CN110016110B - Brush-shaped block polymer and synthesis method and application thereof - Google Patents
Brush-shaped block polymer and synthesis method and application thereof Download PDFInfo
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- 229920000642 polymer Polymers 0.000 title abstract description 11
- 238000001308 synthesis method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- 206010028933 Neonatal diabetes mellitus Diseases 0.000 claims abstract description 38
- 229920001400 block copolymer Polymers 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 238000010791 quenching Methods 0.000 claims abstract description 11
- 208000003013 permanent neonatal diabetes mellitus Diseases 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 8
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 8
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 4
- 239000004305 biphenyl Substances 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 44
- 239000004038 photonic crystal Substances 0.000 claims description 32
- 238000001338 self-assembly Methods 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 239000000049 pigment Substances 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000010438 heat treatment Methods 0.000 description 31
- 239000000243 solution Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 4
- 101150058790 bcp gene Proteins 0.000 description 3
- 101150038746 bcp1 gene Proteins 0.000 description 3
- 101150023633 bcpB gene Proteins 0.000 description 3
- 229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- 238000005034 decoration Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
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- 238000002310 reflectometry Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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Abstract
The invention discloses a brush-shaped block polymer and a synthesis method and application thereof, wherein the synthesis method of the brush-shaped block polymer comprises the following steps: dissolving norbornene monomer NBPM with a biphenyl structure into an organic solvent, adding a G-3 catalyst, stirring at 20-40 ℃ for reaction to homopolymerize the monomer NBPM, then adding the dissolved norbornene monomer NDM with a decyl structure into the reaction solution for continuous reaction to realize copolymerization of the NBPM and the NDM, adding a terminator after the reaction is finished to quench the reaction, and finally obtaining the target brush-shaped block copolymer PNBPM-b-PNDM. The invention can be used in light sensor, light valve, pigment and dye, with high application value.
Description
Technical Field
The invention relates to the technical field of preparation of brush-shaped block copolymers, in particular to a brush-shaped block polymer and a synthesis method and application thereof.
Background
The photonic crystal can regulate and control the propagation of light waves due to the existence of an internal photon forbidden band structure, so that the photonic crystal has great application value, such as special pigment, waveguide, reflective coating and the like. Responsive photonic crystals are a class of materials whose reflected wavelength can change with changes in external physical or chemical conditions. Such materials must have a responsive group present in addition to the periodic structure necessary for conventional photonic crystals. Two methods are common for introducing responsive groups: (1) the photonic crystal structure is directly constructed by using a responsive material as a matrix, for example, a one-dimensional photonic crystal is prepared by using block polymer self-assembly, and a chain segment swells in a solvent atmosphere so as to show the change of reflection wavelength. (2) Firstly, a photonic crystal structure is prepared, and then a responsive material is doped into a matrix to form a stable photonic crystal composite material. According to the requirements, the photonic crystal materials with different responsivities such as Ph, temperature, chemical solvents, electric fields, magnetic fields and the like can be designed and prepared by the two methods.
The temperature sensitive photonic crystal is a responsive photonic crystal material which is widely researched. Since the pioneering work of Asher (a.asher, et al Science 1996,274,959.), numerous temperature sensitive photonic crystal materials with similar structures have been reported. The majority of the hydrogel photonic crystals are temperature-sensitive hydrogel photonic crystals prepared by embedding colloidal crystals into poly (N-isopropylacrylamide) (PNIPAM). Since PNIPAM is a thermosensitive polymer having a lower critical solution temperature (LCST, about 32 ℃), when the temperature is increased, the polymer changes from hydrophilic to hydrophobic, drains water and shrinks in volume, so that the inter-particle distance in the colloidal crystal decreases, resulting in blue-shift of the reflection wavelength. When the temperature is reduced, the state can be restored. Although the photonic crystal material prepared by the method has obvious temperature response behavior, the process is complicated, and a large range of photonic crystal materials are difficult to prepare. Therefore, it is important to invent a simple and feasible low-cost technology for preparing the temperature-responsive one-dimensional photonic crystal material.
The patent discloses a novel brush-shaped block copolymer (PNBPM-b-PNDM), which is a series of one-dimensional photonic crystal materials obtained by self-assembly of simple low-boiling-point solvent films and has obvious temperature response behavior under heating conditions. Is expected to be practically applied to optical sensors and the like.
Disclosure of Invention
The invention aims to provide a brush-shaped block polymer and a synthesis method thereof aiming at the technical defects in the prior art, and the temperature-sensitive one-dimensional photonic crystal prepared by the brush-shaped block polymer through a simple self-assembly mode is expected to be practically applied to the aspects of optical sensors, light valves, pigments and dyes.
The technical scheme adopted for realizing the purpose of the invention is as follows:
the invention relates to a brush block copolymer, which is marked as PNBPM-b-PNDM and has the structural formula as follows:
wherein m is the polymerization degree of NBPM, and m is 100-; n is the polymerization degree of NDM, and n is 100-1500; the degree of main chain polymerization is 200-3000;
wherein: the structural formula of NBPM is:
the structural formula of NDM is:
preferably, m is n.
In another aspect of the present invention, a method for synthesizing the brush block copolymer is also included, comprising the steps of:
dissolving norbornene monomer NBPM with a biphenyl structure into an organic solvent, adding a G-3 catalyst, stirring at 20-40 ℃ for reaction to homopolymerize the monomer NBPM, then adding the dissolved norbornene monomer NDM with a decyl structure into the reaction solution for continuous reaction to realize the copolymerization of the NBPM and the NDM, adding a terminator after the reaction is finished, quenching and reacting, and finally obtaining the target brush-shaped block copolymer PNBPM-b-PNDM.
Preferably, the molar ratio of G-3, NBPM and NDM is: 1:(100-1500):(100-1500).
Preferably, the molar ratio of G-3, NBPM and NDM is: 1:(300-800):(300-800).
In another aspect of the invention, the application of the brush-shaped block copolymer in preparing a temperature-sensitive one-dimensional photonic crystal material is also included.
Preferably, the brush-shaped block copolymer is synthesized into a one-dimensional photonic crystal material through self-assembly.
The brush-shaped block copolymer self-assembly, namely the one-dimensional photonic crystal material has the following characteristics:
when the polymerization degree m of the NBPM is 180-220 and the polymerization degree n of the NDM is 180-220, the self-assembly substance is dark purple before heating and blue after heating, and preferably, m is 200 and n is 200.
When the polymerization degree m of the NBPM is 280-320 and the polymerization degree n of the NDM is 280-320, the self-assembly substance is blue before heating and bright green after heating, and preferably, m is 300 and n is 300.
When the polymerization degree m of the NBPM is 380-420 and the polymerization degree n of the NDM is 380-420, the self-assembly substance is green and red after heating, and preferably, m is 400 and n is 400.
When the polymerization degree m of the NBPM is 480-520 and the polymerization degree n of the NDM is 480-520, the self-assembly material is red before heating and grey brown after heating, and preferably, m is 500 and n is 500.
The brush block copolymer self-assembly method comprises the following steps: the synthesized brush block copolymer (PNBPM-b-PNDM) is uniformly dispersed in Tetrahydrofuran (THF), the mixed solution is coated on a glass sheet, and a polymer film is obtained after the solvent is volatilized at room temperature.
Preferably, the self-assembly method further comprises a thermal quenching step, specifically, the polymer film is placed on a flat plate heating table and kept for 1-24 hours at 50-300 ℃.
The brush block copolymer self-assembly method can regulate and control the color of a polymerization product.
When the polymerization degree m of the NBPM is 180-220 and the polymerization degree n of the NDM is 180-220, the self-assembly substance is dark purple before heating and blue after heating, preferably, m is 200, and n is 200; when the polymerization degree m of the NBPM is 280-320 and the polymerization degree n of the NDM is 280-320, the self-assembly substance is blue before heating and bright green after heating, preferably, m is 300, and n is 300; when the polymerization degree m of the NBPM is 380-420 and the polymerization degree n of the NDM is 380-420, the self-assembly substance is green and red after heating, preferably, m is 400, and n is 400; when the polymerization degree m of the NBPM is 480-520 and the polymerization degree n of the NDM is 480-520, the self-assembly material is red before heating and grey brown after heating, and preferably, m is 500 and n is 500.
Compared with the prior art, the invention has the beneficial effects that:
the synthesis of the brush-shaped block copolymer is obtained by a series of ring-opening metathesis polymerization (ROMP) methods with controllable activity, firstly, a one-dimensional photonic crystal film is prepared by self-assembly of a low-boiling-point solvent, and then, the temperature-sensitive characteristic of the one-dimensional photonic crystal film is researched by heating treatment. Reflection spectrum tests show that the reflection wavelength has obvious red shift after heat treatment, and the reflectivity is reduced to a certain extent, which shows that the material has obvious temperature responsiveness. In addition, a linear relation graph between the main chain polymerization degree and the main reflection wavelength is obtained, and the relation between the material structure and the performance is well combined. The invention can be used in light sensor, light valve, pigment and dye, with high application value.
Drawings
FIG. 1 example 1 synthetic route for brush block copolymer (PNBPM-b-PNDM).
FIG. 2 nuclear magnetic spectrum of brush block copolymer of example 1 (PNBPM-b-PNDM).
FIG. 3 comparative pictures before and after self-assembly heat treatment of brush block copolymer (PNBPM-b-PNDM) of example 2.
FIG. 4 is a reflection spectrum of a photonic crystal film of example 2. A1-A6 and B1-B6 represent the reflectance spectra before and after thermal assembly of BCP1-BCP6, respectively.
Detailed Description
The invention is described in further detail below with reference to the figures and specific examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
The preparation method of the brush-shaped block copolymer BCP1-6 comprises the following steps: the preparation route is shown in figure 1,
the general structural formula of BCP1-6 is:
the synthesis steps of BCP1(m 200, n 200) are as follows:
NBPM (57.6mg, 91.2. mu. mol), 1mL dry methylene chloride, and G-3(0.41mg, 0.46X 10. mu. mol) were added to a 10mL polymerization flask-3mmol) of dichloromethane solution, stirring the reaction solution at room temperature for 30 minutes, adding 1.1mL of dichloromethane solution containing NDM (72.2mg, 91.2. mu. mol) into the reaction solution, and continuing the reaction for 1 hour, wherein the whole addition and reaction process are carried out in a glove box. After the reaction was complete, 1mL of ethyl vinyl ether was added to quench the reaction. The mixture was taken out of the glove box, precipitated in anhydrous methanol, centrifuged, and vacuum-dried to obtain a brush-like block copolymer BCP1 having a polymerization degree of 400 in the main chain, wherein the polymerization degree of NBPM was 200 and the polymerization degree of NDM was 200.
The synthesis of BCP2(m 300, n 300) was as follows:
NBPM (57.6mg, 91.2. mu. mol), 1mL dry methylene chloride, and G-3(0.27mg, 0.31X 10) were added to a 10mL polymerization flask-3mmol) of dichloromethane solution, stirring the reaction solution at room temperature for 30 minutes, adding 1.1mL of dichloromethane solution containing NDM (72.2mg, 91.2. mu. mol) into the reaction solution, and continuing the reaction for 1 hour, wherein the whole addition and reaction process are carried out in a glove box. After the reaction was complete, 1mL of ethyl vinyl ether was added to quench the reaction. The mixture was taken out of the glove box, precipitated in anhydrous methanol, centrifuged, and vacuum-dried to obtain a brush-like block copolymer BCP2 having a polymerization degree of 600 in the main chain of NBPM of 300 and NDM of 300.
The synthesis steps of BCP3(m 400, n 400) are as follows:
NBPM (57.6mg, 91.2. mu. mol), 1mL dry methylene chloride, and G-3(0.21mg, 0.23X 10) were added to a 10mL polymerization flask-3mmol) of dichloromethane solution, stirring the reaction solution at room temperature for 30 minutes, adding 1.1mL of dichloromethane solution containing NDM (72.2mg, 91.2. mu. mol) into the reaction solution, and continuing the reaction for 1 hour, wherein the whole addition and reaction process are carried out in a glove box. After the reaction was complete, 1mL of ethyl vinyl ether was added to quench the reaction. Removing from the glove box, precipitating in anhydrous methanol, centrifuging, and vacuum drying to obtain the final productThe brush block copolymer BCP3 with the chain polymerization degree of 800 is provided, wherein the polymerization degree of NBPM is 400, and the polymerization degree of NDM is 400.
The synthesis of BCP4(m 500, n 500) was as follows:
NBPM (57.6mg, 91.2. mu. mol), 1mL dry methylene chloride, and G-3(0.16mg, 0.18X 10) were added to a 10mL polymerization flask-3mmol) of dichloromethane solution, stirring the reaction solution at room temperature for 30 minutes, adding 1.1mL of dichloromethane solution containing NDM (72.2mg, 91.2. mu. mol) into the reaction solution, and continuing the reaction for 1 hour, wherein the whole addition and reaction process are carried out in a glove box. After the reaction was complete, 1mL of ethyl vinyl ether was added to quench the reaction. The mixture was taken out of the glove box, precipitated in anhydrous methanol, centrifuged, and vacuum-dried to obtain a brush-like block copolymer BCP4 having a polymerization degree of 1000 in the main chain of NBPM of 500 and NDM of 500.
The synthesis of BCP5(m 700, n 700) was as follows:
NBPM (57.6mg, 91.2. mu. mol), 1mL dry methylene chloride, and G-3(0.12mg, 0.13X 10) were added to a 10mL polymerization flask-3mmol) of dichloromethane solution, stirring the reaction solution at room temperature for 30 minutes, adding 1.1mL of dichloromethane solution containing NDM (72.2mg, 91.2. mu. mol) into the reaction solution, and continuing the reaction for 1 hour, wherein the whole addition and reaction process are carried out in a glove box. After the reaction was complete, 1mL of ethyl vinyl ether was added to quench the reaction. The mixture was taken out of the glove box, precipitated in anhydrous methanol, centrifuged, and vacuum-dried to obtain a brush-like block copolymer BCP5 having a backbone polymerization degree of 1400, wherein the polymerization degree of NBPM was 700 and the polymerization degree of NDM was 700.
The synthesis of BCP6(m 1000, n 1000) was as follows:
NBPM (57.6mg, 91.2. mu. mol), 1mL dry methylene chloride, and G-3(0.082 mg, 0.092X 10) were added to a 10mL polymerization flask-3mmol) of dichloromethane solution, stirring at room temperature for 30 minutes, adding 1.1mL of dichloromethane solution containing NDM (72.2mg, 91.2. mu. mol) into the above reaction solution, and continuing the reaction for 1 hour, wherein the whole process of charging and reaction is carried out in a glove box. After the reaction was complete, 1mL of ethyl vinyl ether was added to quench the reaction.The mixture was taken out of the glove box, precipitated in anhydrous methanol, centrifuged, and vacuum-dried to obtain a brush-like block copolymer BCP6 having a polymerization degree of 2000 in the main chain, wherein the polymerization degree of NBPM was 1000 and the polymerization degree of NDM was 1000.
As shown in FIG. 2, which is a nuclear magnetic hydrogen spectrum of block polymer BCP4, it can be seen that all monomers have been completely converted and that all peaks can be well assigned.
Example 2
The synthesized series of brush-shaped block copolymers (BCP1-BCP6) have the following conditions of solvent self-assembly and heat treatment:
and (3) respectively preparing 10mg/mL tetrahydrofuran solution from the synthesized brush-shaped block copolymer (BCP1-BCP6), dripping the mixed solution on a clean horizontal glass sheet, and volatilizing the solvent completely to obtain 6 different polymer films, namely the prepared one-dimensional photonic crystal material. And then, heating the prepared one-dimensional photonic crystal film for 30min at the temperature of 130 ℃ to research the temperature-sensitive characteristic of the one-dimensional photonic crystal film. As shown in FIG. 2, the self-assembly pictures of BCP1-BCP6 before and after heat treatment show obvious light reflection phenomenon and temperature-sensitive behavior. The self-assembly of BCP1 appeared dark purple before heating and blue after heating; the self-assembly of BCP2 appeared blue before heating and bright green after heating; the self-assembly of BCP3 was green and red after heating, and the self-assembly of BCP4 was red before heating and grey brown after heating.
FIG. 3 is a reflection spectrogram of BCP1-BCP6 before and after heat treatment, wherein the reflection wavelength has obvious red shift after heating, and the reflectivity is reduced to a certain extent, which indicates that the temperature-sensitive one-dimensional photonic crystal material is successfully prepared.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A brush block copolymer having the structural formula:
wherein m is the polymerization degree of NBPM, and m is 100-; n is the polymerization degree of NDM, and n is 100-1500; the polymerization degree of the main chain is 200-3000;
wherein: the structural formula of NBPM is:
the structural formula of NDM is:
2. a brush block copolymer according to claim 1, wherein m is n.
3. A brush block copolymer according to claim 1, prepared by the following process: dissolving norbornene monomer NBPM with a biphenyl structure into an organic solvent, adding a G-3 catalyst, stirring at 20-40 ℃ for reaction to homopolymerize the monomer NBPM, then adding the dissolved norbornene monomer NDM with a decyl structure into the reaction solution for continuous reaction to realize copolymerization of the NBPM and the NDM, adding a terminator after the reaction is finished to quench the reaction, and finally obtaining the target brush-shaped block copolymer (PNBPM-b-PNDM).
4. The brush block copolymer of claim 1, wherein the molar ratio of G-3, NBPM, and NDM is: 1:(100-1500):(100-1500).
5. The brush block copolymer of claim 4, wherein the molar ratio of G-3, NBPM, and NDM is: 1:(300-800):(300-800).
6. The method of synthesizing a brush block copolymer according to claim 1, comprising the steps of:
dissolving norbornene monomer NBPM with a biphenyl structure into an organic solvent, adding a G-3 catalyst, stirring at 20-40 ℃ for reaction to homopolymerize the monomer NBPM, then adding the dissolved norbornene monomer NDM with a decyl structure into the reaction solution for continuous reaction to realize copolymerization of the NBPM and the NDM, adding a terminator after the reaction is finished to quench the reaction, and finally obtaining the target brush-shaped block copolymer (PNBPM-b-PNDM).
7. The method of synthesizing a brush block copolymer according to claim 6, wherein the molar ratio of G-3, NBPM and NDM is: 1:(100-1500):(100-1500).
8. The method of synthesizing a brush block copolymer according to claim 7, wherein the molar ratio of G-3, NBPM and NDM is: 1:(300-800):(300-800).
9. Use of the brush block copolymer according to claim 1 for the preparation of a temperature sensitive one-dimensional photonic crystal material.
10. The use of a brush block copolymer according to claim 5 for the preparation of a temperature sensitive one-dimensional photonic crystal material, wherein: the brush-shaped block copolymer is synthesized into a one-dimensional photonic crystal material through self-assembly.
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