CN110818614A - Nitrogen-oxygen stable free radical with aggregation-induced emission function and preparation method thereof - Google Patents
Nitrogen-oxygen stable free radical with aggregation-induced emission function and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a nitrogen-oxygen stable free radical with aggregation-induced emission function and a preparation method thereof, wherein the nitrogen-oxygen stable free radical has the following structure:
Description
Technical Field
The invention relates to a novel nitrogen-oxygen stable free radical and a preparation method thereof.
Background
The nitrogen-oxygen stable free radical has wide application, can be used as a functional group for signal transmission, and can label protein, nucleic acid, lipoid and drug molecules by a spin labeling method. And the nitroxide stable free radical has been successfully used to synthesize bioactive paramagnetic substances for further study of the microstructure and properties of the labeled substances. In addition, part of the nitroxide stable free radicals can be used for carrying out the active controllable free radical polymerization so as to control the molecular weight and the molecular structure of the polymer. However, the functionality of nitroxide stable free radicals is still under further development.
Aggregation-induced emission technology has attracted much attention in recent years. A large number of materials with aggregation-induced emission properties are applied to the fields of organic light-emitting diodes, fluorescence sensors, biological imaging and the like. The combination of groups with aggregation-induced emission properties with various functional groups to derive new compounds is an important direction for the development of aggregation-induced emission technology. So far, no report of combining the aggregation-induced emission group with the nitroxide-stable free radical has been found.
Disclosure of Invention
The first technical problem to be solved by the invention is to provide a nitrogen-oxygen stable free radical with aggregation-induced emission function.
The second technical problem to be solved by the invention is to provide a method for preparing the nitroxide stable free radical.
In order to solve the first technical problem, the technical scheme of the invention is as follows: a nitrogen-oxygen stable free radical with aggregation-induced emission function has the following structure:
in the formula: r1, R2, R3 and R4 are respectively independent to obtain C1-6 alkyl and other elements are heterochain groups optionally substituted; r5 is hydrogen, NH2, carbonyl, hydroxyl, oxygen-linked alkyl, and other elements are optionally substituted heterochain groups.
In order to solve the second technical problem, the technical scheme of the invention is as follows: a method for preparing stable free radical of nitrogen oxygen with aggregation-induced emission function comprises synthesizing tetramethyl piperidine nitroxide free radical with hydroxyl group from tetramethyl piperidine alcohol; synthesizing a tetraphenylethylene intermediate by using 2-bromo-1, 1, 2-triphenylethylene and 4-methylbenzeneboronic acid as raw materials, and brominating to obtain tetraphenylethylene with a benzyl bromide group; then carrying out nucleophilic substitution reaction on the nitroxide self-stabilizing free radical and tetraphenylethylene with a benzyl bromide group at room temperature, wherein the total reaction time is 2-12 h; and purifying by adopting a column chromatography separation method to obtain a nitrogen-oxygen stable free radical product with aggregation-induced emission performance.
The mass ratio of the tetraphenylethylene with benzyl bromide group to the tetramethyl piperidine nitroxide stable free radical with hydroxyl group is preferably 1: 1-1: 5.
Further, a method for preparing a nitroxide stable free radical with aggregation-induced emission function comprises the following steps:
(1) mixing tetramethylpiperidinol, sodium bicarbonate, deionized water, acetone and potassium hydrogen persulfate composite salt, stirring for 2-6 h under an ice bath condition, continuing stirring for 2-6 h at normal temperature, stopping stirring, performing oil-water phase separation, washing an organic phase with ethyl acetate, collecting an ethyl acetate phase, sequentially washing with deionized water and saturated salt water, drying, removing ethyl acetate to obtain a crude product, and performing recrystallization and purification with a mixed solvent of n-heptane and ethyl acetate to obtain an intermediate 1. The preferable feeding amount is as follows: the mass ratio of the tetramethylpiperidinol to the sodium bicarbonate is 0.3-0.7; deionized water, acetone and the like are added in an amount which is 0.5-5 times the weight of the sodium bicarbonate; the potassium hydrogen persulfate composite salt is added in an amount which is 0.5-5 times the mass of the sodium bicarbonate.
(2) Mixing 2-bromo-1, 1, 2-triphenylethylene and 4-methylbenzeneboronic acid, adding the mixture into a reaction bottle, adding a sodium carbonate aqueous solution, tetrahydrofuran and ethylene glycol, stirring uniformly, adding palladium tetrakis (triphenylphosphine) after stirring uniformly, adding nitrogen for protection after removing oxygen, heating to 70-90 ℃, keeping refluxing for 12-24 hours, and naturally cooling to normal temperature. And extracting the reaction liquid by using ethyl acetate, separating liquid, dewatering the organic phase by using a drying agent, standing, and removing the ethyl acetate to obtain a dark green oily intermediate 2. And (3) purifying the intermediate 2 by using a column chromatography separation method by using petroleum ether as an eluent. The preferable feeding amount is as follows: the mass ratio of the 2-bromo-1, 1, 2-triphenylethylene to the 4-methylphenylboronic acid is 1.0-3.0; adding 5-15 times of the mass of 2-bromo-1, 1, 2-triphenylethylene into the sodium carbonate aqueous solution, wherein the mass concentration of the sodium carbonate aqueous solution is 10% -30%; adding tetrahydrofuran in an amount which is 0.3-0.7 times the volume of the sodium carbonate aqueous solution, and adding ethylene glycol in an amount which is 0.05-0.10 times the volume of the sodium carbonate aqueous solution; the addition amount of the tetrakis (triphenylphosphine) palladium is 0.3-0.7 time of the mass of the 2-bromo-1, 1, 2-triphenylethylene.
(3) Dissolving the intermediate 2 in carbon tetrachloride, adding N-bromosuccinimide and benzoyl peroxide, removing oxygen, adding nitrogen for protection, heating to 78-90 ℃, performing reflux reaction for 12-24 hours, cooling to room temperature, pouring a reaction product into a separating funnel, extracting by using a mixed solution of dichloromethane and saturated salt solution, removing water from an organic phase by using a drying agent, and standing; removing the solvent, using petroleum ether as eluent, and purifying the crude product by column chromatography separation method to obtain an intermediate 3. The preferable feeding amount is as follows: the mass fraction of the intermediate 2 dissolved in carbon tetrachloride is 1-10%; adding N-bromosuccinimide in an amount which is 0.4-0.8 times of the mass of the intermediate 2; the benzoyl peroxide is added in an amount of 0.5 to 5 percent of the mass of the N-bromosuccinimide.
(4) Dissolving the intermediate 3 and the intermediate 1 in tetrahydrofuran, and stirring for 2 hours; adding triethylamine, and continuously stirring for 12 hours; separating the upper layer solution, extracting the product with dichloromethane, washing with deionized water and saturated saline solution, removing water and solvent, and purifying by column chromatography to obtain orange red powder target product. The preferable feeding amount is as follows: the mass ratio of the intermediate 3 to the intermediate 1 is 1: 3-1: 5, and the triethylamine accounts for 0.5-2 times of the mass of the intermediate 3.
The invention synthesizes a nitrogen-oxygen stable free radical with aggregation-induced emission performance, the main functional groups of the nitrogen-oxygen stable free radical are tetraphenylethylene and tetramethylpiperidine, the product has strong absorption in an ultraviolet region (220nm-360nm), and has fluorescence emission (400nm-550nm) in a blue-green light region. Under the irradiation of ultraviolet light, the radical does not emit light in a good solvent (such as dichloromethane), but emits intense blue-green fluorescence in a poor solvent (such as water). The free radical can be used for initiating the controllable active free radical polymerization of the styrene monomer, and the obtained polymer also has the property of emitting light under the irradiation of ultraviolet light. The polymer has good aggregation-induced emission performance, and can be used as a fluorescence chemical sensor, a fluorescence probe, a fluorescence contrast material and the like.
Drawings
FIG. 1 is a nuclear magnetic spectrum of the product of the present invention.
FIG. 2 is a fluorescence emission spectrum of the luminescence property of the nitroxide stable free radical of the present invention.
FIG. 3 is a photograph of the luminescence of the nitroxide stable free radical of the present invention under UV light.
FIG. 4 is a graph of the molecular weight and molecular weight distribution GC of the polymer product of example 3.
FIG. 5 is a photograph of the fluorescence properties of the polymer product of example 3.
Detailed Description
EXAMPLE 1 Synthesis of nitroxide stable free radical
(1) After being mixed, 30g of tetramethyl piperidinol, 50g of sodium bicarbonate, 100g of deionized water, 100g of acetone and 100g of potassium hydrogen persulfate composite salt are intensively stirred for 2-6 h under the ice bath condition, and the mixture is continuously stirred for 2h at normal temperature. Stopping stirring, separating oil phase and water phase, washing with appropriate amount of ethyl acetate for 3 times, collecting ethyl acetate phase, washing with appropriate amount of deionized water and saturated saline solution sequentially, and drying with anhydrous sodium sulfate. Removing ethyl acetate by rotary evaporation to obtain a crude product, and then recrystallizing and purifying by using a mixed solvent of n-heptane and ethyl acetate to obtain an intermediate 1, namely 4-amino-2, 2, 6, 6-tetramethylpiperidine 1-oxygen radical.
(2) Adding 2-bromo-1, 1, 2-triphenylethylene (10g) and 4-methylbenzeneboronic acid (5g) into a 250mL three-neck flask, adding 100mL of 2mol/L sodium carbonate aqueous solution and 50mL of tetrahydrofuran, adding a proper amount of ethylene glycol, uniformly stirring by magnetic force, adding 5.2g of tetrakis (triphenylphosphine) palladium, removing oxygen by freezing and pumping for 3 times, adding nitrogen for protection, and heating to 74 ℃. After reflux was maintained for 12h, the reaction was stopped and allowed to cool to ambient temperature. And extracting the mixed solution with ethyl acetate for 3 times, separating the solution, dewatering the organic phase with anhydrous sodium sulfate, and standing for 2 hours. Ethyl acetate was removed by rotary evaporation to give a greenish black oily intermediate 2, i.e. 4-methyl tetraphenylethylene. And (3) purifying the intermediate 2 by using a column chromatography separation method by using petroleum ether as an eluent.
(3) Dissolving the intermediate 2(5g) in 100mL of carbon tetrachloride, adding N-bromosuccinimide (3.0g), adding benzoyl peroxide (0.03g), freezing, exhausting oxygen, adding nitrogen for protection, heating to 78 ℃, keeping reacting for 12h after stable reflux, cooling to room temperature, pouring the reaction liquid into a separating funnel, extracting for 3 times by using a mixed solution of dichloromethane and saturated saline solution, dewatering the organic phase by using anhydrous sodium sulfate, standing for 2h, evaporating the solvent, using petroleum ether as an eluent, and purifying the crude product by using a column chromatography separation method to obtain an intermediate 3.
(4) Intermediate 3(1.0g) and intermediate 1(3.0g) were weighed out and dissolved in 10mL tetrahydrofuran, stirred at room temperature for 2h, added with an appropriate amount of triethylamine, and stirred for 12 h. After the reaction, the upper layer solution was separated, and the product was extracted with dichloromethane, washed with deionized water and a saturated aqueous solution of sodium chloride, and then removed with an anhydrous sodium sulfate solution. Removing the solvent by rotary evaporation, and purifying by column chromatography separation to obtain the target product. The nuclear magnetic spectrum is shown in figure 1.
EXAMPLE 2 luminescent Properties of nitroxide-stabilized free radicals
5mg of nitroxide stable free radical was weighed and dissolved in 5mL of tetrahydrofuran to prepare a mother liquor. And respectively preparing tetrahydrofuran and n-hexane mixed solutions with different proportions, wherein the total volume is 5 mL. Respectively transferring 100 microliters of mother liquor, adding the mother liquor into different mixed solvents, and carrying out fluorescence spectrum analysis after uniformly mixing. It can be observed that, as the proportion of cyclohexane is increased, the nitroxide radicals continuously have and cause the fluorescence intensity to increase, the corresponding fluorescence emission spectrum is shown in figure 2, and the light emission photograph under an ultraviolet lamp is shown in figure 3.
Example 3 controlled living radical polymerization Using nitroxide stable free radical
64mg of nitroxide-stable free radical and 0.0203g of azobisisobutyronitrile are weighed out and 8mL of styrene and 2mL of toluene are metered into the reaction flask, respectively. And (3) removing oxygen in the reaction bottle by bubbling nitrogen, heating the reaction mixture until the temperature is 130 ℃, enabling the reactant to be light yellow, gradually increasing the viscosity of the product along with the increase of the reaction time, changing the liquid substance with lower viscosity into a liquid fluid substance with higher viscosity, and finally changing the liquid substance into a light yellow solid. After 12h of reaction, the monomer conversion rate reached 85%, the reaction was stopped by cooling, and the obtained polymer product was subjected to molecular weight and fluorescence tests, with the results shown in fig. 4 and 5. The polymerization product is dissolved in dichloromethane for ultraviolet test, the polymer is found to have a stronger absorption peak at the position of 250-330nm, the fluorescence performance of the product is tested by taking the wavelength as the excitation light, the product is found to have certain fluorescence emission in the visible light range, and the product has strong fluorescence emission between 450-500 nm. The polymerization product was irradiated with an ultraviolet lamp of 365nm, and the product emitted blue-green fluorescence visible to the naked eye.
Claims (8)
1. A nitrogen-oxygen stable free radical with aggregation-induced emission function has the following structure:
in the formula: r1, R2, R3 and R4 are respectively independent to obtain C1-6 alkyl and other elements are heterochain groups optionally substituted; r5 is hydrogen, NH2, carbonyl, hydroxyl, oxygen-linked alkyl, and other elements are optionally substituted heterochain groups.
2. A method for preparing the nitroxide stable free radical of claim 1, wherein the hydroxy-containing tetramethylpiperidinyloxy radical is synthesized by using tetramethylpiperidinol as a raw material; synthesizing a tetraphenylethylene intermediate by using 2-bromo-1, 1, 2-triphenylethylene and 4-methylbenzeneboronic acid as raw materials, and brominating to obtain tetraphenylethylene with a benzyl bromide group; then carrying out nucleophilic substitution reaction on the nitroxide self-stabilizing free radical and tetraphenylethylene with a benzyl bromide group at room temperature, wherein the total reaction time is 2-12 h; and purifying by adopting a column chromatography separation method to obtain a nitrogen-oxygen stable free radical product with aggregation-induced emission performance.
3. The method as set forth in claim 2, wherein the molar ratio of the tetraphenylethylene having a benzylidene bromide group to the tetramethylpiperidinyloxy stable free radical having a hydroxyl group is 1: 1 to 1: 5.
4. The method of claim 2, comprising the steps of:
(1) mixing tetramethylpiperidinol, sodium bicarbonate, deionized water, acetone and potassium hydrogen persulfate composite salt, stirring for 2-6 h under an ice bath condition, continuing stirring for 2-6 h at normal temperature, stopping stirring, performing oil-water phase separation, washing an organic phase with ethyl acetate, collecting an ethyl acetate phase, washing with deionized water and saturated saline solution in sequence, drying, removing ethyl acetate to obtain a crude product, and performing recrystallization purification with a mixed solvent of n-heptane and ethyl acetate to obtain an intermediate 1;
(2) mixing 2-bromo-1, 1, 2-triphenylethylene and 4-methylbenzeneboronic acid, adding the mixture into a reaction bottle, adding a sodium carbonate aqueous solution, tetrahydrofuran and ethylene glycol, stirring uniformly, adding palladium tetrakis (triphenylphosphine) after stirring uniformly, adding nitrogen for protection after removing oxygen, heating to 70-90 ℃, keeping refluxing for 12-24 hours, and naturally cooling to normal temperature; extracting the reaction liquid by using ethyl acetate, separating liquid, dewatering the organic phase by using a drying agent, standing, and removing the ethyl acetate to obtain a dark green oily intermediate 2; purifying the intermediate 2 by column chromatography separation with petroleum ether as eluent;
(3) dissolving the intermediate 2 in carbon tetrachloride, adding N-bromosuccinimide and benzoyl peroxide, removing oxygen, adding nitrogen for protection, heating to 78-90 ℃, performing reflux reaction for 12-24 hours, cooling to room temperature, pouring a reaction product into a separating funnel, extracting by using a mixed solution of dichloromethane and saturated salt solution, removing water from an organic phase by using a drying agent, and standing; removing the solvent, using petroleum ether as eluent, and purifying the crude product by column chromatography separation to obtain an intermediate 3;
(4) dissolving the intermediate 3 and the intermediate 1 in tetrahydrofuran, and stirring for 2 hours; adding triethylamine, and continuously stirring for 12 hours; separating the upper layer solution, extracting the product with dichloromethane, washing with deionized water and saturated salt solution, removing water and solvent, and purifying with column chromatography to obtain orange red powder as target product.
5. The method of claim 4, wherein the mass ratio of the tetramethylpiperidinol to the sodium bicarbonate is 0.3 to 0.7; deionized water, acetone and the like are added in an amount which is 0.5-5 times the weight of the sodium bicarbonate; the potassium hydrogen persulfate composite salt is added in an amount which is 0.5-5 times the mass of the sodium bicarbonate.
6. The method according to claim 4, wherein the mass ratio of 2-bromo-1, 1, 2-triphenylethylene to 4-methylphenylboronic acid is 1.0 to 3.0; adding 5-15 times of the mass of 2-bromo-1, 1, 2-triphenylethylene into the sodium carbonate aqueous solution, wherein the mass concentration of the sodium carbonate aqueous solution is 10% -30%; adding tetrahydrofuran in an amount which is 0.3-0.7 times the volume of the sodium carbonate aqueous solution, and adding ethylene glycol in an amount which is 0.05-0.10 times the volume of the sodium carbonate aqueous solution; the addition amount of the tetrakis (triphenylphosphine) palladium is 0.3-0.7 time of the mass of the 2-bromo-1, 1, 2-triphenylethylene.
7. The method as set forth in claim 4, wherein the mass fraction of the intermediate 2 dissolved in carbon tetrachloride is 1-10%; adding N-bromosuccinimide in an amount which is 0.4-0.8 times of the mass of the intermediate 2; the benzoyl peroxide is added in an amount of 0.5 to 5 percent of the mass of the N-bromosuccinimide.
8. The method as claimed in claim 4, wherein the mass ratio of the intermediate 3 to the intermediate 1 is 1: 3 to 1: 5, and the mass of triethylamine is 0.5 to 2 times of the mass of the intermediate 3.
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| CN113773265A (en) * | 2021-10-25 | 2021-12-10 | 滨州医学院 | Fluorescent probe for detecting CYP450, preparation method and application thereof |
| CN114703650A (en) * | 2022-04-13 | 2022-07-05 | 邵建平 | Smooth skin-care fabric and preparation method thereof |
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| CN103194215A (en) * | 2013-04-15 | 2013-07-10 | 武汉大学 | Aggregation-induced emission molecule as well as preparation method and use thereof |
| CN108623538A (en) * | 2018-04-28 | 2018-10-09 | 杭州芬得检测技术有限公司 | A kind of piperazine modified tetraphenylethylene derivative and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103194215A (en) * | 2013-04-15 | 2013-07-10 | 武汉大学 | Aggregation-induced emission molecule as well as preparation method and use thereof |
| CN108623538A (en) * | 2018-04-28 | 2018-10-09 | 杭州芬得检测技术有限公司 | A kind of piperazine modified tetraphenylethylene derivative and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773265A (en) * | 2021-10-25 | 2021-12-10 | 滨州医学院 | Fluorescent probe for detecting CYP450, preparation method and application thereof |
| CN114703650A (en) * | 2022-04-13 | 2022-07-05 | 邵建平 | Smooth skin-care fabric and preparation method thereof |
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