CN111808037A - Triazine derivative and synthesis method thereof - Google Patents
Triazine derivative and synthesis method thereof Download PDFInfo
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- CN111808037A CN111808037A CN202010560865.9A CN202010560865A CN111808037A CN 111808037 A CN111808037 A CN 111808037A CN 202010560865 A CN202010560865 A CN 202010560865A CN 111808037 A CN111808037 A CN 111808037A
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Abstract
The invention belongs to the technical field of organic materials, and particularly relates to a triazine derivative and a synthesis method thereof. The triazine derivative comprises 2, 4-dihydroxyalkyl ether-6-hydroxy s-triazine, and the synthesis method comprises the following steps: 1) hydrolyzing the prochlorperazine in a carbonate buffer solution to obtain an intermediate 2-hydroxy-4, 6-dichloro-s-triazine; 2) and adding the intermediate 2-hydroxy-4, 6-dichloros-triazine into a diol monosodium salt solution to obtain a target product 2, 4-dihydroxyalkyl ether-6-hydroxy-s-triazine. The triazine derivatives prepared by the invention are a series of s-triazine derivatives with hydroxyl and hydroxyalkyl, have the characteristics of good alcohol solubility and partial water solubility, so that the pure organic phosphorescent long-afterglow material with the long afterglow characteristic can be obtained, and the triazine derivatives not only can be used for photoelectric functional materials, but also can be used as organic chemical intermediates and can be used as intermediates of pharmaceutical, agricultural chemicals and photoelectric functional materials.
Description
Technical Field
The invention belongs to the technical field of organic materials, and particularly relates to a triazine derivative and a synthesis method thereof.
Background
The s-triazine ring is a benzene ring-like compound with aromaticity, and is formed by alternating 3 carbon atoms and 3 nitrogen atoms. Due to the influence of nitrogen atom lone pair electrons, compared with benzene rings, the electron cloud density on the s-triazine ring is higher, so that the photoelectric property of the compound is stronger, and the compound with the s-triazine ring structure is applied in the field of organic photoelectricity in an expandable manner.
For example, patent CN201611206304.9 discloses a triazine-based compound and an organic electroluminescent device thereof, wherein carbazole with a substituent side group is linked to an s-triazine ring, so that a material with electroluminescent property can be obtained, and the compound can be used for manufacturing a light-emitting layer of an OLED photoelectric element, and has the characteristics of good current and voltage efficiency and high external quantum efficiency. On the other hand, other modifying groups can be connected to three carbon atoms on the s-triazine ring, and s-triazine is a highly symmetrical structure, so that after the same groups are linked at three sites, coupling can be performed, and a crosslinked network polymer can be obtained, as described in patent CN 201510133998.7. And the s-triazine ring has good luminous performance, so that the fluorescent polymer material with good performance can be obtained. Three different modifying groups are linked on three sites of s-triazine, so that different influences can be generated on s-triazine rings, and the performance of the finally obtained luminescent material can be accurately adjusted, thereby expanding the application field of the luminescent material.
However, the existing organic long afterglow materials are all based on carbazole or imide compounds. These compounds are characterized by being essentially lipid soluble and having low solubility in water or alcohol solvents, thus requiring the use of large amounts of organic solvents for their production and handling. Therefore, the development of triazine compounds with good alcohol solubility and water solubility is urgently needed.
Disclosure of Invention
In view of the above problems, the present invention aims to provide a triazine derivative and a synthesis method thereof, wherein the prepared triazine derivative has the characteristics of good alcohol solubility and partial water solubility, and can be used not only for photoelectric functional materials, but also as an organic chemical intermediate.
The technical content of the invention is as follows:
the invention provides a triazine derivative, which comprises 2, 4-dihydroxyalkyl ether-6-hydroxy s-triazine, and the structure of the triazine derivative comprises one of the following components:
wherein R is1，R2The structure of the polyether chain is the same or different, and the polyether chain comprises an alkyl group containing 2-6 carbon atoms and a polyether chain (-CH)2O-)nOr an aryl group.
The triazine derivative is prepared from raw materials including trichlorotriazine and hydroxyl-terminated diol compounds.
The structure of the dihydroxy compound containing the terminal group is as follows:
wherein R has a structure comprising an alkyl group having 2 to 6 carbon atoms and a polyether chain (-CH)2O-)nOr an aryl group;
namely, the terminal dihydroxy compound comprises one of propylene glycol, butanediol, ethylene glycol, diphenol and polyether glycol.
The invention also provides a synthesis method of the triazine derivative, which comprises the following steps:
1) hydrolyzing the prochlorperazine in a carbonate buffer solution to obtain an intermediate 2-hydroxy-4, 6-dichloro-s-triazine;
2) and adding the intermediate 2-hydroxy-4, 6-dichloros-triazine into a diol monosodium salt solution to obtain a target product 2, 4-dihydroxyalkyl ether-6-hydroxy-s-triazine.
The carbonate buffer solution in the step 1) comprises a mixture of sodium carbonate and sodium bicarbonate, and the mixing ratio of the mixture is (2-4): 1;
the hydrolysis reaction conditions in the step 1) comprise that the reaction temperature is 45-55 ℃, and the concentration of a carbonate buffer solution is 0.1-0.2 mol/L;
the diol monosodium salt solution in the step 2) is prepared by adopting a raw material comprising a hydroxyl-terminated diol compound and solid sodium hydride to react, wherein the mass ratio of the reacted substances is 1: (1.5-2);
the preparation conditions of the diol monosodium salt solution comprise that anhydrous 1, 4-dioxane, anhydrous tetrahydrofuran or anhydrous dimethyl sulfoxide is adopted as a reaction solvent under an ice bath condition;
the reaction conditions of the step 2) comprise a dry and closed environment, and the reaction temperature is 80-90 ℃.
The invention has the following beneficial effects:
the triazine derivative is a series of s-triazine derivatives with hydroxyl and hydroxyl alkyl, wherein the s-triazine with room-temperature phosphorescent emission potential is used as a luminescent core, a series of groups are linked to modify the luminescent core so as to obtain a pure organic long-afterglow phosphorescent material with long afterglow characteristics, and the triazine derivative has alcohol solubility and water solubility, is convenient for later treatment and use, has low cost and is environment-friendly by utilizing the characteristic that trichlorooxazine can be hydrolyzed under alkaline conditions and reacting the trichlorooxazine serving as a raw material with sodium alkoxide;
the triazine derivative prepared by the invention has the characteristics of good alcohol solubility and partial water solubility, can be used for photoelectric functional materials, can also be used as an organic chemical intermediate, and can be used as an intermediate of pharmacy, agricultural chemicals and photoelectric functional materials.
Drawings
FIG. 1 is an infrared absorption spectrum (KBr method) of 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine of example 1;
FIG. 2 is a steady state emission spectrum of 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine from example 1;
FIG. 3 is a transient phosphorescence spectrum of 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine of example 1;
FIG. 4 is a graph of the phosphorescence decay for 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine from example 1;
FIG. 5 is a schematic diagram showing the afterglow luminescence of 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine of example 1.
Detailed Description
The present invention is described in further detail in the following description of specific embodiments and the accompanying drawings, it is to be understood that these embodiments are merely illustrative of the present invention and are not intended to limit the scope of the invention, which is defined by the appended claims, and modifications thereof by those skilled in the art after reading this disclosure that are equivalent to the above described embodiments.
All the raw materials and reagents of the invention are conventional market raw materials and reagents unless otherwise specified.
Example 1
The synthesis of triazine derivative 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine:
1) preparation of intermediate 2-hydroxy-4, 6-dichloros-triazine: adding 10.000g of trichlorooxazine into a dry 250mL three-neck spherical flask, adding 50mL of 0.2g/mL carbonate solution (2: 1 of sodium carbonate and sodium bicarbonate), reacting at 50 ℃ for 2 hours, adding diluted hydrochloric acid to adjust the pH of the reaction solution to 7 after the reaction is ended, filtering to obtain a large amount of white solid, and repeatedly washing the white solid with dichloromethane until the mass of the white solid is not changed to obtain 6.924g of a white solid product, wherein the nuclear magnetic resonance hydrogen spectrum of the white solid product is 1H NMR (400MHz, DMSO-d6)11.10(s,1H), and the yield is 69.2%;
2) preparing a monosodium glycol salt solution: adding 10mL of dried 1, 4-dioxane and 1.122g of ethylene glycol (about 1.008mL) into a dried 50mL three-neck spherical flask, stirring the mixed solution, placing the mixed solution in an ice bath condition, adding 0.278g of sodium hydride (0.01mol), and finishing the reaction when no obvious gas is generated;
3) preparation of triazine derivatives: wiping the outer wall of the reaction bottle, transferring the reaction bottle into an oil bath pan, adding 1.000g of the product 2-hydroxy-4, 6-dichloros-triazine obtained in the step 1), heating the reaction bottle to 80 ℃, and reacting the reaction bottle for 12 hours. After the reaction, dilute hydrochloric acid was added to adjust the reaction solution to pH 7, the precipitate was separated by centrifugation, the precipitate was dissolved in anhydrous methanol, insoluble substances were removed, the methanol solution was dropped into an excess of tetrahydrofuran, and the above procedure was repeated until the solid mass was constant, to obtain 1.023g of white pure 2, 4-dihydroxyethyl-6-hydroxy-s-triazine, which had a nuclear magnetic resonance hydrogen spectrum 1H NMR (600MHz, Deuterium Oxide)4.70(s,1H), and the peak at 4.70 was the nuclear magnetic peak of methylene hydrogen on the pendant group of 2, 4-dihydroxyethyl ether-6-hydroxy-s-triazine, and the yield was 78.1%.
The hydrogen spectrum of the product is measured by using heavy water as a deuteration reagent, and the hydroxyl hydrogen peak of the 2, 4-dihydroxyethyl ether-6-hydroxy s-triazine does not show because the hydrogen-deuterium exchange occurs in a heavy water system, so that the hydrogen peak of active hydrogen disappears;
as shown in FIG. 1, the infrared spectrum of the product is determined to have the following characteristics: 3500CM-1Hydroxyl group, methylene group: 3000CM-1And intra-ring C ═ N bond: 3100CM-1Alkyl ether bond: 1275CM-1Isomer N-H bond, 3490CM-1；
As shown in FIG. 2, the excitation wavelength was 365nm and the fluorescence emission wavelength was measured to be 450nm at room temperature;
as shown in FIG. 3, the excitation wavelength was 365nm and the phosphorescence emission wavelength was 510nm at room temperature;
as shown in FIG. 4, the excitation wavelength was 365nm and the detection wavelength was 505nm at room temperature, and the fitted phosphorescence lifetime was 231 ms;
as shown in FIG. 5, when the sample is irradiated at 365nm, the sample can show afterglow luminescence phenomenon, which indicates that the sample has room temperature long afterglow property.
Example 2
The synthesis of triazine derivative 2, 4-dihydroxypropyl ether-6-hydroxy s-triazine:
1) preparation of intermediate 2-hydroxy-4, 6-dichloros-triazine: adding 10.000g of trichlorooxazine into a dry 250mL three-neck spherical flask, adding 50mL of 0.2g/mL carbonate solution (3: 1 of sodium carbonate and sodium bicarbonate), reacting at 45 ℃ for 2 hours, adding dilute hydrochloric acid to adjust the pH of the reaction solution to 7 after the reaction is ended, filtering to obtain a large amount of white solid, and repeatedly washing the white solid with dichloromethane until the mass of the white solid is not changed to obtain 6.863g of a white solid product with the yield of 68.7%;
2) preparing a monosodium glycol salt solution: adding 10mL of dried 1, 4-dioxane and 1.375g of propylene glycol (about 1.328mL) into a dried 50mL three-neck spherical flask, stirring the mixed solution, placing the mixed solution in an ice bath condition, adding 0.312g of sodium hydride (0.01mol), and finishing the reaction when no obvious gas is generated;
3) preparation of triazine derivatives: wiping the outer wall of the reaction bottle, transferring into an oil bath pan, adding 1.000g of the product 2-hydroxy-4, 6-dichloros-triazine in the step 1), heating to 83 ℃, and reacting for 10 hours under dry and closed conditions. After the reaction, dilute hydrochloric acid was added to adjust the reaction solution to pH 7, the precipitate was separated by centrifugation, the precipitate was dissolved in anhydrous methanol, the insoluble matter was removed, the methanol solution was dropped into an excess amount of tetrahydrofuran, and the centrifugation was repeated until the solid mass was constant to obtain 0.979g of white pure 2, 4-dihydroxypropyl-6-hydroxy-s-triazine with a yield of about 66.2%.
Example 3
Synthesis of triazine derivative 2, 4-dihydroxy butyl ether-6-hydroxy s-triazine:
1) preparation of intermediate 2-hydroxy-4, 6-dichloros-triazine: adding 10.000g of trichlorooxazine into a dry 250mL three-neck spherical flask, adding 50mL of 0.1g/mL carbonate solution (2: 1 of sodium carbonate and sodium bicarbonate), reacting at 50 ℃ for 2 hours, adding diluted hydrochloric acid to adjust the pH of the reaction solution to 7 after the reaction is ended, filtering to obtain a large amount of white solid, and repeatedly washing the white solid with dichloromethane until the mass of the white solid is not changed to obtain 6.956g of a white solid product with the yield of 70.2%;
2) preparing a monosodium glycol salt solution: adding 10mL of dry anhydrous tetrahydrofuran and 1.639g of butanediol (about 1.639mL) into a dry 50mL three-neck spherical flask, stirring the mixed solution, placing the mixed solution in an ice bath condition, adding 0.312g of sodium hydride (0.01mol), and finishing the reaction when no obvious gas is generated;
3) preparation of triazine derivatives: wiping the outer wall of the reaction bottle, transferring the reaction bottle into an oil bath pan, adding 1.000g of the product 2-hydroxy-4, 6-dichloros-triazine obtained in the step 1), heating the mixture to 85 ℃, and reacting the mixture for 9 hours under the dry and closed conditions. After the reaction, dilute hydrochloric acid was added to adjust the reaction solution to pH 7, the precipitate was separated by centrifugation, the precipitate was dissolved in anhydrous methanol, the insoluble matter was removed, the methanol solution was dropped into an excess amount of tetrahydrofuran, and the centrifugation was repeated until the solid mass was constant to obtain 0.979g of white pure 2, 4-dihydroxybutyl-6-hydroxy-s-triazine with a yield of about 66.2%.
Example 4
The synthesis of triazine derivative 2, 4-dihydroxyphenyl ether-6-hydroxy s-triazine:
1) preparation of intermediate 2-hydroxy-4, 6-dichloros-triazine: adding 10.000g of trichlorooxazine into a dry 250mL three-neck spherical flask, adding 50mL of 0.2g/mL carbonate solution (3: 1 of sodium carbonate and sodium bicarbonate), reacting at 53 ℃ for 2 hours, adding diluted hydrochloric acid to adjust the pH of the reaction solution to 7 after the reaction is ended, filtering to obtain a large amount of white solid, and repeatedly washing the white solid with dichloromethane until the mass of the white solid is not changed to obtain 7.105g of a white solid product with the yield of 71.8%;
2) preparing a monosodium glycol salt solution: adding 10mL of dry anhydrous dimethyl sulfoxide and 1.1g of diphenol (molecular weight is 400) into a dry 50mL three-neck spherical flask, stirring the mixed solution, placing the mixed solution in an ice bath condition, adding 0.312g of sodium hydride (0.01mol), and finishing the reaction when no obvious gas is generated;
3) preparation of triazine derivatives: wiping the outer wall of the reaction bottle, transferring the reaction bottle into an oil bath pan, adding 1.000g of the product 2-hydroxy-4, 6-dichloros-triazine obtained in the step 1), heating the mixture to 88 ℃, and reacting the mixture for 7 hours under the dry and closed conditions. After the reaction, dilute hydrochloric acid was added to adjust the reaction solution to pH 7, the precipitate was separated by centrifugation, the precipitate was dissolved in anhydrous methanol, the insoluble matter was removed, the methanol solution was dropped into an excess amount of tetrahydrofuran, and the centrifugation was repeated until the solid mass was constant to obtain 0.763g of white pure 2, 4-dihydroxyphenyl ether-6-hydroxy-s-triazine, with a yield of about 36.4%.
Example 5
Synthesis of triazine derivative 2, 4-dihydroxy polyether-6-hydroxy s-triazine:
1) preparation of intermediate 2-hydroxy-4, 6-dichloros-triazine: adding 10.000g of trichlorooxazine into a dry 250mL three-neck spherical flask, adding 50mL of 0.1g/mL carbonate solution (sodium carbonate and sodium bicarbonate are 4:1), reacting at 55 ℃ for 2 hours, adding dilute hydrochloric acid to adjust the pH of the reaction solution to 7 after the reaction is ended, filtering to obtain a large amount of white solid, and repeatedly washing the white solid with dichloromethane until the mass of the white solid is not changed to obtain 7.113g of a white solid product with the yield of 72.4%;
2) preparing a monosodium glycol salt solution: adding 10mL of dry 1, 4-dioxane and 4g of polyether glycol (molecular weight is 400) into a dry 50mL three-neck spherical flask, stirring the mixed solution, placing the mixed solution in an ice bath condition, adding 0.312g of sodium hydride (0.01mol), and finishing the reaction when no obvious gas is generated;
3) preparation of triazine derivatives: wiping the outer wall of the reaction bottle, transferring into an oil bath pan, adding 1.000g of the product 2-hydroxy-4, 6-dichloros-triazine obtained in the step 1), heating to 90 ℃, and reacting for 4 hours under the dry and closed conditions. After the reaction, dilute hydrochloric acid was added to adjust the reaction solution to pH 7, the precipitate was separated by centrifugation, the precipitate was dissolved in anhydrous methanol, the insoluble matter was removed, the methanol solution was dropped into an excess amount of tetrahydrofuran, and the separation by centrifugation was repeated until the solid mass was constant to obtain 2.79g of white pure 2, 4-dihydroxypolyether-6-hydroxy-s-triazine in a yield of about 59.4%.
Claims (9)
1. The triazine derivative is characterized by comprising 2, 4-dihydroxyalkyl ether-6-hydroxy s-triazine, and the structure of the triazine derivative comprises one of the following components:
wherein R is1，R2The structure of the polyether chain is the same or different, and the polyether chain comprises an alkyl group containing 2-6 carbon atoms and a polyether chain (-CH)2O-)nOr an aryl group.
2. The triazine derivative according to claim 1, which is produced from a starting material comprising a trichlorooxazine and a hydroxyl-terminated diol compound.
3. The triazine derivative according to claim 2, wherein the hydroxyl-terminated diol compound has the following structure:
wherein R has a structure comprising an alkyl group having 2 to 6 carbon atoms and a polyether chain (-CH)2O-)nOr an aryl group.
4. A method for synthesizing the triazine derivative as set forth in any one of claims 1 to 3, comprising the steps of:
1) hydrolyzing the prochlorperazine in a carbonate buffer solution to obtain an intermediate 2-hydroxy-4, 6-dichloro-s-triazine;
2) and adding the intermediate 2-hydroxy-4, 6-dichloros-triazine into a diol monosodium salt solution to obtain a target product 2, 4-dihydroxyalkyl ether-6-hydroxy-s-triazine.
5. The method for synthesizing triazine derivatives as claimed in claim 4, wherein the carbonate buffer solution in step 1) comprises a mixture of sodium carbonate and sodium bicarbonate, and the mixing ratio of the carbonate buffer solution to the sodium bicarbonate is (2-4): 1.
6. the method for synthesizing triazine derivatives as claimed in claim 4, wherein the hydrolysis in step 1) is carried out under reaction conditions including a reaction temperature of 45-55 ℃ and a concentration of carbonate buffer solution of 0.1-0.2 mol/L.
7. The method for synthesizing triazine derivatives according to claim 4, wherein the diol monosodium salt solution obtained in step 2) is prepared by reacting a raw material comprising a hydroxyl-terminated diol compound and solid sodium hydride, and the ratio of the amount of the reaction materials is 1: (1.5-2).
8. The method for synthesizing triazine derivatives of claim 7, wherein the diol monosodium salt solution is prepared by using anhydrous 1, 4-dioxane, anhydrous tetrahydrofuran or anhydrous dimethylsulfoxide as a reaction solvent under ice-bath conditions.
9. The method for synthesizing triazine derivatives as claimed in claim 4, wherein the reaction conditions in step 2) include a dry and sealed environment, and the reaction temperature is 80-90 ℃.
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| CN112940241A (en) * | 2021-02-08 | 2021-06-11 | 华南师范大学 | Triazine polymer and preparation method thereof |
| CN113149918A (en) * | 2021-04-12 | 2021-07-23 | 中昊(大连)化工研究设计院有限公司 | Synthetic method of ultraviolet absorbent UV-1600 intermediate |
| CN113713420A (en) * | 2021-08-13 | 2021-11-30 | 宁夏新辰新材料有限公司 | Method for refining and preparing slag wax for coal-based Fischer-Tropsch wax |
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