CN115043743B - Substituted triphenylamine aldehyde, preparation method and application - Google Patents

Substituted triphenylamine aldehyde, preparation method and application Download PDF

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CN115043743B
CN115043743B CN202210870532.5A CN202210870532A CN115043743B CN 115043743 B CN115043743 B CN 115043743B CN 202210870532 A CN202210870532 A CN 202210870532A CN 115043743 B CN115043743 B CN 115043743B
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triphenylamine
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substituted triphenylamine
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CN115043743A (en
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马恒昌
孙雨晴
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Northwest Normal University
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Abstract

The invention discloses a substituted triphenylamine aldehyde and a preparation method thereof, which can be used for a mechanoluminescence organic material, has high fluorescence quantum yield and better crystallization performance, has stable crystal structure and still has high mechanoluminescence performance after being ground for a plurality of times; the invention connects different alkyl groups at the 4-position substitution site of triphenylamine aldehyde, adjusts the molecular stacking structure of the triphenylamine aldehyde, and can obtain the high-sensitivity electroluminescent organic material. And applies the method to fluorescence visualization metal deformation detection.

Description

Substituted triphenylamine aldehyde, preparation method and application
Technical Field
The invention relates to the technical field of organic luminescent materials, in particular to a substituted triphenylamine aldehyde mechanoluminescence material, a preparation method and application thereof.
Background
The mechanism of the mechanoluminescence phenomenon is mainly the piezoelectric effect. For non-centrosymmetric crystals, the crystals fracture under mechanical stimulation, and the surface of the crack accumulates opposite charges, forming an electric field, which generates light by electron bombardment. For a centrosymmetric crystal, the solid surface during the crystal fracture emits electrons, ions and neutral species, which recombine on the crack surface due to the neutralization of the charge and generate energy which causes the molecule to be in an excited state, which produces a "mechanoluminescence" ML phenomenon when transitioning back to the ground state by radiation.
Through extensive research, it was found that the molecular stacking means and intermolecular interactions are critical to whether a molecule has ML behaviour. Generally, the intermolecular interaction is strong and the stacking mode is compact, so that energy loss caused by molecular slippage possibly occurring under the action of external force is avoided, non-radiative transition under the stimulation of external force is restrained, and the generation of ML phenomenon is promoted. However, if the molecules are too tightly packed, the crystals are not easily broken due to the strong rigidity, but rather result in weaker ML. Therefore, it is important to study at present to regulate the molecular stacking mode and intermolecular interaction by reasonable molecular design so as to obtain excellent ML performance.
Disclosure of Invention
The invention aims to provide a substituted triphenylaldehyde mechanoluminescence material and a preparation method thereof, which have stable crystal structure and high fluorescence quantum yield.
A substituted triphenylamine aldehyde having the following general formula (I):
Figure BDA0003760540630000011
wherein R is saturated fatty alkyl (CH 3) n -, wherein n is less than 4.
Specifically, R is hydrogen, methyl, isopropyl, tert-butyl respectively.
A process for preparing substituted triphenylamine aldehyde includes such steps as reacting N, N-dimethylformamide, catalyst and R-substituted triphenylamine to obtain compound of general formula (I).
Specifically, the catalyst is one of phosphorus oxychloride, oxalyl chloride, zinc chloride and thionyl chloride
Specifically, the molar ratio of R-substituted triphenylamine, phosphorus oxychloride and N, N-dimethylformamide is 1: 8-12: 18-22, the reaction temperature is 40-50 ℃ and the reaction time is 3h.
Specifically, when R is isopropyl or tert-butyl, R-substituted triphenylamine is obtained by taking 4-R bromobenzene and aniline as raw materials through Buchwald-Hartwig coupling reaction, wherein R is isopropyl or tert-butyl.
Specifically, when the R-substituted triphenylamine is 4, 4-diisopropyl triphenylamine, the preparation of the 4, 4-diisopropyl triphenylamine comprises the steps of mixing aniline, 4-isopropyl bromobenzene, tri-tert-butyl phosphine tetrafluoroborate and tri (dibenzylideneacetone) dipalladium according to a molar ratio of 1:2.2:0.02:0.01, the reaction temperature is 110-120 ℃ and the time is 12h, and 4, 4-diisopropyl triphenylamine is obtained by extraction and purification.
Specifically, when the R-substituted triphenylamine is 4, 4-di-tert-butyltriphenylamine, the molar ratio of the aniline, 4-tert-butylbromobenzene, tri-tert-butylphosphinothiotetraborate and tris (dibenzylideneacetone) dipalladium is 1:2.2:0.02:0.01, the reaction temperature is 110-120 ℃ and the time is 12 hours, and 4, 4-di-tert-butyl triphenylamine is obtained through extraction and purification.
The substituted triphenylamine aldehyde obtained by the invention is applied to the field of luminescence of the mechanoluminescence material, and the mechanoluminescence material can be applied to damage detection, stress sensing and imaging, anti-counterfeiting encryption and the like.
The invention has the beneficial effects that:
the saturated fatty alkane substituted triphenylamine aldehyde power-induced luminescence organic material provided by the invention has high fluorescence quantum yield and good crystallization performance, and has stable crystal structure and high power-induced luminescence performance after being ground for a plurality of times; the invention connects different alkyl groups at the 4-position substitution site of triphenylamine aldehyde, adjusts the molecular stacking structure of the triphenylamine aldehyde, and can obtain the high-sensitivity electroluminescent organic material. And applies the method to fluorescence visualization metal deformation detection.
Drawings
FIG. 1 is a graph showing the variation of fluorescence spectra of the compounds of examples 1-4 in acetonitrile/water mixed solutions of different proportions;
FIG. 2 is an I/I of the compounds of examples 1-4 in an acetonitrile/water mixture 0 (I is the maximum fluorescence emission intensity under different water integral numbers, I) 0 Maximum fluorescence emission intensity at 0 water volume fraction) versus fw
FIG. 3 is a photograph of the mechanoluminescence of the compounds of examples 1-4;
FIG. 4 is the material electrochemiluminescence spectrum of the compounds of examples 1-4;
FIG. 5 is a photograph showing the deformation of a metal sample detected by the compounds of examples 1 to 4.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
A substituted triphenylamine aldehyde having the following general formula (I):
Figure BDA0003760540630000031
wherein R is saturated fatty alkyl (CH 3) n -, wherein n is less than 4. Specifically, R is hydrogen, methyl, isopropyl, tert-butyl respectively. When the fatty chain is too long, the flexible fatty chain may cause a decrease in crystallization properties of the molecule, even in a liquid state. Selecting saturated fats with n less than 4The reason for fatty alkyl groups is the gradual transition from a less sterically hindered hydrogen atom to a more sterically hindered tertiary butyl group. Compared with tertiary butyl, methyl isopropyl has similar main structure, and only has different numbers of replaced hydrogen atoms, and the influence of molecular accumulation on the mechanoluminescence performance is explored through regulating and controlling the size of a steric hindrance group.
A process for preparing substituted triphenylamine aldehyde includes such steps as reacting N, N-dimethylformamide, catalyst and R-substituted triphenylamine to obtain compound of general formula (I).
Vilsmeier-Haack reaction, the reaction of formylating an aromatic compound containing an active aromatic ring with a di-substituted carboxamide phosphoryl chloride on the aromatic ring in the presence of a catalyst (typically phosphorus oxychloride: POCl 3) is referred to as Vilsmeier reaction, also referred to as Vilsmeier-Haack reaction.
The catalyst is one of phosphorus oxychloride, oxalyl chloride, zinc chloride and thionyl chloride,
specifically, the molar ratio of R-substituted triphenylamine, phosphorus oxychloride and N, N-dimethylformamide is 1: 8-12: 18-22, the reaction temperature is 40-50 ℃ and the reaction time is 3h.
Specifically, when R is isopropyl or tert-butyl, R-substituted triphenylamine is obtained by taking 4-R bromobenzene and aniline as raw materials through Buchwald-Hartwig coupling reaction, wherein R is isopropyl or tert-butyl.
Specifically, when the R-substituted triphenylamine is 4, 4-diisopropyl triphenylamine, the preparation of the 4, 4-diisopropyl triphenylamine comprises the steps of mixing aniline, 4-isopropyl bromobenzene, tri-tert-butyl phosphine tetrafluoroborate and tri (dibenzylideneacetone) dipalladium according to a molar ratio of 1:2.2:0.02:0.01, the reaction temperature is 110-120 ℃ and the time is 12h, and 4, 4-diisopropyl triphenylamine is obtained by extraction and purification.
Specifically, when the R-substituted triphenylamine is 4, 4-di-tert-butyltriphenylamine, the molar ratio of the aniline, 4-tert-butylbromobenzene, tri-tert-butylphosphinothiotetraborate and tris (dibenzylideneacetone) dipalladium is 1:2.2:0.02:0.01, the reaction temperature is 110-120 ℃ and the time is 12 hours, and 4, 4-di-tert-butyl triphenylamine is obtained through extraction and purification.
The substituted triphenylamine aldehyde obtained by the invention is applied to the field of luminescence of the mechanoluminescence material, and the mechanoluminescence material can be applied to damage detection, stress sensing and imaging, anti-counterfeiting encryption and the like.
Example 1
Triphenylamine (2.5 g,10.19 mmol) and N, N-dimethylformamide (8 mL) are added into a 50mL three-neck round bottom flask, phosphorus oxychloride (8 mL) is added dropwise under the protection of nitrogen and stirring in an ice bath, the temperature is raised to 40 ℃ after the dropwise addition, the reaction is carried out for 3 hours, the reaction solution is poured into 500mL distilled water, unreacted phosphorus oxychloride is removed, the mixed solution is filtered by suction, the filter residue is extracted by dichloromethane and water, the organic phase is extracted, dried by anhydrous magnesium sulfate, concentrated after the suction filtration, the mixture is stirred by silica gel, the mixture is subjected to column chromatography separation, petroleum ether and ethyl acetate (volume ratio is 100:1) are taken as eluent, and the white solid compound 1 is obtained, the yield of which is 82.2 percent
Example 2
Methyl triphenylamine (1.1 g,4 mmol) and N, N-dimethylformamide (4 mL) are added into a 50mL three-neck round bottom flask, phosphorus oxychloride (4 mL) is added dropwise under the protection of nitrogen and stirring in an ice bath, the temperature is raised to 40 ℃ after the dropwise addition, the reaction is carried out for 3 hours, the reaction solution is poured into 500mL distilled water, unreacted phosphorus oxychloride is removed, the mixed solution is filtered by suction, the filter residue is extracted by dichloromethane and water, the organic phase is extracted, dried by anhydrous magnesium sulfate, concentrated after the suction filtration, silica gel is used for stirring, column chromatography separation method is used for column chromatography, petroleum ether and ethyl acetate (volume ratio is 100:1) are used as eluent, and the white solid compound 2 is obtained, the yield is 82.5 percent
Example 3
Into a 100mL double flask were added aniline (1.1 g,11.4 mmol), 4-isopropyl bromobenzene (5 g,25.1 mmol), t-Buona (3.6 g,37.6 mmol), pd 2 (dba) 3 (348 mg,0.228 mmol), tri-tert-butylphosphine tetrafluoroborate (133 mg, 0.458 mL) under argon. Toluene (35 mL) was then dried by flash evaporation and refluxed overnight with stirring. After the reaction, cooling to room temperature, and evaporating toluene. The obtained solid methylene chloride is dissolved, extracted by adding water, dried by magnesium sulfate, filtered by suction and concentrated. The crude product was purified by flash column chromatography (silica gel) eluting with petroleum ether/ethyl acetate (volume ratio 50:1) to give the product 4, 4-diisopropylester as a white solidTriphenylamine.
Adding 4, 4-isopropyl triphenylamine (0.3 g,4 mmol) and N, N-dimethylformamide (4 mL) into a 50mL three-port round bottom flask, dropwise adding phosphorus oxychloride (4 mL) under nitrogen protection and ice bath stirring, heating to 40 ℃ after the dropwise addition, reacting for 3 hours, pouring the reaction solution into 500mL distilled water, removing unreacted phosphorus oxychloride, filtering the mixed solution, extracting the filter residue with dichloromethane and water, extracting an organic phase, drying with anhydrous magnesium sulfate, concentrating after the filtering, stirring with silica gel, passing through a column chromatography separation method, and using petroleum ether and ethyl acetate (volume ratio is 100:1) as a eluent to obtain a pale yellow solid compound 3, wherein the yield is 70.5 percent
Example 4
Into a 100mL double flask were charged aniline (1.1 g,11.4 mmol), 4-tert-butylbromobenzene (5.35 g,25.1 mmol), t-Buona (3.6 g,37.6 mmol), pd 2 (dba) 3 (348 mg,0.228 mmol), tri-tert-butylphosphine tetrafluoroborate (133 mg, 0.458 mL) under argon. Toluene (35 mL) was then dried by flash evaporation and refluxed overnight with stirring. After the reaction, cooling to room temperature, and evaporating toluene. The obtained solid methylene chloride is dissolved, extracted by adding water, dried by magnesium sulfate, filtered by suction and concentrated. The crude product was purified by flash column chromatography (silica gel) eluting with petroleum ether/ethyl acetate (volume ratio 50:1) to give the product tert-butyltriphenylamine as a white solid.
Tert-butyltriphenylamine (0.3 g,4 mmol) and N, N-dimethylformamide (4 mL) are added into a 50mL three-neck round bottom flask, phosphorus oxychloride (4 mL) is added dropwise under the protection of nitrogen and stirring in an ice bath, the temperature is raised to 40 ℃ after the dropwise addition, the reaction is carried out for 3 hours, the reaction solution is poured into 500mL distilled water, unreacted phosphorus oxychloride is removed, the mixed solution is filtered by suction, the filter residue is extracted by dichloromethane and water, the organic phase is extracted, dried by anhydrous magnesium sulfate, concentrated after the suction filtration, the mixture is stirred by silica gel, the mixture is subjected to column chromatography separation, petroleum ether and ethyl acetate (volume ratio is 100:1) are taken as eluent, and a pale yellow solid compound 4 is obtained, the yield of which is 73 percent
Figure BDA0003760540630000051
Performance testing
The compound 4 prepared in example 4 was used for performance testing to characterize the relationship between the aggregation state and the mechanoluminescence performance.
Compound 4 was first configured to 1X 10 -5 The fluorescence emission spectrum of the acetonitrile solution of mol/L in a dilute solution state is tested by a fluorescence spectrometer. Meanwhile, the fluorescence spectrum of the compound 4 in a crystal state is tested by a fluorescence spectrometer, and in order to further study the aggregation state behavior of the compound 4, the fluorescence spectrum of the compound 4 in a mixed solvent of different acetonitrile/water is tested. The poor solvent (water) was added to the good solvent (acetonitrile), and the aggregation state of the molecules was changed, and the fluorescence spectrum was also changed, so that the influence of the aggregation of the molecules on the photoluminescence wavelength and fluorescence intensity was studied by this change. The results are shown in FIG. 1 (four plots 1-4 show the total water fraction f for compounds 1-4, respectively) w Photoluminescence spectra tested at 0-95% respectively). As the water content increases, the fluorescence intensity of compounds 1 to 4 shows a gradual decrease (distorted intramolecular charge transfer effect) followed by a gradual increase (AIE phenomenon), and the results indicate that compounds 1 to 4 are typical AIE molecules. FIG. 2 is a line graph showing I/I in acetonitrile/water mixture as 1-4 0 (I is the maximum fluorescence emission intensity under different water integral numbers, I) 0 Maximum fluorescence emission intensity at 0 water volume fraction) and f w Is a graph of the relationship of (1).
The mechanochromatic luminescence spectra of compounds 1-4 were tested using a marine optical CCD and the results are shown in FIG. 4 (the mechanochromatic luminescence spectra of compounds 1-4 under two different forces).
The material was processed into a desired shape using wire cut electric discharge 316L stainless steel, and then sequentially sanded with 400, 600, 800, 1000, 1500, 2000 mesh sandpaper on a sample grinder, and then the metal surface was polished with a diamond polish of 0.5 μm until scratches disappeared. 0.5g of the powder of the mechanoluminescence molecule 4 was dissolved in 5mL of methylene chloride solvent, and a 316L stainless steel sample was immersed in the solution so that the mechanoluminescence molecule 4 was uniformly adhered to the surface of the sample. The result is shown in FIG. 5 (visual metal deformation schematic)
The above-described embodiments are only illustrative of one of the preferred modes of the present invention, and are not intended to limit the scope of the present invention, and various modifications and improvements made by those skilled in the art to the technical solution of the present invention should fall within the scope of protection defined by the claims of the present invention without departing from the spirit of the design of the present invention.

Claims (7)

1. A substituted triphenylamine aldehyde characterized by the following general formula (I):
Figure FDA0004170326690000011
wherein R is isopropyl.
2. A process for the preparation of the substituted triphenylamine aldehyde of claim 1, wherein: n, N-dimethylformamide, catalyst and R-substituted triphenylamine are reacted by Vilsmeier-Haack to give the compound of formula (I).
3. A process for the preparation of a substituted triphenylamine aldehyde as defined in claim 2, wherein: the catalyst is one of phosphorus oxychloride, oxalyl chloride, zinc chloride and thionyl chloride.
4. A process for the preparation of a substituted triphenylamine aldehyde as defined in claim 2, wherein: the molar ratio of the R-substituted triphenylamine, the catalyst and the N, N-dimethylformamide is 1: 8-12: 18-22, the reaction temperature is 40-50 ℃ and the reaction time is 3h.
5. A process for the preparation of a substituted triphenylamine aldehyde as defined in claim 4, wherein: when R is isopropyl, the R-substituted triphenylamine is obtained by taking 4-R bromobenzene and aniline as raw materials through Buchwald-Hartwig coupling reaction, wherein R is isopropyl.
6. A process for the preparation of a substituted triphenylamine aldehyde as defined in claim 5, wherein: when the R-substituted triphenylamine is 4, 4-diisopropyltriphenylamine, the preparation of the 4, 4-diisopropyltriphenylamine comprises the steps of mixing aniline, 4-isopropylbromobenzene, tri-tert-butylphosphine tetrafluoroborate and tris (dibenzylideneacetone) dipalladium according to a molar ratio of 1:2.2:0.02:0.01, the reaction temperature is 110-120 ℃ and the time is 12h, and 4, 4-diisopropyl triphenylamine is obtained by extraction and purification.
7. A mechanoluminescence material comprising the substituted triphenylaldehyde of claim 1.
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