Chiral enantiomer detection device as well as preparation method and application thereof

Abstract

The invention belongs to the field of thin film semiconductor materials, and particularly relates to a chiral enantiomer detection device and a preparation method and application thereof.The detection device comprises a detection mechanism and an analysis system, the analysis system is connected with the detection mechanism, and the analysis system is used for monitoring electric signal changes of the detection mechanism; the detection mechanism comprises at least one R-configuration detection sheet and at least one S-configuration detection sheet, the R-configuration detection sheet comprises an R-configuration chiral metal organic framework film, and the S-configuration detection sheet comprises an S-configuration chiral metal organic framework film; the chiral metal organic framework film is provided with a chiral pore channel, and the chiral pore channel can be selectively combined with a chiral substance with an opposite configuration. The chiral metal organic framework film provided by the invention has different combining capacities for chiral substances with different configurations, and the detection of chiral enantiomers can be intuitively and quickly completed in a mode of detecting a photoconductivity value.

Description

Technical Field

[0001] The present invention belongs to the field of thin film semiconductor materials, and in particular relates to a chiral enantiomer detection device and a preparation method and application thereof, and specifically relates to a method and application of preparing a chiral metal organic framework semiconductor thin film into a detection device with a chiral substance detection function. Background Art

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

[0003] Traditional methods for detecting chiral enantiomers include chromatography and nuclear magnetic resonance. Chromatography usually requires complex sample pretreatment and a long separation process. Although nuclear magnetic resonance technology has high accuracy, the instrumentation is expensive and the analysis time is long. In addition, these traditional methods cannot meet the requirements of high-throughput analysis and real-time monitoring.

[0004] Therefore, it is necessary to develop new chiral enantiomer detection technologies, and the new technology extensions should have the following characteristics:

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

[0006] 2. Rapid and high-throughput analysis: It has the ability of rapid analysis and can complete 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: Chiral enantiomers can be detected instantly and non-destructively 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: Reduce the need for expertise and cumbersome sample handling to improve the ease of use and operability of detection.

[0009] In addition, the cost-effectiveness of the technology is also a consideration, making it more feasible and widely used.

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

[0011] In summary, there is still an urgent need to develop new chiral recognition materials through technological expansion and innovation, starting from improving the sensitivity, speed, accuracy of chiral enantiomer detection and the simplicity and reliability of the production and manufacturing links. The materials should be highly selective and sensitive, and be able to interact specifically with the target chiral enantiomer. They can be used to construct new sensors to detect chiral enantiomers by measuring the electrochemical, optical, electronic or magnetic signals caused by the interaction. Summary of the invention

[0012] In order to improve the deficiencies of the prior art, the present invention provides a chiral enantiomer detection device based on a chiral metal organic framework film, and a preparation method and application thereof.

[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 is connected to the detection mechanism, and the analysis system is used to monitor the change of the electrical signal of the detection mechanism;

[0014] The detection mechanism includes at least one R-configuration detection piece and at least one S-configuration detection piece, the R-configuration detection piece includes an R-configuration chiral metal organic framework film, and the S-configuration detection piece includes an S-configuration chiral metal organic framework film; the chiral metal organic framework film has a chiral channel, and the chiral channel can selectively bind to a chiral substance of the opposite configuration.

[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-configured detection piece.

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

[0018] According to an embodiment of the present invention, the number of the R-configuration detection pieces is the same as the number of the S-configuration detection pieces.

[0019] According to an embodiment of the present invention, the R-configuration detection piece and the S-configuration detection piece have the same size.

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

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

[0022] According to an embodiment of the present invention, the right-handed metal organic framework film can selectively bind 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 with chiral carbon or spatial chirality, two or more carboxylic acid or pyridine coordination nodes, 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 has no specific requirements 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 grown by liquid phase epitaxial layer-by-layer assembly and has a specific growth orientation.

[0028] According to the embodiment of the present invention, the thickness of the chiral metal organic framework film can be customized from 0.05 to 2 microns according to the number of prepared layers.

[0029] According to the embodiments of the present invention, chiral metal organic framework films of different thicknesses have no significant effect on the detection of chiral enantiomeric 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 connected to the first power supply. The signal acquisition component is connected to the signal processor via a cable. The signal collector is connected to the detection electrode for collecting 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 for providing voltage to the detection piece so that a current is formed in the loop formed by the detection piece 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 a control function, wherein the control function can be implemented in the form of touch, voice or buttons. For example, the display and control component is a display with a touch function.

[0034] According to an embodiment of the present invention, the detection device further comprises an ultraviolet irradiator, which is used to irradiate the detection mechanism to cause the detection mechanism to produce an obvious change in resistance value, such as an ultraviolet mercury lamp or an ultraviolet LED.

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

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

[0037] According to an embodiment of the present invention, the chiral enantiomer is avoided from contact with corrosive liquids such as dimethylformamide, so as not to affect the stability of the circuit in the device.

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

[0039] As an example, the monitoring circuit consists of two groups of input electrodes connected to a knife switch, an output electrode connected to an S / R chiral metal organic framework film detection device, and a detector with S or R chirality determined by the switch is connected to an analysis system.

[0040] As an example, the analysis system is composed of an analog-to-digital converter chip (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 the implementation scheme of the present invention, the analog-to-digital conversion chip uses the AD5940 impedance measurement collector developed by ADI, which is capable of 8-bit data acquisition to meet the real-time detection requirements of subtle photoconductivity changes caused by light.

[0042] According to the implementation scheme of the present invention, the microcontroller unit for logic analysis uses the STM32F103 series microcontroller unit of STMicroelectronics, 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 the implementation scheme of the present invention, there is no special requirement for the display screen, as long as the resolution is greater than or equal to 64p and can fully display the test results, and there is no restriction on color or monochrome screen.

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

[0045] In a second aspect, the present invention further provides a method for preparing the chiral metal organic framework film, comprising the following steps:

[0046] A metal salt solution and an organic ligand solution are cyclically sprayed on the surface of a supporting substrate to form a chiral metal organic framework film by liquid phase epitaxy.

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

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

[0049] According to an embodiment of the present invention, the spray coating process may be performed under an inert atmosphere or under a ventilated environment.

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

[0051] According to an embodiment of the present invention, before cyclically spraying the metal salt solution and the organic ligand solution on the surface of the supporting substrate, the following step is also included: molecular-level functional group modification of the supporting substrate to expose the active sites of the functional groups on the surface of the supporting substrate.

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

[0053] According to an embodiment of the present invention, the rigid substrate is selected from alumina, silica 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 a textile material.

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

[0056] In a third aspect, the present invention further provides an application of the chiral metal organic framework film and / or chiral enantiomer detection device in the detection of chiral substances.

[0057] In a fourth aspect, the present invention further provides a method for detecting a chiral substance using the chiral enantiomer detection device, comprising the following steps:

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

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

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

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

[0062] According to an embodiment of the present invention, before the detection mechanism is immersed in the solution formed by the substance to be detected, the following step is also included: testing the electrical signal of the detection mechanism before being immersed 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 an analysis system comprises the following steps: irradiating the dried detection mechanism with ultraviolet light, the analysis system reading the electrical signal of the detection mechanism, subtracting the reference electrical signal, and determining the chirality of the substance to be detected.

[0064] According to an embodiment of the present invention, the wavelength of the ultraviolet light is 300-350 nm and 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 detected for 30 to 120 seconds, for example, 60 seconds.

[0066] The present invention makes full use of the chiral spatial environment of the chiral metal organic framework, prepares it into a continuous thin film as a detection layer, and utilizes its different binding abilities to chiral substances of different configurations. The detection of chiral enantiomers is intuitively and quickly completed by detecting the photoconductivity value, thereby solving the problems of traditional detector detection devices such as complex structure, difficult preparation and environmental unfriendliness.

[0067] The method of the present invention is flexible in operation and clear in principle. Its core detection layer is obtained by liquid phase epitaxial layer-by-layer self-assembly process, which can be used for high-quality and large-area film batch preparation. The chiral metal organic framework film does not need additional treatment and can be directly used for chiral enantiomer detection after device packaging and integration.

[0068] Beneficial Effects

[0069] 1. The present invention provides a chiral enantiomer detector made of a chiral metal organic framework film, which utilizes the chiral channel environment rich in the chiral metal organic framework film material to have different selective binding abilities for chiral substances of different configurations, and directly and quickly judges the chirality of the substance to be tested through real-time electrical signals of portable circuits. At the same time, the liquid phase epitaxial layer-by-layer assembly technology is used to effectively improve the uniformity, flatness and orientation of the metal organic framework film, overcoming the problem that the traditional chiral metal organic framework powder material lacks continuity and restricts the application of devices.

[0070] 2. Fast and accurate detection of chiral enantiomers: Chiral metal organic framework films have different binding abilities to chiral substances of different configurations. By detecting the photoconductivity value, the detection of chiral enantiomers can be completed intuitively and quickly. Compared with traditional detectors, this method avoids problems such as complex structure, difficult preparation, and environmental unfriendliness, and provides an efficient method for detecting chiral enantiomers.

[0071] 3. Flexible operation and clear principle: This method is flexible in operation and has a clear principle. It uses liquid phase epitaxial layer-by-layer self-assembly process to obtain the detection layer, overcoming the difficulty of preparing devices due to the original materials being mostly in powder form. It obtains a layer-by-layer assembled film with a dense structure and uniform morphology, greatly enriching the application scenarios of its original materials and enabling high-quality, large-area film batch preparation. This flexibility and clear principle make the detection of chiral enantiomers more feasible and reliable.

[0072] 4. Direct application in chiral enantiomer detection: After the chiral metal organic framework film is packaged and integrated into a device, it can be directly used for the detection of chiral enantiomers without additional processing. This integrated design simplifies the operation process, improves the efficiency and convenience of detection, and makes the detection of chiral enantiomers more practical and popularizable.

[0073] 5. This innovation has reached high industry standards in terms of structure and performance, especially highlighting the application of metal organic framework as a crystalline chemical material in the field of optical detection research, showing broad development prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0074] Figure 1 XRD diffraction patterns of the chiral metal organic framework detection sheets with R and S configurations prepared in Example 1 of the present invention;

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

[0076] Figure 3 The UV-visible light absorption data of the R and S configuration detection sheets described in Example 1 of the present invention after being combined with L or D configuration tryptophan at the same time;

[0077] Figure 4 The overall diagram of the detection device assembled for Example 2 of the present invention, including the detection piece and the external power supply and analysis circuit;

[0078] Figure 5 The detection device assembled for Example 2 of the present invention collects resistance value information during actual work and displays the schematic diagram on the display screen. DETAILED DESCRIPTION

[0079] The following will further describe the chiral enantiomer detector detection device of the present invention and its preparation method and application in combination with specific embodiments. It should be understood that the following embodiments are only exemplary descriptions and explanations of the present invention and should not be interpreted as limiting the scope of protection of the present invention. All technologies realized based on the above content of the present invention are included in the scope of protection of the present invention.

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

[0081] In order to verify the effectiveness and reliability of the results of the present invention, the test instruments used in the following examples are as follows:

[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-visible spectrophotometer;

[0086] (6) UV mercury lamp;

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

[0088] Example 1 Preparation of Chiral Enantiomer Detection Sheet

[0089] S1. First, use an AUY120 analytical balance to weigh copper acetate and H2BDA (chiral ligand 2,2-dimethoxy-1,1-binaphthyl-5,5-dicarboxylic acid). Then, dissolve copper acetate and H2BDA in ethanol solutions to prepare metal salt solutions with concentrations of 2mmol / L and H2BDA solutions with concentrations of 0.5mmol / L, respectively. Next, mix concentrated sulfuric acid and hydrogen peroxide in a volume ratio of 3:1 to prepare a fresh piranha solution. Immerse the insulating ceramic substrate in the piranha solution and heat it at 80°C for 30 minutes. After the treatment is completed, rinse with deionized water and place the treated insulating substrate on a support frame.

[0090] S2. In a nitrogen atmosphere with an air pressure of 0.2 MPa, the metal salt solution prepared in step S1 is sprayed for 20 seconds (the spraying amount is about 4 mL), and then the solution is kept for 30 seconds after spraying; the ethanol cleaning solution is sprayed for 10 seconds, and then the solution is kept for 10 seconds; the H2BDA solution is sprayed for 30 seconds (the spraying amount is about 5 mL), and then the solution is kept for 30 seconds; the ethanol cleaning solution is sprayed for 10 seconds, and then the solution is kept for 10 seconds.

[0091] S3. Repeat step S2 for 5 to 100 times according to the required film thickness, approximately corresponding to a thickness ranging from 0.1 to 2 microns, until a chiral metal organic framework film of the required thickness is obtained, and the chiral metal organic framework film is the chiral enantiomer detection film.

[0092] See also Figure 1 The figure shows the XRD spectrum of the chiral metal organic framework film prepared in this embodiment, where the fitted XRD data is the X-ray diffraction peak of the powdered material without special orientation growth simulated according to the crystal structure of the material, and has more diffraction peaks. The chiral metal organic framework film prepared by the liquid phase epitaxial layer-by-layer assembly method shows that in the direction perpendicular to the growth substrate, it grows along the preferred orientation of the

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

[0093] The film prepared in this embodiment has microscopic framework pores. The pore size is estimated to be about 1.56 nanometers by measuring its framework structure.

[0094] Test Example 1 Taking R-Cu(BDA)SURMOF and S-Cu(BDA)SURMOF as examples, the specific absorption of different configurations is illustrated.

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

[0096] Take L and D configurations of tryptophan (Trp) as an example to demonstrate the function of the chiral enantiomer detection film. Prepare two pieces of R and S configurations of chiral metal organic framework films (R-Cu(BDA)SURMOF and S-Cu(BDA)SURMOF), respectively, and immerse them in the prepared 1mM L-tryptophan and D-tryptophan ethanol solutions for 1 minute, then rinse them with pure ethanol and blow dry with nitrogen, and then record the absorption of the samples in the UV-visible light band using a PerkinElmer Lambda 365 UV-visible spectrophotometer.

[0097] like Figure 3 As shown in the left figure, the ultraviolet absorption of R-Cu(BDA)SURMOF increased significantly after being immersed in tryptophan solution. According to the Lambert-Beer 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 has a better binding ability to L-configuration tryptophan due to its R-configuration chiral space environment. In the same time, it binds more molar amounts of L-Trp, so its light absorption is improved. On the contrary, Figure 3 As shown in the right figure, the S-Cu(BDA) chiral metal organic framework film has a better binding ability for D-configuration tryptophan and binds more molar amounts of D-Trp in the same time. It can be seen that the chiral metal organic framework film detection piece prepared by the present invention can selectively bind to chiral substances with opposite configurations.

[0098] Example 2 Chiral Enantiomer Detector

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

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

[0101] The sizes of the R detection piece and the S detection piece are the same or different. In this embodiment, the R detection piece and the S detection piece 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 the display and control component are connected to the first power supply. The signal acquisition component is connected to the display and control component through the signal processor. The signal collector is connected to the detection mechanism to collect the photoelectric signal of the detection mechanism. In this embodiment, a double-sided knife switch (such as Figure 5 As shown in component 2), the detection mechanism is connected to the second power supply and is used to provide voltage to the detection piece so that a test current is formed in the loop formed by the detection piece and the signal collector.

[0103] The first power supply and the second power supply are DC power supplies, and 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 control component is a display with a control function, wherein the control function can be realized by touch, voice or button. In this embodiment, the display control component is a display with a touch function.

[0105] The detector further comprises an ultraviolet irradiator, which is used to irradiate the detection mechanism so that the detection mechanism produces an obvious resistance value, such as an ultraviolet mercury lamp or an ultraviolet LED lamp.

[0106] Test Example 2: Detection of unknown chiral tryptophan configuration

[0107] This test example uses the chiral enantiomer detector in Example 2 to detect the unknown chiral configuration of tryptophan.

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

[0109] The "Base" stage is used to calibrate the detection piece 1 (the left half of the detection piece 1 is an R-configuration chiral metal-organic framework film, and the right side is an S-configuration metal-organic framework film) to eliminate the difference in working base resistance values ​​of the two different configurations of the detection pieces due to preparation reasons, which affects the subsequent sensitive analysis of the photoconductivity data caused by the chiral substance; the "Test" stage is used to test the configuration of the object to be tested, and the results are corrected through the "Base" stage.

[0110] Specifically, the "Base" stage includes the following steps: switch to the "Base" option under the main menu in the display 4, and measure the resistance values ​​of the left and right sides (R detection piece and S detection piece) of the detection piece 1 under the irradiation of the ultraviolet mercury lamp by coordinating the left and right options of the knife switch. After the process is controlled by button 6, the light resistance values ​​of the S detection piece and the R detection piece will be recorded, and the microprocessor MCU 5 under the display screen will perform zeroing processing so that the base resistance value is recorded as 0. The display screen data of each step is recorded in Figure 5 Left side.

[0111] Before the "Test" stage, immerse the R probe and the S probe into the prepared 1 mM tryptophan ethanol solution of unknown chirality, let it stand for 1 minute, then take it out, wash the R probe and the S probe with pure ethanol, blow dry with nitrogen, and then reconnect the probe to the analysis system.

[0112] "Test" stage: Select the "Test" option under the main menu, and use button 6 in combination with the knife switch to measure the resistance changes of the R probe and the S probe after contact with unknown chiral tryptophan under the irradiation of ultraviolet mercury lamp. At this time, the data displayed on the screen is the test data after deducting the basic resistance measured in the "Base" stage.

[0113] Since it has been concluded through ultraviolet-visible spectrum research in Test Example 1 that the chiral metal organic framework material of R configuration has a better binding ability to L configuration tryptophan, while the chiral metal organic framework material of S configuration has a better binding ability to D configuration tryptophan. Therefore, if the unknown chiral substance to be tested is of L configuration, it will be more combined in the chiral metal organic framework film of R configuration, hindering the conduction of current and generating a greater resistance, so that the resistance value measured by the R detection piece is greater than the resistance value measured by the S detection piece, which can prove that the unknown chiral substance is of L configuration; if the unknown chiral substance to be tested is of D configuration, it will be more combined in the chiral metal organic framework film of S configuration, hindering the conduction of current, so that the increment of the base resistance measured by the S detection piece is greater than the measured value of the R detection piece.

[0114] In this embodiment, if 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 12.4. Therefore, the MCU can be used to analyze the comparison values ​​and obtain the result: the chirality of the amino acid to be tested is L configuration.

[0115] The above examples are used to illustrate the specific implementation of the present invention. However, the protection scope of the present invention is not limited to the above exemplary implementation. Any modification, equivalent substitution, improvement, etc. made by those skilled in the art within the spirit and principle of the present invention shall be included in the protection scope 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, wherein the analysis system is connected to the detection mechanism and is used to monitor changes in electrical signals of the detection mechanism; The detection mechanism includes at least one R-configuration detection piece and at least one S-configuration detection piece, wherein the R-configuration detection piece is composed of an R-configuration chiral metal organic framework film, and the S-configuration detection piece is composed of an S-configuration chiral metal organic framework film; the chiral metal organic framework film has a chiral channel, and the chiral channel can selectively bind to a chiral substance of the opposite configuration.

2. The chiral enantiomer detection device according to claim 1, characterized in that: The chiral ligand is selected from chiral ligands with chiral carbon or spatial chirality and two or more carboxylic acid or pyridine coordination nodes. Preferably, the chiral metal organic frame thin film is grown 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 or 2, characterized in that: 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 display and control component via the signal processor. The signal collector is connected to the detection mechanism for collecting electrical signals from the detection mechanism. Preferably, the detection device further comprises a circularly polarized light source, which is used to illuminate the detection mechanism so as to cause the detection mechanism to produce an obvious change in photoconductivity resistance.

4. A method for preparing a chiral metal organic framework film according to any one of claims 1 to 3, characterized in that: The following steps are involved: A metal salt solution and an organic ligand solution are sprayed on the surface of a supporting substrate in a circular manner in sequence to form a chiral metal organic framework film by liquid phase epitaxy.

5. The method for preparing a chiral metal organic framework thin film according to claim 4, characterized in that: Before cyclically spraying the metal salt solution and the organic ligand solution on the surface of the supporting substrate, the method further includes the following steps: performing molecular-level functional group modification on the supporting substrate so that the active sites of the functional groups are exposed on the surface of the supporting substrate.

6. The method for preparing a chiral metal organic framework thin film according to claim 4 or 5, characterized in that: The supporting substrate for growing the chiral metal organic framework film is selected from a rigid substrate and / or a flexible substrate. Preferably, the rigid substrate is selected from alumina, silica or quartz. Preferably, the flexible substrate is selected from at least one of polyethylene terephthalate, polyimide, polydimethylsiloxane, polyvinyl alcohol, polyethylene naphthalate or a textile material.

7. Use of the chiral enantiomer detection device according to any one of claims 1 to 3 and / or the chiral metal organic framework film according to any one of claims 4 to 6 in the detection of chiral substances.

8. A method for detecting a chiral substance using the chiral enantiomer detection device according to any one of claims 1 to 3, comprising the following steps: The detection mechanism is immersed in a solution formed by the substance to be detected, taken out, rinsed and dried, and then the photoelectric signal of the detection mechanism is read through an analysis system. Preferably, before drying, the method further comprises the following step: washing the soaked detection mechanism. Preferably, the washing comprises flushing the surface of the detection mechanism with a solvent, and preferably the solvent is selected from ethanol, methanol, ethyl acetate or a mixture of several thereof.

9. The method for detecting chiral substances according to claim 8, characterized in that: Reading the electrical signal of the detection mechanism by the analysis system comprises the following steps: irradiating the dried detection mechanism with ultraviolet light, and the analysis system reading the electrical signal of the detection mechanism to determine the chirality of the substance to be detected. Preferably, before the detection mechanism is immersed in the solution formed by the substance to be detected, the following step is also included: testing the electrical signal of the detection mechanism before being immersed in the solution and using it as a reference electrical signal.

10. The method for detecting chiral substances according to claim 8 or 9, characterized in that: Reading the electrical signal of the detection mechanism by the analysis system includes the following steps: irradiating the dried detection mechanism with ultraviolet light, the analysis system reading the electrical signal of the detection mechanism, subtracting the reference electrical signal, and determining the chirality of the substance to be detected. Preferably, the detection mechanism is immersed in the solution formed by the substance to be detected for 30 to 120 seconds.

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