A chiral enantiomer detection device, its preparation method and application

Abstract

This invention belongs to the field of thin-film semiconductor materials, and particularly relates to a chiral enantiomer detection device, its preparation method, and its application. The detection device includes a detection mechanism and an analysis system. The analysis system is connected to the detection mechanism and is used to monitor changes in the electrical signal of the detection mechanism. The detection mechanism includes at least one R-configuration detector and at least one S-configuration detector. The R-configuration detector includes an R-configuration chiral metal-organic framework (MOF) film, and the S-configuration detector includes an S-configuration chiral MOF film. The chiral MOF film has chiral channels that can selectively bind chiral substances with opposite configurations. The chiral MOF film of this invention has different binding capabilities for chiral substances with different configurations. By detecting photoconductivity values, chiral enantiomers can be detected intuitively and quickly.

Description

Technical Field

[0001] This invention belongs to the field of thin-film semiconductor materials, and particularly relates to a chiral enantiomer detection device, its preparation method and application, specifically to a method and application for preparing a chiral metal-organic framework semiconductor thin film into a detection device with chiral substance detection function. Background Technology

[0002] Chiral enantiomers are an important concept in chemistry, referring to compounds with the same molecular formula and linkage but mirror-symmetric spatial configurations. Chiral enantiomers exhibit significant differences in chemical properties and biological activities. For example, different chiral enantiomers of the same compound can have significantly different pharmacological effects, side effects, and toxicities. Therefore, the detection and separation of chiral enantiomers are of great significance in drug development, medicinal chemistry, pesticide design, food safety, and environmental monitoring.

[0003] Traditional methods for detecting chiral enantiomers include chromatography and nuclear magnetic resonance (NMR). Chromatography typically requires complex sample pretreatment and a lengthy separation process. While NMR technology offers high accuracy, the equipment is expensive and the analysis time is long. Furthermore, these traditional methods cannot meet the requirements of high-throughput analysis and real-time monitoring.

[0004] Therefore, there is a need to develop new chiral enantiomer detection techniques, and these new techniques should have the following characteristics:

[0005] 1. High sensitivity and high selectivity: It can detect and distinguish very low concentrations of chiral enantiomers and eliminate the influence of other interfering substances. This can be achieved by introducing new detection principles, designing new recognition elements or molecules, and optimizing sensor structure.

[0006] 2. Rapid and high-throughput analysis: It has the ability to perform rapid analysis, enabling the detection of a large number of samples in a short time, which helps to improve experimental efficiency and is suitable for high-throughput screening and large-scale sample analysis.

[0007] 3. Real-time monitoring and non-destructive testing: It can perform instantaneous and non-destructive testing of chiral enantiomers during sample processing or in practical applications, which is of great significance for monitoring reaction kinetics, the generation and transformation of reaction intermediates, and online quality control.

[0008] 4. Simplified operation and cost-effectiveness: Reduces the need for specialized knowledge and cumbersome sample handling to improve the ease of use and operability of testing.

[0009] In addition, the cost-effectiveness of the technology is also a factor to consider, making it more feasible and widely applicable.

[0010] In recent years, cutting-edge research in this field has focused on chiral organic polymer fluorescent probes. Although they can detect chiral substances through chemical reactions such as color changes, the deviceization problem still needs to be solved, and this approach restricts its further digitalization and integration development.

[0011] In summary, there is still an urgent need to expand and innovate technologies to improve the sensitivity, speed, accuracy, and simplicity and reliability of chiral enantiomer detection, and to develop new chiral recognition materials with high selectivity and sensitivity, capable of specific interactions with target chiral enantiomers. These materials can be used to construct novel sensors that detect chiral enantiomers by measuring the electrochemical, optical, electronic, or magnetic signals caused by the interactions. Summary of the Invention

[0012] To address the shortcomings of existing technologies, this invention provides a chiral enantiomer detection device based on chiral metal-organic framework thin films, its preparation method, and its application.

[0013] In a first aspect, the present invention provides a chiral enantiomer detection device, the detection device comprising a detection mechanism and an analysis system, the analysis system being connected to the detection mechanism and used to monitor changes in the electrical signal of the detection mechanism;

[0014] The detection mechanism includes at least one R-configuration detector and at least one S-configuration detector. The R-configuration detector includes an R-configuration chiral metal-organic framework film, and the S-configuration detector includes an S-configuration chiral metal-organic framework film. The chiral metal-organic framework film has chiral channels that can selectively bind chiral substances with opposite configurations.

[0015] According to an embodiment of the present invention, the analysis system is connected to the analysis system via an external monitoring circuit.

[0016] According to an embodiment of the present invention, the detection mechanism includes at least one R-shaped detection element.

[0017] According to an embodiment of the present invention, the detection mechanism includes at least one S-shaped detection element.

[0018] According to an embodiment of the present invention, the number of detector elements in the R configuration is the same as that in the S configuration.

[0019] According to an embodiment of the present invention, the R-configuration detector piece is the same size as the S-configuration detector piece.

[0020] As an example, the detection mechanism includes an R-shaped detection element and an S-shaped detection element.

[0021] According to an embodiment of the present invention, the left-handed metal-organic framework thin film is capable of selectively binding L-configuration molecules.

[0022] According to an embodiment of the present invention, the right-handed metal-organic framework film is capable of selectively binding D-configuration molecules.

[0023] According to an embodiment of the present invention, the chiral metal-organic framework film is composed of chiral ligands and metal nodes connected by coordination bonds.

[0024] According to an embodiment of the present invention, the chiral ligand is selected from chiral ligands having two or more carboxylic acid or pyridyl coordination nodes having chiral carbon or spatial chirality, for example, BDA (2,2-dimethoxy-1,1-binaphthyl-5,5-dicarboxylic acid, H2BDA).

[0025] According to an embodiment of the present invention, the metal ion is not specifically required and can be selected from at least one of Zn, Cu, Fe, etc.

[0026] As an example, the chiral metal-organic framework film may be a Zn(BDA) film or a Cu(BDA) film.

[0027] According to an embodiment of the present invention, the chiral metal-organic frame thin film is obtained by liquid-phase epitaxial layer-by-layer assembly growth and has a specific growth orientation.

[0028] According to an embodiment of the present invention, the thickness range of the chiral metal-organic framework film can be customized from 0.05 to 2 micrometers depending on the number of layers prepared.

[0029] According to embodiments of the present invention, chiral metal-organic framework films of different thicknesses have no significant effect on the detection of chiral enantiomer configurations, but may affect the minimum detection limit.

[0030] According to an embodiment of the present invention, the analysis mechanism includes a signal processor, a display and control component, a first power supply, and a signal acquisition component. The signal processor and the display and control component are both connected to the first power supply. The signal acquisition component is connected to the signal processor via a ribbon cable. The signal acquisition component is connected to a detection electrode for acquiring photoelectric signals.

[0031] According to an embodiment of the present invention, a monitoring circuit is provided between the signal collector and the detection mechanism, and the detection mechanism is connected to a second power supply to provide voltage to the detection element, so that current is formed in the circuit formed by the detection element and the signal collector.

[0032] According to an embodiment of the present invention, the first power supply and the second power supply are DC power supplies. For example, the first power supply uses a 5V DC power supply and the second power supply uses a 3.3V DC power supply.

[0033] According to an embodiment of the present invention, the display and control component is a display with control functions, wherein the control functions can be implemented by touch, voice or buttons. For example, the display and control component is a display with touch functions.

[0034] According to an embodiment of the present invention, the detection device further includes an ultraviolet irradiator for irradiating the detection mechanism to cause a significant change in the resistance value of the detection mechanism, such as an ultraviolet mercury lamp or an ultraviolet LED.

[0035] According to an embodiment of the present invention, the detection device further includes a polarizer and a quarter-glass slide for generating polarized light.

[0036] According to an embodiment of the present invention, the chiral enantiomer is soluble in a volatile solution with poor conductivity, the solution being selected from one or more of methanol, ethanol, and ethyl acetate.

[0037] According to an embodiment of the present invention, the chiral enantiomer is prevented from contacting corrosive liquids such as dimethylformamide to avoid affecting the stability of the circuit in the device.

[0038] According to an embodiment of the present invention, the monitoring circuit and analysis system have the functions of independently providing bias voltage and monitoring changes in photoconductivity, and can process and analyze signals from different chiral metal-organic framework thin film sensors for comparative analysis.

[0039] As an example, the monitoring circuit consists of two sets of input electrodes connected to a knife switch, and output electrodes connected to an S / R chiral metal-organic framework thin film detection device. The switch determines whether the detector has S or R chirality and is connected to the analysis system.

[0040] As an example, the analysis system consists of an analog-to-digital converter (ADC), a microcontroller unit (MCU) for logic analysis, a display screen, a power supply, a printed circuit board (PCB), and control buttons soldered on the PCB.

[0041] According to an embodiment of the present invention, the analog-to-digital converter chip is the AD5940 impedance measurement acquisition unit developed by ADI, which is capable of 8-bit data acquisition and meets the real-time detection requirements for subtle photoconductivity changes caused by illumination.

[0042] According to an embodiment of the present invention, the microcontroller unit for logic analysis is selected from the STMicroelectronics STM32F103 series microcontroller unit, which is mainly used to analyze and compare the photoconductivity data recorded by the ADC, calculate the test results, and display them on the display screen in real time.

[0043] According to an embodiment of the present invention, the display screen has no special requirements; it only needs to have a resolution of 64p or higher and be able to display the test results completely. It is not limited to a color or monochrome screen.

[0044] According to an embodiment of the present invention, the control button is a relay switch, which can be programmed to control the MCU processor to perform up and down operations.

[0045] Secondly, the present invention also provides a method for preparing the above-mentioned chiral metal-organic framework thin film, comprising the following steps:

[0046] A chiral metal-organic framework thin film is formed by cyclically spraying metal salt solution and organic ligand solution onto the surface of a supporting substrate and then performing liquid-phase epitaxy.

[0047] According to an embodiment of the present invention, the amount of the metal salt solution sprayed each time is 1 to 5 ml, and the spraying time is 5 to 30 seconds.

[0048] According to an embodiment of the present invention, the amount of organic ligand solution sprayed each time is 1 to 5 ml, and the spraying time is 5 to 30 seconds.

[0049] According to an embodiment of the present invention, the spraying process can be carried out in an inert atmosphere or in a ventilated environment.

[0050] According to an embodiment of the present invention, the spraying process is carried out under normal pressure.

[0051] According to an embodiment of the present invention, before cyclically spraying the metal salt solution and organic ligand solution onto the surface of the support substrate, the following step is further included: modifying the support substrate with molecular-level functional groups so that the active sites of the functional groups are exposed on the surface of the support substrate.

[0052] According to an embodiment of the present invention, the supporting substrate for the growth of the chiral metal-organic framework thin film is selected from rigid substrates and / or flexible substrates.

[0053] According to an embodiment of the present invention, the rigid substrate is selected from alumina, silicon dioxide or quartz.

[0054] According to an embodiment of the present invention, the flexible substrate is selected from at least one of polyethylene terephthalate, polyimide, polydimethylsiloxane, polyvinyl alcohol, polyethylene naphthalate, or textile materials.

[0055] According to an embodiment of the present invention, the thickness of the supporting substrate is 50-600 nm, preferably 100-500 nm, for example, the thickness of the silicon dioxide substrate is 500 nm.

[0056] Thirdly, the present invention also provides an application of the above-mentioned chiral metal-organic framework thin film and / or chiral enantiomer detection device in the detection of chiral substances.

[0057] Fourthly, the present invention also provides a method for detecting chiral substances using the above-described chiral enantiomer detection device, comprising the following steps:

[0058] The detection mechanism is immersed in a solution formed by the substance to be tested, then removed, rinsed, and dried before the electrical signal of the detection mechanism is read by an analysis system.

[0059] According to an embodiment of the present invention, before drying, the following step is further included: washing the soaked detection mechanism.

[0060] According to an embodiment of the present invention, the washing includes rinsing the surface of the detection structure with a solvent that is non-corrosive to the detection sheet and volatile, such as a mixture of one or more selected from ethanol, methanol, and ethyl acetate.

[0061] According to an embodiment of the present invention, reading the electrical signal of the detection mechanism by the analysis system includes the following steps: irradiating the dried detection mechanism with ultraviolet light, reading the electrical signal of the detection mechanism by the analysis system, and determining the chirality of the substance to be tested.

[0062] According to an embodiment of the present invention, before immersing the detection mechanism in the solution formed by the substance to be tested, the following steps are further included: testing the electrical signal of the detection mechanism before immersion in the solution, and using it as a reference electrical signal.

[0063] According to an embodiment of the present invention, reading the electrical signal of the detection mechanism by the analysis system includes the following steps: irradiating the dried detection mechanism with ultraviolet light, reading the electrical signal of the detection mechanism by the analysis system, subtracting the reference electrical signal, and determining the chirality of the substance to be tested.

[0064] According to an embodiment of the present invention, the wavelength of the ultraviolet light is 300-350 nm, and it is provided by a mercury lamp or an ultraviolet LED light source.

[0065] According to an embodiment of the present invention, the detection mechanism is immersed in the solution formed by the substance to be tested for 30 to 120 seconds, for example, 60 seconds.

[0066] This invention fully utilizes the chiral spatial environment of chiral metal-organic frameworks to fabricate them into continuous thin films as detection layers. By leveraging their different binding capabilities to chiral substances with different configurations, the invention enables the intuitive and rapid detection of chiral enantiomers through the measurement of photoconductivity values. This solves the problems of traditional detector detection devices, such as complex structures, difficult fabrication, and environmental unfriendliness.

[0067] The method described in this invention is flexible in operation and clear in principle. Its core detection layer is obtained using a liquid-phase epitaxial layer-by-layer self-assembly process, enabling high-quality, large-area batch preparation of thin films. The chiral metal-organic framework thin film requires no additional processing and can be directly used for chiral enantiomer detection after device-level packaging and integration.

[0068] Beneficial effects

[0069] 1. This invention provides a chiral enantiomer detector made of a chiral metal-organic framework (MOF) thin film. It utilizes the chiral porous environment inherent in the MOF material to selectively bind chiral substances with different configurations, directly and rapidly determining the chirality of the analyte through a portable circuit and real-time electrical signal. Simultaneously, the use of liquid-phase epitaxial layer-by-layer assembly technology effectively improves the uniformity, flatness, and orientation of the MOF thin film, overcoming the challenge of lack of continuity in traditional chiral MOF powder materials, which restricts their device applications.

[0070] 2. Rapid and accurate chiral enantiomer detection: Chiral metal-organic framework thin films exhibit varying binding capabilities to chiral substances with different configurations. By detecting photoconductivity values, chiral enantiomers can be detected intuitively and rapidly. Compared to traditional detectors, this method avoids issues such as complex structures, difficult fabrication, and environmental unfriendliness, providing a highly efficient method for chiral enantiomer detection.

[0071] 3. Flexible Operation and Clear Principle: This method is flexible in operation and has a clear principle. It uses a liquid-phase epitaxial layer-by-layer self-assembly process to obtain the detector layer, overcoming the difficulty of fabricating devices from materials that are mostly in powder form. It yields dense, uniformly morphologically assembled layer-by-layer thin films, greatly enriching the application scenarios of the original materials and enabling high-quality, large-area batch fabrication of thin films. This flexibility and clear principle make chiral enantiomer detection more feasible and reliable.

[0072] 4. Direct application to chiral enantiomer detection: After being integrated into a device-like package, chiral metal-organic framework films can be directly used for chiral enantiomer detection without additional processing. This integrated design simplifies the operation process, improves detection efficiency and convenience, and makes chiral enantiomer detection more practical and widely applicable.

[0073] 5. This innovation has reached high industry standards in terms of structure and performance, and in particular highlights the application of metal-organic frameworks as a crystalline chemical material in the field of optical detection research, demonstrating broad development prospects. Attached Figure Description

[0074] Figure 1 The XRD diffraction patterns of the R and S configuration chiral metal-organic framework detectors prepared in Example 1 of this invention;

[0075] Figure 2 This is a SEM image of the chiral metal-organic framework thin film detector layer prepared in Example 1 of the present invention;

[0076] Figure 3 The data provided are the ultraviolet-visible absorption data of the R and S configuration detectors described in Example 1 of this invention after binding with L or D configuration tryptophan at the same time.

[0077] Figure 4 This is an overall diagram of the detection device assembled according to Embodiment 2 of the present invention, including the detection chip and external power supply and analysis circuit;

[0078] Figure 5 The schematic diagram shows the resistance value information collected by the detection device assembled in Embodiment 2 of the present invention during actual operation, displayed on the screen. Detailed Implementation

[0079] The following detailed description, in conjunction with specific embodiments, provides a more comprehensive overview of the chiral enantiomer detector detection device, its fabrication method, and its applications. It should be understood that the following embodiments are merely illustrative and explanatory of the invention and should not be construed as limiting the scope of protection of the invention. All technologies implemented based on the above description of the invention are covered within the scope of protection intended by the invention.

[0080] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0081] To verify the effectiveness and reliability of the results of this invention, the following test instruments were used in the characterization of the embodiments:

[0082] (1) Rigaku X-Ray MiniFlex 600 powder diffractometer;

[0083] (2) ZEISS Gemini 300 field emission scanning electron microscope;

[0084] (4) AUY120 analytical balance;

[0085] (5) PerkinElmer Lambda 365 UV-Vis spectrophotometer;

[0086] (6) Ultraviolet mercury lamp;

[0087] (6) Keithely 2400 semiconductor analysis system.

[0088] Example 1: Preparation of chiral enantiomer detector strips

[0089] S1. First, copper acetate and H2BDA (chiral ligand 2,2-dimethoxy-1,1-binaphthyl-5,5-dicarboxylic acid) were weighed using an AUY120 analytical balance. Then, copper acetate and H2BDA were dissolved separately in ethanol solutions to prepare metal salt solutions with concentrations of 2 mmol / L and H2BDA solutions with concentrations of 0.5 mmol / L, respectively. Next, concentrated sulfuric acid and hydrogen peroxide were mixed in a 3:1 volume ratio to prepare a fresh piranha solution. The insulating ceramic substrate was immersed in the piranha solution and heated at 80°C for 30 minutes. After treatment, the substrate was rinsed with deionized water and placed on a support frame.

[0090] S2. Under a nitrogen atmosphere with a pressure of 0.2 MPa, spray the metal salt solution prepared in step S1 for 20 seconds (approximately 4 mL), and then hold for 30 seconds; spray the ethanol cleaning solution for 10 seconds, and then hold for 10 seconds; spray the H2BDA solution for 30 seconds (approximately 5 mL), and then hold for 30 seconds; spray the ethanol cleaning solution for 10 seconds, and then hold for 10 seconds.

[0091] S3. According to the required film thickness, repeat step S2 5 to 100 times, which approximately corresponds to a thickness from 0.1 to 2 micrometers, until the chiral metal-organic framework film of the required thickness is obtained. This chiral metal-organic framework film is the chiral enantiomer detector.

[0092] See Figure 1 The image shows the XRD pattern of the chiral metal-organic framework thin film prepared in this embodiment. The fitted XRD data represents the X-ray diffraction peaks of the powdered material without specific orientation growth, which are simulated based on the crystal structure of the material, and exhibit numerous diffraction peaks. The chiral metal-organic framework thin film prepared by liquid-phase epitaxial layer-by-layer assembly shows that, perpendicular to the growth substrate, it grows along the preferred orientation of the

[100] crystal phase, which matches the fitted XRD data well, proving that the prepared material is the target chiral metal-organic framework thin film. Figure 2 The images show the SEM front and cross-sectional views of the chiral metal-organic framework film prepared in this embodiment. As can be seen from the images, the chiral metal-organic framework film prepared by this invention has a smooth morphology and a uniform and dense structure, which has obvious advantages over powder spin coating.

[0093] The thin film prepared in this embodiment has microstructured pores, and the pore size is estimated to be approximately 1.56 nanometers based on the measurement of its framework structure.

[0094] Test Example 1 uses R-Cu(BDA)SURMOF and S-Cu(BDA)SURMOF as examples to illustrate the specific absorption of different configurations.

[0095] In this test example, except that the selected substrate is a transparent quartz substrate, the preparation methods of R-Cu(BDA)SURMOF and S-Cu(BDA)SURMOF are basically the same as those in Example 1.

[0096] Using L- and D-configurations of tryptophan (Trp) as examples, the function of chiral enantiomer detectors is demonstrated. Two chiral metal-organic framework films (R-Cu(BDA)SURMOF and S-Cu(BDA)SURMOF) with R and S configurations were prepared. Each film was immersed in a prepared 1 mM ethanol solution of L-tryptophan and D-tryptophan, respectively, for 1 minute. After removal, the films were rinsed with pure ethanol and dried with nitrogen. The absorption of the samples in the UV-Vis band was then recorded using a PerkinElmer Lambda 365 UV-Vis spectrophotometer.

[0097] like Figure 3 As shown in the left figure, the ultraviolet absorption of R-Cu(BDA)SURMOF significantly increased after immersion in a tryptophan solution. According to Lambert-Beer's law, the amount of light absorbed is proportional to the amount of substance. Therefore, in the same experimental process, the R-Cu(BDA) chiral metal-organic framework film, due to its R-configuration chiral spatial environment, has a better binding capacity for L-configuration tryptophan, binding more molar amounts of L-Trp in the same time, thus increasing its absorbance. Conversely, as... Figure 3 As shown in the right figure, the S-Cu(BDA) chiral metal-organic framework film has a better binding capacity for D-configuration tryptophan, binding more molar amounts of D-Trp in the same time. Therefore, it can be seen that the chiral metal-organic framework film detector prepared in this invention can selectively bind chiral substances with opposite configurations.

[0098] Example 2: Chiral Enantiomer Detector

[0099] See Figure 4 The diagram shown is a schematic of the structure of the chiral enantiomer detector in this embodiment. The chiral enantiomer detector includes a detection mechanism and an analysis system. The analysis system is used to monitor changes in the electrical signal of the detector.

[0100] The detection mechanism includes at least one R-configuration detector (hereinafter referred to as R detector) and at least one S-configuration detector (hereinafter referred to as S detector). The specific number of detectors is set according to actual needs. In this embodiment, it includes one R-configuration detector (R-Cu(BDA)SURMOF prepared in Test Example 1) and one S-configuration detector (S-Cu(BDA)SURMOF prepared in Test Example 1).

[0101] The R and S detectors may have the same or different dimensions. In this embodiment, the R and S detectors are rectangular with a thickness of 1 mm, a length of 10 mm, and a width of 5 mm.

[0102] The analysis mechanism includes a signal processor, a display and control component, a first power supply, and a signal acquisition component. The signal processor and display and control component are both connected to the first power supply. The signal acquisition component is connected to the display and control component via the signal processor. The signal acquisition unit is connected to the detection mechanism and is used to acquire the photoelectric signals from the detection mechanism. In this embodiment, a double-sided knife switch (such as...) is provided between the signal acquisition unit and the detection mechanism. Figure 5 As shown in component 2), the detection mechanism is connected to the second power supply to provide voltage to the detection chip, so that a test current is formed in the circuit formed by the detection chip and the signal acquisition device.

[0103] The first power supply and the second power supply are DC power supplies. The power supply specifications are selected according to actual needs. In this embodiment, the first power supply uses a 5V DC power supply and the second power supply uses a 3.3V DC power supply.

[0104] The display and control component is a display with control functions, which can be implemented through touch, voice, or buttons. In this embodiment, the display and control component is a display with touch functions.

[0105] The detector also includes an ultraviolet irradiator, which is used to irradiate the detection mechanism to produce a significant resistance value, such as an ultraviolet mercury lamp or an ultraviolet LED lamp.

[0106] Test Example 2: Detection of tryptophan conformation with unknown chirality

[0107] This test case uses the chiral enantiomer detector from Example 2 to detect the configuration of tryptophan with unknown chirality.

[0108] The test is divided into two phases: the "Base" phase and the "Test" phase.

[0109] The “Base” stage is used to calibrate detector 1 (the left half of detector 1 is an R-configuration chiral metal-organic framework film, and the right half is an S-configuration metal-organic framework film) to eliminate the difference in the working base resistance value caused by the fabrication of the two different detector configurations, which affects the photoconductivity data caused by chiral substances in subsequent sensitive analysis; the “Test” stage is used to test the configuration of the analyte and correct the results through the “Base” stage.

[0110] Specifically, the "Base" stage includes the following steps: Switch to the "Base" option under the main menu on display 4; by using the left and right options of the switch, measure the resistance values ​​of the left and right sides (R and S detectors) of detector 1 under ultraviolet mercury lamp irradiation; after controlling the process via button 6, the light resistance values ​​of the S and R detectors are recorded; and the microprocessor MCU 5 below the display screen performs zeroing processing, so that the base resistance value is recorded as 0. The display data for each step is recorded in... Figure 5 Left side.

[0111] Before the “Test” stage, the R and S detectors were immersed in a prepared 1 mM unknown chiral tryptophan ethanol solution, left to stand for 1 minute, then removed, washed with pure ethanol, and dried with nitrogen gas. After that, the detectors were reconnected to the analysis system.

[0112] "Test" stage: Select the "Test" option under the main menu. Use button 6 in conjunction with the knife switch to measure the resistance change of the R and S detectors after contact with the unknown chiral tryptophan under ultraviolet mercury lamp irradiation. The data displayed on the screen at this time is the test data after deducting the baseline resistance value measured in the "Base" stage.

[0113] As demonstrated in Test Example 1 using UV-Vis spectroscopy, R-configuration chiral metal-organic frameworks exhibit better binding affinity for L-configuration tryptophan, while S-configuration chiral metal-organic frameworks show better binding affinity for D-configuration tryptophan. Therefore, if the substance with unknown chirality is L-configuration, it will bind more extensively within the R-configuration chiral metal-organic framework film, hindering current conduction and generating greater resistance. This results in the resistance measured by the R detector being greater than that measured by the S detector, confirming that the substance with unknown chirality is L-configuration. Conversely, if the substance with unknown chirality is D-configuration, it will bind more extensively within the S-configuration chiral metal-organic framework film, hindering current conduction. This results in the increase in resistance measured by the S detector after deducting the baseline being greater than the value measured by the R detector.

[0114] In this embodiment, as Figure 5As shown on the right, the measured value of the R probe under the "Test" option is 20.8, which is greater than the measured value of the S probe of 12.4. Therefore, the result can be obtained by analyzing and comparing the values ​​through the MCU: the chirality of the amino acid to be tested is L configuration.

[0115] The specific embodiments of the present invention have been described above by way of example. However, the scope of protection of the present invention is not limited to the above exemplary embodiments. Any modifications, equivalent substitutions, improvements, etc., made by those skilled in the art within the spirit and principles of the present invention should be included within the scope of protection of the claims of the present invention.

Claims

1. A chiral enantiomer detection device, characterized in that, The detection device includes a detection mechanism and an analysis system. The analysis system is connected to the detection mechanism and is used to monitor changes in the electrical signal of the detection mechanism. The detection mechanism includes at least one R-configuration detector and at least one S-configuration detector. The R-configuration detector is composed of an R-configuration chiral metal-organic framework film, and the S-configuration detector is composed of an S-configuration chiral metal-organic framework film. The chiral metal-organic framework film has chiral channels that can selectively bind chiral substances with opposite configurations.

2. The chiral enantiomer detection device according to claim 1, characterized in that, The chiral ligands are selected from chiral ligands with chiral carbon or spatial chirality and two or more carboxylic acid or pyridyl coordination nodes; The chiral metal-organic frame thin film is obtained by liquid-phase epitaxial layer-by-layer assembly and has a dense film structure and a specific growth orientation.

3. The chiral enantiomer detection device according to claim 1, characterized in that, The analysis system includes a signal processor, a display and control component, a first power supply, and a signal acquisition component. The signal processor and the display and control component are both connected to the first power supply. The signal acquisition component is connected to the display and control component through the signal processor. The signal acquisition component is connected to the detection mechanism and is used to acquire the electrical signals of the detection mechanism. The detection device also includes a circularly polarized light source, which is used to illuminate the detection mechanism, causing a significant change in the photoresistivity of the detection mechanism.

4. The chiral enantiomer detection apparatus according to any one of claims 1-3, characterized in that, The method for preparing the chiral metal-organic framework thin film includes the following steps: A chiral metal-organic framework thin film is formed by sequentially spraying metal salt solution and organic ligand solution onto the surface of a supporting substrate through liquid phase epitaxy.

5. The chiral enantiomer detection device according to claim 4, characterized in that, Before cyclically spraying the metal salt solution and organic ligand solution onto the surface of the support substrate, the following steps are also included: modifying the support substrate with molecular-level functional groups so that the active sites of the functional groups are exposed on the surface of the support substrate.

6. The enantiomer detection apparatus according to claim 5, characterized in that, The supporting substrate for the growth of the chiral metal-organic framework thin film is selected from rigid substrates and / or flexible substrates; The rigid substrate is selected from alumina, silicon dioxide, or quartz; The flexible substrate is selected from at least one of polyethylene terephthalate, polyimide, polydimethylsiloxane, polyvinyl alcohol, polyethylene naphthalate, or textile materials.

7. The application of the chiral enantiomer detection device according to any one of claims 1-6 in the detection of chiral substances.

8. A method for detecting chiral substances using the chiral enantiomer detection apparatus according to any one of claims 1-6, comprising the following steps: The detection mechanism is immersed in a solution formed by the substance to be tested, then removed, rinsed, and dried before the photoelectric signal of the detection mechanism is read by an analysis system. Before drying, the following steps are also included: washing the soaked detection mechanism; The washing process includes rinsing the surface of the detection mechanism with a solvent selected from one or a mixture of ethanol, methanol, and ethyl acetate.

9. The method for detecting chiral substances according to claim 8, characterized in that, The steps of reading the electrical signal of the detection mechanism by the analysis system are as follows: irradiating the dried detection mechanism with ultraviolet light, reading the electrical signal of the detection mechanism by the analysis system, and determining the chirality of the substance to be tested; Before immersing the detection mechanism into the solution formed by the substance to be tested, the following steps are also included: testing the electrical signal of the detection mechanism before immersion in the solution, and using it as a reference electrical signal.

10. The method for detecting chiral substances according to claim 9, characterized in that, The steps of reading the electrical signal of the detection mechanism by the analysis system are as follows: the detection mechanism is dried by ultraviolet light, the analysis system reads the electrical signal of the detection mechanism, the reference electrical signal is subtracted, and the chirality of the substance to be tested is determined. The detection mechanism is immersed in the solution formed by the substance to be tested for 30 to 120 seconds.

Images