CN114736363B - Fluorescent polymers and methods of modulating the luminescent color of fluorescent polymers - Google Patents
Fluorescent polymers and methods of modulating the luminescent color of fluorescent polymers Download PDFInfo
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Abstract
The invention relates to a fluorescent polymer and a method for regulating and controlling the luminescence color of the fluorescent polymer, belonging to the field of polymer luminescent materials. The invention particularly relates to a polymer with a molecular skeleton containing tertiary amine and vinyl ether groups or vinyl ether and other non-traditional chromophores, which can realize the change of fluorescent color from blue light to red light by controlling the structure of the polymer (adjusting the distance between the tertiary amine and the vinyl ether groups or the vinyl ether groups in the main chain of the polymer), and can be applied to the fields of anti-counterfeiting, ion detection, cell imaging and the like. The color-controllable fluorescent polymer is prepared based on the click reaction of diol or triol and activated alkyne monomer through hydroxyl and alkyne. The non-traditional fluorescent polymer prepared by the invention has the characteristics of adjustable fluorescence of a polymer structure, has the advantages of mild polymerization reaction conditions, simple and efficient system, environmental friendliness and the like, is suitable for large-scale production and application, and has a huge application prospect.
Description
Technical Field
The invention belongs to the field of polymer luminescent materials, and particularly relates to a polymer with a molecular skeleton containing tertiary amine, vinyl ether group or vinyl ether and other non-traditional chromophores and a preparation method thereof. Relates to a fluorescent polymer and a method for regulating and controlling the luminous color by the fluorescent polymer.
Background
The fluorescent small molecules have the defects of difficult separation, high toxic and side effects, easy pollution, unrepeatable use and the like, so that the application range and the scene of the fluorescent small molecules are greatly limited. In order to overcome the limitations of fluorescent small molecules, people aim at fluorescent polymers with excellent performance. The fluorescent polymer chromophore is bonded in the molecular weight in a covalent bond form, and has the advantages of difficult falling off, uniform distribution and excellent optical performance. Meanwhile, the fluorescent polymer has the advantages of good mechanical property, easy processing and the like, and is widely applied.
The traditional fluorescent polymers all carry larger conjugated systems and have rigid plane structures, and have the inherent defects of difficult preparation, poor hydrophilicity, high toxicity and the like, so that the application of the fluorescent polymers is limited to a certain extent. In recent years, researchers have found that a class of polymers without conventional chromophores also exhibit significant photoluminescent properties in the aggregated state. Such non-conventional luminescent materials do not contain conventional pi-conjugated chromophores, and only contain electron-rich heteroatoms (e.g., N, O, S, P atoms and/or unsaturated bonds) non-conventional chromophores. Compared with non-traditional polymer fluorescent materials, the non-traditional fluorescent materials have the advantages of easy preparation, stable structure, good hydrophilicity and biocompatibility and the like, and become ideal candidate materials for sensor, biology and medical application. However, most of the non-traditional fluorescent polymer materials emit fluorescence mainly in blue or green areas, and it is difficult to realize the structure to regulate the light emitting color of the non-traditional fluorescent polymer. Therefore, the realization of the structural control of the luminescence color of the non-traditional fluorescent polymer has important significance for understanding the luminescence mechanism, and is beneficial to widening the application fields, in particular to aspects of anti-counterfeiting, biological imaging, photodynamic therapy and the like.
Disclosure of Invention
The invention aims at solving the defect that the non-traditional fluorescent polymer is difficult to realize the achievement of long-wavelength and red fluorescent materials through structural control, and provides a non-traditional fluorescent polymer material with adjustable luminous color from a blue light region to a red light region and a preparation method thereof. The non-traditional fluorescent polymer is a non-traditional chromophore (the structure of which is shown as formula 1) containing tertiary amine, vinyl ether group or vinyl ether and the like in a molecular skeleton, has aggregation-induced luminescence and excitation wavelength-dependent red shift characteristics, is prepared through hydroxyl-alkynyl click polymerization reaction, and can regulate and control the excitation wavelength and the emission wavelength of the polymer through a polymer structure, so that the change of fluorescent color from blue light to red light is realized through the control of the polymer structure, and the non-traditional fluorescent polymer can be used in the fields of anti-counterfeiting, ion detection and biomedical.
Any linear and branched polymer having a molecular skeleton containing these structural units can be used, and m in the structural units can be adjusted to control the luminescence color of the fluorescent polymer, the luminescence color varies from a blue light region to a red light region, and the smaller the m value, i.e., the shorter the distance between the tertiary amine and the vinyl ether group or between the tertiary amine and the vinyl ether group. The closer the emission wavelength of the fluorescent polymer is to the red light region, the more favorable the red light region material is obtained. n is the number of the polymer chain structural units and is not particularly limited.
The distance between the tertiary amine and vinyl ether group of the polymer main chain or the distance between the vinyl ether group is realized by hydroxyl-alkyne click polymerization reaction of an alcohol monomer and activated alkyne monomers with different carbon chain lengths or alcohol and activated alkyne monomers with different carbon chain lengths.
Wherein the alcohol monomer is diol or triol, such as 2-methyl-1, 3-propanediol, N-methyldiethanolamine or triethanolamine, and the ester group activated alkyne with different carbon chain lengths is ethylene glycol dipropionate, 1, 4-butanediol dipropionate and 1, 6-hexanediol dipropionate; or carbonyl-activated alkynes are bis (acetyl dipropyl alkyne), bis (butyryl dipropyl alkyne) and bis (hexanoyl dipropyl alkyne).
Wherein the activated alkyne monomer is alkyne activated by ester groups or carbonyl groups, and the alcohols with different carbon chain lengths are ethylene glycol, 1, 4-butanediol, 1, 5-pentanediol and 1, 6-hexanediol.
Further, the structural units contained in the linear or branched fluorescent polymer are:
when m=3, 2 and 1, the blue light, the green light and the red light respectively correspond to the blue light, the green light and the red light materials, and the light emitting color of the non-traditional fluorescent polymer is regulated and controlled by the polymer structure.
Further, the structural units contained in the linear or branched fluorescent polymer are:
when m=3, 2 and 1, the blue light, the green light and the red light respectively correspond to the blue light, the green light and the red light materials, and the light emitting color of the non-traditional fluorescent polymer is regulated and controlled by the polymer structure.
Further, the structural units contained in the linear or branched fluorescent polymer are:
when m=3, 2 and 1, the polymer structure is realized to regulate the luminous color of the non-traditional fluorescent polymer corresponding to blue light, blue light and green light materials respectively.
Further, the structural units contained in the linear or branched fluorescent polymer are:
when m=6, 5, 4, 2, corresponding to blue light, blue light and green light materials, respectively, the polymer structure is realized to regulate the luminescence color of the non-traditional fluorescent polymer.
Compared with the prior art, the invention has the beneficial effects that:
the non-traditional fluorescent polymer prepared by the invention can realize the change of fluorescent color from blue light to red light through the control of a polymer structure (adjusting the distance between the tertiary amine of the polymer main chain and the vinyl ether group or the vinyl ether group), has the characteristic of adjustable fluorescence of the polymer structure, has the advantages of mild polymerization reaction condition, simple and efficient system, environmental friendliness and the like, and can be applied to the fields of anti-counterfeiting, ion detection, cell imaging and the like.
Drawings
FIG. 1 nuclear magnetic hydrogen spectra of polymers LP-1, LP-2 and LP-3.
FIG. 2 shows the fluorescence chromatograms of polymers LP-1, LP-2 and LP-3 at 40mg/mL of (a) ultraviolet, (b) emission spectrum and (c) at the respective excitation wavelengths.
FIG. 3 nuclear magnetic resonance hydrogen spectra of polymers LP-3, LP-4 and LP-5.
FIG. 4 emission spectra of polymers LP-4, LP-5 and LP-6 at 40 mg/mL.
FIG. 5 emission spectra of polymers LP-7, LP-8 and LP-9 at 40 mg/mL.
FIG. 6 emission spectra of polymers LP-10, LP-11, LP-12 and LP-13 at 40 mg/mL.
FIG. 7 nuclear magnetic resonance hydrogen spectra of polymers BP-1, BP-2 and BP-3.
FIG. 8 emission spectra of polymers BP-1, BP-2 and BP-3 at 20 mg/mL.
Detailed Description
All monomers are commercially available or readily synthesized.
For example wherein the ester alkyne monomer is activatedReference may be made to the synthesis of publication (Polymer Chemistry,2020,11 (14): 2568-2575).
Example 1:
n-methyldiethanolamine (0.119 g,1 equiv) was mixed with 1, 6-hexanediol dipropionate (0.222 g,1 equiv), 1, 4-butanediol dipropionate (0.194 g,1 equiv) or ethylene glycol dipropionate (0.166 g,1 equiv) monomers, respectively, at 25 ℃. After the reaction was completed, three groups of the mixture were precipitated with n-hexane to obtain three groups of polymers LP-1 (m=3), LP-2 (m=2) and LP-3 (m=1) of different structures, respectively. The resulting polymer structure was confirmed by nuclear magnetism (fig. 1). The maximum absorption peak and the emission peak of the obtained LP-1, LP-2 and LP-3 in 40mg/mL tetrahydrofuran solution are subjected to obvious red shift in sequence, the maximum excitation wavelengths of the obtained LP-1, LP-2 and LP-3 in 40mg/mL tetrahydrofuran solution are respectively 380, 450 and 560nm, and the maximum emission wavelengths are respectively 460, 522 and 607nm, which correspond to blue light, green light and red light materials respectively (figure 2), which shows that the method can prepare the change of the luminescence color from the blue light area to the red light area by using the tertiary amine-containing diol and the ester with different carbon chain lengths to activate alkyne, and realize the regulation of the luminescence color of the non-traditional fluorescent polymer by using the polymer structure (changing the distance between the tertiary amine and vinyl ether groups).
Example 2:
n-methyldiethanolamine (0.119 g,1 equiv) was mixed with bis (hexanoyl dipropyl) (0.190 g,1 equiv), bis (butyryl dipropyl) (0.162 g,1 equiv) or bis (acetyl dipropyl) (0.134 g,1 equiv) monomers, respectively, at 25 ℃. After the reaction was completed, three groups of mixtures were precipitated with n-hexane to obtain three groups of linear polymers LP-4 (m=3), LP-5 (m=2) and LP-6 (m=1) of different structures, respectively. The resulting polymer structure was confirmed by nuclear magnetism (fig. 3). The maximum emission peaks of LP-4, LP-5 and LP-6 obtained by fluorescence spectrum test in 40mg/mL tetrahydrofuran solution are obviously red shifted in sequence, and the maximum emission wavelengths of LP-4, LP-5 and LP-6 are 465, 527 and 610nm respectively (figure 4), which shows that the method can prepare polymers with different emission wavelengths by using the diol containing tertiary amine and carbonyl activated alkyne with different carbon chain lengths, and realize the regulation of the luminous color of non-traditional fluorescent polymers by using the polymer structure (changing the distance between tertiary amine and vinyl ether groups).
Example 3:
2-methyl-1, 3-propanediol (0.104 g,1 equiv) was mixed with 1, 6-hexanediol dipropionate (0.222 g,1 equiv), 1, 4-butanediol dipropionate (0.1940 g,1 equiv) or ethylene glycol dipropionate (0.166 g,1 equiv) monomer at 25℃using 1, 4-diazabicyclo [2.2.2] octane (0.01 g,0.1 equiv) as a catalyst. After the reaction is finished, the three groups of mixtures are respectively settled by normal hexane to obtain three groups of polymers LP-7, LP-8 and LP-9 with different structures. The maximum emission peaks of LP-7, LP-8 and LP-9 obtained by fluorescence spectrum test in 40mg/mL tetrahydrofuran solution are obviously red shifted in sequence, and the maximum emission wavelengths of LP-7, LP-8 and LP-9 are 432, 475 and 525nm respectively (figure 5), which shows that polymers with different emission wavelengths can be prepared by hydroxyl-alkyne click polymerization of diols without tertiary amine and alkynes with different carbon chain lengths, and the purpose of regulating and controlling the luminous color of non-traditional fluorescent polymers by a polymer structure (changing the distance between vinyl ether groups) is realized.
Example 4:
ethylene glycol dipropionate (0.166 g,1 equiv) was reacted with 1, 6-hexanediol (0.118 g,1 equiv), 1, 5-pentanediol (0.104 g,1 equiv), 1, 4-butanediol (0.090 g,1 equiv), ethylene glycol (0.062 g,1 equiv) or at 25℃with 1, 4-diazabicyclo [2.2.2] octane (0.01 g,0.1 equiv) as a catalyst, and the four groups of mixtures were each precipitated with n-hexane to give four groups of polymers of different structures, LP-10 (m=6), LP-11 (m=5), LP-12 (m=4) and LP-13 (m=2). The maximum emission peaks of the LP-10, LP-11, LP-12 and LP-13 obtained through fluorescence spectrum test in 40mg/mL tetrahydrofuran solution are subjected to obvious red shift in sequence, and the maximum emission wavelengths of the LP-10, LP-11, LP-12 and LP-13 are 428, 430, 480 and 530nm (figure 6), and the method prepares polymers with different emission wavelengths through hydroxyl-alkyne click polymerization by using ester activated alkyne and alcohols with different carbon chain lengths, and realizes the regulation of the luminous color of non-traditional fluorescent polymers through a polymer structure (changing the distance between vinyl ether groups).
Example 5
Triethanolamine (0.149 g,1 equiv) was reacted with 1, 6-hexanediol dipropionate (0.222 g,1 equiv), 1, 4-butanediol dipropionate (0.194 g,1 equiv), or ethylene glycol dipropionate (0.166 g,1 equiv) monomer, respectively, at 25℃with mixing and stirring. After 24h of reaction, the three groups of mixtures were respectively precipitated with diethyl ether to give three groups of branched polymers BP-1 (m=3), BP-2 (m=2) and BP-3 (m=1) of different structures. The resulting polymer structure was confirmed by nuclear magnetism (fig. 7). The maximum emission peaks of BP-1, BP-2 and BP-3 obtained by fluorescence spectrum test in 20mg/mL tetrahydrofuran solution are obviously red shifted in sequence, the maximum emission wavelengths of BP-1, BP-2 and BP-3 in 20mg/mL tetrahydrofuran solution are 432, 471 and 573nm respectively (figure 8), which shows that branched polymers with different emission wavelengths are prepared by hydroxyl-alkyne click polymerization of tertiary amine-containing triols and ester-activated alkynes with different carbon chain lengths, and the polymer structure (changing the distance between groups of tertiary amine and vinyl ether) is realized to regulate and control the luminous color of non-traditional fluorescent polymers.
Claims (7)
1. A luminescent color-tunable fluorescent polymer, characterized in that: the fluorescent polymer is a linear and branched polymer with a molecular main chain containing tertiary amine and vinyl ether groups or vinyl ether structures;
the structural unit general formula of the linear or branched polymer in which the molecular main chain contains tertiary amine and vinyl ether group structure is as follows:
the structural unit general formula of the linear or branched polymer in which the molecular main chain contains vinyl ether group structure is as follows:
wherein m is 1 to 6.
2. A method for controlling the luminescence color of a fluorescent polymer, characterized in that the excitation wavelength and the emission wavelength of the polymer are controlled by controlling the distance between tertiary amine and vinyl ether group or the distance between vinyl ether in the structural unit of the fluorescent polymer according to claim 1, so that the change of the luminescence color from blue light region to red light region is controlled by the structure of the polymer.
3. The method for controlling the luminescence color of the fluorescent polymer according to claim 2, wherein the distance between the main chain tertiary amine and the vinyl ether group or the distance between the vinyl ethers in the structural unit of the fluorescent polymer is realized by hydroxyl-alkyne click polymerization reaction of an alcohol monomer and an activated alkyne monomer with different carbon chain lengths or an alcohol with different carbon chain lengths and an activated alkyne monomer.
4. The method of modulating the luminescent color of a fluorescent polymer of claim 2, wherein the linear or branched fluorescent polymer comprises structural units of the formula:
when m=3, 2 and 1, the blue light, the green light and the red light respectively correspond to the blue light, the green light and the red light materials, and the light emitting color of the non-traditional fluorescent polymer is regulated and controlled by the polymer structure.
5. The method of modulating the luminescent color of a fluorescent polymer of claim 2, wherein the linear or branched fluorescent polymer comprises structural units of the formula:
when m=3, 2 and 1, the blue light, the green light and the red light respectively correspond to the blue light, the green light and the red light materials, and the light emitting color of the non-traditional fluorescent polymer is regulated and controlled by the polymer structure.
6. The method of modulating the luminescent color of a fluorescent polymer of claim 2, wherein the linear or branched fluorescent polymer comprises structural units of the formula:
when m=3, 2 and 1, the polymer structure is realized to regulate the luminous color of the non-traditional fluorescent polymer corresponding to blue light, blue light and green light materials respectively.
7. The method of modulating the luminescent color of a fluorescent polymer of claim 2, wherein the linear or branched fluorescent polymer comprises structural units of the formula:
when m=6, 5, 4, 2, corresponding to blue light, blue light and green light materials, respectively, the polymer structure is realized to regulate the luminescence color of the non-traditional fluorescent polymer.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012177021A2 (en) * | 2011-06-24 | 2012-12-27 | Lg Chem, Ltd. | Polymeric fluorescent material |
| CN110358064A (en) * | 2019-07-11 | 2019-10-22 | 陕西师范大学 | A kind of transmitting fluorescent polymer preparation of non-conjugated systems and test method |
| CN110483773A (en) * | 2019-08-22 | 2019-11-22 | 苏州大学 | Polyvinyl thioethers ester and the preparation method and application thereof |
| CN110845714A (en) * | 2019-11-19 | 2020-02-28 | 常州大学 | Water-soluble aggregation-induced emission polymer and preparation method and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012177021A2 (en) * | 2011-06-24 | 2012-12-27 | Lg Chem, Ltd. | Polymeric fluorescent material |
| CN110358064A (en) * | 2019-07-11 | 2019-10-22 | 陕西师范大学 | A kind of transmitting fluorescent polymer preparation of non-conjugated systems and test method |
| CN110483773A (en) * | 2019-08-22 | 2019-11-22 | 苏州大学 | Polyvinyl thioethers ester and the preparation method and application thereof |
| CN110845714A (en) * | 2019-11-19 | 2020-02-28 | 常州大学 | Water-soluble aggregation-induced emission polymer and preparation method and application thereof |
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