CN119080706B - Synthesis method and application of aggregation-induced emission body with mechanochromic emission property - Google Patents
Synthesis method and application of aggregation-induced emission body with mechanochromic emission propertyInfo
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Abstract
本发明公开了一类具有机械致变色发光性质的α‑氰基乙烯类聚集诱导发射型发光体的合成方法与应用。α‑氰基乙烯类机械致变色荧光团能够在外界机械刺激后立即触发荧光颜色瞬态响应，因此被广泛应用于光敏传感器、有机发光二极管(OLED)、荧光探针、多色快速响应代码和全方位的信息加密系统等领域。该系列化合物合成路线简单，反应产率较高，所使用的原料廉价、易合成，产物热稳定性好，无需特殊的保存条件，整体合成效率高。该方法更易于工业化应用推广。
The present invention discloses a synthesis method and application of a class of α-cyanoethylene aggregation-induced emission-type luminophores with mechanochromic luminescence properties. α-cyanoethylene mechanochromic fluorophores can trigger a transient fluorescence color response immediately after external mechanical stimulation and are therefore widely used in fields such as photosensors, organic light-emitting diodes (OLEDs), fluorescent probes, multi-color rapid response codes, and comprehensive information encryption systems. This series of compounds has a simple synthesis route, a high reaction yield, and uses inexpensive and easily synthesized raw materials. The products have good thermal stability, do not require special storage conditions, and have a high overall synthesis efficiency. This method is more easily promoted for industrial application.
Description
Technical Field
The invention belongs to the technical field of luminescent materials, and in particular relates to a synthesis method and application of an aggregation-induced emission body with mechanochromic emission property
Background
Mechanochromism (MFC) materials are used as hot spots in the research field of novel intelligent materials, and intelligent regulation and control of solid state luminescence performance of the materials are always power to be explored. The research shows that the color-changing materials under the special response mechanism can generate double changes of apparent and fluorescent colors after external stimuli such as extrusion, grinding, friction and the like. However, most organic fluorophores can cause fluorescence quenching due to the tight pi-pi accumulation between solid molecules, so that the application prospect of the organic fluorophores as solid-state emission devices is greatly limited, and the transition from a crystalline phase to an amorphous phase is difficult to realize through a molecular accumulation mode, so that the design of an aggregation-induced emission type luminophore with adjustable appearance or emission color and mechanochromic luminescence property at a solid level is still a outstanding challenge. In 2001, tang Benzhong academy first focused on the concept of induced luminescence (AIE) so that solid molecules in the focused state still maintain good emission properties, and later studies indicate that fluorescence color changes can be induced by mechanical force stimulation. Based on the theoretical research of mechanical color change induced by cyanoethylene functionalization, AIE fluorophor with different color increasing effects is introduced at two sides by utilizing a cyanostilbene core, so that the adjustable mechanical color change effect carrying AIE characteristics is effectively realized, and the method becomes an important strategy for obtaining an ideal intelligent MFC material with the aggregation-induced emission body with the mechanical color change luminescence property.
Disclosure of Invention
The invention aims to introduce a macromolecular AIE (AIE) fluorophore cluster at the tail end of a cyanoethylene unit with excellent mechanochromism effect so as to realize good solid state color change property, designs a Dicyanodiphenylethylene (DCPV) small molecule system with adjustable Intramolecular Charge Transfer (ICT) property between a typical substituent and a core, and provides a simple and effective synthesis strategy for obtaining an aggregation-induced type luminophor with mechanochromism luminescence property. Because they can trigger fluorescent color transient response immediately after external mechanical stimulus, they are widely used in the fields of photosensitive sensors, organic Light Emitting Diodes (OLEDs), fluorescent probes, multi-color fast response codes, and omnibearing information encryption systems. The invention prepares the 4,4 '-dibromo dicyanostilbene (BrDCPV) intermediate by using 4,4' -dibromo diphenyl ketone as a raw material through Knoevenagel condensation reaction, and under the condition of alkali catalysis, brDCPV realizes heating reflux in a toluene and ethanol mixed system, and prepares a class of alpha-cyanoethylene mechanochromic fluorophor through Suzuki coupling reaction, thereby providing a new thought for synthesizing an aggregation-induced emission type illuminant with mechanochromic luminescence property.
In order to further optimize the traditional aggregation-induced emission micromolecules and add unique mechanochromism, the aggregation-induced emission body with mechanochromism luminescence property has the following structural formula:
Wherein R is one of triphenyltriazine, tetraphenyl ethylene and triphenylamine. The alpha-cyanoethylene mechanochromic fluorophore can trigger fluorescent color transient response immediately after external mechanical stimulation, so that the alpha-cyanoethylene mechanochromic fluorophore is widely applied to the fields of photosensitive sensors, organic Light Emitting Diodes (OLED), fluorescent probes, multicolor quick response codes, omnibearing information encryption systems and the like.
In order to prepare the aggregation-induced emission body with the mechanochromic emission property more efficiently, the technical scheme of the invention provides a simple and easy cyanoethylene functional synthesis idea, which comprises the following steps:
And the first step is synthesis. The obtained 4,4' -dibromodicyanostilbene (BrDCPV) intermediate is used as a raw material, brDCPV is heated and refluxed in a toluene and ethanol mixed system under the condition of alkali catalysis, and a class of alpha-cyanoethylene mechanochromic fluorophor is prepared through Suzuki coupling reaction, and the reaction formula is as follows:
And the second step, extraction. After the reaction is finished, extracting the cooled reaction product for 2-3 times by using a good solvent, collecting an organic phase solution, washing the collected organic phase solution with saturated saline water for 2-3 times in sequence, and then drying the organic phase solution with anhydrous magnesium sulfate to obtain a mixed solution of a crude reaction product and the good solvent;
And thirdly, purifying. The mixture of the crude reaction product and the good solvent is distilled under reduced pressure until a small amount of solvent remains, and the pure product is further obtained by a silica gel column chromatography with methylene chloride/petroleum ether (V/v=1:2) as eluent.
The invention uses various raw materials as commercial reagents, has low price, simple intermediate preparation, good thermal stability, no need of special preservation conditions, simple integral synthesis route, higher yield and less pollution.
In order to better prepare the alpha-cyanoethylene mechanochromic fluorophore, the preferable technical scheme is that the molar ratio of the intermediate BrDCPV to the R-pinacol ester in the first step is 1:2.5, the solvent is toluene and ethanol, the reaction temperature is reflux, and the reaction time is 24 hours.
In order to improve the extraction efficiency of the reactant, the preferred technical scheme is that the good solvent in the second step is dichloromethane.
In order to improve the purification efficiency, the preferred technical scheme is that the eluent used for column chromatography purification is dichloromethane and petroleum ether (V/V=1:2), and the product and impurities can be well separated in the system.
In order to better popularize and apply the aggregation-induced emission body with mechanochromic emission property, the aggregation-induced emission body is proposed to be applied to the fields of photosensitive sensors, organic Light Emitting Diodes (OLED), fluorescent probes, multicolor quick response codes, omnibearing information encryption systems and the like.
The invention has the advantages and beneficial effects that:
1. The invention provides an aggregation-induced emission type luminophor with mechanochromatic luminescence property, which further optimizes the traditional aggregation-induced luminescence micromolecules and adds unique mechanochromatic fluorescence color change characteristics, and the series of compounds have potential application values in the fields of photosensitive sensors, organic Light Emitting Diodes (OLED), fluorescent probes, multicolor quick response codes, omnibearing information encryption systems and the like.
2. The invention takes 4,4' -dibromodicyanostilbene as a raw material, realizes heating reflux in a toluene and ethanol mixed system under the condition of alkali catalysis, prepares a class of alpha-cyanoethylene mechanochromic fluorophor through Suzuki coupling reaction, and provides a new thought for synthesizing an aggregation-induced emission type illuminant with mechanochromic luminescence property.
3. The method has the advantages that various raw materials used in the synthesis are cheap and easy to obtain, the preparation of the intermediate is simple, the performance is stable, no special preservation condition is needed, related reagents and solvents are common commercial reagents, the cost is low, the whole synthesis route is simple, the yield is high, the pollution is small, the method comprises three steps of synthesis, extraction and purification, and the purification only needs to be washed by the solvent, so that the method simplifies the synthesis steps compared with other aggregation-induced emission bodies, and is easier to industrially apply and popularize.
Drawings
FIG. 1 is a structure of a synthetic compound;
FIG. 2 is a graph comparing fluorescence emission spectra of TADCPV in different volume ratios of solutions (water and tetrahydrofuran).
FIG. 3 is a fluorescence emission spectrum of TADCPV raw powders by milling-fumigation cycles.
Fig. 4 is a TADCPV solid powder fatigue resistance test.
Detailed Description
The following describes the embodiments of the present invention further with reference to the drawings and examples. The following examples are only for more clearly illustrating the technical aspects of the present invention, and are not intended to limit the scope of the present invention. The procedures, conditions, reagents, experimental methods, test methods, etc. for carrying out the present invention are common knowledge and common knowledge in the art, except for the following specific references, and the present invention is not limited in particular. The data presented in the examples below include specific operations and reaction conditions and products. The purity of the product is analyzed and identified through nuclear magnetism, high-resolution mass spectrum and PXRD powder diffraction technology, and the structure is accurately characterized.
An alpha-cyanoethylene mechanochromic fluorophore having the structural formula:
wherein R is one of triphenyltriazine, tetraphenyl ethylene and triphenylamine.
The synthesis method of the mechanochromism fluorophore with alpha-cyanoethylene comprises the following steps:
And the first step is synthesis. The obtained 4,4' -dibromodicyanostilbene (BrDCPV) intermediate is used as a raw material, brDCPV is heated and refluxed in a toluene and ethanol mixed system under the condition of alkali catalysis, and a class of alpha-cyanoethylene mechanochromic fluorophor is prepared through Suzuki coupling reaction, and the reaction formula is as follows:
And the second step, extraction. After the reaction is finished, extracting the cooled reaction product for 2-3 times by using a good solvent, collecting an organic phase solution, washing the collected organic phase solution with saturated saline water for 2-3 times in sequence, and then drying the organic phase solution with anhydrous magnesium sulfate to obtain a mixed solution of a crude reaction product and the good solvent;
And thirdly, purifying. The mixture of the crude reaction product and the good solvent is distilled under reduced pressure until a small amount of solvent remains, and the pure product is further obtained by a silica gel column chromatography with methylene chloride/petroleum ether (V/v=1:2) as eluent.
In order to better prepare the alpha-cyanoethylene mechanochromic fluorophore, the preferable technical scheme is that the molar ratio of the intermediate BrDCPV to the R-pinacol ester in the first step is 1:2.5, the solvent is toluene and ethanol, the reaction temperature is reflux, and the reaction time is 24 hours.
In order to improve the extraction efficiency of the reactant, the preferred technical scheme is that the good solvent in the second step is dichloromethane.
In order to improve the purification efficiency, the preferred technical scheme is that the eluent used for column chromatography purification is dichloromethane and petroleum ether (V/V=1:2), and the product and impurities can be well separated in the system.
In order to better popularize and apply the aggregation-induced emission body with mechanochromic emission property, the aggregation-induced emission body is proposed to be applied to the fields of photosensitive sensors, organic Light Emitting Diodes (OLED), fluorescent probes, multicolor quick response codes, omnibearing information encryption systems and the like.
Example 1
Taking the synthesis of compound TADCPV as an example, the chemical reaction formula is shown below:
Intermediate BrDCPV (388.3 mg,1 mmol), 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine (1.305 g,3 mmol), K 2CO3 (11.4 g/40mL, 2M) and Pd (PPh 3)4 (115.6 mg,0.1 mmol) were added to toluene (40 mL) and ethanol (20 mL) was added to the mixture, the reaction mixture was then heated to reflux under N 2 for 24 hours, the crude product cooled to room temperature and quenched with water (60 mL), the mixture was extracted with dichloromethane (3X 80 mL), the combined extracts were washed with water and brine, dried over MgSO 4 and concentrated, and the crude product was further purified by silica gel column chromatography with DCM/PE (1:2) as eluent to give 548mg of light yellow solid TADCPV (64.6%; melting point 137-139 ℃ C.).
1H NMR(400MHz,CDCl3,ppm)δH＝7.04–7.14(m,17H,TPE–H),7.38–7.43(t,4H,TPE–H)7.48–7.51(d,2H,J＝8.4Hz,Ar–H),7.65–7.68(m,4H,Ar-H),7.85–7.87(d,J＝8.4Hz,2H,Ar–H);13C NMR(100MHz,CDCl3,ppm):δC＝80.2,114.3,126.4,126.5,126.3,126.9,127.1,127.7,127.9,130.7,131.3,131.4,132.0,132.1,136.2,136.9,137.6,140.2,140.3,143.5,143.6,143.7,143.9 144.7,145.1,174.0,196.0;FAB-MS:m/z calcd for C52H36N4890.3661[M+];found 890.3651[M+].
Example 2
Example 2 differs from example 1 in that intermediate BrDCPV and 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine are fed in a molar ratio of 1:2, example 1 is 1:3, the yield of the target compound TADCPV is 45.2% separated, a portion of starting material BrDCPV remains in the middle, and test data are identical to example 1.
Example 3
Example 3 differs from example 1 in that the molar ratio of intermediate BrDCPV to 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine is 1:2.5, example 1 is 1:3, the yield of the target compound TADCPV is 60.2% and the test data are identical to example 1.
Example 4
Example 4 differs from example 1 in that the reaction temperature was room temperature, the reaction temperature of example 1 was reflux, and the yield of the objective compound TADCPV was isolated in 18%, and the test data were the same as in example 1.
Example 5
Example 5 differs from example 1 in that the reaction temperature was 60 ℃, the reaction temperature was reflux, and the yield of the objective compound TADCPV was isolated as 32.6%, and the test data were the same as in example 1.
Example 5
Example 5 differs from example 1 in that the reaction time was 12 hours, the reaction time was 24 hours in example 1, and the yield of the objective compound TADCPV was isolated in 40.2%, and the test data were the same as in example 1.
Example 6
Example 6 differs from example 1 in that the reaction time was 36 hours, the reaction time was 24 hours in example 1, and the yield of the objective compound TADCPV was isolated in 66.2% and the test data was the same as in example 1.
The drugs used in this example were all commercial chemicals.
Experimental results indicate that example 1 is the best reaction synthesis condition, and that although example 3 yields close to example 1 and example 3 inputs less starting material, example 3 also has some intermediate BrDCPV remaining, not completely reacted, example 6 yields slightly higher than example 1, but suffers from longer reaction times. Thus, the reaction conditions of example 1 were determined to be optimal, i.e., a molar ratio of the main reactants of 1:3, a reaction temperature of reflux, and a reaction time of 24 hours.
Example 7
Aggregation-induced emission and mechanochromism properties of the target compound TADCPV in example 1 were tested:
The first step is to prepare 11 parts of target compound TADCPV of example 1 in the form of solutions with concentration of 1X 10 -7 mol/L, wherein the solvent is a mixture of water (poor solvent) and tetrahydrofuran (good solvent), and the volume ratio of tetrahydrofuran to water is 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, 1:99 respectively;
and secondly, respectively carrying out fluorescence test on 11 parts of solution of the target compound TADCPV by using a fluorescence spectrum analyzer.
The experimental results showed that the peak value of the maximum fluorescence emission intensity of the objective compound TADCPV showed a tendency to be increased with the increase of the volume content of water in the solvent as shown in FIG. 3, and the phenomenon of fluorescence surge was shown when the water content reached 99%, and the maximum peak value of the maximum fluorescence emission intensity was shown to be increased by about 4 times as compared with the THF solution having the initial water content of 0%, and the peak values of the maximum fluorescence emission intensities of the objective compounds TPEDCPV and TPADCPV were also measured by the same method to be increased with the increase of the volume content of water in the solvent, and the maximum fluorescence emission intensity was shown to be increased when the water content was 99%, and the fluorescence ratio was increased by about 20 times and 330 times. The three target compounds prepared by the synthesis method show remarkable aggregation-induced emission enhancement effect.
And thirdly, respectively preparing an original powder sample of three target products, sample powder subjected to mechanical grinding and a sample obtained by dispersing and evaporating a methylene dichloride solvent after grinding, respectively carrying out fluorescence emission wavelength test on a solid sample in three states by utilizing a fluorescence spectrum analyzer, wherein the maximum fluorescence emission peaks of the three target compounds are respectively shown to be blue shifted and then reduced to an initial state, thereby realizing perfect reversible circulation of mechanochromism, and then respectively carrying out 10 times of anti-fatigue test, wherein excellent reversibility is shown, and the three target compounds prepared by the synthesis method disclosed by the invention all show reversible mechanochromism.
The foregoing is merely a preferred embodiment of the present invention, and it should be noted that it will be apparent to those skilled in the art that several modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the scope of the invention.
Claims (6)
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| CN109280033A (en) * | 2017-07-21 | 2019-01-29 | 香港科技大学 | Preparation and application of tetraphenylpyrazine-based nitrile vinyl functionalized AIE molecule |
| CN113912517A (en) * | 2021-10-29 | 2022-01-11 | 河南大学 | A kind of mechanochromic and mechanoluminescent color-changing compound and its preparation method and application |
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| CN109280033A (en) * | 2017-07-21 | 2019-01-29 | 香港科技大学 | Preparation and application of tetraphenylpyrazine-based nitrile vinyl functionalized AIE molecule |
| CN113912517A (en) * | 2021-10-29 | 2022-01-11 | 河南大学 | A kind of mechanochromic and mechanoluminescent color-changing compound and its preparation method and application |
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