4, characterized in that, The organic solvent is any one or any combination of two of ethanol, acetone, butanone, or acetonitrile.

7. The preparation method according to claim 4, characterized in that, The grinding time is 10-20 minutes.

8. The preparation method according to claim 4, characterized in that, Based on a solid mixture obtained after grinding of 15-30 mg, the amount of organic solvent added for dissolution is 2-5 mL.

9. The preparation method according to claim 4, characterized in that, The evaporation and crystallization are carried out under dark conditions, and the evaporation and crystallization time is 7-15 days.

10. The application of the 2-aminoterephthalate dimethyl ester-tetracyanophenyl eutectic according to any one of claims 1-3 in improving the thermal stability and fluorescence performance regulation of solid-state luminescent materials.

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