CN110003488B - Amphiphilic aggregation-induced emission hyperbranched polyphosphoric acid amide and synthesis method thereof - Google Patents
Amphiphilic aggregation-induced emission hyperbranched polyphosphoric acid amide and synthesis method thereof Download PDFInfo
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- 238000004220 aggregation Methods 0.000 title claims abstract description 24
- 230000002776 aggregation Effects 0.000 title claims abstract description 24
- 238000001308 synthesis method Methods 0.000 title abstract description 8
- 150000001408 amides Chemical class 0.000 title description 42
- 229920000137 polyphosphoric acid Polymers 0.000 title description 35
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000004985 diamines Chemical class 0.000 claims abstract description 8
- 238000004020 luminiscence type Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 238000001291 vacuum drying Methods 0.000 claims description 11
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000010189 synthetic method Methods 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 238000000502 dialysis Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
- 230000007613 environmental effect Effects 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000010644 ester aminolysis reaction Methods 0.000 abstract description 2
- 238000007306 functionalization reaction Methods 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 108020004459 Small interfering RNA Proteins 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 229920001109 fluorescent polymer Polymers 0.000 description 1
- 238000001476 gene delivery Methods 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- -1 polychlorinated phosphate ester Chemical class 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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Abstract
本发明涉及一种双亲性聚集诱导发光超支化聚磷酰胺及合成方法，以磷酸三乙酯与二元胺为原料通过简单可控的酯的胺解法合成超支化聚磷酰胺。所合成的超支化聚磷酰胺中不含苯环，只含有胺基和P＝O键，具有良好的生物相容性和生物降解性，且这类超支化聚磷酰胺可发射明亮的蓝色荧光，并具有聚集诱导发光特性。本专利报道的超支化聚磷酰胺具有合成及提纯工艺简便、过程可控、三废污染少，且产品的稳定性好、毒性低、生物降解性好、环境友好性以及荧光强度高。易于进行修饰实现功能化、荧光强度高、应用范围广等特征。
The invention relates to an amphiphilic aggregation-induced luminescence hyperbranched polyphosphoramid and a synthesis method. The hyperbranched polyphosphoramid is synthesized by a simple and controllable ester aminolysis method using triethyl phosphate and diamine as raw materials. The synthesized hyperbranched polyphosphoramids do not contain benzene rings, but only contain amine groups and P=O bonds. They have good biocompatibility and biodegradability, and this type of hyperbranched polyphosphoramids can emit bright blue. Fluorescence, and has aggregation-induced luminescence properties. The hyperbranched polyphosphoramide reported in this patent has the advantages of simple synthesis and purification process, controllable process, less pollution of three wastes, good product stability, low toxicity, good biodegradability, environmental friendliness and high fluorescence intensity. It is easy to be modified to achieve functionalization, high fluorescence intensity, and wide application range.
Description
Technical Field
The invention belongs to the field of high-molecular luminescent materials, and relates to amphiphilic aggregation-induced emission hyperbranched polyphosphoric acid amide 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. The polyphosphazene amide as a novel polymer 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 polyphosphazene amide has a definite three-dimensional structure and a large number of active groups with modifiable tail ends, and is a very good gene delivery tool.
Xu et al [ Royal Society of Chemistry,2015,5:50425] A dendritic polyphosphamide was synthesized by click Chemistry using ethyl dichlorophosphate and N- (2-aminoethyl) -N- (1-methyl) -1, 2-ethylenediamine as starting materials and used for gene and siRNA delivery. Ye et al (Polymer Degradation and Stability,2017,142: 29) use phenyl dichlorophosphate and melamine as raw materials to synthesize a hyperbranched polyphosphoric acid amide. In the existing synthesis method of the polyphosphoric acid amide, phosphorus oxychloride or polychlorinated phosphate ester is used as a raw material and reacts with polyamine to prepare the polyphosphoric acid amide. HCl generated in the synthesis process reacts with triethylamine to generate salt, and the salt is removed through suction filtration. In the reaction process, acetonitrile and other solvents are added to ensure that the reaction is smoothly carried out. 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 polyphosphoric acid amide is limited. Therefore, the simple and environment-friendly synthesis process of the polyphosphoric acid amide has great application prospect. In addition, no report on the fluorescence property of the polyphosphazene amide exists at present, so that the characterization means after the gene loading of the polyphosphazene amide is complicated. If a polyphosphoric amide 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 using polyphosphoric amide as a 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 amphiphilic aggregation-induced emission hyperbranched polyphosphazene and a synthesis method thereof, and develops a plurality of amphiphilic hyperbranched polyphosphazenes with aggregation-induced emission characteristics, and the synthesized hyperbranched polyphosphazene can emit bright blue fluorescence.
Technical scheme
An amphiphilic aggregation-induced emission hyperbranched polyphosphazene amide is characterized in that: triethyl phosphate and diamine are used as raw materials, the molar ratio is 2: 1-4, the triethyl phosphate and the diamine are obtained through an ester aminolysis reaction, and the structural formula of the obtained amphiphilic aggregation-induced luminescence hyperbranched polyphosphoric acid amide is as follows:
the diamines include, but are not limited to, ethylenediamine, 1, 6-hexanediamine, propylenediamine, urea, 1, 5-diaminopentane, 1, 7-diaminoheptane.
A synthetic method of the amphiphilic aggregation-induced emission hyperbranched polyphosphoric acid amide is characterized by comprising the following steps:
step 1: mixing triethyl phosphate and diamine in a molar ratio of 2: 1-4;
step 2: under the protection of nitrogen, heating to 70-180 ℃, and stirring for reaction for 9-18 h;
and step 3: dissolving the product in ethanol, dialyzing, rotary evaporating and vacuum drying to obtain the amphiphilic aggregation-induced luminescent hyperbranched polyphosphoric acid amide.
A use method of the amphiphilic aggregation-induced emission hyperbranched polyphosphazene is characterized by comprising the following steps: dissolving amphiphilic aggregation-induced emission hyperbranched polyphosphazene in water, and emitting bright blue fluorescence under the irradiation of ultraviolet light; increasing the wavelength of the ultraviolet light causes a red shift.
A use method of the amphiphilic aggregation-induced emission hyperbranched polyphosphazene is characterized by comprising the following steps: dissolving amphiphilic aggregation-induced emission hyperbranched polyphosphoric acid amide in an organic solvent, and emitting bright blue fluorescence under ultraviolet irradiation; increasing the wavelength of the ultraviolet light causes a red shift.
Advantageous effects
The invention provides amphiphilic aggregation-induced emission hyperbranched polyphosphoric acid amide and a synthesis method thereof. The synthesized hyperbranched polyphosphoric acid amide does not contain benzene rings, only contains amino and P ═ O bonds, has good biocompatibility and biodegradability, and can emit bright blue fluorescence and has aggregation-induced luminescence characteristics. The hyperbranched polyphosphoric acid amide reported in the patent has the advantages of simple and convenient synthesis and purification process, controllable process, less three-waste pollution, good stability of the product, low toxicity, good biodegradability, environmental friendliness and high fluorescence intensity. Easy modification and realization of functionalization, high fluorescence intensity, wide application range and the like.
The hyperbranched polyphosphoric acid amide synthesized by the invention can be dissolved in water or an organic reagent, and can emit bright blue fluorescence under the irradiation of ultraviolet light. The synthesis method has the characteristics of simple process, controllable structure, no need of catalyst solvent, environmental friendliness and the like. The synthesized hyperbranched polyphosphoric acid amide has good biocompatibility, biodegradability and easy modification, and has aggregation-induced emission characteristics, so that the hyperbranched polyphosphoric acid amide has wide application prospects in the aspects of DNA/RNA (deoxyribonucleic acid/ribonucleic acid) transportation, cell imaging, drug delivery and the like.
Drawings
FIG. 1 shows the excitation spectrum and the emission spectrum of a pure amino-terminated hyperbranched polyphosphazene. As can be seen, the maximum excitation wavelength is 397nm, at which the fluorescence intensity is strongest, and the corresponding emission wavelength is 442 nm.
Detailed Description
The invention will now be further described with reference to the following examples and drawings:
example 1
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and ethylenediamine (14.42g) in a molar ratio of 1:1.6 under the protection of nitrogen, mixing, slowly heating to 80 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 2
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and ethylenediamine (16.23g) in a molar ratio of 1:1.8 under the protection of nitrogen, mixing, slowly heating to 80 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 3
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and ethylenediamine (18.03g) in a molar ratio of 1:2 under the protection of nitrogen, mixing, slowly heating to 80 ℃, 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 4
The preparation method of the terminal ethoxy hyperbranched polyamino ester comprises the following steps: reacting triethyl phosphate (27.32g) and ethylenediamine (12.62g) in a molar ratio of 1:1.4 under the protection of nitrogen, mixing, slowly heating to 80 ℃, stirring at the temperature, reacting for 10 hours, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 5
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and 1, 6-hexamethylene diamine (27.89g) in a molar ratio of 1:1.6 under the protection of nitrogen, mixing, slowly heating to 120 ℃, stirring at the temperature, reacting for 12 hours, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 6
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and 1, 3-propane diamine (17.31g) in a molar ratio of 1:1.6 under the protection of nitrogen, mixing, slowly heating to 110 ℃, stirring at the temperature, reacting for 11 hours, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 7
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and urea (14.41g) in a molar ratio of 1:1.6 under the protection of nitrogen, mixing, slowly heating to 110 ℃, stirring at the temperature, reacting for 11h, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 8
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and 1, 5-diaminopentane (24.52g) in a molar ratio of 1:1.6 under the protection of nitrogen, mixing, slowly heating to 130 ℃, stirring at the temperature, reacting for 14h, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
Example 9
The preparation method of the amino-terminated hyperbranched polyphosphoric acid amide comprises the following steps: reacting triethyl phosphate (27.32g) and 1, 7-diaminoheptane (31.26g) in a molar ratio of 1:1.6 under the protection of nitrogen, mixing, slowly heating to 150 ℃, stirring at the temperature, reacting for 16h, dissolving the product in ethanol, dialyzing, rotary evaporating, and vacuum drying to obtain the amino-terminated hyperbranched polyphosphoric acid amide.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295778A (en) * | 2011-06-30 | 2011-12-28 | 西安交通大学 | Hyperbranched polyphosphoramidate and preparation method thereof |
| CN107151316A (en) * | 2017-06-20 | 2017-09-12 | 西北工业大学 | The hyperbranched polycarbonates and preparation method of the carbonyl end-blocking of energy emitting bright fluorescence |
| CN108727576A (en) * | 2018-05-29 | 2018-11-02 | 西北工业大学 | A kind of hyperbranched poly amino ester and preparation method that can emit multicolor fluorescence |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0700792A2 (en) * | 2007-12-07 | 2010-04-28 | Peter Dr Anna | Process for the preparation of amine functional phosphoric amides and their use as flame retardant and curing agent for epoxy resing |
| WO2012112899A1 (en) * | 2011-02-17 | 2012-08-23 | Vanderbilt University | Enhancement of light emission quantum yield in treated broad spectrum nanocrystals |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295778A (en) * | 2011-06-30 | 2011-12-28 | 西安交通大学 | Hyperbranched polyphosphoramidate and preparation method thereof |
| CN107151316A (en) * | 2017-06-20 | 2017-09-12 | 西北工业大学 | The hyperbranched polycarbonates and preparation method of the carbonyl end-blocking of energy emitting bright fluorescence |
| CN108727576A (en) * | 2018-05-29 | 2018-11-02 | 西北工业大学 | A kind of hyperbranched poly amino ester and preparation method that can emit multicolor fluorescence |
Non-Patent Citations (2)
| Title |
|---|
| Fluorescence emission from hyperbranched polycarbonate without conventional chromohpores;Yuqun Du, et al;《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY》;20180618;第364卷;第415-423页 * |
| Synthesis and properties of a novel hyperbranched polyphosphoramidate using an A2+CB2 approach;Yuhong Liu, et al;《POLYMER INTERNATIONAL》;20120803;第62卷(第3期);第390-396页 * |
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