CN113307908A - Temperature and light dual-responsiveness dendritic polymer microspheres containing DASAs and preparation method thereof - Google Patents
Temperature and light dual-responsiveness dendritic polymer microspheres containing DASAs and preparation method thereof Download PDFInfo
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Abstract
The invention discloses temperature and light dual-responsiveness dendritic polymer microspheres containing DASAs and a preparation method thereof, and discloses a method for realizing water-phase reversible photochromism of Donor-Acceptor Stenhouse Adducts (DASAs). The temperature-sensitive dendronized polymer microspheres containing DASAs are prepared by combining the crowding effect, the vermicular topological structure and the temperature-sensitive characteristic of the alkoxy ether dendronized polymer and the physical appearance of the polymer microspheres, so that a limited microenvironment is constructed, and the reversible photochromic regulation of photochromic elements DASAs in a water phase is successfully realized. The method for constructing the limited microenvironment provided by the invention ensures that the DASAs have high isomerization speed in the water phase and are completely reversible. The regulation and control mode has the characteristics of multiplicity, environmental friendliness, simplicity, flexibility and the like. Therefore, the method has potential application value in the fields of biological medicine, molecular probes, environmental monitoring, optical devices, intelligent display and the like.
Description
Technical Field
The invention relates to a method for realizing reversible photochromism of DASAs in a water phase and application thereof, in particular to a branched polymer microsphere and a preparation method thereof, which are applied to the technical field of organic photochromic compound processes.
Background
Donor-Acceptor Stenhouse Adducts (DASAs) are a class of organic photochromic compounds formed by linking a Donor moiety (typically an aliphatic amine or an aromatic amine) and an Acceptor moiety (typically meldrum's acid, barbituric acid, indandione, and the like) via a polyene bridge. According to the difference between the donor and the acceptor, the DASA can be divided into a first generation DASA, a second generation DASA and a third generation DASA. DASAs undergo photoisomerization under visible light irradiation, resulting in significant changes in physical or chemical properties, such as color, hydrophilicity and hydrophobicity, and size (Helmy S, Leibfarth F A, et al]J Am Chem Soc,2014,136(23) 8169-. Compared with conventional organic photochromic materials such as azobenzene, spiropyran, diarylethene, etc., DASAs are attracting much attention because of their advantages of visible light response, high sensitivity, simple synthesis, low cost, etc. To date, studies on the photochromic properties of DASAs, in particular the first generation of DASAs formed by fatty amines as donors and by michaelis acid or barbituric acid as acceptors, have been mostly limited to organic solvents, and achieving reversible isomerization in the aqueous phase has been extremely challenging, which has largely limited their application in the biomedical field. Mukherjee et al reported that DASAs are soluble in water in PdIIReversible isomerization can be achieved in the confined environment provided by the 8-molecule container. (Saha R, Devaraj A, et al. Unnuual behavor of donor-acceptor stenhouse additives in defined space of a water-soluble Pd (II)8molecular vessel [ J]J Am Chem Soc,2019,141: 8638-8645.). Zhang et al (Li W, Zhang A, et al. Thermosponsive polymers with tunable lower critical solution temperature [ J)]Chem Commun,2008: 5523) reports a class of alkoxy ether dendrimers, which have unique topological structure and excellent temperature-sensitive property and can form a certain hydrophobic micro-scale in waterEnvironment, has a solvent shielding effect, and can realize envelope release of guest molecules (Wu.D, Zhang A, et al. Thermoresponsive cationic polymerized and conjugated nanoparticles [ J.]Polym Chem,2020,11, 4105) and control of the chirality of chiral polymers (Zhao Y, Zhang A, et al Stimuli-responsive poly (phenyl acetyl ethylene) microparticles with tunable chirality [ J]Eur Polym J,2019: 275-27.). Therefore, how to better realize reversible photochromism of DASAs in aqueous phase becomes a technical problem to be solved urgently.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to overcome the defects in the prior art, and provides temperature and light dual-responsive dendritic polymer microspheres containing DASAs and a preparation method thereof, so that reversible photochromism of the DASAs in a water phase is realized. The temperature-sensitive dendronized polymer microspheres containing DASAs are prepared by combining the crowding effect, the vermicular topological structure and the temperature-sensitive characteristic of the alkoxy ether dendronized polymer and the physical appearance of the polymer microspheres, so that a limited microenvironment is constructed, and reversible photochromism of the DASAs in a water phase is realized. The invention provides a temperature and light dual-responsive dendritic polymer microsphere. The obtained dendritic polymer microspheres combine the temperature-sensitive characteristic of the alkoxy ether branched polymer and the photosensitive characteristic of DASAs, and have dual stimulation responsiveness of temperature and visible light.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of temperature and light dual-responsive dendritic polymer microspheres containing DASAs comprises the following steps:
a. heating and irradiating by ultraviolet light for 1-6 h to obtain blue-emitting microsphere dispersion liquid;
b. and (b) dissolving the activated furan derivative in tetrahydrofuran, slowly adding the dissolved activated furan derivative into the microsphere dispersion prepared in the step a, stirring and reacting at the temperature of not lower than 60 ℃ for not more than 4 hours to gradually change the color of the microsphere dispersion into a purple product solution, and performing centrifugal washing to obtain the purple DASAs-containing temperature and light dual-responsive dendritic polymer microspheres.
Preferably, in the step a, the structural formula of the alkoxy ether branched polymer is represented by P (Gn-N) x-co-PMy, and the structural formula is as follows:
wherein Gn is an alkoxy ether dendron with one generation of n ═ 1 or two generations of n ═ 2, x: y ═ 100: 1-10: 1, and x and y are integers of 1-100.
Further preferably, Gn has the formula:
preferably, in said step a, the aqueous solution of the alkoxylated ether dendrimers is placed in a water bath at 30-50 ℃ for heating.
Preferably, in said step b, not more than 20 times the molar amount of the activated furan derivative is dissolved in tetrahydrofuran. It is further preferred that 10 to 20 times the molar amount of the activated furan derivative is dissolved in tetrahydrofuran.
Preferably, in said step b, the reaction is stirred at 30-60 ℃ for not more than 1-4 h.
The invention discloses temperature and light dual-responsive dendritic polymer microspheres containing DASAs, which are prepared by a preparation method of the temperature and light dual-responsive dendritic polymer microspheres containing DASAs.
Preferably, the temperature and light dual-responsive dendritic polymer microspheres containing DASAs construct a restricted microenvironment, thereby realizing reversible photochromism of DASAs in an aqueous phase.
Preferably, the temperature and light dual responsive dendrimeric microspheres of the present invention containing DASAs have a radius of no greater than 120 nm.
Preferably, the hydrodynamic radius of the DASAs-containing temperature and light dual-responsive dendronized polymer microspheres is adjustable within the range of 20-60 ℃.
Compared with the prior art, the invention has the following obvious and prominent substantive characteristics and remarkable advantages:
1. the method for realizing reversible photochromism of the DASAs in the aqueous phase can realize reversible isomerization of the DASAs in the aqueous phase, and is expected to expand the application of the DASAs in the field of biological medicines;
2. according to the invention, salicylic acid groups are introduced into the temperature-sensitive alkoxy ether branched polymer, and the microspheres are stabilized by further photocrosslinking after being aggregated into spheres under the action of temperature-sensitive induction of the polymer, so that the obtained microspheres are more uniform in size;
3. the dendronized polymer microsphere provided by the invention has dual responsivity of temperature and light.
Drawings
FIG. 1 shows nuclear magnetic hydrogen spectrum characterization (CDCl) of polymer P (N-M-NH)3,25℃，500MHz)。
FIG. 2 is a graph showing the transmittance of an aqueous solution of polymer P (N-M-NH) at a concentration of 0.5 Wt% as a function of temperature.
FIG. 3 is a graph of hydrodynamic particle size of 0.5 Wt% concentration of polymeric microspheres P (N-M-NH) -NP versus temperature.
FIG. 4 is an AFM topography of polymer microsphere N-NPs.
FIG. 5 is an AFM topography of the polymer microsphere N-NP-DASA.
FIG. 6 is a UV-VIS spectrum of an aqueous solution of polymer microsphere N-NP-DASA at a concentration of 0.5 Wt% showing the change of absorbance with time under the irradiation of visible light at a temperature of 25 ℃.
FIG. 7 is a UV-Vis spectrum of 0.5 Wt% polymer microsphere N-NP-DASA water solution under 45 deg.C heating and dark heating conditions with time-dependent absorbance change.
FIG. 8 is a schematic diagram of a process for preparing microspheres of the present invention, which can be used as follows.
Detailed Description
The synthesis of the branched alkoxy ether monomers was carried out with reference to the literature (Li W, Zhang A, et al. effective synthesis of first-and second-generation, water-soluble branched polymers [ J ]. Macromolecules,2008,41(1): 43-49.).
The present invention is further illustrated by the following examples, which are not intended to limit the scope of the present invention in any way. The invention utilizes1The method of H NMR is used for representing the structure of the polymer, the temperature-sensitive aggregation behavior and the appearance of the polymer microsphere are represented by using dynamic light scattering DLS and an atomic force microscope AFM, and the characteristics of the light response and the temperature response of the polymer microsphere are represented by using an ultraviolet visible spectrometer.
The above-described scheme is further illustrated below with reference to specific embodiments, which are detailed below:
the first embodiment is as follows:
in this example, referring to fig. 8, a method for preparing temperature and light dual-responsive dendrimeric microspheres containing DASAs includes the following steps:
a. adopting alkoxy ether dendritic polymer, putting the aqueous solution of the polymer in a water bath at 35 ℃, heating and irradiating by ultraviolet light for 3 hours to obtain blue-emitting microsphere dispersion liquid;
b. and (b) dissolving 20 times of molar amount of activated furan derivative in tetrahydrofuran, slowly adding the activated furan derivative into the microsphere dispersion prepared in the step a, stirring and reacting at 40 ℃ for 4 hours to gradually change the color of the microsphere dispersion into a purple product solution, and performing centrifugal washing to obtain the purple temperature and light dual-responsive dendritic polymer microspheres containing DASAs.
In the step a, the structural general formula of the alkoxy ether branched polymer is represented as P (Gn-N) x-co-PMy, and the structural formula is as follows:
wherein x and y are 100: 1-10: 1, and x and y are integers of 1-100; the structural formula of Gn is:
this example provides temperature and light dual responsive dendrimeric microspheres. The obtained dendritic polymer microspheres combine the temperature-sensitive characteristic of the alkoxy ether branched polymer and the photosensitive characteristic of DASAs, and have dual stimulation responsiveness of temperature and visible light. The embodiment realizes reversible photochromism of DASAs in the aqueous phase, combines the crowding effect, the worm-shaped topological structure and the temperature-sensitive characteristic of the alkoxy ether dendritic polymer and the physical appearance of the polymer microspheres into a whole, prepares the temperature-sensitive branched polymer microspheres containing the DASAs, constructs a limited microenvironment, and further realizes reversible photochromism of the DASAs in the aqueous phase.
Example two:
this embodiment is substantially the same as the first embodiment, and is characterized in that:
in this example, P (N-M-NH) was prepared according to the above synthetic route, and a temperature sensitive dendrimeric polymer P (N-M-NH) with a concentration of 0.5 Wt% was placed in a cuvette for turbidity test, and the polymer had a certain temperature sensitive behavior. The transmittance of the aqueous copolymer solution was measured with respect to temperature using a UV-Vis spectrum, and a haze curve was obtained as shown in FIG. 2. According to the full spectrum scanning test of the copolymer, the copolymer has no absorption at the wavelength lambda of 700nm, so that the transmittance at the wavelength lambda of 700nm is selected as a turbidity test, the temperature range is 20-35 ℃, and the temperature rising speed is 0.2 ℃/min to study the temperature-sensitive behavior. The results show that the phase transition temperature is 26.5 ℃ and that the solution becomes turbid when the temperature reaches above the phase transition temperature. And when the temperature drops below the phase transition temperature, the solution returns to be clear.
Example three:
this embodiment is substantially the same as the previous embodiment, and is characterized in that:
in this example, the present example relates to temperature response characteristic experiments of the polymeric microspheres. The polymer microsphere N-NP was prepared as an aqueous solution with a concentration of 0.5 Wt%, and the hydrodynamic particle size change with temperature was studied by dynamic light scattering DLS, as shown in FIG. 3. The testing temperature range is 20-60 ℃, the hydrodynamic radius of the polymer microsphere N-NP is 110nm at the temperature of 20 ℃, the size of a single microsphere is gradually reduced along with the temperature rise due to dehydration shrinkage of the dendritic alkoxy ether units, the hydrodynamic radius is reduced to 43nm when the temperature reaches 60 ℃, and the size of the microsphere is gradually restored to the original 110nm when the temperature is reduced from 60 ℃ to 20 ℃.
Example four:
this embodiment is substantially the same as the previous embodiment, and is characterized in that:
in this example, the present example relates to an apparent morphology characterization experiment of the polymeric microspheres. Polymer microspheres N-NP and N-NP-DASA are prepared into water solution with the concentration of 0.01mg/mL, the water solution is dripped on a mica sheet, and AFM shooting is carried out after the water solution is thoroughly dried in a nitrogen atmosphere. From the photographs, it can be clearly seen that both N-NP as shown in FIG. 4 and N-NP-DASA as shown in FIG. 5 are spherical shapes with uniform size. The size of microsphere N-NP is 90nm, and the size of microsphere N-NP-DASA is 120 nm.
Example five:
this embodiment is substantially the same as the previous embodiment, and is characterized in that:
in this example, this example relates to photochromic reversible isomerization experiments for the polymeric microspheres. The polymer microsphere N-NP-DASA is prepared into an aqueous solution with the concentration of 0.5 Wt%, and then the aqueous solution is placed into a cuvette for testing, wherein the maximum absorption wavelength of an ultraviolet absorption spectrum is 559 nm. And the absorbance at the wavelength is gradually reduced along with the increase of the illumination time, and the color of the microsphere aqueous solution is gradually changed from purple to colorless. After illumination, the solution is changed into a colorless N-NP-DASA solution, the solution is heated in a water bath kettle at 45 ℃ in a dark place, the absorbance gradually rises along with the increase of time, and the absorbance can be restored to the initial value before illumination, which shows that the DASAs can be completely and reversibly isomerized in the water phase under the higher-level hydrophobic limited microenvironment provided by the microspheres.
Example six:
this embodiment is substantially the same as the previous embodiment, and is characterized in that:
in this example, referring to fig. 8, a method for preparing temperature and light dual-responsive dendrimeric microspheres containing DASAs includes the following steps:
a. adopting alkoxy ether dendritic polymer, putting the aqueous solution of the polymer in a water bath at 35 ℃, heating and irradiating by ultraviolet light for 6 hours to obtain microsphere dispersion liquid emitting blue light;
b. and (b) dissolving 10 times of molar amount of activated furan derivative in tetrahydrofuran, slowly adding the activated furan derivative into the microsphere dispersion prepared in the step a, stirring and reacting at 60 ℃ for 1 hour to gradually change the color of the microsphere dispersion into a purple product solution, and performing centrifugal washing to obtain the purple DASAs-containing temperature and light dual-responsive dendritic polymer microspheres.
The embodiment realizes reversible photochromism of DASAs in the aqueous phase, combines the crowding effect, the worm-shaped topological structure and the temperature-sensitive characteristic of the alkoxy ether dendritic polymer and the physical appearance of the polymer microspheres into a whole, prepares the temperature-sensitive branched polymer microspheres containing the DASAs, constructs a limited microenvironment, and further realizes reversible photochromism of the DASAs in the aqueous phase.
In summary, the above examples implement a method of Donor-Acceptor Stenhouse Adducts (DASAs) aqueous phase reversible photochromism. The temperature-sensitive dendronized polymer microspheres containing DASAs are prepared by combining the crowding effect, the vermicular topological structure and the temperature-sensitive characteristic of the alkoxy ether dendronized polymer and the physical appearance of the polymer microspheres, so that a limited microenvironment is constructed, and the reversible photochromic regulation of photochromic elements DASAs in a water phase is successfully realized. The method of construction of a confined microenvironment provided by the above examples allows DASAs to isomerize rapidly and completely reversibly in the aqueous phase. The regulation and control mode has the characteristics of multiplicity, environmental friendliness, simplicity and flexibility. Therefore, the method has potential application value in the fields of biological medicine, molecular probes, environmental monitoring, optical devices, intelligent display and the like.
The embodiments of the present invention have been described above with reference to the accompanying drawings, but the present invention is not limited to the above embodiments, and various changes can be made according to the purpose of the invention, and any changes, modifications, substitutions, combinations or simplifications made according to the spirit and principle of the technical solution of the present invention should be replaced with equivalents as long as the object of the present invention is met, and the technical principle and the inventive concept of the present invention are not departed from the scope of the present invention.
Claims (8)
1. A preparation method of temperature and light dual-responsive dendritic polymer microspheres containing DASAs is characterized by comprising the following steps:
a preparation method of temperature and light dual-responsive dendritic polymer microspheres containing DASAs comprises the following steps:
a. heating and irradiating by ultraviolet light for 1-6 h to obtain blue-emitting microsphere dispersion liquid;
b. and (b) dissolving the activated furan derivative in tetrahydrofuran, slowly adding the dissolved activated furan derivative into the microsphere dispersion prepared in the step a, stirring and reacting at the temperature of not lower than 60 ℃ for not more than 4 hours to gradually change the color of the microsphere dispersion into a purple product solution, and performing centrifugal washing to obtain the purple DASAs-containing temperature and light dual-responsive dendritic polymer microspheres.
2. The method of claim 1, wherein the temperature and light dual-responsive dendrimeric microspheres containing DASAs are prepared: in the step a, the structural general formula of the alkoxy ether branched polymer is represented as P (Gn-N) x-co-PMy, and the structural formula is as follows:
wherein Gn is an alkoxy ether dendron with one generation of n ═ 1 or two generations of n ═ 2, x: y ═ 100: 1-10: 1, and x and y are integers of 1-100.
3. The method of claim 2, wherein the temperature and light dual-responsive dendrimeric microspheres containing DASAs are prepared: the structural formula of Gn is:
4. the method of claim 1, wherein the temperature and light dual-responsive dendrimeric microspheres containing DASAs are prepared: in said step b, not more than 20 times the molar amount of the activated furan derivative is dissolved in tetrahydrofuran.
5. A temperature and light dual-responsive dendritic polymer microsphere containing DASAs, which is characterized in that: the temperature and light dual-responsive dendrimeric microspheres containing DASAs according to claim 1.
6. The temperature and light dual-responsive dendrimeric microspheres containing DASAs according to claim 5, wherein: a confined microenvironment is constructed to allow reversible photochromism of DASAs in the aqueous phase.
7. The temperature and light dual-responsive dendrimeric microspheres containing DASAs according to claim 5, wherein: the radius is not more than 120 nm.
8. The temperature and light dual-responsive dendrimeric microspheres containing DASAs according to claim 5, wherein: the hydrodynamic radius of the DASAs-containing temperature and light dual-responsive dendritic polymer microspheres is 43-110nm and adjustable within the range of 20-60 ℃.
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