CN109134748B - Functionalized polymer optical switch and synthesis method thereof - Google Patents
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Abstract
The invention discloses a functionalized polymer optical switch and a synthesis method thereof, belonging to the technical field of new materials. A method for synthesizing a functionalized polymer optical switch comprises the steps of synthesizing a double-bond modified azobenzene derivative and a double-bond modified succinimide derivative, taking the double-bond modified azobenzene derivative and the double-bond modified succinimide derivative as raw materials, adding hydroxyethyl methacrylate and N-vinyl pyrrolidone as chain diluents, and carrying out free radical polymerization to obtain the functionalized polymer optical switch. The DMSO solution of the copolymer has the capability of forward and reverse transformation of more than 100 times, and has the characteristics of an optical switch.
Description
Technical Field
The invention belongs to the technical field of new materials, relates to synthesis of azobenzene copolymers and research on photoresponse characteristics of the azobenzene copolymers, and particularly relates to a functionalized polymer photoswitch and a synthesis method thereof.
Background
The discovery of azobenzene compounds dates back to 19 th century, and the azobenzene compounds have been regarded as important color developers, intermediates, dyes or colorants in various industries such as chemical industry, food, medicine, light industry and the like. Azobenzene has two isomers, trans isomer and cis isomer. The different spatial arrangements lead to different physical and chemical properties, the photoisomerization reaction of azobenzenes inducing a sharp change in dipole moment (. mu.s)Trans-azobenzene0.5D, and μCis-azobenzene3.1D), which in turn determines the hydrophobic and hydrophilic character of the trans and cis isomers. The trans-azobenzene is not a planar structure, the included angle N-N-C-C of the two faces is about 17.5 degrees, and the plane occupied by one benzene ring in the cis-azobenzene forms an included angle of 56 degrees with the plane of the other benzene ring. Therefore, the distances between the two most distant carbon atoms in cis and trans isomers of azobenzene are 0.9 and 0.5nm, respectively. The ultraviolet-visible absorption spectrum of trans-azobenzene is characterized by 3 main bandsThe band at 228nm results from a pi-pi transition localized on the phenyl group; (2) the band at 318nm results from symmetry allowing pi-pi transitions delocalized over the entire molecule including the two nitrogen atoms; (3) the band at 440nm originates from a n-pi transition that occurs with symmetric forbidden blocking on the central nitrogen atom. However, the UV-visible absorption spectrum of cis-azobenzene is clearly distinguished compared to trans-azobenzene, with the 260nm band resulting from the symmetrically allowed π - π transition, while this band of the trans-isomer is at 318 nm.
With the research and understanding of the mechanism and characteristics of the photoisomerization reaction of azobenzene, azobenzene derivatives have received a great deal of attention, both theoretically and experimentally. Azobenzene achieves its reversible transformation under optically driven conditions, a property that makes it, as a functional element of optical switch response, have been used not only for the synthesis of smart polymers, liquid crystal materials, molecular switches and molecular machines, but also are rapidly penetrating into various aspects of chemical biological systems research and analysis.
However, azobenzene molecules also have the disadvantage of photobleaching, i.e. this ultraviolet light-driven reversible transition loses its reversible properties after several reversible changes, and the range of application of small molecules is always influenced by their solubility, intermolecular stacking and their toxicity.
Disclosure of Invention
In order to overcome the technical problems, the invention provides an azobenzene macromolecule, wherein double bonds are modified by azobenzene molecules, and the azobenzene macromolecule and other functional monomers are subjected to free radical copolymerization to obtain a macromolecular optical switch with excellent performances; wherein the introduction of the specific functionalized monomer makes it possible to have a functionalizable character.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for synthesizing a functionalized polymer optical switch comprises the following steps:
(1) double bond-modified azobenzene derivative (P)AZO) The synthesis of (2):
azobenzene containing an active hydrogen substituent and acryloyl chloride are used as raw materials to react to obtain a double-bond modified azobenzene derivative; reacting acyl chloride group on acryloyl chloride with active hydrogen on azobenzene substituent to obtain double bond modified azobenzene derivative, washing with water, extracting, distilling under reduced pressure, vacuum drying to obtain pure product,
(2) synthesis of double bond modified succinimide derivative (NAS)
Taking acryloyl chloride and N-hydroxysuccinimide as raw materials, and reacting to obtain a double-bond modified succinimide derivative; the double-bond modified succinimide derivative is obtained by the reaction of acyl chloride groups on acryloyl chloride and hydroxyl groups on N-hydroxysuccinimide, the derivative has the characteristic of functionalization by reacting with amino groups, and a pure product is obtained by the processes of water washing, extraction, reduced pressure distillation, vacuum drying and the like,
(3) the functionalized polymer optical switch is prepared by taking double-bond modified azobenzene derivative and double-bond modified succinimide derivative as raw materials, selecting two flexible hydrophilic monomers of hydroxyethyl methacrylate (HEMA) and N-vinyl pyrrolidone (NVP) as chain diluents and carrying out free radical polymerization.
The further technical scheme is that in the step (1), the specific synthesis method comprises the following steps:
dissolving azobenzene containing an active hydrogen substituent in an anhydrous nonpolar oil phase solvent in a dry environment, wherein the concentration of the azobenzene is 0.1-10M, dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the dropwise adding speed is 1-15mL/h, and the content of the acryloyl chloride: the mol ratio of azobenzene is 1.5:1-1:1, the reaction time is 2-12h, after the reaction is finished, excess ethylenediamine is added into the system, the system is washed by saturated salt water for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified azobenzene derivative.
In a further technical scheme, the azobenzene containing the active hydrogen substituent is one of p-aminoazobenzene, p-hydroxyazobenzene and p-carboxyazobenzene;
the anhydrous nonpolar oil phase solvent is one of dichloromethane, trichloromethane and tetrahydrofuran;
the concentration of the azobenzene is 0.5-3M;
the acryloyl chloride: the molar ratio of azobenzene is 1.2:1-1: 1;
the dropping speed is 2-10 mL/h;
the reaction time is 4-8 h;
in a further technical scheme, the azobenzene containing the active hydrogen substituent is one of p-aminoazobenzene and p-hydroxyazobenzene, preferably p-aminoazobenzene;
the anhydrous nonpolar oil phase solvent is one of dichloromethane and trichloromethane, and dichloromethane is preferred;
the concentration of the azobenzene is 1-2M;
the acryloyl chloride: the molar ratio of azobenzene is 1.1: 1;
the dropping speed is 5 mL/h;
the reaction time is 4-6 h.
The further technical scheme is that in the step (2), the specific synthesis method comprises the following steps:
dissolving N-hydroxysuccinimide in an anhydrous nonpolar oil phase solvent in a dry environment, and dropwise adding acryloyl chloride into the system under an ice bath condition, wherein the dropwise adding speed is 1-15mL/h, and the content of the acryloyl chloride: the molar ratio of N-hydroxysuccinimide is 1.5:1-1:1, the reaction time is 2-12h, excessive ethylenediamine is added into the system after the reaction is finished, the system is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified succinimide derivative.
In a further technical scheme, the anhydrous nonpolar oil phase solvent is one of dichloromethane, trichloromethane and tetrahydrofuran;
the concentration of the N-hydroxysuccinimide is 0.1-10M;
the acryloyl chloride: the molar ratio of the N-hydroxysuccinimide is 1.2:1-1: 1;
the dropping speed is 2-10 mL/h;
the reaction time is 4-8 h;
in a further technical scheme, the anhydrous nonpolar oil phase solvent is one of dichloromethane and trichloromethane, preferably dichloromethane;
the concentration of the N-hydroxysuccinimide is 0.5-3M, preferably 1-2M;
the acryloyl chloride: the molar ratio of N-hydroxysuccinimide is 1.1: 1;
the dropping speed is 5 mL/h;
the reaction time is 4-6 h.
In a further technical scheme, the free radical polymerization in the step (3) adopts solution polymerization, and the specific method comprises the following steps:
adding four monomers of double-bond modified azobenzene derivative, double-bond modified succinimide derivative, hydroxyethyl methacrylate and N-vinyl pyrrolidone into a reaction system containing a solvent, introducing nitrogen to remove oxygen, uniformly mixing, adding an initiator, sealing at 50-90 ℃ for reaction, precipitating the polymer by using ether after the reaction is finished for 5-48h, filtering the obtained precipitate, and freeze-drying to obtain the azobenzene copolymer (P)AZO) (ii) a Wherein the total concentration of the monomers is 0.05-2M; 2-25 parts of double bond modified azobenzene derivative, 5-25 parts of double bond modified succinimide derivative, 20-55 parts of hydroxyethyl methacrylate and 20-50 parts of N-vinyl pyrrolidone, wherein the total parts of the monomers are 100; the initiator is one of benzoyl peroxide and azodiisobutyronitrile; the mole number of the initiator is 1-10% of the total mole number of the monomers.
The solvent is one of dioxane and tetrahydrofuran, preferably dioxane;
the total concentration of the monomers is 0.1-1M, preferably 0.1-0.5M;
5-20 parts of double bond modified azobenzene derivative, 10-20 parts of double bond modified succinimide derivative, 30-50 parts of hydroxyethyl methacrylate and 10-40 parts of N-vinyl pyrrolidone, wherein the total parts of the monomers are 100;
preferably, the total parts of the monomers are 100, 15-17 parts of double bond modified azobenzene derivatives, 15-17 parts of double bond modified succinimide derivatives, 40-45 parts of hydroxyethyl methacrylate and 20-30 parts of N-vinyl pyrrolidone;
the initiator is benzoyl peroxide;
the mole number of the initiator is 2-5%, preferably 5% of the total mole number of the monomers;
the reaction temperature is 60-80 ℃, and preferably 70 ℃;
the reaction time is 10-24h, preferably 16-24 h;
the freeze drying condition is-50 deg.C and 7-8 Pa.
Advantageous effects
Compared with the prior art, the invention has the following remarkable advantages:
the invention provides an azobenzene copolymer used in the fields of molecular switches, biological diagnosis and the like. The DMSO solution of this copolymer has a capability of forward and reverse transformation of 100 times or more, and has characteristics of an optical switch (as can be seen from fig. 1 of example 1). Although unmodified paraaminoazobenzene (comparative example 1) can achieve a reversible cis-trans transformation under the action of UV light, this transformation is 1 weaker than 1 and is largely depleted, completely losing its reversible cis-trans transformation capability after undergoing 7 cis-trans transformations. The invention has great social benefit and economic benefit.
Drawings
FIG. 1 shows P in example 1AZOSolution uv-vis absorption spectrum: an illumination response time (a) and a recovery time (b); pAZOCirculating absorbance (c), P, at 350nm/320nmAZOCyclic UV light response time and recovery time under visible light (d).
Fig. 2 is a graph of the UV absorption spectra of AZO in comparative example 1 with UV illumination at different cycle times: an irradiation time (a, c) and a recovery time (b, d), wherein (a, b) cycles for a first time; (c, d) a seventh cycle.
FIG. 3 is the absorbance cycling parameter (a) at 400nm for AZO in comparative example 1, the cycling UV light response time for AZO in DMF solution and the recovery time in the dark (b).
Detailed Description
The invention is explained in more detail below with reference to the figures and examples.
Example 1
A method for synthesizing a functionalized polymer optical switch comprises the following steps:
step (1): dissolving a certain amount of p-aminoazobenzene in dichloromethane in a dry environment, wherein the concentration is 1.3M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the content of the acryloyl chloride: the mol ratio of azobenzene is 1.1:1, the dropping speed is 5mL/h, excessive ethylenediamine is added after 6h of reaction, the mixture is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified azobenzene derivative.
Step (2): dissolving a certain amount of N-hydroxysuccinimide in dichloromethane in a dry environment, wherein the concentration of the N-hydroxysuccinimide is 1.3M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the acryloyl chloride: the mol ratio of N-hydroxysuccinimide is 1.1:1, the dropping speed is 5mL/h, excessive ethylenediamine is added after 6h of reaction, saturated saline water is used for washing for a plurality of times to remove unreacted acyl chloride and ethylenediamine, ethyl acetate is used for extracting a product, and the product is subjected to reduced pressure distillation and vacuum drying to obtain the pure double-bond modified succinimide derivative.
And (3): the monomers were added to the dioxane-containing reaction system in amounts such that the total concentration of the final monomers was 0.25M, where PAZO16.7 parts of NAS, 16.6 parts of NAS, 41.7 parts of HEMA and 25.0 parts of NVP, introducing nitrogen to remove oxygen, uniformly mixing the monomers, adding an initiator BPO, and concentrating the mole number of the initiator BPO to be 5 percent of the total mole number of the monomers; sealing the reaction at 70 deg.C for 24 hr, precipitating the polymer with diethyl ether, filtering the precipitate, and freeze drying (-50 deg.C, 7-8 Pa) to obtain azobenzene copolymer (P)AZO)。
Example 2
A method for synthesizing a functionalized polymer optical switch comprises the following steps:
step (1): dissolving a certain amount of p-hydroxyazobenzene in chloroform in a dry environment, wherein the concentration is 0.1M, and dropwise adding acryloyl chloride into the system under an ice bath condition, wherein the ratio of the content of the acryloyl chloride: the mol ratio of azobenzene is 1.5:1, the dropping speed is 15mL/h, excessive ethylenediamine is added after 12h of reaction, saturated saline water is used for washing for a plurality of times to remove unreacted acyl chloride and ethylenediamine, ethyl acetate is used for extracting products, and the products are subjected to reduced pressure distillation and vacuum drying to obtain the pure double-bond modified azobenzene derivative.
Step (2): dissolving a certain amount of N-hydroxysuccinimide in chloroform in a dry environment, wherein the concentration is 0.1M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the acryloyl chloride: the mol ratio of N-hydroxysuccinimide is 1.5:1, the dropping speed is 15mL/h, excessive ethylenediamine is added after 12h of reaction, saturated saline water is used for washing for a plurality of times to remove unreacted acyl chloride and ethylenediamine, ethyl acetate is used for extracting a product, and the product is subjected to reduced pressure distillation and vacuum drying to obtain the pure double-bond modified succinimide derivative.
And (3): adding a certain amount of monomers into a reaction system containing dioxane to ensure that the total concentration of the final monomers is 0.05M, wherein the total concentration of PAZO is 2 parts, the total concentration of NAS is 5 parts, the total concentration of HEMA is 43 parts, the total concentration of NVP is 50 parts, introducing nitrogen to remove oxygen, uniformly mixing the monomers, and adding an initiator AIBN, wherein the mole number of the initiator AIBN is 1 percent of the total mole number of the monomers; after the reaction is carried out for 10h under the condition of 80 ℃, the polymer is precipitated by ether, and the obtained precipitate is filtered and then is frozen and dried (-50 ℃, 7-8 Pa) to obtain the azobenzene copolymer.
Example 3
A method for synthesizing a functionalized polymer optical switch comprises the following steps:
step (1): dissolving a certain amount of p-carboxyazobenzene in tetrahydrofuran in a dry environment, wherein the concentration is 10M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the acryloyl chloride: the mol ratio of azobenzene is 1.2:1, the dropping speed is 10mL/h, after 2h of reaction, excess ethylenediamine is added, the mixture is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified azobenzene derivative.
Step (2): dissolving a certain amount of N-hydroxysuccinimide in tetrahydrofuran in a dry environment, wherein the concentration is 10M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the acryloyl chloride: the mol ratio of N-hydroxysuccinimide is 1.2:1, the dropping speed is 10mL/h, after 2h of reaction, excess ethylenediamine is added, the mixture is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified succinimide derivative.
And (3): the monomers were added to the dioxane-containing reaction system in amounts such that the total concentration of the final monomers was 0.25M, where P AZO5 parts of NAS, 50 parts of HEMA and 40 parts of NVP, introducing nitrogen to remove oxygen, uniformly mixing the monomers, and adding an initiator BPO (hydrogen peroxide oxide), wherein the mole number of the initiator BPO is 10% of the total mole number of the monomers; after the reaction is carried out for 16h under the condition of sealing at the temperature of 70 ℃, the polymer is precipitated by ether, and the obtained precipitate is filtered and then is frozen and dried (-50 ℃, 7-8 Pa) to obtain the azobenzene copolymer.
Example 4
A method for synthesizing a functionalized polymer optical switch comprises the following steps:
step (1): dissolving a certain amount of p-aminoazobenzene in dichloromethane in a dry environment, wherein the concentration is 5M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the content of the acryloyl chloride: the mol ratio of azobenzene is 1:1, the dropping speed is 1mL/h, after 8h of reaction, excess ethylenediamine is added, the mixture is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified azobenzene derivative.
Step (2): dissolving a certain amount of N-hydroxysuccinimide in dichloromethane in a dry environment, wherein the concentration is 5M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the mass ratio of the acryloyl chloride: the mol ratio of N-hydroxysuccinimide is 1:1, the dropping speed is 1mL/h, after 8h of reaction, excess ethylenediamine is added, the mixture is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified succinimide derivative.
And (3): adding a certain amount of monomer to the reaction system containing dioxane to make the total concentration of the final monomer be 0.1M, wherein PAZO25 parts of NAS, 30 parts of HEMA and 20 parts of NVP, introducing nitrogen to remove oxygen, uniformly mixing the monomers, and adding an initiator BPO (hydrogen peroxide oxide), wherein the mole number of the initiator BPO is 2% of the total mole number of the monomers; after the reaction is carried out for 24h under the sealing condition at the temperature of 60 ℃, the polymer is precipitated by ether, and the obtained precipitate is filtered and then is frozen and dried (-50 ℃, 7-8 Pa) to obtain the azobenzene copolymer.
Example 5
A method for synthesizing a functionalized polymer optical switch comprises the following steps:
step (1): dissolving a certain amount of p-aminoazobenzene in dichloromethane in a dry environment, wherein the concentration is 3M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the ratio of the content of the acryloyl chloride: the mol ratio of azobenzene is 1.1:1, the dropping speed is 6mL/h, excessive ethylenediamine is added after 4h of reaction, the mixture is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified azobenzene derivative.
Step (2): dissolving a certain amount of N-hydroxysuccinimide in dichloromethane in a dry environment, wherein the concentration is 3M, and dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the mass ratio of the acryloyl chloride: the mol ratio of N-hydroxysuccinimide is 1.1:1, the dropping speed is 6mL/h, excessive ethylenediamine is added after 4h of reaction, saturated saline water is used for washing for a plurality of times to remove unreacted acyl chloride and ethylenediamine, ethyl acetate is used for extracting a product, and the product is subjected to reduced pressure distillation and vacuum drying to obtain the pure double-bond modified succinimide derivative.
And (3): adding a certain amount of monomer to the reaction system containing dioxane to make the total concentration of the final monomer be 0.5M, wherein PAZO16.7 parts of NAS, 16.6 parts of NAS, 41.7 parts of HEMA and 25.0 parts of NVP, introducing nitrogen to remove oxygen, uniformly mixing the monomers, and adding an initiator BPO, wherein the mole number of the initiator BPO is 10 percent of the total mole number of the monomers; after the reaction was carried out at 80 ℃ for 24 hours under sealed conditions, the polymer was precipitated with diethyl etherAnd filtering the obtained precipitate, and freeze-drying at (-50 ℃ C., 7-8 Pa) to obtain the azobenzene copolymer.
The comparison was made with unmodified p-aminoazobenzene as the product of example 1 and with unmodified p-aminoazobenzene as comparative example 1.
The experimental method is as follows:
the azobenzene copolymer was dissolved in DMSO to give a solution of about 0.1mg/mL, and the aminoazobenzene was dissolved in DMF to give a solution of 0.03 mg/mL. And (3) placing the solution in a sample pool of ultraviolet spectrum, and detecting the ultraviolet spectrum of the solution after ultraviolet irradiation of 30w 365nm for a specific time until the detected ultraviolet spectrum does not change along with the irradiation time. The UV lamp was turned off and the UV spectrum of the solution, i.e., the conformational return, was measured at intervals. This process is repeated to detect the nature of these chemicals as optical switches.
Claims (10)
1. A method for synthesizing a functionalized polymer optical switch is characterized in that: the method comprises the following steps:
(1) synthesis of double bond-modified azobenzene derivatives
Azobenzene containing an active hydrogen substituent and acryloyl chloride are used as raw materials to react to obtain a double-bond modified azobenzene derivative;
(2) synthesis of double bond modified succinimide derivative
Taking acryloyl chloride and N-hydroxysuccinimide as raw materials, and reacting to obtain a double-bond modified succinimide derivative;
(3) the functionalized polymer optical switch is obtained by taking double-bond modified azobenzene derivative and double-bond modified succinimide derivative as raw materials, adding hydroxyethyl methacrylate and N-vinyl pyrrolidone as chain diluents and carrying out free radical polymerization.
2. The method of claim 1, wherein the method comprises the steps of: the specific synthesis method of the step (1) comprises the following steps:
dissolving azobenzene containing an active hydrogen substituent in an anhydrous nonpolar oil phase solvent in a dry environment, wherein the concentration of the azobenzene is 0.1-10M, dropwise adding acryloyl chloride into the system under the ice bath condition, wherein the dropwise adding speed is 1-15mL/h, and the content of the acryloyl chloride: the mol ratio of azobenzene is 1.5:1-1:1, the reaction time is 2-12h, after the reaction is finished, excess ethylenediamine is added into the system, the system is washed by saturated salt water for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified azobenzene derivative.
3. The method of claim 2, wherein the method comprises the steps of:
the azobenzene containing the active hydrogen substituent is one of para-amino azobenzene, para-hydroxy azobenzene and para-carboxyl azobenzene;
the anhydrous nonpolar oil phase solvent is one of dichloromethane, trichloromethane and tetrahydrofuran;
the concentration of the azobenzene is 0.5-3M;
the acryloyl chloride: the molar ratio of azobenzene is 1.2:1-1: 1;
the dropping speed is 2-10 mL/h;
the reaction time is 4-8 h.
4. The method of claim 3, wherein the method comprises the steps of:
the azobenzene containing the active hydrogen substituent is one of para-amino azobenzene and para-hydroxy azobenzene;
the anhydrous nonpolar oil phase solvent is one of dichloromethane and trichloromethane;
the concentration of the azobenzene is 1-2M;
the acryloyl chloride: the molar ratio of azobenzene is 1.1: 1;
the dropping speed is 5 mL/h;
the reaction time is 4-6 h.
5. The method of claim 1, wherein the method comprises the steps of: the specific synthesis method of the step (2) is as follows:
dissolving N-hydroxysuccinimide in an anhydrous nonpolar oil phase solvent in a dry environment, and dropwise adding acryloyl chloride into the system under an ice bath condition, wherein the dropwise adding speed is 1-15mL/h, and the content of the acryloyl chloride: the molar ratio of N-hydroxysuccinimide is 1.5:1-1:1, the reaction time is 2-12h, excessive ethylenediamine is added into the system after the reaction is finished, the system is washed by saturated saline solution for a plurality of times to remove unreacted acyl chloride and ethylenediamine, the product is extracted by ethyl acetate, and the product is vacuum-dried after reduced pressure distillation to obtain the pure double-bond modified succinimide derivative.
6. The method of claim 5, wherein the method comprises the steps of:
the anhydrous nonpolar oil phase solvent is one of dichloromethane, trichloromethane and tetrahydrofuran;
the concentration of the N-hydroxysuccinimide is 0.1-10M;
the acryloyl chloride: the molar ratio of the N-hydroxysuccinimide is 1.2:1-1: 1;
the dropping speed is 2-10 mL/h;
the reaction time is 4-8 h.
7. The method of claim 6, wherein the method comprises the steps of: the anhydrous nonpolar oil phase solvent is one of dichloromethane and trichloromethane;
the concentration of the N-hydroxysuccinimide is 0.5-3M;
the acryloyl chloride: the molar ratio of N-hydroxysuccinimide is 1.1: 1;
the dropping speed is 5 mL/h;
the reaction time is 4-6 h.
8. The method of claim 1, wherein the method comprises the steps of: the free radical polymerization in the step (3) adopts solution polymerization, and the specific method comprises the following steps:
adding four monomers of double-bond modified azobenzene derivatives, double-bond modified succinimide derivatives, hydroxyethyl methacrylate and N-vinyl pyrrolidone into a reaction system containing a solvent, introducing nitrogen to remove oxygen, uniformly mixing, adding an initiator, sealing at the temperature of 50-90 ℃ for reaction, precipitating a polymer by using ether after the reaction is finished for 5-48h, filtering the obtained precipitate, and freeze-drying to obtain an azobenzene copolymer; wherein the total concentration of the monomers is 0.05-2M; 2-25 parts of double bond modified azobenzene derivative, 5-25 parts of double bond modified succinimide derivative, 20-55 parts of hydroxyethyl methacrylate and 20-50 parts of N-vinyl pyrrolidone, wherein the total parts of the monomers are 100; the initiator is one of benzoyl peroxide and azodiisobutyronitrile; the mole number of the initiator is 1-10% of the total mole number of the monomers.
9. The method of claim 8, wherein the method comprises:
the solvent is one of dioxane and tetrahydrofuran;
the total concentration of the monomers is 0.1-1M;
5-20 parts of double bond modified azobenzene derivative, 10-20 parts of double bond modified succinimide derivative, 30-50 parts of hydroxyethyl methacrylate and 10-40 parts of N-vinyl pyrrolidone, wherein the total parts of the monomers are 100;
the initiator is benzoyl peroxide;
the mole number of the initiator is 2-5% of the total mole number of the monomers;
the reaction temperature is 60-80 ℃;
the reaction time is 10-24 h;
the freeze drying condition is-50 deg.C and 7-8 Pa.
10. A functionalizable polymer optical switch made according to the synthetic method of any one of claims 1-9.
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