5-dimethylaminoisophthalic acid and tetracyanobenzene co-crystal compound, preparation method and application thereof

Abstract

This invention discloses a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenylene, its preparation method, and its applications. The chemical formula of the invented eutectic compound is C5. 30 H 24 N6O8 has a monoclinic crystal system, space group P21 / n, with cell parameters α = 90°, β = 101.461(3)°, γ = 90°, and cell volume. This invention uses a solvent evaporation method for preparation, which features simple processing, mild conditions, good crystal quality, and complete crystal habit. The eutectic compound provided by this invention can serve as a potential luminescent material.

Description

Technical Field

[0001] This invention belongs to the fields of organic chemistry and crystallography, and specifically relates to a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenylene, its preparation method and application. Background Technology

[0002] Supramolecular chemistry is often described as "Lego chemistry," where each Lego brick represents a molecular component. These components attract each other through weak non-covalent interactions such as electrostatics, hydrogen bonds, coordination bonds, hydrophobic interactions, cation-π interactions, anion-π interactions, π-π stacking interactions, and solvation effects, ultimately forming a supramolecular aggregate. In 1987, C. J. Dedersen, DJ. Cram, and J. M. Lehn were awarded the Nobel Prize in Chemistry for their major contributions in designing and synthesizing molecules with highly selective structure-specific interactions, which played a crucial role in the development of supramolecular chemistry. Since then, supramolecular chemistry has officially become a widely accepted branch of chemistry. To some extent, supramolecular chemistry has significantly expanded the boundaries and research areas of classical chemistry, extending the study of covalent bonds between atoms to non-covalent interactions between molecules, deepening our understanding of the structure and physicochemical properties of matter.

[0003] Crystal engineering originated from organic chemistry and physical chemistry and is an important component of molecular engineering. The concept of crystal engineering was first proposed by Professor R. Pepinsky of Pennsylvania State University at the American Physical Society meeting in August 1955. In the 1990s, supramolecular chemistry and crystal engineering intersected and mutually promoted each other, truly realizing "chemistry beyond the molecular level." Cocrystals are an important part of crystal engineering research. The earliest report on cocrystals can be traced back to the p-benzoquinone-hydroquinone cocrystal synthesized by the famous chemist F. Wohler in 1844. After a period of silence, the term cocrystal was first proposed by J. Schmidt and W. Snippes in 1967, and subsequently popularized by M.C. Etter. A cocrystal is a single-phase crystalline solid material formed by two or more different molecular or ionic compounds in a fixed stoichiometric ratio, which is different from both solvates and simple salts.

[0004] Organic light-emitting materials (OLEDs) have potential applications not only in light-emitting diodes (LEDs), field-effect transistors (FETs), photovoltaic devices, sensors, solid-state lasers, optical waveguides, and information storage, but also hold immense importance in research fields such as biology, chemistry, materials science, and translational research. 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 altering the spatial arrangement of organic fluorescent molecules. However, due to the complexity of the spatial structure of molecules when forming solids, the emission color of materials is often unpredictable. Therefore, how to rationally design the interaction modes and stacking arrangements of organic molecules within a molecular solid, thereby modulating its optical properties, is one of the important challenges facing the field of organic light-emitting materials.

[0005] Dimethyl 5-aminoisophthalate (DMAI) is a compound with the molecular formula C1. 10 H 11 NO4, with a molecular weight of 209.2, is generally soluble in ethyl acetate and dichloromethane, but sparingly soluble in water and methanol. It is commonly used as a raw material for synthesizing novel sweeteners and certain chiral drug intermediates, as well as as an intermediate for clinical drugs and chemical raw materials. According to literature reports, dimethyl 5-aminoisophthalate is also an organic light-emitting material with two crystal forms, named DMAI-B and DMAI-G. DMAI-B emits bright blue fluorescence under ultraviolet light irradiation, with a maximum emission peak at 420 nm, a fluorescence lifetime of 3.59 ns, and an absolute fluorescence quantum yield of approximately 0.14. DMAI-G emits green fluorescence under ultraviolet light irradiation, with a maximum emission peak at 500 nm, a fluorescence lifetime of 4.0 ns, and an absolute fluorescence quantum yield of up to 0.38.

[0006] Therefore, in order to expand its applications, it is essential to regulate the luminescence properties of dimethyl 5-aminoisophthalate compounds in multiple dimensions. Summary of the Invention

[0007] This invention provides a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenylene with modulated fluorescence emission properties, its preparation method, and its applications. This invention utilizes solvent evaporation to prepare an organic eutectic fluorescent material based on dimethyl 5-aminoisophthalate. The process is simple, the conditions are mild, the reproducibility is good, and the resulting crystal product has high crystallinity and complete crystal habit, making it suitable for large-scale production and providing guidance for the development of organic light-emitting crystal materials.

[0008] One of the objectives of this invention is to provide a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenyl.

[0009] The present invention provides a co-crystal compound of dimethyl 5-aminoisophthalate and tetracyanobenzene, wherein the molecular formula of the co-crystal compound is C2. 30 H 24 N6O8;

[0010] The crystal structure of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene is a monoclinic crystal system, space group P21 / n, with unit cell parameters of... α = 90°, β = 101.461(3)°, γ = 90°, and the unit cell volume is

[0011] Preferably, the X-ray powder diffraction pattern of the eutectic is shown in the attached figure. Figure 1 At 2θ diffraction angles of 6.3±0.2°, 7.8±0.2°, 9.2±0.2°, 9.9±0.2°, 10.6±0.2°, 12.7±0.2°, 14.2±0.2°, 15.4±0.2°, 15.6±0.2°, 16.8±0.2°, 17.1±0.2°, 18.0±0.2°, 18.6±0.2°, and 19.6±0.2°, Characteristic peaks are observed at 20.1±0.2°, 21.4±0.2°, 23.1±0.2°, 23.7±0.2°, 24.1±0.2°, 25.0±0.2°, 25.5±0.2°, 26.6±0.2°, 27.6±0.2°, 27.9±0.2°, 28.1±0.2°, 28.5±0.2°, 29.5±0.2°, and 30.0±0.2°.

[0012] The X-ray powder diffraction pattern of the eutectic compound of 5-aminoisophthalate and tetracyanobenzene of this invention was obtained using a Rigaku D / max-2500 X-ray powder diffractometer (Japan). The testing method is as follows: 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.

[0013] This invention uses a Rigaku Saturn 70CCD diffractometer to determine the single-crystal structure of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene at 113 K, and a graphite monochromator with MoKα rays. Data was collected using multi-scan scanning, and data restoration and absorption correction were performed using the ShelXL package. The space group was determined based on the system's extinction rules and verified by refined results. All crystal structures were solved using ShelXL via the direct method, and the structures were corrected using the full-matrix least squares method with the SHELXL-2018 / 3 program. Hydrogen atom coordinates were incorporated from theoretical calculations, thus successfully resolving the crystal structure of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenylene, as shown in the attached figure. Figure 2 As shown, the asymmetric unit contains two 5-aminoisophthalate dimethyl ester molecules and one tetracyanobenzene molecule, and the crystal stacking structure along the a-axis is shown in the attached figure. Figure 3 As shown in Table 1, the crystallographic parameters of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenylene are shown below.

[0014] Table 1

[0015]

[0016]

[0017] A second objective of this invention is to provide a method for preparing the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanophenyl as described in one objective, the method comprising the following steps:

[0018] A mixed solution containing dimethyl 5-aminoisophthalate and tetracyanobenzene raw materials at a temperature of 30-50℃ is evaporated and crystallized at 10-25℃ to obtain a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene.

[0019] Preferably, the method for preparing the mixed solution includes: mixing 5-aminoisophthalate dimethyl ester raw material and tetracyanophenyl raw material in an organic solution under ultrasonic action to obtain a mixed solution.

[0020] Preferably, the molar ratio of the 5-aminoisophthalate dimethyl raw material to the tetracyanobenzene raw material is 1:(0.5-1.5).

[0021] Preferably, the organic solvent includes any one or a combination of at least two of methanol, ethanol, n-propanol, isopropanol, acetone, butanone, or acetonitrile.

[0022] Preferably, based on the addition amount of 0.1 mmol of dimethyl 5-aminoisophthalate raw material, the addition amount of the organic solvent is 2-5 mL.

[0023] Preferably, the evaporation and crystallization time is 5-7 days.

[0024] Preferably, the preparation method further includes solid-liquid separation of the mixture obtained after evaporation and crystallization.

[0025] As a preferred embodiment of the present invention, the method for preparing the eutectic compound includes the following:

[0026] (1) Under the action of ultrasound, 0.1 mmol of dimethyl 5-aminoisophthalate solid raw material and 0.05-0.15 mmol of tetracyanobenzene solid raw material are mixed and added to a certain volume of organic solvent. The reaction temperature is set at 30-50℃ and heated until fully dissolved to obtain a solution.

[0027] (2) The solution was allowed to stand at 10-25℃ for 5-7 days to slowly evaporate, yielding a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene. The product was an orange blocky crystal; microscopic photographs are attached. Figure 4 The crystal products have high crystallinity and complete crystal structure.

[0028] A third objective of this invention is to provide an application of the co-crystal compound of dimethyl 5-aminoisophthalate and tetracyanobenzene as described in one objective in the regulation of fluorescence properties.

[0029] The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene of this invention exhibits a bright rose color under ultraviolet light irradiation, with a maximum emission wavelength of 641 nm, as shown in the attached figure. Figure 5 As shown, the emission wavelength exhibits a significant red shift compared to dimethyl 5-aminoisophthalate. The average fluorescence lifetime of the cocrystal compound of dimethyl 5-aminoisophthalate and tetracyanobenzene is 1.46 ns, as shown in the attached figure. Figure 6 As shown, the quantum yield is 0.19%. This invention uses tetracyanobenzene as a ligand to form an organic eutectic with dimethyl 5-aminoisophthalate through weak hydrogen bonds and π-π interactions, altering the spatial arrangement of the original dimethyl 5-aminoisophthalate and preparing a eutectic solid-state luminescent material with excellent properties. This eutectic material exhibits significant control over its luminescent properties, including emission color, emission wavelength, average fluorescence lifetime, and quantum yield. Attached Figure Description

[0030] Figure 1 X-ray diffraction pattern of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene of this invention.

[0031] Figure 2 The present invention relates to the asymmetric unit of the 5-aminoisophthalate dimethyl ester and tetracyanophenyl eutectic compound.

[0032] Figure 3 The crystal packing structure of the eutectic compound of 5-aminoisophthalate and tetracyanophenyl ester along the a-axis direction of this invention.

[0033] Figure 4Microscopic photograph of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene of this invention.

[0034] Figure 5 The fluorescence spectrum of the co-crystal compound of 5-aminoisophthalate and tetracyanobenzene of this invention.

[0035] Figure 6 The fluorescence lifetime of the co-crystal compound of 5-aminoisophthalate and tetracyanobenzene of this invention. Detailed Implementation

[0036] The following detailed description, through specific embodiments, further illustrates the above-described content of the present invention. However, it should not be construed as limiting the scope of the present invention to the following embodiments. All technologies implemented based on the above-described content of the present invention fall within the scope of the present invention.

[0037] Example 1

[0038] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.05 mmol of solid tetracyanobenzene were mixed and added to 2 mL of methanol. The reaction temperature was 30 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was left to stand at 10 °C and slowly evaporated for 5 days to obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0039] The X-ray powder diffraction pattern of the product prepared in Example 1 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.3°, 7.8°, 9.2°, 9.9°, 10.6°, 12.7°, 14.2°, 15.4°, 15.6°, 16.8°, 17.1°, 18.0°, 18.6°, 19.6°, 20.1°, 21.4°, 23.1°, 23.7°, 24.1°, 25.0°, 25.5°, 26.6°, 27.6°, 27.9°, 28.1°, 28.5°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs and accompanying images are shown. Figure 4 Similar (Note: This appendix) Figure 4 The color image was originally orange, but has been adjusted to grayscale for submission requirements. The crystalline product exhibits high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light, with an emission wavelength of 641 nm, similar to the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0040] Example 2

[0041] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.05 mmol of solid tetracyanobenzene were mixed and added to 4 mL of acetone. The reaction temperature was 40 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was left to stand at 15 °C and slowly evaporated for 6 days to obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0042] The X-ray powder diffraction pattern of the product prepared in Example 2 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.4°, 7.8°, 9.2°, 9.9°, 10.7°, 12.6°, 14.2°, 15.6°, 15.6°, 16.8°, 17.3°, 18.0°, 18.6°, 19.6°, 20.1°, 21.4°, 23.1°, 23.9°, 24.1°, 25.0°, 25.5°, 26.6°, 27.6°, 27.9°, 28.1°, 28.5°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs and accompanying images are shown. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0043] Example 3

[0044] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.1 mmol of solid tetracyanobenzene were mixed and added to 5 mL of ethanol. The reaction temperature was 40 °C. The mixture was heated until fully dissolved to obtain a solution. The solution was allowed to stand at 15 °C and slowly evaporated for 6 days to obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0045] The X-ray powder diffraction pattern of the product prepared in Example 3 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.2°, 7.8°, 9.2°, 9.8°, 10.6°, 12.7°, 14.2°, 15.4°, 15.4°, 16.8°, 17.1°, 18.0°, 18.4°, 19.6°, 20.1°, 21.2°, 23.1°, 23.7°, 24.1°, 25.0°, 25.3°, 26.6°, 27.4°, 27.9°, 28.1°, 28.3°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs and accompanying images are shown. Figure 4Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0046] Example 4

[0047] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.15 mmol of solid tetracyanobenzene were mixed and added to 5 mL of acetonitrile. The reaction temperature was 45 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was then allowed to stand at 25 °C for 5 days to slowly evaporate, yielding a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0048] The X-ray powder diffraction pattern of the product prepared in Example 4 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.3°, 7.8°, 9.2°, 9.9°, 10.6°, 12.6°, 14.2°, 15.4°, 15.6°, 16.7°, 17.1°, 18.0°, 18.6°, 19.6°, 20.1°, 21.2°, 23.1°, 23.7°, 24.1°, 25.0°, 25.4°, 26.6°, 27.6°, 27.9°, 28.1°, 28.5°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs are attached. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0049] Example 5

[0050] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.15 mmol of solid tetracyanobenzene were mixed and added to 5 mL of isopropanol. The reaction temperature was 50 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was then allowed to stand at 10 °C for 7 days to slowly evaporate and obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0051] The X-ray powder diffraction pattern of the product prepared in Example 5 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.3°, 7.8°, 9.2°, 9.9°, 10.6°, 12.7°, 14.2°, 15.4°, 15.6°, 16.8°, 17.1°, 18.0°, 18.6°, 19.6°, 20.1°, 21.4°, 23.1°, 23.7°, 24.1°, 25.0°, 25.5°, 26.6°, 27.6°, 27.9°, 28.1°, 28.5°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs and accompanying images are shown. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0052] Example 6

[0053] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.1 mmol of solid tetracyanobenzene were mixed and added to 3 mL of butanone. The reaction temperature was 30 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was then allowed to stand at 10 °C for 6 days to slowly evaporate and obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0054] The X-ray powder diffraction pattern of the product prepared in Example 6 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.3°, 7.8°, 9.2°, 9.9°, 10.6°, 12.7°, 14.2°, 15.4°, 15.6°, 16.8°, 17.1°, 18.0°, 18.6°, 19.6°, 20.1°, 21.4°, 23.1°, 23.7°, 24.1°, 25.0°, 25.5°, 26.6°, 27.6°, 27.9°, 28.1°, 28.5°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs and accompanying images are shown. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0055] Example 7

[0056] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.15 mmol of solid tetracyanobenzene were mixed and added to 5 mL of n-propanol. The reaction temperature was 50 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was left to stand at 15 °C and slowly evaporated for 5 days to obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0057] The X-ray powder diffraction pattern of the product prepared in Example 7 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.4°, 7.8°, 9.2°, 9.9°, 10.7°, 12.6°, 14.2°, 15.6°, 15.6°, 16.8°, 17.3°, 18.0°, 18.6°, 19.6°, 20.1°, 21.4°, 23.1°, 23.9°, 24.1°, 25.0°, 25.5°, 26.6°, 27.6°, 27.9°, 28.1°, 28.5°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs are attached. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0058] Example 8

[0059] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.05 mmol of solid tetracyanobenzene were mixed and added to 2 mL of ethanol. The reaction temperature was 45 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was then allowed to stand at 20 °C for 5 days to slowly evaporate and obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0060] The X-ray powder diffraction pattern of the product prepared in Example 8 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.2°, 7.8°, 9.2°, 9.8°, 10.6°, 12.7°, 14.2°, 15.4°, 15.4°, 16.8°, 17.1°, 18.0°, 18.4°, 19.6°, 20.1°, 21.2°, 23.1°, 23.7°, 24.1°, 25.0°, 25.3°, 26.6°, 27.4°, 27.9°, 28.1°, 28.3°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs are attached. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0061] Example 9

[0062] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.05 mmol of solid tetracyanobenzene were mixed and added to 2 mL of butanone. The reaction temperature was 40 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was then allowed to stand at 20 °C for 6 days to slowly evaporate and obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0063] The X-ray powder diffraction pattern of the product prepared in Example 9 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.2°, 7.8°, 9.2°, 9.8°, 10.6°, 12.7°, 14.2°, 15.4°, 15.4°, 16.8°, 17.1°, 18.0°, 18.4°, 19.6°, 20.1°, 21.2°, 23.1°, 23.7°, 24.1°, 25.0°, 25.3°, 26.6°, 27.4°, 27.9°, 28.1°, 28.3°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs are attached. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0064] Example 10

[0065] Under ultrasonic treatment, 0.1 mmol of solid 5-aminoisophthalate and 0.05 mmol of solid tetracyanobenzene were mixed and added to 2 mL of acetonitrile. The reaction temperature was 35 °C, and the mixture was heated until it was fully dissolved to obtain a solution. The solution was then allowed to stand at 10 °C for 6 days to slowly evaporate and obtain a eutectic compound of 5-aminoisophthalate and tetracyanobenzene.

[0066] The X-ray powder diffraction pattern of the product prepared in Example 10 is represented by 2θ. Characteristic peaks are observed at 2θ diffraction angles of 6.2°, 7.8°, 9.2°, 9.8°, 10.6°, 12.7°, 14.2°, 15.4°, 15.4°, 16.8°, 17.1°, 18.0°, 18.4°, 19.6°, 20.1°, 21.2°, 23.1°, 23.7°, 24.1°, 25.0°, 25.3°, 26.6°, 27.4°, 27.9°, 28.1°, 28.3°, 29.5°, and 30.0°. The product is an orange blocky crystal. Microscopic photographs are attached. Figure 4 Similarly, the crystalline products exhibit high crystallinity and complete crystal habit. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene displays a bright rose color under ultraviolet light irradiation; the emission wavelength of the eutectic is 641 nm, similar to that of the attached... Figure 5 Similarly, compared to dimethyl 5-aminoisophthalate, the emission wavelength shows a significant red shift. The average fluorescence lifetime of the eutectic is 1.46 ns, compared to the attached... Figure 6 Similarly, the quantum yield is 0.19%.

[0067] This invention discloses and proposes the preparation and application of a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene. 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 aspects 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 eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene, characterized in that, The molecular formula of the eutectic compound is C 30 H 24 N6O8; The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene has a monoclinic crystal system, space group P21 / n, with cell parameters a = 7.6502(3) Å, b = 22.7523(7) Å, c = 18.2160(5) Å, α = 90°, β = 101.461(3) °, γ = 90°, and a cell volume of 3107.45(18) Å. 3 ; The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene exhibits a bright rose color under ultraviolet light irradiation, with a maximum emission wavelength of 641 nm.

2. The eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene according to claim 1, characterized in that, In the X-ray powder diffraction pattern of the eutectic compound, at 2θ diffraction angles of 6.3±0.2°, 7.8±0.2°, 9.2±0.2°, 9.9±0.2°, 10.6±0.2°, 12.7±0.2°, 14.2±0.2°, 15.4±0.2°, 15.6±0.2°, 16.8±0.2°, 17.1±0.2°, 18.0±0.2°, 18.6±0.2°, and 1... Characteristic peaks are observed at 9.6±0.2°, 20.1±0.2°, 21.4±0.2°, 23.1±0.2°, 23.7±0.2°, 24.1±0.2°, 25.0±0.2°, 25.5±0.2°, 26.6±0.2°, 27.6±0.2°, 27.9±0.2°, 28.1±0.2°, 28.5±0.2°, 29.5±0.2°, and 30.0±0.2°.

3. The method for preparing the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene according to claim 1 or 2, characterized in that, The preparation method includes the following steps: A mixed solution containing dimethyl 5-aminoisophthalate and tetracyanobenzene raw materials at a temperature of 30-50℃ is evaporated and crystallized at 10-25℃ to obtain a eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene.

4. The preparation method according to claim 3, characterized in that, The method for preparing the mixed solution includes: mixing dimethyl 5-aminoisophthalate raw material and tetracyanobenzene raw material in an organic solution under ultrasonic action to obtain a mixed solution.

5. The preparation method according to claim 4, characterized in that, The molar ratio of the 5-aminoisophthalate dimethyl ester raw material to the tetracyanobenzene raw material is 1:(0.5-1.5).

6. The preparation method according to claim 4, characterized in that, The organic solvent includes any one or a combination of at least two of methanol, ethanol, n-propanol, isopropanol, acetone, butanone, or acetonitrile.

7. The preparation method according to claim 4, characterized in that, Based on an addition amount of 0.1 mmol of dimethyl 5-aminoisophthalate raw material, the addition amount of the organic solvent is 2-5 mL.

8. The preparation method according to claim 3, characterized in that, The evaporation and crystallization process takes 5-7 days.

9. The preparation method according to claim 3, characterized in that, The preparation method further includes solid-liquid separation of the mixture obtained after evaporation and crystallization.

10. The application of the eutectic compound of dimethyl 5-aminoisophthalate and tetracyanobenzene according to claim 1 or 2 in the regulation of fluorescence properties.

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