A low-temperature-processed flexible organic crystalline compound and a preparation method thereof

By developing low-temperature flexible organic crystal compounds THEAT, the problems of brittleness and difficulty in processing of organic materials at low temperatures have been solved, flexibility and operability in extreme environments have been achieved, and the development of optical signal transmission and modulation technology has been promoted, which is suitable for optoelectronics, wearable devices and biocompatible sensors.

CN118993940BActive Publication Date: 2025-10-21JILIN UNIVERSITY
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Patent Information

Application Number
CN202411092838.8
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-08-09
Publication Date
2025-10-21
Estimated Expiration
2044-08-09

AI Technical Summary

Technical Problem

Existing organic materials become brittle and difficult to process at low temperatures, limiting their application in extreme environments, especially in maintaining flexibility and operability. Optical signal transmission and modulation in low-temperature environments also face challenges.

Method used

A low-temperature flexible organic crystal compound, 2,3,5-trifluoro-6-((2-(2-hydroxyethoxy)ethyl)amino)terephthalonitrile (THEAT), was developed. Through specific synthesis and processing methods, it maintains flexibility and processability in the temperature range of 298K to 77K. A spectral sensing system was constructed by combining an ultraviolet light source and an optical signal receiver to achieve real-time two-dimensional motion detection, and the spectral output was modulated by changing the crystal width.

Benefits of technology

THEAT maintains flexibility and processability at low temperatures and is used in optoelectronics, wearable devices, and biocompatible sensors. It enables flexible transmission and modulation of optical signals and is suitable for optical communications and sensing in extreme environments, promoting the cross-integration development of materials science.

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Abstract

The application relates to the technical field of organic crystals, and particularly discloses a low-temperature-processed flexible organic crystal compound and a preparation method thereof, which comprises a low-temperature flexible organic crystal compound, the low-temperature flexible organic crystal compound is 2,3,5-trifluoro-6-((2-(2-hydroxyethoxy)ethyl)amino) p-phenylenedinitrile (THEAT), and the low-temperature flexible organic crystal compound exhibits flexibility and processability in a temperature range of 298K to 77K; the application exhibits good flexibility and processability of THEAT in a temperature range of 298K to 77K, the feature enables the material to still maintain physical performance and operability in a low-temperature environment, the low-temperature flexible and processable combination overcomes the shortcomings that traditional organic materials are brittle and difficult to process in a low-temperature environment, the low-temperature flexibility and processability make THEAT and similar materials have wide application prospects in multiple fields such as wearable devices, biocompatible sensors and soft robotics, and promote the cross integration and innovative development of material science.
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Description

Technical Field

[0001] The invention belongs to the technical field of organic crystals, and in particular relates to a low-temperature processed flexible organic crystal compound and a preparation method thereof. Background Art

[0002] Flexible organic crystals have attracted much attention due to their potential applications in optoelectronics, sensing, and soft robotics. The unique properties of these materials, such as lightness and bendability, make them advantageous for the development of next-generation wearable devices and biocompatible sensors.

[0003] However, how to develop materials that can maintain flexibility, functionality and processability under low temperature conditions remains a key challenge in this field. Most organic materials, including polymers, become brittle and difficult to process at low temperatures, which hinders their application in extreme environments such as space exploration and polar research, especially when materials are required to remain flexible and operable. In addition, precise control and modulation of optical signals under these extreme conditions are also crucial to promoting the development of optical communication and sensing technologies. Optical signal transmission and modulation in low temperature environments face unique challenges, such as the thermal shrinkage effect of materials and the temperature dependence of optical properties. Therefore, there is an urgent need for innovative materials that can combine low-temperature flexibility, processability and adjustable optical properties. Summary of the Invention

[0004] The object of the present invention is to provide a low-temperature processed flexible organic crystal compound and a preparation method thereof, so as to solve the problems raised in the above background technology.

[0005] To achieve the above object, the present invention provides the following technical solutions:

[0006] A low-temperature processed flexible organic crystal compound comprising:

[0007] Low-temperature flexible organic crystal compounds;

[0008] The low-temperature flexible organic crystal compound is 2,3,5-trifluoro-6-((2-(2-hydroxyethoxy)ethyl)amino)terephthalonitrile (THEAT);

[0009] The low-temperature flexible organic crystal compound exhibits flexibility and processability within a temperature range of 298K to 77K.

[0010] A method for synthesizing a low-temperature flexible organic crystal compound comprises the following steps:

[0011] S1. Dissolve tetrafluoroterephthalonitrile (2.01 g) in 50 ml of tetrahydrofuran;

[0012] S2. Add 2-(2-aminoethoxy)-1-ethanol (1.05 g) and 4 ml of triethylamine solution and stir at room temperature;

[0013] S3. Monitor the reaction by thin layer chromatography. After about 8 hours, evaporate the tetrahydrofuran using a rotary evaporator.

[0014] S4. The reaction mixture was dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo;

[0015] S5. The crude compound was purified by column chromatography using ethyl acetate and dichloromethane (1:5) as eluent to obtain a light yellow product with a yield of 75%.

[0016] A method for growing decimeter-scale crystals of a low-temperature flexible organic crystal compound comprises the following steps:

[0017] S1: Dissolve the purified THEAT in dichloromethane;

[0018] S2: Carefully add cyclohexane as the upper layer at a volume ratio of dichloromethane:cyclohexane (1:4);

[0019] S3: Slowly diffuse with the solvent until high-quality crystals are formed.

[0020] A method for processing low-temperature flexible organic crystal compound crystals at room temperature, comprising the following steps:

[0021] S1. Place the crystal on a clean silicon wafer;

[0022] S2. Use a sharp blade to cut the crystal;

[0023] S3, using a fine needle tip to peel the crystal;

[0024] S4. Apply external force to the crystal to bend it.

[0025] A method for processing low-temperature flexible organic crystal compound crystals at low temperature comprises the following steps:

[0026] S1. Immerse the crystal in liquid nitrogen to lower its temperature to 77K;

[0027] S2, using a pre-cooled sharp knife to cut the crystal immersed in liquid nitrogen;

[0028] S3, using a pre-cooled needle tip to peel the crystal immersed in liquid nitrogen;

[0029] S4. Apply external force to the crystal in a liquid nitrogen environment to bend it.

[0030] A wavelength modulator comprises a low temperature flexible organic crystalline compound crystal, wherein the spectral output is modulated by varying the width of the crystal.

[0031] A method for wavelength modulation using a low-temperature flexible organic crystal compound crystal comprises the following steps:

[0032] S1, cutting the crystal into structures of different widths;

[0033] S2, input optical signal from one end of the crystal;

[0034] S3. Modulate the output wavelength by selecting crystal sections of different widths.

[0035] A spectral sensing system for real-time two-dimensional motion detection in a cryogenic environment, comprising:

[0036] Low-temperature flexible organic crystal compound crystal, ultraviolet light source for excitation and optical signal receiver.

[0037] A method for detecting two-dimensional motion in a low-temperature environment using a low-temperature flexible organic crystal compound crystal comprises the following steps:

[0038] S1, placing the crystal in a low temperature environment;

[0039] S2, scanning the UV light source in the X-axis direction to excite different positions of the crystal;

[0040] S3, inserting and scanning the UV light source in the Y-axis direction to excite different depths of the crystal;

[0041] S4. Analyze the change pattern of the collected spectral signal in real time to track the movement of the object in the X-axis and Y-axis directions.

[0042] Compared with the prior art, the present invention has the following beneficial effects:

[0043] (1) THEAT exhibits good flexibility and processability in the temperature range of 298K to 77K. This property enables the material to maintain its physical properties and operability in low-temperature environments, overcoming the shortcomings of traditional organic materials that become brittle and difficult to process at low temperatures. The combination of low-temperature flexibility and processability gives THEAT and similar materials broad application prospects in multiple fields such as wearable devices, biocompatible sensors, and soft robotics, promoting the cross-integration and innovative development of materials science.

[0044] (2) Flexibility and processability make THEAT have potential application value in the field of optoelectronics. For example, it can be used to develop flexible optoelectronic devices to meet the needs of optical signal transmission and modulation in special environments (such as space and polar regions).

[0045] (3) By combining with ultraviolet light sources and optical signal receivers, THEAT crystals can be used to construct spectral sensing systems in low-temperature environments and realize real-time two-dimensional motion detection, which is of great significance for scientific research (such as polar ecological monitoring) and engineering applications (such as robotic exploration).

[0046] (4) By changing the width of the THEAT crystal, the spectral output can be modulated. This feature provides new ideas and methods for optical communication and spectral modulation technology, and improves the flexibility and controllability of optical signal transmission. The successful synthesis and performance demonstration of THEAT provides new strategies and ideas for the design and synthesis of low-temperature flexible organic crystal materials, and promotes further development in this field.

[0047] (5) In extreme low temperature environments, such as space exploration and polar research, the flexibility and processability of materials are crucial. The development of THEAT provides new material options for these fields, solving the problem of limited performance of existing materials at low temperatures. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] Figure 1 is the chemical structure diagram of the THEAT compound of the present invention;

[0049] Figure 2 is the chemical structure diagram of the THAT compound of the present invention;

[0050] Figure 3 is the crystal structure diagram of the present invention;

[0051] Figure 4 A processing diagram of the crystal of the present invention;

[0052] Figure 5 This is a diagram of an optical waveguide experiment of the present invention;

[0053] Figure 6 FIG is an application diagram of the crystal of the present invention in wavelength modulator and motion detection;

[0054] in Figure 3 a and b are the crystal molecular structures measured at 298K (a) and 100K (b), respectively. c is the stacking structure of the crystal along the (100) plane at 100K. d is the stacking structure of the crystal along the (001) plane at 100K, as well as the expansion and contraction directions of the outer and inner arcs during the bending process. e and f are the hydrogen bond interaction types at 100K (e) and 298K (f), respectively.

[0055] in Figure 4a is a schematic diagram of organic crystals being cut into different lengths, b is a diagram of THEAT being cut into different lengths at room temperature, c is a schematic diagram of crystals being cut into different widths, d is a diagram of THEAT being peeled into different widths at room temperature, e and f are transmission micrographs of THEAT of different thicknesses being peeled to different widths (150 μm (e) and 200 μm (f)), g is a scanning electron micrograph of THEAT after processing, h is a diagram of THEAT bending under external force, i is a diagram after PDMS processing, j is a diagram of THEAT being cut into different lengths at low temperature, k is a diagram of THEAT being cut into different widths at low temperature, and l is a diagram of THEAT bending under external force at low temperature;

[0056] in Figure 5 Figures ad are images of THEAT with different widths used as waveguides: 0.372 mm (a), 0.300 mm (b), 0.228 mm (c), and 0.072 mm (d); e is a graph showing the relationship between the crystal width, emission peak position, and excitation position and the distance of the collected light signal; fg are images of THEAT with different widths used as waveguides in a bent state: 0.372 mm (f) and 0.072 mm (g); hi are the normalized fluorescence spectra collected at different excitation positions, and panels h and i correspond to the crystals in panels f and g, respectively; jk are images of THEAT with different widths used as waveguides in a bent state at low temperature (77 K): 0.372 mm (j) and 0.072 mm (k); lm is the normalized fluorescence spectra collected at different excitation positions, and panels l and m correspond to the crystals in panels j and k, respectively;

[0057] in Figure 6 Figure a is a schematic diagram of THEAT wavelength modulators of different widths, b is a schematic diagram of the spectral sensing system for real-time monitoring of two-dimensional motion in a low-temperature environment, c is a photograph of THEAT excited by ultraviolet light in the X direction, d is the normalized fluorescence spectrum collected at different excitation positions, e is a linear graph of shift position and spectral change, f is a photograph of THEAT excited by ultraviolet light along the Y direction, g is the normalized fluorescence spectrum collected at different depths, h is a linear graph of depth position and spectral change, i is a decimeter-level photograph of THEAT optical signal transmission, j is the normalized fluorescence spectrum collected at different excitation positions, and k is a linear graph of excitation position and spectral change. DETAILED DESCRIPTION

[0058] The following will clearly and completely describe the technical solutions in the embodiments of the present invention in conjunction with the accompanying drawings. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0059] Example 1:

[0060] See also Figures 1 to 6 A low-temperature processed flexible organic crystal compound comprising:

[0061] Low-temperature flexible organic crystal compounds;

[0062] The low-temperature flexible organic crystal compound is 2,3,5-trifluoro-6-((2-(2-hydroxyethoxy)ethyl)amino)terephthalonitrile (THEAT);

[0063] The low-temperature flexible organic crystal compounds exhibit flexibility and processability in the temperature range of 298K to 77K.

[0064] The crystals formed by the compound can achieve a controllable spectral red shift that is proportional to the crystal width.

[0065] The compound is able to form ultra-long, flexible organic crystals exceeding 10 centimeters in length.

[0066] A method for synthesizing a low-temperature flexible organic crystal compound comprises the following steps:

[0067] S1. Dissolve tetrafluoroterephthalonitrile (2.01 g) in 50 ml of tetrahydrofuran;

[0068] S2. Add 2-(2-aminoethoxy)-1-ethanol (1.05 g) and 4 ml of triethylamine solution and stir at room temperature;

[0069] S3. Monitor the reaction by thin layer chromatography. After about 8 hours, evaporate the tetrahydrofuran using a rotary evaporator.

[0070] S4. The reaction mixture was dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo;

[0071] S5. The crude compound was purified by column chromatography using ethyl acetate and dichloromethane (1:5) as eluent to obtain a light yellow product with a yield of 75%.

[0072] A method for growing decimeter-scale crystals of a low-temperature flexible organic crystal compound comprises the following steps:

[0073] S1: Dissolve the purified THEAT in dichloromethane;

[0074] S2: Carefully add cyclohexane as the upper layer at a volume ratio of dichloromethane:cyclohexane (1:4);

[0075] S3: Slowly diffuse with the solvent until high-quality crystals are formed.

[0076] A method for processing low-temperature flexible organic crystal compound crystals at room temperature, comprising the following steps:

[0077] S1. Place the crystal on a clean silicon wafer;

[0078] S2. Use a sharp blade to cut the crystal;

[0079] S3, using a fine needle tip to peel the crystal;

[0080] S4. Apply external force to the crystal to bend it.

[0081] The optical performance of the crystal is tested in a low-temperature environment after processing, including measuring the spectral red shift and optical loss coefficient.

[0082] A method for processing low-temperature flexible organic crystal compound crystals at low temperature comprises the following steps:

[0083] S1. Immerse the crystal in liquid nitrogen to lower its temperature to 77K;

[0084] S2, using a pre-cooled sharp knife to cut the crystal immersed in liquid nitrogen;

[0085] S3, using a pre-cooled needle tip to peel the crystal immersed in liquid nitrogen;

[0086] S4. Apply external force to the crystal in a liquid nitrogen environment to bend it.

[0087] A wavelength modulator comprises a low temperature flexible organic crystalline compound crystal, wherein the spectral output is modulated by varying the width of the crystal.

[0088] A method for wavelength modulation using a low-temperature flexible organic crystal compound crystal comprises the following steps:

[0089] S1, cutting the crystal into structures of different widths;

[0090] S2, input optical signal from one end of the crystal;

[0091] S3. Modulate the output wavelength by selecting crystal sections of different widths.

[0092] A spectral sensing system for real-time two-dimensional motion detection in a cryogenic environment, comprising:

[0093] Low-temperature flexible organic crystal compound crystal, ultraviolet light source for excitation and optical signal receiver.

[0094] The crystals retain their flexibility and optical properties at temperatures as low as 77 K.

[0095] A method for detecting two-dimensional motion in a low-temperature environment using a low-temperature flexible organic crystal compound crystal comprises the following steps:

[0096] S1. Place the crystal in a low temperature environment;

[0097] S2, scanning the UV light source in the X-axis direction to excite different positions of the crystal;

[0098] S3, inserting and scanning the UV light source in the Y-axis direction to excite different depths of the crystal;

[0099] S4. Analyze the change pattern of the collected spectral signal in real time to track the movement of the object in the X-axis and Y-axis directions.

[0100] 2,3,5-Trifluoro-6-((3-hydroxypropyl)amino)terephthalonitrile (THAT)

[0101] Scheme 1: The purified product was dissolved in a dichloromethane solution and added to a test tube. Then, n-hexane solvent (volume ratio of 1:2) was carefully added to the upper layer. After the solvent slowly diffused, high-quality centimeter-scale ribbon-shaped THAT crystals were obtained. THAT crystals have excellent elasticity and can be repeatedly bent under external force without breaking. The abundant intermolecular hydrogen bonds not only play a key role in buffering external stress, but also facilitate the formation of high-quality large-size crystals.

[0102] Scheme 2: Further introduce strong polar groups to increase intramolecular hydrogen bonds and synthesize 2,3,5-trifluoro-6-((2-(2-hydroxyethoxy)ethyl)amino)terephthalonitrile (THEAT) molecules. Through crystal growth (dichloromethane:cyclohexane = 1:4), high-quality decimeter-scale strip-shaped THEAT crystals are obtained, which far exceeds the length of previously reported elastic organic crystals. The 10-centimeter-long THEAT crystal can be bent by both hands. At 298K, the maximum absorption peak positions of THAT and THEAT crystals are 409nm and 389nm, respectively. At 77K, the maximum emission peak positions of THAT and THEAT crystals are 466nm and 467nm, respectively. nm and 467nm, THEAT crystals are repeatedly bent at room temperature and low temperature, and can be wound on a capillary glass tube without breaking. In order to quantitatively evaluate the mechanical bendability of the crystals, a reported method was used to determine the maximum expansion and contraction ratios (maximum elastic strain, εmax) of the inner and outer arcs when the bent crystals were free of cracks. The method is to wrap crystals of different thicknesses on a cylinder (with a diameter of 0.52 mm) to form a semicircle; the maximum applicable thickness (0.101 mm) corresponds to εmax. Therefore, the calculated εmax of THEAT crystals at room temperature is 6.98%, and at low temperature is 7.74%.

[0103] The THEAT crystal grows along the a-axis, with the bendable crystal plane being the (010) plane. The asymmetric unit of the crystal contains one molecule, and the torsion angle of the side chain differs by only 0.32° at 298K and 100K (e.g. Figure 3 After LN gas was blown into the frozen crystal, the crystal axis shortened isotropically (the a, b and c axes shortened by -0.8%, -0.9% and -1.6%, respectively) (as shown in a and b in Figure 2). Figure 3 b), the molecular layer is connected by hydrogen bonds OH...O CH…N Connect along the

[100] direction (such as Figure 3 c), and forms a stable structure on the (001) plane (as shown in Figure 3 d), the close presence of electronegative N, O, and F atoms on the benzene molecule forms a rich hydrogen bond network between multiple molecules. When the crystal is subjected to external stress, the distance between the outer arc molecules increases to disperse the energy of the external stress, while the inner arc molecules become closer due to compression. and CH…F The hydrogen bond network prevents the molecular layers from sliding, thus ensuring that the crystal can bend without breaking at room and low temperatures (e.g. Figure 3 e), the intermolecular forces and types of interactions are roughly the same at low temperatures compared to those at 298 K, which further explains the ability of the crystal to maintain bending at low temperatures (e.g. Figure 3 f).

[0104] like Figure 4 As shown in a and b, the crystal is placed on a silicon wafer and cut with a blade. The crystal can be cut into different lengths at room temperature. The crystal is subjected to pressure during cutting and the tip is split. This may be due to the destruction of the weak interaction force between the crystal molecular layers, as shown in Figure 4 As shown in c and d, the crystal is processed into different widths by peeling at the crack with the needle tip. In order to prove that crystals of different thicknesses can be peeled, a crystal with a width of 404 μm and a thickness of about 150 μm can be split to a minimum width of 80 μm (as shown in Figure 4 Similarly, a crystal with a thickness of 200 μm can also be processed into different widths (as shown in Figure 4 f), as shown Figure 4 As shown in g, the crystal surface was observed to be flat and undamaged under a scanning microscope, and it could still be bent repeatedly (as shown in Figure 4 h), as shown in Figure 4 As shown in Fig. 1, polydimethylsiloxane (PDMS) is placed in liquid nitrogen and then processed with scissors. PDMS will break brittlely under external force, making processing difficult. On the contrary, the crystal in liquid nitrogen (77K) is still easy to process and can be cut and peeled into smaller sizes (such as Figure 4 j and k in the figure), and it can still maintain good elasticity at low temperatures (as shown in Figure 4 The above experiments demonstrate the processability of the crystal at room temperature and low temperature.

[0105] In order to determine the optical waveguide properties of the processed crystals, the optical loss coefficient (OLC) of THEAT crystals with different widths was evaluated. Figure 5 In the ad, the optical waveguides of THEAT crystals with the same length and thickness but different widths (0.372 mm, 0.300 mm, 0.228 mm, and 0.072 mm) were tested. The emission intensity decreased with increasing distance from the illumination point, which was attributed to the optical loss ( Figure 5 ad), by using a 355nm laser to uniformly illuminate the crystal from different positions and capturing the emission spectrum at the end of the crystal, the emission spectrum that varies with distance was obtained. After fitting the collected data using the previous method, the OLCs of the emission peaks were calculated to be: 0.372mm width is 0.199dBmm^-1, 0.300mm width is 0.161dBmm^-1, 0.228mm width is 0.123dBmm^-1, and 0.072mm width is 0.106dBmm^-1. As the distance from the irradiation point to the signal collection position increases, the emission spectrum gradually redshifts, with a maximum redshift wavelength of 62nm. This is attributed to the self-absorption of THEAT. The optical loss of the crystal gradually decreases with decreasing width, and self-absorption also decreases, resulting in a gradual decrease in the redshift of the wavelength ( Figure 5 e), the change of crystal width and wavelength presents an exponential relationship, the change of crystal width and wavelength presents an exponential relationship, Figure 5 In f and g, optical loss experiments were conducted on different widths of THEAT (0.372 mm and 0.072 mm) in the bent state. Calculations show that in the bent state, the OLC of the emission peak with a width of 0.372 mm is 0.1208 dBmm^-1, and that of the THEAT with a width of 0.072 mm is 0.200 dBmm^-1. The wavelength changes of different widths in the bent state are consistent with those in the straight state. Figure 5 In j and k, crystals of different widths can maintain optical signal transmission at low temperature (77K), and the wavelength red shift increases with the increase of width. Under low temperature (77K) conditions, the OLC of the crystal with a width of 0.372mm is 0.282dBmm^-1, and the OLC of THEAT with a width of 0.072mm is 0.205dBmm^-1. The above experiments prove the optical signal transmission capability of the processed crystal in bent and straight states, as well as at room temperature and low temperature conditions.

[0106] exist Figure 6In a, since the width of the crystal affects the degree of redshift of the wavelength, the crystal is cut into structures of different widths. When the input light enters the crystal from the left, the output signal changes, which shows that a wavelength modulator can be prepared. Figure 6 In b, a spectral sensing system is designed. Based on the red shift phenomenon of the light signal in the crystal emission spectrum, the two-dimensional movement of the object in the low-temperature environment is monitored in real time. The crystal is placed in liquid nitrogen, and an optical signal receiver is installed on its left end. By controlling the scanning of the ultraviolet light source in the X-axis and Y-axis, the crystal can be excited and its spectral signal can be collected. In the X-axis direction, the ultraviolet light source scans horizontally to excite different positions of the crystal and generate corresponding spectral signals. The change pattern of these signals is analyzed in real time to accurately track the movement of the object in the X-axis direction. Similarly, a vertically inserted ultraviolet light source is used to scan the Y-axis direction, and the position change of the object on the Y-axis is detected by analyzing the spectral response at different depths. Figure 4 In c, the crystal was placed on one side of a 3.2 cm × 3.2 cm rectangle and irradiated with ultraviolet light along the X-axis. Spectral signals at different positions were collected. The maximum red shift of the spectrum was 23 nm, and the position of the red shift was linearly related to the wavelength ( Figure 6 d, e), using a vertically inserted UV light source to illuminate the Y-axis direction, collecting spectral signals corresponding to different depths, the maximum value of the spectrum red shift is 7 nanometers, and the depth and spectrum are linearly related ( Figure 6 g, h), and also cultivated an ultra-long flexible organic crystal with a length of 10.25 cm, exceeding the commonly reported 2 to 3 cm. As the distance between the ultraviolet excitation and the signal collection position increases, the spectrum of the crystal can be red-shifted by up to 52 nanometers ( Figure 6 j), while the linear relationship between the excitation position and the emission wavelength remains ( Figure 6 k), these unique optical properties make this crystal capable of monitoring the motion of a larger range of two-dimensional objects in a cryogenic environment.

[0107] A new type of flexible organic crystal (THEAT) exhibits excellent mechanical and optical properties at both room temperature and cryogenic conditions. THEAT crystals remain elastic and processable at 77K, overcoming the brittleness of organic materials typically present at low temperatures. These crystals display unique optical waveguide properties, including a controllable spectral redshift phenomenon that is proportional to the crystal width, allowing for precise modulation of optical signals with spectral redshifts up to 62nm. Ultra-long THEAT crystals exceeding 10 cm in length have been cultivated, maintaining excellent optical signal transmission properties. These properties demonstrate the potential of THEAT crystals as wavelength modulators and spectral sensing systems, enabling real-time two-dimensional motion detection in cryogenic environments. THEAT crystals combine low-temperature processability with tunable optical properties, and are expected to be applied in space exploration, cryogenic sensing, and optical communications.

[0108] While embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions, and variations may be made to these embodiments without departing from the principles and spirit of the invention, and that the scope of the invention is defined by the appended claims and their equivalents.

Claims

1. A low-temperature processed flexible organic crystal compound, characterized in that: include: Low-temperature flexible organic crystal compounds; The low-temperature flexible organic crystal compound is 2,3,5-trifluoro-6-((2-(2-hydroxyethoxy)ethyl)amino)terephthalonitrile, namely THEAT; The low-temperature flexible organic crystal compound exhibits flexibility and processability within a temperature range of 77K to 298K.

2. A method for synthesizing a low-temperature flexible organic crystal compound, characterized in that: The following steps are involved: S1, dissolving 2.01 g of tetrafluoroterephthalonitrile in 50 ml of tetrahydrofuran; S2. Add 1.05 g of 2-(2-aminoethoxy)-1-ethanol and 4 ml of triethylamine solution and stir at room temperature; S3. Monitor the reaction by thin layer chromatography. After 8 hours, evaporate the tetrahydrofuran using a rotary evaporator. S4. The reaction mixture was dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo; S5. The crude compound was purified by column chromatography using ethyl acetate and dichloromethane in a ratio of 1:5 as eluent to obtain a light yellow product with a yield of 75%.

3. A method for growing decimeter-scale crystals of low-temperature flexible organic crystal compounds, characterized in that: The following steps are involved: S1: Dissolve the purified THEAT in dichloromethane; S2: Carefully add cyclohexane as the top layer at a volume ratio of 1:4 dichloromethane:cyclohexane; S3: Slowly diffuses with the solvent until crystals form.

4. A method for processing low-temperature flexible organic crystal compound crystals at room temperature, characterized in that: The following steps are involved: S1. Place the crystal on a clean silicon wafer; S2. Use a sharp blade to cut the crystal; S3, using a fine needle tip to peel the crystal; S4. Apply external force to the crystal to bend it.

5. A method for processing low-temperature flexible organic crystal compound crystals at low temperature, characterized in that: The following steps are involved: S1. Immerse the crystal in liquid nitrogen to lower its temperature to 77K; S2, using a pre-cooled sharp knife to cut the crystal immersed in liquid nitrogen; S3, using a pre-cooled needle tip to peel the crystal immersed in liquid nitrogen; S4. Apply external force to the crystal in a liquid nitrogen environment to bend it.

6. A wavelength modulator, characterized in that: These include low-temperature flexible organic crystalline compound crystals in which the spectral output can be modulated by varying the width of the crystal.

7. A method for wavelength modulation using a low-temperature flexible organic crystal compound crystal, characterized in that: The following steps are involved: S1, cutting the crystal into structures of different widths; S2, input optical signal from one end of the crystal; S3. Modulate the output wavelength by selecting crystal sections of different widths.

8. A spectral sensing system for real-time two-dimensional motion detection in a low-temperature environment, characterized in that: include: Low-temperature flexible organic crystal compound crystal, ultraviolet light source for excitation and optical signal receiver.

9. A method for two-dimensional motion detection in a low-temperature environment using a low-temperature flexible organic crystal compound crystal, characterized in that: The following steps are involved: S1, placing the crystal in a low temperature environment; S2, scanning the UV light source in the X-axis direction to excite different positions of the crystal; S3, inserting and scanning the UV light source in the Y-axis direction to excite different depths of the crystal; S4. Analyze the change pattern of the collected spectral signal in real time to track the movement of the object in the X-axis and Y-axis directions.

Citation Information

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