CN102585212A - Preparation method of novel fluorescence polymer containing nitrogen - Google Patents
Preparation method of novel fluorescence polymer containing nitrogen Download PDFInfo
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- CN102585212A CN102585212A CN2011100205370A CN201110020537A CN102585212A CN 102585212 A CN102585212 A CN 102585212A CN 2011100205370 A CN2011100205370 A CN 2011100205370A CN 201110020537 A CN201110020537 A CN 201110020537A CN 102585212 A CN102585212 A CN 102585212A
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Abstract
The invention provides a preparation method of novel fluorescence polymer containing nitrogen, which is simple to implement and low in cost. The product is easy to degrade, has the advantages of polyamidoamine dendrimer, overcomes the shortcomings of the polyamidoamine dendrimer and has wide application prospect in the fields of green lighting and environment-friendly materials and biomedicine. A polymerization system comprises micromolecule amine, acrylics and solvent. The three reactants are respectively added into a reaction container through a one-step method and are stirred under magnetic force under the temperature ranging from -10 DEG C to 50 DEG C for 0.5 day to 15 days, wherein the volume ratio of the micromolecule amine and the acrylics in the mixed liquid is 1:10-10:1. An obtained polymer has two obvious fluorescence peaks at the 370nm position and the 450nm position, and the transmitting peak at the 370nm position is higher in strength. The preparation method is simple to implement, and directly adopts alcohols as the solvent in the following fluorescence research without post-processing work like purification.
Description
Technical field
The present invention relates to a kind of preparation method of novel nitrogen-containing fluorescent polymer.
Background technology
The fluorescence emission light that to be molecule produce when the lower relaxation of electronic state of another kind of energy from a kind of electronic state; The generation of fluorescence depends on the The Nomenclature Composition and Structure of Complexes and the residing environment thereof of molecule; Wherein two prerequisites are: first; Molecule must have the frequency identical with irradiates light, and molecule can absorb light the energy of son, make its electron excitation to high-energy state; The second, molecule must have high fluorescence efficiency, makes the energy of absorption change into the photon energy of fluorescence form again, and does not consume with radiationless mode.Typical organic fluorescent substance all has molecular rigidity structure and electron conjugated structure, aromatic ring or have having of conjugation unsaturated group and be beneficial to and strengthen the extinction ability and improve fluorescence efficiency, thus produce intensive fluorescence.Traditional organic fluorescent substance is general water-soluble relatively poor, and biocompatibility is low and toxic side effect is high, to a certain degree limit the application of traditional organic fluorescent substance.
This research group one type of itrogenous organic substance that does not have typical fluorophor of discovery can be launched intense fluorescence; Compare with traditional organic fluorescent substance; The characteristic that the nitrogenous organic fluorescence thing of this type not only has good biocompatibility, water-soluble height and is easy to degrade; Also have the functional modification of being easy to and the simple relatively advantage of preparation, so wide application prospect is arranged at green luminescent material and biomedicine field.
The method of this type of nitrogenous fluorescent polymer luminescence mechanism of traditional research mainly is to start with from tree-like polymer.Main employing is dispersed method, convergence method, is dispersed convergence common method, solid-phase synthesis etc. in preparation.The method of dispersing progressively adds cladon from the nuclear beginning and carries out reaction repeated, connects end group at last and constructs dendrimer.But along with algebraically increases, cause reaction not exclusively easily, cause the part-structure defective, and their structure, performance are similar, separate very difficulty.Convergence method is the synthetic of ecto-entad, and per step has only limited functional group to participate in reaction, helps reacting completely; It is simpler than dispersing method to make separation; Defective reduces in the structure of dendrimer, and it can settle functional group neatly in the dendrimer periphery, and is slower but molecular weight increases; Synthetic big structure time space obstacle is very big, causes productive rate low.Above-mentioned several method has all been prepared the perfect tree-like polymer of structure, but their drawback is that the preparation process is loaded down with trivial details, complicated operation, and the comparatively difficulty of purifying makes product purity lower.Although the tree-like polymer of synthetic has more textural defect, but still can send intense fluorescence under proper condition.
This research group has synthesized a kind of hyperbranched nitrogenous fluorescent polymer first, and this method is simple, and cost is lower; And product be easy to the degraded, its primary structure is identical with tree-like polymer, has possessed the advantage that tree-like polymer possessed; And remedied the preparation tree-like high molecular weak point; Though defective is more on the structure, still can send intense fluorescence under proper condition, therefore have more wide application space.Synthetic and research for this type of hyperbranched nitrogenous fluorescent polymer does not also appear in the newspapers.
Summary of the invention
The objective of the invention is to solve the prior art defective, a kind of method for preparing the novel nitrogen-containing fluorescent polymer is provided.Present method is synthesized a kind of novel hyperbranched nitrogenous fluorescent polymer, and method technology is simple, is easy to degraded, and the hyperbranched polymer fluorescence intensity prepared is high, is the method for the nitrogenous fluorescent polymer of preparation of a kind of economy, efficient, environmental protection.
The present invention adopts single stage method synthesis of super branched polymer with nitrogen: small molecule amine, esters of acrylic acid were joined respectively in 1: 10 by volume～10: 1 in the reaction vessel of solvent; In-10～50 ℃; Magnetic agitation polymerase 10 .5～15d finally obtains thick product.
The volume ratio of small molecule amine and esters of acrylic acid is 1: 10～10: 1 among the present invention.
Temperature of reaction is a room temperature-10～50 ℃ among the present invention.
Preparation time among the present invention is 0.5～15d
Small molecule amine among the present invention is selected from one or more mixtures in quadrol, tn, the tetramethylenediamine.
Esters of acrylic acid among the present invention is selected from one or more mixtures in methyl acrylate, ethyl propenoate, the Bing Xisuandingzhi.
Solvent among the present invention is selected from methyl alcohol, ethanol, terepthaloyl moietie, 1, one or more mixtures in 2-Ucar 35, propyl carbinol, Virahol, propyl carbinol, the primary isoamyl alcohol.
Description of drawings
Fig. 1 and Fig. 2 are the fluorescence spectrum of embodiment 1 product.
Embodiment
Embodiment 1
With the 10mL quadrol, the 10mL methyl acrylate, 10mL methyl alcohol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Embodiment 2
With the 10mL quadrol, the 10mL ethyl propenoate, 10mL ethanol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Embodiment 3
With the 15mL quadrol, the 10mL Bing Xisuandingzhi, the 10mL propyl carbinol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Embodiment 4
With the 10mL tn, the 15mL methyl acrylate, 10mL methyl alcohol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Embodiment 5
With the 15mL tn, the 10mL ethyl propenoate, 10mL ethanol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Embodiment 6
With the 10mL tn, the 10mL Bing Xisuandingzhi, the 10mL propyl carbinol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Embodiment 7
With the 10mL tetramethylenediamine, the 10mL methyl acrylate, 10mL methyl alcohol is added in the reaction vessel, and in-10～50 ℃, polymerase 10 .5～15d can obtain hyperbranched fluorescent polymer under magnetic agitation.
Claims (7)
1. the preparation method of a novel nitrogen-containing fluorescent polymer is characterized in that: join small molecule amine, esters of acrylic acid and solvent in the reaction vessel respectively; Wherein, the volume ratio of small molecule amine and esters of acrylic acid is 1: 10～10: 1 in the mixed solution, and under-10～50 ℃, magnetic agitation polymerase 10 .5～15d forms thick polymkeric substance;
Described small molecule amine is selected from one or more mixtures in quadrol, tn, the tetramethylenediamine;
Used esters of acrylic acid is selected from one or more mixtures in methyl acrylate, ethyl propenoate, the Bing Xisuandingzhi;
Used solvent is methyl alcohol, ethanol, terepthaloyl moietie, 1,2-Ucar 35, propyl carbinol, Virahol, propyl carbinol, primary isoamyl alcohol.
2. method according to claim 1 is characterized in that: the volume ratio of described small molecule amine and esters of acrylic acid is 1: 10～10: 1.
3. method according to claim 1 is characterized in that: said temperature is-10～50 ℃.
4. method according to claim 1 is characterized in that: the described reaction times is 0.5～15d.
5. method according to claim 1 is characterized in that: described small molecule amine is selected from one or more the mixture in quadrol, tn, the tetramethylenediamine.
6. method according to claim 1 is characterized in that: described esters of acrylic acid is selected from one or more the mixture in methyl acrylate, ethyl propenoate, the Bing Xisuandingzhi;
7. method according to claim 1 is characterized in that: the fluorescence excitation of described polymkeric substance and emission peak positions be respectively at Ex 300, Em 370nm and Ex 345, Em 450nm.
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| CN2011100205370A CN102585212A (en) | 2011-01-10 | 2011-01-10 | Preparation method of novel fluorescence polymer containing nitrogen |
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| CN2011100205370A CN102585212A (en) | 2011-01-10 | 2011-01-10 | Preparation method of novel fluorescence polymer containing nitrogen |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101220154A (en) * | 2008-01-31 | 2008-07-16 | 上海交通大学 | Crosslinked polyalcohol membrana body material, method for producing the same and process of using |
| CN101531800A (en) * | 2009-04-14 | 2009-09-16 | 东华大学 | Method for preparing poly(amidoamine)/carbon nanometer tube composite material for cancer cell targeting diagnosis |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101220154A (en) * | 2008-01-31 | 2008-07-16 | 上海交通大学 | Crosslinked polyalcohol membrana body material, method for producing the same and process of using |
| CN101531800A (en) * | 2009-04-14 | 2009-09-16 | 东华大学 | Method for preparing poly(amidoamine)/carbon nanometer tube composite material for cancer cell targeting diagnosis |
Non-Patent Citations (2)
| Title |
|---|
| 刘军安等: "聚酰胺-胺型树状大分子的合成及pH值对其荧光性能的影响", 《华中师范大学学报（自然科学版）》, vol. 41, no. 1, 30 March 2007 (2007-03-30) * |
| 郝利玲等: "一种新型树状大分子的合成及表征", 《山西大学学报（自然科学版）》, vol. 32, no. 1, 15 February 2009 (2009-02-15) * |
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Application publication date: 20120718 |