Multifunctional Molecular Sensor for Detecting Polar, Viscosity or Hydrazine Components in Soil or Water Body, and Preparation and Application Thereof

Abstract

The present invention discloses a multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water, and its preparation and application. The structure of the molecular sensor provided by the present invention contains multiple rotatable aromatic rings and conjugated structures, and has typical twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) characteristics. It can not only respond to the polarity and viscosity of soil or water, but even to hydrazine, a pollutant. It has multiple response functions and can assist in evaluating the physical state of the microenvironment, the microplastic adsorption behavior and the degree of contamination by hydrazine in soil and water through the detection results, and can be used as one of the important evaluation tools for soil and water safety monitoring.

Description

Technical Field

[0001] The present invention relates to the field of molecular sensor design, and particularly relates to a multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water, and its preparation and application. Background Art

[0002] Soil is an important guarantee for the survival of various crops in agricultural production, which contains many granular substances, organic substances, water, microorganisms, oxygen, etc. The three substances of solid, liquid and gas together form a unified whole. In recent years, with the changes in the production environment, the improvement of production speed, the application of production tools and other realities, the soil has been seriously damaged. Soil health and water body safety have become hot issues in agriculture. In modern agricultural production, in order to increase soil temperature, maintain soil moisture, maintain the soil microenvironment, avoid pest invasion and the occurrence of certain diseases, a large amount of plastic film and even soil amendments are used. These substances are still very easy to remain in the soil after being treated by various means. In fact, microplastics through fragmentation and decomposition have become important hazards in the soil. The ineradicable microplastics not only cause serious damage to soil properties (such as the pore structure of the soil, the water evaporation rate, dissolved organic carbon, phosphorus content, etc.), but also transfer to crops through the soil, enter the human food chain, and cause harm to the human body. For example, a variety of plasticizers can transfer to wheat grains and then enter the human body. On the other hand, the residual microplastics also have obvious inhibitory or reducing effects on the diversity of the soil microbial community and the activities of some hydrolases and dehydrogenases, causing damage to the soil carbon, phosphorus and nitrogen cycling paths; not only that, many soil micro-animals have their oxidative stress and reproductive growth states severely disturbed after being forced to ingest microplastics, resulting in a sharp decline in survival rate; furthermore, the presence of microplastics will directly affect the growth processes of many terrestrial plants (including sorghum, wheat, mung beans, broad beans, lettuce, etc.), and cause ecological toxicity and genotoxicity, seriously changing the natural state of soil plant growth and posing potential ecological risks to the terrestrial ecosystem. From a chemical perspective, most microplastics come from substances such as polyethylene (PE), polypropylene (PP), polystyrene (PS), etc. The hydrophobicity on their surfaces can enrich persistent organic pollutants (such as polycyclic aromatic hydrocarbons, polychlorinated biphenyls, polybrominated diphenyl ethers, etc.) in the surrounding water bodies, that is, there is an obvious adsorption behavior. There is not only the adsorption of pollutants by the crystalline region and the amorphous region, but also the change in adsorption behavior caused by temperature changes. More importantly, the changes in viscosity and polarity caused by the adsorption behavior in the water microenvironment. In addition to the various hazards brought by microplastics, hydrazine (hydrazine) is widely used in the preparation of modern pesticides, modern chemical pharmaceutical engineering and modern industrial manufacturing due to its strong alkalinity and reducibility. It is an indispensable synthetic raw material, but due to unreasonable post-treatment, it is transferred to the soil. As a

[0003] Highly toxic chemicals not only cause persistent harm to the soil, but may even enter the human food chain, seriously endangering human health. Thus, extensive testing of soil safety helps to comprehensively understand the degree of harm to the soil and water in a certain area, and can also provide an effective basis for evaluating the ecological risks in the soil and water environment.

[0004] Most traditional methods for monitoring soil and water safety are based on mass spectrometry, electrochemistry, electrophoresis, chromatography, and fluorescence metrology analysis. These methods strongly rely on fixed laboratory equipment for relevant detections and generally have defects such as cumbersome sample preparation, low detection efficiency, a relatively troublesome detection process, and a certain time lag, making it difficult to meet the current demand for portable, real-time, intuitive, and efficient visualization monitoring. On the other hand, based on the current pollution situation of soil and water, it is difficult to meet the need to detect multiple pollutants simultaneously, and its practical application is greatly restricted. In contrast, fluorescence analysis technology based on the mechanism of photoluminescence can achieve on-site and real-time monitoring at the sampling point through a portable handheld device. It is not only convenient to operate, has high detection sensitivity, can achieve non-destructive detection, but also has low and controllable costs, a wide range of applicable scenarios, and strong applicability. Monitoring polar substances, viscosity, and hydrazine pollutants in soil and water through obvious changes in optical signals makes it possible for visual monitoring of soil and water safety. However, so far, there is rarely a multifunctional molecular tool that can simultaneously achieve the above detection functions.

[0005] Therefore, there is an urgent need to develop a molecular tool that can be used to monitor the polarity changes, viscosity changes in the microenvironment caused by microplastic adsorption, and hydrazine content in the microenvironment of soil and water, which is of great significance for the ecological risk assessment and environmental safety monitoring of soil and water. Summary of the Invention

[0006] To overcome the deficiencies and defects of the prior art, the primary object of the present invention is to provide a multifunctional molecular sensor for detecting polar substances, viscosity, or hydrazine components in soil or water. This molecular sensor has multiple freely rotatable conjugated structures, not only has a typical aggregation-induced emission (AIE) effect, but also has a twisted intramolecular charge transfer (TICT) effect, and also has the ability to respond to hydrazine.

[0007] Another object of the present invention is to provide a preparation method for the above multifunctional molecular sensor. This method is simple, fast, environmentally friendly, cost controllable, and has a high yield, suitable for large-scale production and preparation.

[0008] Another object of the present invention is to provide the application of the above multifunctional molecular sensor in the detection of polar substances, viscosity, or hydrazine components in soil or water.

[0009] The objects of the present invention are achieved through the following technical solutions:

[0010] A multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water bodies. The multifunctional molecular sensor is 2-(3-(4'-(diphenylamine)-(1,1'-biphenyl]-4-yl)allylidene)malononitrile, abbreviated as DPABAM, with the molecular formula C 30 H 21 N3, with a molecular weight of 423.17, and has the following structural formula:

[0011]

[0012] The multifunctional molecular sensor 2-(3-(4'-(diphenylamine)-(1,1'-biphenyl]-4-yl)allylidene)malononitrile (DPABAM) provided by the present invention has the molecular formula C 30 H 21 N3, with a molecular weight of 423.17. This multifunctional molecule appears as an orange powder, is easily soluble in various organic solvents such as acetonitrile, tetrahydrofuran, acetone, and dichloromethane, and generally exists in an aggregated state in water bodies. This multifunctional molecular tool is in powder form at room temperature, exhibits good photo-stability and pH-stability, has a relatively stable chemical structure at room temperature, is easy to store, and has a very low storage cost. From a molecular structure perspective, this molecule DPABAM is composed of a triphenylamine donor (D) and a malononitrile acceptor (A) connected by a cinnamaldehyde derivative, presenting a typical D-A structure. And due to the presence of a relatively long conjugated structure in the molecule, it shows a certain flexibility as a whole, exhibits a typical TICT phenomenon, and can thus sense changes in polarity in soil and water bodies. At the same time, there are many aromatic rings and conjugated structures that can rotate freely in this molecular structure. It can rotate freely in solvents with low viscosity, causing the excited-state energy to dissipate in the form of mechanical rotation, and the optical signal is very weak. In a microenvironment with high viscosity, the excited-state energy can be consumed through radiative transition, thereby releasing a strong optical signal. Moreover, this phenomenon intensifies with the increase in the viscosity of the microenvironment, and can be used as a tool for sensing the microenvironment viscosity in soil and water bodies, providing data reference for the monitoring of microenvironment viscosity. On the other hand, the malononitrile group in its molecular structure has a very good light response effect on hydrazine, a pollutant. Because it can react chemically with hydrazine, which leads to changes in the molecular structure, resulting in changes in the absorption and emission wavelengths of the molecule, and thus can effectively detect hydrazine pollutants in soil and water bodies, which is also very effective for evaluating the safety level of soil and water bodies. In summary, due to the ingenious structural design, this molecular sensor can visually detect the polarity, viscosity, and hydrazine concentration in soil and water bodies from multiple angles. The specific mechanism schematic diagram is as shown in the appendix Figure 1 as follows.

[0013] The present invention also provides a method for preparing the above-mentioned multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water bodies, comprising the following steps:

[0014] (1) Dissolve 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein in ethanol, stir evenly to obtain Solution 1;

[0015] (2) Dissolve malononitrile in ethanol, stir mechanically to obtain Solution 2;

[0016] (3) Mix Solution 1 and Solution 2 in ethanol, heat and react for a period of time under an inert gas atmosphere. After the reaction is completed, the product is purified to obtain an orange powder, which is the multifunctional molecular sensor.

[0017] The reaction equation for the preparation is as follows:

[0018]

[0019] Preferably, the molar ratio of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein described in step (1); to malononitrile described in step (2) is 1:(1-20).

[0020] Preferably, in step (1), the concentration of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein is 1 M-38 M; and the concentration of malononitrile described in step (2) is 1 M-66 M.

[0021] Preferably, the inert gas described in step (3) is helium, argon or neon, the heating temperature is 35°C-80°C, and the reaction time is 3 h-72 h.

[0022] Preferably, the purification process described in step (3) includes removing the reaction solvent by vacuum distillation, using low-temperature crystallization to precipitate the product, and centrifuging to separate the solid and liquid to obtain an orange solid, which is dried to obtain the orange powder.

[0023] More preferably, the low temperature used in the purification process is -40°C-0°C, the precipitation time is 1 h-36 h, the centrifugation speed is 1000 rpm-8000 rpm, the centrifugation time is 1 min-30 min, the precipitate is taken out and dried, the drying temperature is 50°C-100°C, and the drying time is 1 h-24 h.

[0024] The present invention also provides the application of the above-mentioned multifunctional molecular sensor in detecting polar, viscosity or hydrazine components in soil or water bodies, and the multifunctional molecular sensor can be prepared into an aggregated molecular device or a solid-state sensor device.

[0025] The multifunctional molecular sensor provided by the present invention can be used to detect the polarity, viscosity or hydrazine component content in the microenvironment of soil and water bodies. Through the detection results, it can assist in evaluating the physical state of the microenvironment, the adsorption behavior of microcapsules, and the degree of hydrazine pollution in soil and water bodies, and can be used as one of the important evaluation tools for soil and water body safety monitoring. The multifunctional molecular sensor provided by the present invention has practical application value in aspects such as ecological risk assessment and environmental safety monitoring, and can also promote the innovative design of the chemical structure of functional molecular sensors.

[0026] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0027] (1) The molecular sensor (DPABAM) provided by the present invention is a molecular device with multiple response functions. It can not only respond to the polarity and viscosity of soil and water bodies, but also respond to hydrazine, a pollutant. Its molecular structure contains multiple rotatable aromatic rings and conjugated structures, and has typical twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) characteristics, which are particularly suitable for being prepared into aggregated devices, especially solid-state sensor devices.

[0028] (2) The raw materials required for the molecular tool (DPABAM) provided by the present invention are widely sourced and inexpensive. It can be prepared by a one-step method. Ethanol is used as the reaction reagent during the preparation process, which is relatively friendly to the environment, and the final yield is also high. It is suitable for large-scale preparation. The post-treatment process is obtained by centrifugal precipitation and drying, with low cost and can be achieved without relying on any expensive equipment.

[0029] (3) The molecular tool (DPABAM) prepared by the present invention has relatively stable light signal intensity within a wide pH range, good light stability, high sensitivity to polarity, viscosity and hydrazine, and its chemical structure is stable, suitable for use under long-term irradiation and subsequent long-term storage.

[0030] (4) The molecular tool (DPABAM) provided by the present invention can be used in many scenarios in soil and water bodies. It can not only be prepared into an aggregated molecular device for use in a humid atmosphere, but also be prepared into a solid-state device for use in a dry environment, with good universality and great application potential. Brief Description of the Drawings

[0031] Figure 1 It is a schematic diagram of the structure and detection mechanism of the multifunctional molecular sensor provided by the present invention;

[0032] Figure 2 It is the mass spectrum of the molecular sensor DPABAM obtained in Example 1;

[0033] Figure 3Photostability test chart of the molecular sensor DPABAM in Example 4;

[0034] Figure 4 pH stability test chart of the molecular sensor DPABAM in Example 4;

[0035] Figure 5 Specificity test chart of the molecular sensor DPABAM in Example 4;

[0036] Figure 6 Emission spectrum chart of the molecular sensor DPABAM in different polar solvents in Example 5;

[0037] Figure 7 Emission spectrum chart of the molecular sensor DPABAM in different viscosity atmospheres in Example 5;

[0038] Figure 8 Spectrum chart of the molecular sensor DPABAM before and after responding to hydrazine in Example 5. Detailed implementation manners

[0039] The present invention will be further described below through specific implementation manners. The following examples are specific implementation manners of the present invention, but the implementation manners of the present invention are not limited by the following examples. Any changes, modifications, substitutions, combinations, and simplifications made without departing from the spirit and principle of the present invention shall be equivalent replacement manners and are all included in the protection scope of the present invention.

[0040] The raw materials used in the embodiments of the present invention are all commercially available.

[0041] Example 1:

[0042] A preparation method of a multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water body, comprising the following steps:

[0043] (1) Dissolve 375 mg of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein in ethanol, stir evenly to obtain Solution 1, and control its concentration to be 1 M;

[0044] (2) Dissolve 330 mg of malononitrile in ethanol, stir mechanically to obtain Solution 2, and control its concentration to be 33 M;

[0045] (3) Mix Solution 1 and Solution 2 in ethanol, control the molar ratio of the two to be 1:5, heat to 60 °C in an argon atmosphere, react for 24 h. After the reaction is completed, remove the reaction solvent by distillation under reduced pressure, and precipitate the product at -20 °C for 12 h,

[0046] The mixture was centrifuged at a speed of 4000 rpm for 15 min, and the precipitate was dried at 80° C. for 12 h to obtain an orange powder, namely the multifunctional molecular sensor DPABAM, with a yield of 84%.

[0047] The relative molecular mass was tested by mass spectrometry and the MS (ESI) was obtained: m / z 423.17683 [M] + (As attached Figure 2 ), and the calculated relative molecular mass MS: m / z 423.17355 [M] + The results are basically the same, and the obtained product can be seen from the mass spectrum to be the target compound.

[0048] Embodiment 2:

[0049] A method for preparing a multifunctional molecular sensor for detecting polarity, viscosity or hydrazine components in soil or water comprises the following steps:

[0050] (1) Dissolve 375 mg of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein in ethanol and stir evenly to obtain solution 1, the concentration of which is controlled to be 19 M;

[0051] (2) Dissolve 66 mg of malononitrile in ethanol and stir mechanically to obtain solution 2, the concentration of which is controlled to be 1 M;

[0052] (3) Solution 1 and solution 2 were mixed in ethanol, and the molar ratio of the two was controlled to be 1:1. The mixture was heated to 80°C in a helium atmosphere and reacted for 3 hours. After the reaction was completed, the reaction solvent was removed by distillation. The product was precipitated at -40°C for 1 hour, taken out and centrifuged. The centrifugal speed was controlled to 1000 rpm and the centrifugation was performed for 30 minutes. The precipitate was taken out and dried at 100°C for 1 hour to obtain an orange powder, namely the multifunctional molecular sensor DPABAM, with a yield of 78%.

[0053] Embodiment 3:

[0054] A method for preparing a multifunctional molecular sensor for detecting polarity, viscosity or hydrazine components in soil or water comprises the following steps:

[0055] (1) Dissolve 375 mg of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)propenal in ethanol and stir evenly to obtain solution 1, the concentration of which is controlled to be 38 M;

[0056] (2) Dissolve 1320 mg of malononitrile in ethanol and stir mechanically to obtain solution 2, the concentration of which is controlled to be 66 M;

[0057] (3) Mix Solution 1 and Solution 2 in ethanol, control the molar ratio of the two to be 1:20, heat to 35 °C in a neon atmosphere, react for 72 h. After the reaction is completed, remove the reaction solvent by distillation under reduced pressure. The product is precipitated at low temperature at 0 °C for 36 h, taken out and centrifuged. Control the centrifugation speed to be 8000 rpm, centrifuge for 1 min, take out the precipitate and dry it. The drying temperature is 50 °C and the drying time is 24 h, obtaining an orange powder, namely the multifunctional molecular sensor DPABAM, with a yield of 75%.

[0058] Example 4:

[0059] Spectroscopic performance test of the prepared multifunctional molecular sensor.

[0060] (1) Photostability test of the multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water:

[0061] Dissolve 0.85 mg of the molecular sensor DPABAM (prepared in Example 1) fully in dimethyl sulfoxide to prepare a 2 mM mother solution to be tested. During the photostability test, dilute the molecular sensor to 10 μM, and expose it fully to an excitation wavelength of 480 nm and irradiate for 0 - 60 min, and test the corresponding fluorescence intensity at different time intervals. The test results are as shown in the appendix Figure 3 shown. As can be seen from the appendix Figure 3 It can be seen that within the tested time range, the optical signal intensity of the molecular sensor has always remained relatively stable, with a very small change amplitude, indicating that continuous irradiation with an excitation light source will not cause unnecessary photobleaching phenomenon, and it can work under the excitation light source for a long time.

[0062] (2) pH stability test of the multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water:

[0063] Dissolve 0.42 mg of the molecular sensor DPABAM (prepared in Example 1) fully in dimethyl sulfoxide to prepare a 1 mM mother solution to be tested. During the specific test process, control the concentration of the molecular sensor to be 10 μM, and add it to solvents with different pH values, including six solvents with pH values of 3.0, 5.0, 6.8, 7.4, 9.0, and 12.0, and test their fluorescence intensities respectively. The test results are as shown in the appendix Figure 4 shown. As can be seen from the appendix Figure 4 It can be seen that within a relatively wide pH range, its fluorescence intensity does not change much, and the optical signal is stable, indicating that it is suitable for use in soils and waters with various pH atmospheres.

[0064] (3)Specific test of the multifunctional molecular sensor for detecting polar, viscosity or hydrazine components in soil or water bodies:

[0065] Fully dissolve 2.12 mg of the molecular sensor DPABAM (prepared in Example 1) in dimethyl sulfoxide to prepare a 5 mM mother liquor to be tested. During the specific test process, control the concentration of the molecular sensor at 10 μM and add it to deionized water, Na + , K + , Ca 2+ , Mg 2+ , NO3 - , SO4 2- , CO3 2- , L-cysteine (Cys), homocysteine (Hcy), glutathione (GSH), glycerol respectively, and test its fluorescence intensity. The specific test results are as shown in Appendix Figure 5 . As can be seen from Appendix Figure 5 , the fluorescence signal intensity shows weak fluorescence intensity in the solutions containing 10 additives such as Na + , K + etc., which is similar to the fluorescence intensity of the control deionized water and shows little change, indicating that the molecular sensor is suitable for use in complex soil and water atmospheres. On the other hand, when it is added to glycerol, it is found that its fluorescence signal intensity increases sharply, indicating that the molecular sensor can have a very significant response effect on soils and water bodies with higher viscosity, and the specificity of the molecular sensor is excellent.

[0066] Example 5:

[0067] Polarity, viscosity, and hydrazine response tests of the prepared multifunctional molecular sensor.

[0068] (1)Spectroscopic test of the multifunctional molecular sensor in different polar solvent atmospheres:

[0069] Fully dissolve 0.42 mg of the molecular sensor DPABAM (prepared in Example 1) in dimethyl sulfoxide to prepare a 1 mM mother liquor to be tested. During the specific test process, control the concentration of the molecular sensor at 10 μM and add it to solvents with different polarities, including deionized water, toluene, methanol, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetonitrile, and test its fluorescence intensity. The test results are as shown in Appendix Figure 6 . As can be seen from Appendix Figure 6It can be seen that when the molecular sensor is in a deionized water atmosphere, its fluorescence intensity is relatively stronger than that in other solvents. This may be due to its typical AIE characteristics. Since it belongs to a large conjugated hydrophobic structure, it is prone to aggregation in water, and thus the intramolecular rotation is restricted. Instead, it releases optical signals through radiative pathways, resulting in enhanced fluorescence. In addition, by comparing the wavelength values corresponding to the fluorescence spectral peaks of the molecular sensor in different solvents, it can be found that its emission peak redshifts from 547.9 nm in toluene to 562.1 nm in deionized water. This may be because it has TICT characteristics, showing typical solvent effects.

[0070] (2)Spectroscopic tests of the multifunctional molecular sensor in atmospheres with different viscosities:

[0071] Specifically, 1.68 mg of the molecular sensor DPABAM (prepared in Example 1) was dissolved in a certain volume of dimethyl sulfoxide to prepare a mother solution to be tested. During the test, the above molecular sensor DPABAM was further diluted to 10 μM, and it was added to high-viscosity glycerol and low-viscosity deionized water respectively, and the fluorescence signal intensity was measured. The test results are as shown in the appendix Figure 7 shown. As can be seen from the appendix Figure 7 When the molecular sensor is in high-viscosity glycerol, its fluorescence intensity increases sharply. Compared with the low-viscosity deionized water atmosphere, its fluorescence intensity is enhanced by about 33 times, indicating that it has a sensitive response to viscosity.

[0072] (3)Responsiveness test of the multifunctional molecular sensor to hydrazine:

[0073] At room temperature, the concentration of the molecular sensor DPABAM was controlled to be 10 μM, and it was added to the test solution containing hydrazine, and the change in its absorption wavelength was measured. The test results are as shown in the appendix Figure 8 shown. As can be seen from the appendix Figure 8 Before the response, the peak wavelength of the absorption spectrum is around 496.5 nm. After the response, the absorbance near 496.5 nm decreases significantly, and a shoulder peak appears near 386.5 nm, showing an obvious blue shift phenomenon. This may be because the molecular structure has changed, resulting in a change in the intramolecular push-pull electrons, and thus the absorbance has changed. It also indicates that the molecular sensor has indeed changed with hydrazine.

[0074] In summary, the present invention provides a molecular sensor 2-(3-(4'-(diphenylamine)-(1,1'-biphenyl]-4-yl)allylidene)malononitrile (DPABAM). Due to its novel structural design, typical electron-donating and electron-withdrawing structure, a large number of rotatable aromatic rings and conjugated structures, and a certain response ability to hydrazine, it can exhibit the detection ability for polarity, viscosity, and hydrazine, showing a multi-functional response effect. At the same time, it has good photo-stability, pH-stability, and chemical stability, is easy to store for a long time without requiring too high storage costs. The preparation process also conforms to the current concept of green environmental protection, basically avoiding the use of toxic chemical reagents, with a wide source of raw materials, a high yield in the preparation process, and is suitable for large-scale popularization and application. This molecular sensor can be used even in the aggregated state or solid state, can be processed into solid-state devices for application, and can be widely used in soil and water bodies, with high universality.

Claims

1. Application of a multifunctional molecular sensor in detecting polar, viscosity or hydrazine components in soil or water body, characterized in that, The multifunctional molecular sensor has the following structural formula: 。 2. The application according to claim 1, wherein The preparation method of the multifunctional molecular sensor comprises the following steps: (1) Dissolve 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein in ethanol and stir evenly to obtain Solution 1; (2) Dissolve malononitrile in ethanol and stir mechanically to obtain Solution 2; (3) Mix Solution 1 and Solution 2 in ethanol, heat and react for a period of time under an inert gas atmosphere. After the reaction is completed, the product is purified to obtain an orange powder, which is the multifunctional molecular sensor.

3. The application according to claim 2, characterized in that, The molar ratio of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein described in step (1) to malononitrile described in step (2) is 1:(1 - 20).

4. The application according to claim 2, characterized in that, In step (1), the concentration of 3-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)acrolein is 1 M - 38 M; in step (2), the concentration of malononitrile described is 1 M - 66 M.

5. The application according to claim 2, characterized in that, The inert gas described in step (3) is helium, argon or neon, the heating temperature is 35°C - 80°C, and the reaction time is 3 h - 72 h.

6. The application according to claim 2, characterized in that, The purification process described in step (3) includes removing the reaction solvent by vacuum distillation, using the low-temperature crystallization method to precipitate the product, separating the solid and liquid by centrifugation to obtain an orange solid, and drying to obtain an orange powder.

7. The application according to claim 6, characterized in that, The low temperature used in the purification process is -40°C - 0°C, the precipitation time is 1 h - 36 h, the centrifugation speed is 1000 rpm - 8000 rpm, the centrifugation time is 1 min - 30 min, take out the precipitate and dry it, the drying temperature is 50°C - 100°C, and the drying time is 1 h - 24 h.

8. The application according to claim 1, characterized in that, The multifunctional molecular sensor is fabricated into an aggregated molecular device or a solid-state sensor device.

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