CN114634546B - High-luminous-power electrochromic material from red to near infrared and preparation method thereof - Google Patents

Abstract

The invention belongs to the field of high-luminescence mechanochromic materials, and proposes a high-luminescence mechanochromic material ranging from red to near-infrared and a preparation method thereof. Step 1, weighing 7-bromo-4-aldehyde benzo[c] [1,2,5] thiadiazole, triphenylamine boric acid, tetrakistriphenylphosphopalladium and sodium carbonate, and sodium carbonate is configured into sodium carbonate aqueous solution, the above raw materials are dissolved in chromatographic toluene and tetrahydrofuran; then by extraction, Filtration, column chromatography and rotary evaporation obtain 7-triphenylamine-4-formyl benzo[c][1,2,5]thiadiazole; step 2, intermediate product, cholesterol formamidophenylacetonitrile and sodium methylate solution in ethanol; the filter cake was rinsed three times with ethanol, and dried to obtain a red powder, the target product. The present invention has relatively large mechanotropic ratio discoloration, which can be used as a fluorescent pressure sensing probe, and has the following characteristics: high fluorescence efficiency (44.3%), simple synthesis, quantitative determination of the relationship between pressure and emission wavelength, and large discoloration range , the material has great application potential in pressure sensing systems.

Description

A kind of highly luminescent mechanochromic material from red to near infrared and its preparation method

technical field

The invention belongs to the field of high-luminescence mechanochromic materials, in particular to a preparation method of high-luminescence mechanochromic materials ranging from red to near infrared.

Background technique

In recent years, organic near-infrared (680nm-900nm) fluorescent dyes have been widely used in biological imaging, pressure sensing, infrared It has broad application prospects in the fields of camouflage, anti-counterfeiting detection and fluorescence recognition.

So far, many types of near-infrared fluorescent probes have been reported. According to their structures, these materials can be divided into: stilbene nitriles, difluoroborons, tetraphenylethylenes, aromatic acid cyanines, thiazocyanines, etc. Azines, BODIPYs, etc. For example (Chem.Eur.J.,2014,21,2474-2479) reported a compound pCN-TPA with an electron-donating-electron-withdrawing structure centered on stilbene nitrile, which exhibited The luminescence at 508nm can gradually redshift to 618nm under the action of static pressure, and the redshift can reach 110nm, and it can return to the initial state after the static pressure is released. (Chem.Commun., 2016, 52, 3836-3839) synthesized a cyano-substituted stilbene derivative structure CzCNDSB, with an initial luminescence at 529nm, which can be red-shifted from 155nm to 684nm under the action of external static pressure. Realize the change from green to deep red, and the luminescence can return to the original state after the static pressure is removed. (Angew.Chem.Int.Ed., 2020, 59, 15267-15267) Using the co-crystal strategy, the derivatives of anthracene and fluorobenzene were fumigated with a solvent to obtain a co-crystal, which can Realize luminescence at 554nm, and can redshift 92nm to 646nm (transition from green to red) under the action of static pressure.

However, there are relatively few static piezochromic materials with high fluorescence quantum efficiency and in the near-infrared region. The key to constructing high-contrast near-infrared deep red to near-infrared color-changing range is to suppress the intermolecular π-π interaction under pressure.

Contents of the invention

The present invention aims to solve the problems recorded in the background technology, and provides a preparation method of a high-luminescence mechanochromic material ranging from red to near infrared.

In order to achieve the above object, the present invention adopts the following technical scheme: a preparation method of a high-luminescence mechanochromic material from red to near infrared, comprising the following steps:

Synthesis of step 1, intermediate product 7-triphenylamine-4-formyl benzo[c][1,2,5]thiadiazole:

Weigh 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole, triphenylamine boric acid, tetrakistriphenylphosphopalladium and sodium carbonate, and configure sodium carbonate into sodium carbonate solution, Dissolve the above raw materials in chromatographic toluene and tetrahydrofuran; under the protection of nitrogen atmosphere, reflux and stir the reaction. When a large amount of red solid particles are precipitated, confirm the reaction progress by spotting the plate. If the reaction is complete, stop the reaction; then extract, filter, Column chromatographic separation and rotary evaporation to obtain red powder, that is, 7-triphenylamine-4-formylbenzo[c][1,2,5]thiadiazole;

Step 2, the synthesis of target product:

Dissolve the intermediate product, cholesterol formamidophenylacetonitrile and sodium methoxide in ethanol; under the protection of nitrogen atmosphere, stir the reaction at 60°C, and stop the reaction when a large amount of solid particles are precipitated; then put the ethanol solution of the product into the refrigerator Perform cooling and precipitation, and filter after the solid precipitation is complete. The filter cake obtained by filtration is rinsed with ethanol for 3 times, and dried to obtain a red powder, which is the target product.

The target product is a color-changing dye in the near-infrared region, benzothiadiazole cholesterol carboxamidophenylacetonitrile derivative, and its chemical formula is: C ₆₁ H ₆₇ N ₅ O ₂ S.

In a preferred embodiment of the present invention, the molar ratio of 7-bromo-4-formylbenzo[c][1,2,5]thiadiazole to triphenylamine boric acid is 1:1-1:1.5; 7 -Bromo-4-formyl benzo[c][1,2,5]thiadiazole:sodium carbonate:toluene:tetrahydrofuran ratio is: 10mmol:0.8-1.2mmol:50-60ml:30-40ml, wherein The concentration of sodium carbonate solution is 3mol/L.

In a preferred embodiment of the present invention, in step 1, the reflux stirring reaction time is 12-24 hours, and the reaction temperature is 80-100°C.

In a preferred embodiment of the present invention, the extract is dichloromethane, and the eluent for column chromatography is petroleum ether and dichloromethane.

In a preferred embodiment of the present invention, in step 2, the mol ratio of cholesterol formamidophenylacetonitrile and intermediate product is 1:1-1:1.3; Cholesterol formamidophenylacetonitrile: sodium methylate: chromatographic ethanol is 3mmol: 0.3-0.6mmol: 30-50ml.

In a preferred embodiment of the present invention, in step 2, the stirring reaction time is 10-12h.

In a preferred embodiment of the present invention, in step 2, the temperature in the refrigerator is -10-0° C., and the time for putting in the refrigerator is 2-3 hours.

In a preferred embodiment of the present invention, in step 2, the volume molar ratio of ethanol and cholesterol carboxamidophenylacetonitrile used for each rinsing is 2:1, and the number of rinsing times is 3-6 times.

In a preferred embodiment of the present invention, a high-luminescence mechanochromic material ranging from red to near-infrared prepared by the above method is applied to a pressure detection material.

The principle of the present invention and its beneficial effects: the static pressure-induced proportional color-changing material provided by the present invention has obvious color changes (red becomes near infrared), and is sensitive to external stimuli. The color changes ratiometrically and can be used in pressure sensing elements and optical recording.

Molecules form a unique dimer stack when they aggregate, and non-conjugated cholesterol can inhibit the strong π-π interaction between molecules during the tight packing process.

Compared with the prior art, the fluorescence efficiency of most near-infrared fluorescent molecules is low, and the synthesis is relatively complicated. The near-infrared fluorescent molecules of the present invention have high fluorescence efficiency (44.3%), produce a 157nm spectral red shift, and are simple to synthesize, which will greatly enhance the The application potential of materials in the field of pressure detection.

Additional aspects and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention.

Description of drawings

The above and/or additional aspects and advantages of the present invention will become apparent and understandable from the description of the embodiments in conjunction with the following drawings, wherein:

Fig. 1 is the fluorescence spectrogram of static pressure-induced ratiometric discoloration of near-infrared benzothiadiazole cholesterol carboxamidophenylacetonitrile fluorescent dye under 0atm-2.0GPa;

Fig. 2 is the fluorescence spectrogram of the near-infrared benzothiadiazole cholesterol carboxamidophenylacetonitrile fluorescent dye static pressure-induced ratiometric discoloration under the pressure of 2.6-7GPa;

Fig. 3 is a graph showing the relationship between the static pressure and the spectrum of the near-infrared benzothiadiazole cholesterol carboxamidophenylacetonitrile fluorescent dye of the present invention.

Figure 4 is the unique dimer packing that molecules form.

Detailed ways

Embodiments of the present invention are described in detail below, and examples of the embodiments are shown in the drawings, wherein the same or similar reference numerals denote the same or similar elements or elements having the same or similar functions throughout. The embodiments described below by referring to the figures are exemplary only for explaining the present invention and should not be construed as limiting the present invention.

In describing the present invention, it should be understood that the terms "longitudinal", "transverse", "vertical", "upper", "lower", "front", "rear", "left", "right", The orientations or positional relationships indicated by "vertical", "horizontal", "top", "bottom", "inner", "outer", etc. are based on the orientation or positional relationship shown in the drawings, and are only for the convenience of describing the present invention and simplified descriptions, rather than indicating or implying that the device or element referred to must have a specific orientation, be constructed and operate in a specific orientation, and thus should not be construed as limiting the invention.

In the description of the present invention, unless otherwise specified and limited, it should be noted that the terms "installation", "connection" and "connection" should be understood in a broad sense, for example, it can be mechanical connection or electrical connection, or two The internal communication of each element may be directly connected or indirectly connected through an intermediary. Those skilled in the art can understand the specific meanings of the above terms according to specific situations.

The present application provides a method for preparing a high-luminescence mechanochromic material from red to near-infrared, comprising the following steps:

Step 1, synthesis of intermediate (II) 7-triphenylamine-4-formyl benzo[c][1,2,5]thiadiazole:

Its synthetic route is as follows:

The specific operation is: weigh 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole, triphenylamine boric acid, tetrakistriphenylphosphopalladium and sodium carbonate, and configure the sodium carbonate into Sodium carbonate aqueous solution, the above raw materials are dissolved in chromatographic toluene and tetrahydrofuran, in which, 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole (Ⅲ) and triphenylamine boric acid (Ⅳ) The molar ratio of 1:1-1:1.5; 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole:sodium carbonate:chromatographic toluene:chromatographic tetrahydrofuran is 10mmol:0.8-1.2 mmol: 50-60ml: 30-40ml; under the protection of nitrogen atmosphere, the reaction time of reflux stirring is 12-24h. When a large amount of red solid particles are precipitated, confirm the reaction progress by spotting the plate, and terminate the reaction when it is confirmed that the reaction is basically completed; then The reaction solution was extracted, filtered, separated by silica gel column chromatography, washed with petroleum ether: dichloromethane = 2:1, and rotary evaporated under reduced pressure to obtain a red powder, which is the product intermediate (II);

Step 2, the synthesis of target product (I):

Its synthetic route is as follows:

The specific operation is: take intermediate (Ⅱ), cholesterol formamidophenylacetonitrile (Ⅴ) and sodium methylate and dissolve them in chromatographic ethanol, wherein the molar ratio of cholesterol formamidophenylacetonitrile (Ⅴ) to intermediate (Ⅱ) 1:1-1:1.3; cholesterol formamidophenylacetonitrile (Ⅴ): sodium methoxide: chromatographic ethanol: 3mmol: 0.3-0.6mmol: 30-50ml. Under the protection of nitrogen atmosphere, stir and react at 60°C for 8-12h, and stop the reaction when a large amount of solid particles are precipitated; then put the reaction system into the refrigerator at -20-0°C for 8-10h, then filter the filter cake, and use ethanol to filter the cake Rinse 3-6 times, the volume molar ratio (L/mol) of ethanol and cholesterol carboxamidophenylacetonitrile used for each rinsing is 2:1, obtain red powder after drying, namely target product benzothiadiazole Cholesterol formamidophenylacetonitrile derivatives (I). Wherein, (I) molecular weight 933.5g/mol; (II) molecular weight 407g/mol; (V) molecular weight 544g/mol;

Material (II) and (V) feed ratio control 1:1 or (II) is slightly excessive, but not more than 1:1.3; The amount control range of catalyst sodium methoxide is: cholesterol formamidophenylacetonitrile (V): sodium methoxide = 1mmol: 0.1-0.2mmol. Many near-infrared fluorescent molecules have been reported before, and these molecules generally have low fluorescence quantum efficiency, and there is a problem of complex synthesis, while the target molecule in the present invention has a high fluorescence quantum efficiency, and the synthesis is simple, which greatly increases the Great application potential as a pressure sensing system.

The experimental method is as follows:

Experimental method 1

Step 1, synthesis of intermediate (Ⅱ): Weigh 1.3g (6mmol) of 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole (Ⅲ), triphenylamine boronic acid (Ⅳ ) 1.8g (6.2mmol), tetrakistriphenylphosphopalladium 0.25g (0.22mmol) and sodium carbonate solution (3mol/L) were dissolved in chromatographic toluene (50ml) and tetrahydrofuran (30ml), under nitrogen atmosphere protection, 80 The reaction time was 12 hours under reflux and stirring at ℃. When a large amount of red solid particles were precipitated, the plate was spotted to determine the reaction progress, and the reaction was terminated. After the reaction, all the crude products were dissolved with dichloromethane, transferred, washed with water, and the organic phase was taken, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the powdered product and the coarse silica gel powder were mixed and loaded into the column In this method, the ratio of dichloromethane and petroleum ether 1:2 was used as the eluent for column chromatography to obtain 1.68 g of the product intermediate (Ⅱ), with a yield of 70%.

Step 2. Weigh 0.2g (0.55mmol) of intermediate (II), 0.31g (0.55mmol) of cholesterol formamidophenylacetonitrile (V) and 0.054g (1mmol) of sodium methoxide and dissolve them in 40ml of chromatographic ethanol. Under the protection of nitrogen atmosphere, the reaction was stirred at 60° C. for 10 h, and the reaction was terminated when a large amount of solid particles were precipitated. Then put the ethanol solution of the product into -10°C refrigerator for 2h, and filter after the solid precipitation was complete, and rinse the filter cake obtained by filtration with ethanol (20mL×3) times, and obtain a total of 0.30g of red powder after drying. The rate is 63.6%. , that is, the target product benzothiadiazole cholesterol carboxamidophenylacetonitrile derivative (I).

The characterization data are as follows: ¹ H NMR (400MHz, CDCl ₃ ) δ8.72(d, J=7.6Hz, 1H), 8.49(s, 1H), 7.94(d, J=8.8Hz, 2H), 7.84(d, J=7.6Hz, 1H), 7.79(d, J=8.8Hz, 2H), 7.54(d, J=8.8Hz, 2H), 7.34(t, J=8.4Hz, 4H), 7.23(m, 6H) ,7.11(t,J=7.6Hz,2H),6.77(s,1H),5.44(d,J=4.8Hz,1H),4.67(m,1H),2.41(m,2H),1.61(m, 12H), 1.36(m, 3H), 1.16(m, 8H), 1.07(m, 6H), 0.94(d, J=6.4Hz, 3H), 0.89(dd, J=2.0Hz, J=1.6Hz, 6H), 0.71(s, 3H); [M]+934.4986.

Experimental method 2

Step 1, synthesis of intermediate (II): Weigh 2.11 g (10 mmol) of 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole (III), triphenylamine boronic acid (IV ) 2.89g (10mmol), 0.25g (0.22mmol) of tetraphenylphosphorous palladium and sodium carbonate solution (3mol/L) were dissolved in chromatographic toluene (50ml) and tetrahydrofuran (30ml), under nitrogen atmosphere protection, 100 ℃ The reaction time was 20 h under reflux and stirring. When a large amount of red solid particles were precipitated, the plate was confirmed to confirm the reaction progress, and the reaction was terminated. After the reaction, all the crude products were dissolved with dichloromethane, transferred, washed with water, and the organic phase was taken, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the powdered product and the coarse silica gel powder were mixed and loaded into the column In this method, the ratio of dichloromethane and petroleum ether 1:2 was used as the eluent for column chromatography to obtain 3.2 g of the product intermediate (Ⅱ), with a yield of 78.6%.

Step 2. Weigh 0.795g (1.95mmol) of intermediate (II), 0.816g (1.5mmol) of cholesterol formamidophenylacetonitrile (V) and 0.008g (0.15mmol) of sodium methoxide and dissolve them in 50ml of chromatographic ethanol. Under the protection of nitrogen atmosphere, the reaction was stirred at 60° C. for 10 h, and the reaction was terminated when a large amount of solid particles were precipitated. Then put the ethanol solution of the product in a refrigerator at 0°C for 3 hours, and filter after the solid precipitation is complete. The filter cake obtained by filtration is rinsed with ethanol (20mL×5) times, and after drying, a total of 1.1g of red powder is obtained. was 89.1%. , that is, the target product benzothiadiazole cholesterol carboxamidophenylacetonitrile derivative (I).

Experimental method 3

Step 1, synthesis of intermediate (II): Weigh 1.06 g (5 mmol) of 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole (III), triphenylamine boronic acid (IV ) 1.70g (7.5mmol), tetrakistriphenylphosphopalladium 0.25g (0.22mmol) and sodium carbonate solution (3mol/L) were dissolved in chromatographic toluene (60ml) and tetrahydrofuran (40ml), under nitrogen atmosphere protection, 90 The reaction time was 20 h under reflux and stirring at ℃. When a large amount of red solid particles were precipitated, the plate was spotted to determine the reaction progress, and the reaction was terminated. After the reaction, all the crude products were dissolved with dichloromethane, transferred, washed with water, and the organic phase was taken, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the powdered product and the coarse silica gel powder were mixed and loaded into the column In this method, the ratio of dichloromethane and petroleum ether 1:2 was used as the eluent for column chromatography to obtain 1.65 g of the product intermediate (Ⅱ), with a yield of 80.5%.

Step 2. Weigh 0.619g (1.52mmol) of intermediate (II), 0.4265g (1.5mmol) of cholesterol formamidophenylacetonitrile (V) and 0.016g (0.3mmol) of sodium methoxide and dissolve them in 40ml of chromatographic ethanol. Under the protection of nitrogen atmosphere, the reaction was stirred at 60° C. for 11 h, and the reaction was terminated when a large amount of solid particles were precipitated. Then put the ethanol solution of the product into -20 ℃ refrigerator for 10h to cool and precipitate, and filter after the solid precipitation is complete, and filter the filter cake obtained by filtering with ethanol (20mL×4) times, and dry to obtain a red powder with a total of 1.02 g, the yield is 73%. , that is, the target product benzothiadiazole cholesterol carboxamidophenylacetonitrile derivative (I).

Experimental method 4

Step 1, synthesis of intermediate (II): Weigh 2.11 g (10 mmol) of 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole (III), triphenylamine boronic acid (IV ) 2.92g (10.1mmol), tetrakistriphenylphosphopalladium 0.25g (0.22mmol) and sodium carbonate solution (3mol/L) were dissolved in chromatographic toluene (55ml) and tetrahydrofuran (40ml), under nitrogen atmosphere protection, 95 The reaction time was 24 hours under reflux and stirring at ℃. When a large amount of red solid particles were precipitated, the reaction process was determined by spotting the plate, and the reaction was terminated. After the reaction, all the crude products were dissolved with dichloromethane, transferred, washed with water, and the organic phase was taken, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the powdered product and the coarse silica gel powder were mixed and loaded into the column In the process, the ratio of dichloromethane and petroleum ether 1:2 was used as the eluent for column chromatography to obtain 3.4 g of the product intermediate (Ⅱ), with a yield of 76%.

Step 2. Weigh 0.619g (1.52mmol) of intermediate (II), 0.816g (1.5mmol) of cholesterol formamidophenylacetonitrile (V) and 0.054g (1mmol) of sodium methoxide and dissolve them in 30ml of chromatographic ethanol. Under the protection of nitrogen atmosphere, the reaction was stirred at 60° C. for 12 h, and the reaction was terminated when a large amount of solid particles were precipitated. Then put the ethanol solution of the product in a -10°C refrigerator for 10 hours, and filter after the solids were completely precipitated. The filter cake obtained by filtering was rinsed with ethanol (20mL×6) times, and after drying, a total of 0.954g of red powder was obtained. The rate is 68.0%. , that is, the target product benzothiadiazole cholesterol carboxamidophenylacetonitrile derivative (I).

The above experimental mode 1 to experimental mode 4, the target product benzothiadiazole cholesterol carboxamidophenylacetonitrile derivatives (I) obtained, as shown in Figure 4, the molecules formed a unique dimer stacking, in n-hexane In the mixed solution of tetrahydrofuran/tetrahydrofuran, red flaky crystals were obtained by solvent volatilization, and the emission spectra under different pressures were explored, and the relationship between the intensity and wavelength of the fluorescence emission spectrum and the static pressure was roughly clarified, as shown in Figure 1 and Figure 2 As shown: the crystal can emit red to near-infrared fluorescence. As the pressure increases, the fluorescence intensity decreases continuously, and the color of the fluorescence gradually changes from red to near-infrared. This phenomenon indicates that this material can be used in the field of pressure sensors or information storage. In addition, the spectrum is processed to obtain the peak position of the luminescence, and the linear fitting is obtained to obtain the relationship between the static pressure and the peak position of the fluorescence emission spectrum, as shown in Figure 3: in the process of increasing the static pressure, the luminescence of the red crystal gradually turns red shift, and its luminous position has a certain linear relationship with the static pressure. The relationship between pressure and spectrum is 22.1nm/GPa, and the wavelength change is 157nm. This material can be used for pressure sensing elements.

In summary, the static pressure-induced proportional color-changing material provided by the present invention has obvious color changes (as shown in Figure 3, at 1atm-7Gpa, as the pressure increases, the wavelength redshifts from 650nm to 806nm, and the redshift reaches 156nm, by red to near-infrared, so the color change is obvious), and is sensitive to external stimuli (as can be seen from the spectrograms in Figures 1 and 2, as the pressure increases, the fluorescence intensity decreases significantly). It produces a ratiometric change in color upon application of static pressure and is used in pressure sensing elements and optical recording.

Most near-infrared fluorescent molecules have low fluorescence efficiency, and the synthesis is relatively complicated. The near-infrared fluorescent molecule of the present invention has high fluorescence efficiency (44.3%) and simple synthesis, which greatly increases the huge application potential as a pressure sensing system

In the description of this specification, descriptions referring to the terms "preferred embodiment", "one embodiment", "some embodiments", "examples", "specific examples" or "some examples" etc. mean that the embodiments are combined A specific feature, structure, material, or characteristic described by or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiment or example. Furthermore, the specific features, structures, materials or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.

Although the embodiments of the present invention have been shown and described, those skilled in the art can understand that various changes, modifications, substitutions and modifications can be made to these embodiments without departing from the principle and spirit of the present invention. The scope of the invention is defined by the claims and their equivalents.

Claims (10)

1. A method for preparing a high-luminescence mechanochromic material from red to near-infrared, comprising the following steps: step 1, intermediate product 7-triphenylamine-4-formyl benzo[c][1, Synthesis of 2,5]thiadiazole, the structural formula of 7-triphenylamine-4-formyl benzo[c][1,2,5]thiadiazole is: Weigh 7-bromo-4-formyl benzo[c][1,2,5]thiadiazole, triphenylamine boric acid, tetrakistriphenylphosphopalladium and sodium carbonate, and configure sodium carbonate into sodium carbonate solution, Dissolve the above raw materials in chromatographic toluene and tetrahydrofuran; under the protection of nitrogen atmosphere, reflux and stir the reaction. When a large amount of red solid particles are precipitated, confirm the reaction progress by spotting the plate. If the reaction is complete, stop the reaction; then extract, filter, Column chromatographic separation and rotary evaporation to obtain red powder, that is, 7-triphenylamine-4-formylbenzo[c][1,2,5]thiadiazole; Step 2, the synthesis of target product: Dissolve the intermediate product, cholesterol formamidophenylacetonitrile and sodium methoxide in chromatographic ethanol; under the protection of nitrogen atmosphere, stir the reaction at 60°C, and stop the reaction when a large amount of solid particles are precipitated; then put the chromatographic ethanol solution of the product Put it into the refrigerator for cooling and precipitation, and filter after the solid precipitation is complete. The filter cake obtained by filtration is rinsed with ethanol for 3 times, and after drying, a red powder is obtained, which is the target product. Diazole cholesterol formamidophenylacetonitrile derivatives; the structural formula of benzothiadiazole cholesterol formamidophenylacetonitrile derivatives is: Wherein: the structural formula of cholesteryl formamidophenylacetonitrile is: 2. the preparation method of the high-luminescence mechanochromic material from red to near-infrared as claimed in claim 1, it is characterized in that, 7-bromo-4-formyl benzo[c][1,2,5]thiophene The molar ratio of oxadiazole to triphenylamine boronic acid is 1:1-1:1.5; the amount of 7-bromo-4-formylbenzo[c][1,2,5]thiadiazole: sodium carbonate: toluene: tetrahydrofuran The ratio is: 10mmol:0.8-1.2mmol:50-60ml:30-40ml, wherein the concentration of sodium carbonate solution is 3mol/L. 3. The method for preparing high-luminescence mechanochromic materials ranging from red to near-infrared according to claim 2, characterized in that in step 1, the reflux stirring reaction time is 12-24 hours, and the reaction temperature is 80-100°C. 4. as claimed in claim 3 by the preparation method of the high luminescence mechanochromic material of red to near-infrared, it is characterized in that, extract is methylene chloride, and the eluent of column chromatography separation is sherwood oil and methylene dichloride . 5. as claimed in claim 4 from red to the preparation method of near-infrared high-luminescence mechanochromic material, it is characterized in that, in step 2, the mol ratio of cholesteryl formamidophenylacetonitrile and intermediate product is 1:1- 1:1.3; Cholesterol formamidophenylacetonitrile: sodium methoxide: chromatographic ethanol is 3mmol: 0.3-0.6mmol: 30-50ml. 6. The method for preparing a high-luminescence mechanochromic material from red to near-infrared according to claim 5, characterized in that, in step 2, the stirring reaction time is 10-12h. 7. The method for preparing a high-luminescence mechanochromic material from red to near-infrared as claimed in claim 6, wherein in step 2, the temperature in the refrigerator is -10-0°C, and the time to put it into the refrigerator is 2-3h. 8. the preparation method of the high-luminescence mechanochromic material from red to near-infrared as claimed in claim 7, it is characterized in that, in step 2, the ethanol that each rinsing is used and the volume mole of cholesterol formamidophenylacetonitrile The ratio is 2:1, and the number of rinses is 3-6 times. 9. A C ₆₁ H ₆₇ N ₅ O ₂ S prepared by any one of the methods of claims 1-8, whose structural formula is: 10. A high-luminescence mechanochromic material from red to near-infrared prepared by any one of the methods of claims 1-8 applied to a pressure detection material.