CN110540650A - Aggregation-induced emission polyphosphate and synthesis method thereof - Google Patents
Aggregation-induced emission polyphosphate and synthesis method thereof Download PDFInfo
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- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
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Abstract
the invention relates to an aggregation-induced emission polyphosphate and a synthesis method thereof, wherein phosphate or phosphite ester and dihydric alcohol or trihydric alcohol react by a simple ester exchange polycondensation method according to a certain molar ratio to obtain hydroxyl-terminated hyperbranched polyphosphate or linear polyphosphate. The synthesized polyphosphate ester can emit bright blue fluorescence under the irradiation of ultraviolet light. Under the irradiation of light with different wavelengths, fluorescence with different wavelengths can be emitted, and the emitted fluorescence can cover almost the whole visible light range. The synthesized hyperbranched polyphosphate has the characteristic of delayed fluorescence, and the fluorescence life reaches microsecond level. And has aggregation-induced emission properties. The method has the characteristics of simple process, controllable structure, no need of solvent, environmental friendliness and the like. The synthesized polyphosphate ester has good biocompatibility, biodegradability and easy modification, and has aggregation-induced emission characteristics, so that the polyphosphate ester has wide application prospects in the aspects of DNA/RNA (deoxyribonucleic acid/ribonucleic acid) transportation, cell imaging, drug delivery and the like.
Description
Technical Field
the invention belongs to the field of high-molecular luminescent materials, and relates to aggregation-induced emission polyphosphate ester and a synthesis method thereof.
Background
In recent years, with the increasing awareness of environmental protection, the non-traditional fluorescent polymers without benzene ring and other large-pi conjugated structures have received much attention from academia and industry because they have good biocompatibility, biodegradability and environmental friendliness. The polymers can emit fluorescence under certain conditions, and have wide application prospects in the fields of cell fluorescence imaging, gene vectors, drug controlled release and the like. As a novel polymer, the polyphosphate ester has good biocompatibility, biodegradability, modifiability and thermal stability, and is widely applied to the fields of DNA/RNA delivery, flame retardant materials and the like. The hyperbranched polyphosphate has a definite three-dimensional structure and a large number of active groups with modifiable tail ends, and has wide application in biomedicine and the like.
The traditional polyphosphate ester is mostly prepared by adopting a polycondensation method and using phosphoryl dihalide or trihalo and polyhydric alcohol or polyhydric phenol, small molecules such as HCl and the like can be generated in the synthetic process of the method, extra auxiliary agents such as triethylamine are required to be added, and salt generated by reaction is removed by suction filtration. Solvents such as acetonitrile are added during the reaction to facilitate the reaction, and Synthesis of poly (lactic acid) -poly (phenyl phosphate) via direct polycondensation and its purification, journal of Polymer Research, 2009. 16, (3) p.255-261. The synthetic method has the disadvantages that the purification of the product is complicated after the reaction, and the phosphorus oxychloride or the polychlorinated phosphate is toxic or corrosive, so that the industrial production of the polyphosphate ester is limited. Or by ring-opening polymerization or olefin metathesis, which mostly requires the addition of expensive and toxic catalysts, the documents Chen, D.and J.Wang, Synthesis and catalysis of Block Copolymer of polyphosphates and Poly (ε -caprolactones), 2006.39(2): p.473-475. Therefore, the simple environment-friendly polyphosphate ester synthesis process has great application prospect. In addition, no report on the fluorescence property of polyphosphate exists at present, so that the characterization means after the gene is loaded by the polyphosphate is complex. If a polyphosphate ester carrier with aggregation-induced emission performance can be developed, simple visualization of characterization can be realized, so that the technical means of gene therapy by taking polyphosphate ester as the carrier is greatly improved.
Disclosure of Invention
Technical problem to be solved
In order to avoid the defects of the prior art, the invention provides an aggregation-induced emission polyphosphate and a synthesis method thereof, and the polyphosphate with aggregation-induced emission characteristics has good biocompatibility, easy biodegradation, environmental friendliness and high fluorescence intensity.
Technical scheme
An aggregation-induced emission polyphosphate, characterized in that: the polyphosphate ester comprises hyperbranched polyphosphate ester or linear polyphosphate ester; the hyperbranched polyphosphate is as follows: phosphate and dihydric alcohol or phosphorous acid diester and trihydric alcohol in a molar ratio of 2: 1-4 are subjected to ester exchange polycondensation to obtain hyperbranched polyphosphate, and the structural formula of the hyperbranched polyphosphate is as follows:
The linear polyphosphate is: performing ester exchange polycondensation reaction on a phosphorous acid diester and dihydric alcohol in a molar ratio of 2: 1-4 to obtain linear polyphosphate, wherein the structural formula of the linear polyphosphate is as follows:
Wherein:
The phosphate esters include, but are not limited to, trimethyl phosphate or triethyl phosphate.
The phosphorous acid diester includes but is not limited to dimethyl phosphite, diethyl phosphite.
the dihydric alcohol includes, but is not limited to, ethylene glycol, 1, 3-propanediol, 1, 4-butanediol, neopentyl glycol, or diethanolamine.
The trihydric alcohols include, but are not limited to, glycerol or triethanolamine.
A method for preparing aggregation-induced emission polyphosphate according to any one of claims 1 to 5, which is characterized by comprising the following steps:
1. Preparing hyperbranched polyphosphate ester: mixing phosphate and dihydric alcohol in a molar ratio of 2: 1-4, heating to 70-180 ℃, stirring at the temperature, and reacting for 6-18 h; then dissolving in ethanol, dialyzing, rotary steaming and vacuum drying to obtain hyperbranched polyphosphate;
Or mixing the phosphorous acid diester and the trihydric alcohol according to the molar ratio of 2: 1-4, heating to 70-180 ℃, stirring at the temperature, and reacting for 6-18 hours; then dissolving in ethanol, dialyzing, rotary steaming and vacuum drying to obtain hyperbranched polyphosphate;
2. Preparing linear polyphosphate ester: mixing phosphorous acid diester and dihydric alcohol according to a molar ratio of 2: 1-4, heating to 70-180 ℃, stirring at the temperature, and reacting for 6-18 h; then dissolving in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain linear polyphosphate ester;
The reaction was carried out under nitrogen protection.
Advantageous effects
the invention provides an aggregation-induced emission polyphosphate and a synthesis method thereof, wherein phosphate or phosphite ester and dihydric alcohol or trihydric alcohol react by a simple ester exchange polycondensation method according to a certain molar ratio to obtain hydroxyl-terminated hyperbranched polyphosphate or linear polyphosphate. The synthesized polyphosphate ester can emit bright blue fluorescence under the irradiation of ultraviolet light. Under the irradiation of light with different wavelengths, fluorescence with different wavelengths can be emitted, and the emitted fluorescence can cover almost the whole visible light range. The synthesized hyperbranched polyphosphate has the characteristic of delayed fluorescence, and the fluorescence life reaches microsecond level. And has aggregation-induced emission properties.
The invention relates to a plurality of aggregation-induced emission polyphosphate esters and a synthesis method thereof. Under the protection of nitrogen, phosphate ester and dihydric alcohol or phosphorous diester and trihydric alcohol or phosphorous diester and dihydric alcohol react by a simple ester exchange polycondensation method according to a certain molar ratio to obtain polyphosphate ester. The synthesized polyphosphate ester can emit bright blue fluorescence under the irradiation of ultraviolet light. Under the irradiation of light with different wavelengths, fluorescence with different wavelengths can be emitted, and the emitted fluorescence can cover almost the whole visible light range. And the synthesized polyphosphate ester has the characteristic of delayed fluorescence, and the fluorescence lifetime reaches microsecond level. And has aggregation-induced emission properties. The synthesis method has the characteristics of simple process, controllable structure, no need of solvent, environmental friendliness and the like. The synthesized polyphosphate ester has good biocompatibility, biodegradability and easy modification, and has aggregation-induced emission characteristics, so that the polyphosphate ester has wide application prospects in the aspects of DNA/RNA (deoxyribonucleic acid/ribonucleic acid) transportation, cell imaging, drug delivery and the like.
the invention provides a plurality of polyphosphate esters capable of emitting bright fluorescence and a preparation method thereof. Phosphate or phosphite ester and dihydric alcohol or trihydric alcohol are used as raw materials to synthesize hyperbranched/linear polyphosphate through a simple and controllable ester exchange polycondensation method. As the phosphate or phosphite ester is used as the raw material, the use of corrosive phosphorus oxychloride is avoided, so that the reaction condition is simple and easy to operate. The by-product alcohol generated at the same time can be removed by a distillation method and can be recovered under the condensation effect. The recovered alcohol may be used for other purposes. Compared with the method that by-product hydrogen chloride generated by using phosphorus oxychloride is removed by using acid-binding agents such as triethylamine and the like, the method simplifies the synthesis steps and saves a large amount of cost. The synthesized hyperbranched/linear polyphosphate does not contain benzene rings, only contains hydroxyl and P ═ O bonds, has good biocompatibility and biodegradability, and can emit bright blue fluorescence and has aggregation-induced luminescence characteristics. The light emission range of which can cover the whole visible light spectrum. And the fluorescence lifetime reaches microsecond level, and the delayed fluorescence characteristic is realized. The hyperbranched/linear polyphosphate ester reported in the patent has the characteristics of simple and convenient synthesis and purification process, controllable process, less three-waste pollution, good stability, low toxicity, good biodegradability, easy modification, functionalization realization, high fluorescence intensity, wide application range and the like.
Drawings
FIG. 1 shows the excitation and emission spectra of pure hydroxy-terminated hyperbranched polyphosphates
FIG. 2 is a graph of the fluorescence lifetime of pure hydroxy-terminated hyperbranched polyphosphate
Detailed Description
the invention will now be further described with reference to the following examples and drawings:
The invention comprises the following steps: firstly, the polyphosphate ester with terminal hydroxyl/ethoxy/methoxy is synthesized through ester exchange polycondensation. In addition, no solvent, catalyst and the like are used in the whole synthesis process, and the synthesized polyphosphate ester can emit bright blue fluorescence in a pure sample or in a solution.
In addition, the reaction involved in the present invention is not simple and can be determined according to different reaction conditions, specific implementation conditions and repeated tests.
Example 1
the preparation method of the hydroxyl-terminated hyperbranched polyphosphate ester comprises the following steps: reacting triethyl phosphate (27.32g) and ethylene glycol (14.90g) in a molar ratio of 1:1.6 under the protection of nitrogen, adding a sample, slowly heating to 130 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain the hydroxyl-terminated hyperbranched polyphosphate.
Example 2
The preparation method of the hydroxyl-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and ethylene glycol (16.76g) in a molar ratio of 1:1.8 under the protection of nitrogen, adding a sample, slowly heating to 130 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain the hydroxyl-terminated hyperbranched polyphosphate.
Example 3
the preparation method of the hydroxyl-terminated hyperbranched polyphosphate ester comprises the following steps: reacting triethyl phosphate (27.32g) and ethylene glycol (18.62g) in a molar ratio of 1:2 under the protection of nitrogen, adding a sample, slowly heating to 130 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain the hydroxyl-terminated hyperbranched polyphosphate.
Example 4
The preparation method of the terminal ethoxy hyperbranched polyphosphate ester comprises the following steps: reacting triethyl phosphate (27.32g) and ethylene glycol (13.03g) in a molar ratio of 1:1.4 under the protection of nitrogen, adding a sample, slowly heating to 130 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 5
the preparation method of the hydroxyl-terminated hyperbranched polyphosphate ester comprises the following steps: reacting triethyl phosphate (27.32g) and 1, 3-propylene glycol (18.26g) in a molar ratio of 1:1.6 under the protection of nitrogen, adding a sample, slowly heating to 135 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain the hydroxyl-terminated hyperbranched polyphosphate.
Example 6
The preparation method of the hydroxyl-terminated hyperbranched polyphosphate ester comprises the following steps: reacting triethyl phosphate (27.32g) and 1, 4-butanediol (21.63g) in a molar ratio of 1:1.6 under the protection of nitrogen, adding a sample, slowly heating to 140 ℃, stirring at the temperature, reacting for 11 hours, dissolving the product in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain the amino-terminated hyperbranched polyphosphate.
example 7
the preparation method of the hydroxyl-terminated hyperbranched polyphosphate ester comprises the following steps: under the protection of nitrogen, dimethyl phosphite (16.51g) and glycerol (11.05g) react according to a molar ratio of 1:0.8, a sample is added, the temperature is slowly raised to 90 ℃, stirring is carried out at the temperature, reaction is carried out for 8 hours, a product is dissolved in ethanol, dialysis, rotary evaporation and vacuum drying are carried out, and the hydroxyl-terminated hyperbranched polyphosphate is obtained.
Example 8
The preparation method of the hydroxyl-terminated hyperbranched polyphosphate ester comprises the following steps: under the protection of nitrogen, reacting dimethyl phosphite (16.51g) with triethanolamine (17.90g) in a molar ratio of 1:0.8, adding a sample, slowly heating to 70 ℃, stirring at the temperature, reacting for 7 hours, dissolving the product in ethanol, dialyzing, rotary evaporating, and drying in vacuum to obtain the hydroxyl-terminated hyperbranched polyphosphate.
Example 9
the preparation method of the hydroxyl-terminated linear polyphosphate ester comprises the following steps: under the protection of nitrogen, dimethyl phosphite (16.51g) and ethylene glycol (10.24g) react according to a molar ratio of 1:1.1, after a sample is added, the temperature is slowly raised to 120 ℃, stirring is carried out at the temperature, reaction is carried out for 8 hours, and a product is dissolved in ethanol, dialyzed, rotary evaporated and dried in vacuum, so that hydroxyl-terminated linear polyphosphate is obtained.
Example 10
The preparation method of the hydroxyl-terminated linear polyphosphate ester comprises the following steps: under the protection of nitrogen, dimethyl phosphite (16.51g) and 1, 3-propylene glycol (12.56g) react according to a molar ratio of 1:1.1, a sample is added, then the temperature is slowly raised to 120 ℃, stirring is carried out at the temperature, reaction is carried out for 8 hours, and a product is dissolved in ethanol, dialyzed, rotary evaporated and dried in vacuum, so that the hydroxyl-terminated linear polyphosphate is obtained.
Example 11
The preparation method of the hydroxyl-terminated linear polyphosphate ester comprises the following steps: under the protection of nitrogen, dimethyl phosphite (16.51g) and diethanol amine (17.35g) react according to a molar ratio of 1:1.1, after a sample is added, the temperature is slowly raised to 70 ℃, stirring is carried out at the temperature, the reaction is carried out for 6 hours, and a product is dissolved in ethanol, dialyzed, rotary evaporated and dried in vacuum, so that the hydroxyl-terminated linear polyphosphate is obtained.
Claims (6)
1. An aggregation-induced emission polyphosphate, characterized in that: the polyphosphate ester comprises hyperbranched polyphosphate ester or linear polyphosphate ester; the hyperbranched polyphosphate is as follows: phosphate and dihydric alcohol or phosphorous acid diester and trihydric alcohol in a molar ratio of 2: 1-4 are subjected to ester exchange polycondensation to obtain hyperbranched polyphosphate, and the structural formula of the hyperbranched polyphosphate is as follows:
The linear polyphosphate is: performing ester exchange polycondensation reaction on a phosphorous acid diester and dihydric alcohol in a molar ratio of 2: 1-4 to obtain linear polyphosphate, wherein the structural formula of the linear polyphosphate is as follows:
Wherein:
2. The aggregation-induced emission polyphosphate according to claim 1, wherein: the phosphate esters include, but are not limited to, trimethyl phosphate or triethyl phosphate.
3. The aggregation-induced emission polyphosphate according to claim 1, wherein: the phosphorous acid diester includes but is not limited to dimethyl phosphite, diethyl phosphite.
4. The aggregation-induced emission polyphosphate according to claim 1, wherein: the dihydric alcohol includes, but is not limited to, ethylene glycol, 1, 3-propanediol, 1, 4-butanediol, neopentyl glycol, or diethanolamine.
5. The aggregation-induced emission polyphosphate according to claim 1, wherein: the trihydric alcohols include, but are not limited to, glycerol or triethanolamine.
6. A method for preparing aggregation-induced emission polyphosphate according to any one of claims 1 to 5, which is characterized by comprising the following steps:
1. Preparing hyperbranched polyphosphate ester: mixing phosphate and dihydric alcohol in a molar ratio of 2: 1-4, heating to 70-180 ℃, stirring at the temperature, and reacting for 6-18 h; then dissolving in ethanol, dialyzing, rotary steaming and vacuum drying to obtain hyperbranched polyphosphate;
or mixing the phosphorous acid diester and the trihydric alcohol according to the molar ratio of 2: 1-4, heating to 70-180 ℃, stirring at the temperature, and reacting for 6-18 hours; then dissolving in ethanol, dialyzing, rotary steaming and vacuum drying to obtain hyperbranched polyphosphate;
2. Preparing linear polyphosphate ester: mixing phosphorous acid diester and dihydric alcohol according to a molar ratio of 2: 1-4, heating to 70-180 ℃, stirring at the temperature, and reacting for 6-18 h; then dissolving in ethanol, dialyzing, performing rotary evaporation, and performing vacuum drying to obtain linear polyphosphate ester;
The reaction was carried out under nitrogen protection.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115806673A (en) * | 2022-12-29 | 2023-03-17 | 华南理工大学 | Hyperbranched polyphosphate ester material containing thioether bonds as well as preparation method and application thereof |
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| CN103665383A (en) * | 2013-11-07 | 2014-03-26 | 江苏雅克科技股份有限公司 | Oligomeric phosphate compound and preparation method |
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| JPS4828757B1 (en) * | 1969-03-07 | 1973-09-04 | ||
| CN101585919A (en) * | 2009-06-25 | 2009-11-25 | 上海交通大学 | Hyperbranched polyphosphate with biocompatibility and method for synthesizing the same |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115806673A (en) * | 2022-12-29 | 2023-03-17 | 华南理工大学 | Hyperbranched polyphosphate ester material containing thioether bonds as well as preparation method and application thereof |
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