CN109337671B - Layered photochromic film and preparation method thereof - Google Patents

Layered photochromic film and preparation method thereof Download PDF

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CN109337671B
CN109337671B CN201811363901.1A CN201811363901A CN109337671B CN 109337671 B CN109337671 B CN 109337671B CN 201811363901 A CN201811363901 A CN 201811363901A CN 109337671 B CN109337671 B CN 109337671B
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photochromic film
layered
layered photochromic
montmorillonite
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CN109337671A (en
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刘兆阅
甘孟轲
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Beijing University of Aeronautics and Astronautics
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

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Abstract

The layered photochromic thin film of the present invention contains montmorillonite as a host material, cations represented by the following formula I and quaternary ammonium cations represented by the following formula II, and is easily obtained without polymerization, stable and not liable to phase separation

Description

layered photochromic film and preparation method thereof
Technical Field
The invention relates to the field of photochromism, in particular to a photochromism film and a preparation method thereof.
Background
Photochromic molecules have the characteristic of photoinduced reversible color change and have potential application in the fields of optical information storage, optical switches, chemical sensing and the like. The spiropyran is a common organic photochromic molecule, and reversible structural isomerization between colorless closed-loop spiropyran and colored open-loop body cyanine can be generated by illumination. In general, a film is further used in which a spiropyran molecule is dispersed in a host material, and for example, patent document 1 discloses a polymer film in which a spiropyran molecule is dispersed in a high-molecular monomer and then polymerized by high-molecular polymerization. However, the preparation method of the photochromic film is complicated, the process is complex, and in addition, the defect of weak luminous intensity of photochromic caused by low concentration of spiropyran molecules exists, so that the wide application of the photochromic film is limited. Further, there is disclosed a polymer film obtained by dispersing a spiropyran directly in a polymer material as a host material, and such a production method is simple, but the spiropyran and the polymer material are not directly linked, and therefore the polymer film obtained in this way has disadvantages such as poor stability and easy phase separation.
Patent document 1: CN107099282A
Disclosure of Invention
The present inventors have made extensive studies to solve at least some of the problems of the photochromic thin film materials of the prior art and to obtain a stable photochromic thin film material which is less likely to cause phase separation, etc., and have found that at least one of the above-mentioned problems can be solved by the layered photochromic thin film of the present invention, thereby completing the present invention.
The invention provides a layered photochromic film and a preparation method thereof. Specifically, the present invention includes the following.
The first aspect of the present invention provides a layered photochromic film comprising montmorillonite as a host material, and cations represented by formula I and quaternary ammonium cations represented by formula II.
In another aspect of the present invention, there is provided a method for preparing a layered photochromic thin film, comprising the steps of:
An ion exchange step of subjecting a precursor of a cation represented by the following formula I and a precursor of a quaternary ammonium cation represented by the following formula II to ion exchange with montmorillonite.
The layered photochromic thin film of the present invention is obtained by ion-exchanging a precursor of a cation represented by formula I, a precursor of a quaternary ammonium cation represented by formula II, and montmorillonite. Preferably, the montmorillonite has a lamellar structure. In the present invention, a precursor of a cation represented by formula I and a precursor of a quaternary ammonium cation represented by formula II are mixed with montmorillonite, cations such as potassium, sodium, and calcium in the montmorillonite are ion-exchanged with the cation represented by formula I and the quaternary ammonium cation represented by formula II to cause an intercalation reaction, so that the montmorillonite which is originally in a lamellar structure is exfoliated and the cation represented by formula I is fixed on the surface thereof, thereby making it possible to disperse a high-concentration photoluminescent material in the montmorillonite as a host material. Wherein, by containing the precursor of the quaternary ammonium cation shown in the formula II in the mixing process, the concentration of the precursor of the cation shown in the formula I in the obtained layered photochromic film can be further increased, so that the active sites of the interaction between the montmorillonite nanosheet and the precursor of the cation shown in the formula I are increased.
The layered photochromic film contains cations shown in a formula I, exists in a closed-loop form under the irradiation of visible light, and is light yellow as a whole; under the condition of ultraviolet light or darkness, the laminated photochromic film exists in an open-loop form, and the whole laminated photochromic film is purple red.
The layered photochromic film of the invention does not need to be polymerized by high molecules usually adopted in the prior art, and can simplify the process flow. And because the cations shown in the formula I are fixed on the surface of the montmorillonite, compared with the photochromic film prepared by directly mixing the cations and the montmorillonite without bonding, the layered photochromic film has stable performance and does not generate phase separation.
Drawings
FIG. 1: TEM topography of the layered photochromic thin film obtained in example 1.
FIG. 2: AFM profiles of the layered photochromic thin films obtained in example 1.
FIG. 3: SEM topographic surface and cross sectional views of the layered photochromic thin film obtained in example 1; wherein fig. 3(a) is an SEM image of the surface of the layered photochromic thin film obtained in example 1, fig. 3(B) is a partially enlarged view of fig. 3(a), and fig. 3(C) is an SEM image of a cross-section of the layered photochromic thin film obtained in example 1.
FIG. 4: the photochromic performance of the layered photochromic thin film obtained in example 1 and the corresponding ultraviolet reflection spectrum thereof. Wherein, fig. 4(a) is a color state diagram (purple red) of the layered photochromic film 1 (the cation shown in the formula I is in the ring-opening structure) just prepared, fig. 4(B) is a color state diagram (light yellow) of the layered photochromic film 1 (the cation shown in the formula I is in the ring-closing structure after being irradiated by visible light), and fig. 4(C) is a color state diagram (purple red) of the layered photochromic film 1 (the cation shown in the formula I is in the ring-opening structure) after being irradiated by ultraviolet light after being irradiated by the visible light. Fig. 4(D) is an ultraviolet reflectance spectrum of the layered photochromic thin film 1 in the state corresponding to fig. 4(a), 4(B), and 4 (C). In FIG. 4(D), the uppermost curve is after visible light irradiation, the middle curve is after ultraviolet light irradiation, and the lowermost curve is immediately after production.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but as a more detailed description of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Further, for numerical ranges in this disclosure, it is understood that the upper and lower limits of the range, and each intervening value therebetween, is specifically disclosed. Every smaller range between any stated value or intervening value in a stated range and any other stated or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference herein for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control. Unless otherwise indicated, "%" is percent by weight.
the "precursor of cation represented by formula I" in the present invention means a compound capable of generating or releasing cation represented by formula I, and examples thereof include cation represented by formula I as a cation and other anion (e.g., Br)-、Cl-) A compound of (a).
The "precursor of quaternary ammonium cation represented by the formula II" in the present invention means a compound capable of generating or releasing cation represented by the formula II, and examples thereof include cation represented by the formula II as a cation and other anion (e.g., Br)-、Cl-) A compound of (a).
[ layered photochromic film ]
The layered photochromic film of the present invention contains montmorillonite as a host material, cations represented by the following formula I, and quaternary ammonium cations represented by the following formula II.
The photochromic active molecule used in the layered photochromic film of the present invention comprisesHas the structure shown in the formula I. The precursor of the photochromic active molecule may be Br-Or Cl-The anion is a compound having a structure represented by formula I as a cation. With Br-the compound as an anion may be simply referred to as "compound 1" in the present invention. With Cl-The compound as an anion may be simply referred to as "compound 2" in the present invention. One or a combination of two of the above-mentioned compounds may be used in the present invention.
In the layered photochromic film, the quaternary ammonium cation shown in the formula II has the function of improving the dispersity of the montmorillonite nanosheets, so that the active sites of the interaction between the montmorillonite nanosheets and photochromic active molecules are increased. Examples of the anion contained in the precursor of the quaternary ammonium cation represented by the formula II include Br-Or Cl-. With Br-The compound as an anion and the compound having the structure represented by formula II as a cation may be simply referred to as "compound 3" in the present invention. With Cl-The compound which is an anion and the compound having the structure represented by the formula II as a cation may be simply referred to as "compound 4" in the present invention. One or a combination of two of the above compounds may be used in the present invention.
The montmorillonite contained in the layered photochromic film of the invention as a host material preferably has a lamellar structure, and in the invention, a guest molecule of a structure shown in formula I containing a quaternary ammonium group and a compound molecule of a cation shown in formula II containing a quaternary ammonium group are used for carrying out ion exchange with the montmorillonite so as to fix photochromic active molecules on the surface of the montmorillonite. As the montmorillonite used in the layered photochromic film of the present invention, from the viewpoint of improving its fixing ability to obtain a layered photochromic film having a large photochromic strength, it is preferable to use two-dimensional montmorillonite nanosheets, the transverse dimension of which is usually greater than 100nm or up to several micrometers or even more, for example, between 10 and 8000nm, preferably between 15 and 1000 nm. The thickness can be as thin as a single or a few atomic layers, for example up to less than 5nm, on the other hand more than 0.01nm, more preferably more than 0.1 nm. Due to the advantages of ultrahigh specific surface area, multiple spatial sites, easy film formation and the like of the two-dimensional montmorillonite nanosheets, the layered photochromic film with high photochromic strength, simple and convenient manufacturing process and excellent stability can be obtained by adopting the two-dimensional montmorillonite nanosheets as a main material.
[ method for producing layered photochromic film ]
The preparation method of the layered photochromic film comprises the following steps: an ion exchange step of performing ion exchange between a precursor having a structure represented by the following formula I, a precursor having a quaternary ammonium cation represented by the following formula II and montmorillonite,
in the ion exchange step, the quaternary ammonium groups of the precursor having the structure shown in formula I and the quaternary ammonium groups of the precursor having the structure shown in formula II are subjected to an ion exchange reaction with montmorillonite, so that the photochromic active molecules are fixed on the surface of the montmorillonite. The two precursor molecules may be in the form of a mixed solution obtained by first dissolving them in water, and the aforementioned montmorillonite may be in the form of a suspension previously suspended in water. Preferably, the reaction temperature in the ion exchange step is 50 to 90 ℃, preferably 60 to 80 ℃.
the method for producing a layered photochromic film of the present invention may further comprise at least one of the following steps:
A centrifugal separation step of performing centrifugal separation on the solution after the ion exchange step at room temperature, and removing the suspension to obtain a precipitate;
a washing step of washing the precipitate obtained in the centrifugal separation step with, for example, a chloroform/methanol mixed solvent to wash the precipitate;
a dispersing step of sufficiently stirring and dispersing the precipitate subjected to the washing step in chloroform;
And a step of forming the layered photochromic thin film by suction-filtering the precipitate obtained in the dispersion step onto a filter membrane and then peeling the filter membrane.
In the centrifugal separation step, the product after the ion exchange reaction is subjected to centrifugal separation to remove the suspension, thereby obtaining a precipitate as a reaction product.
The cleaning step washes the precipitate, and improves the purity of the reaction product. The solvent used for washing is preferably a chloroform/methanol mixed solvent, and the blending ratio of chloroform to methanol in the chloroform/methanol mixed solvent can be determined by those skilled in the art according to the common knowledge in the art, and may be, for example, 1: 1. The above-described washing step may be repeated 2 or more times in order to obtain a layered photochromic thin film having a small content of impurities, but the above-described washing step is preferably 5 or less times in view of improving the efficiency of the production process and reducing the loss of the reaction product.
the dispersion step is carried out in chloroform, and the stirring time is, for example, 2 to 72 hours, preferably 12 hours or more, more preferably 24 hours or more from the viewpoint of sufficient stirring, and preferably 48 hours or less from the viewpoint of efficiency of stirring, as long as the precipitate is sufficiently dispersed in chloroform.
In the above-mentioned forming step, as the filtration membrane to be used, a filtration membrane made of a material such as polyethylene or nylon can be used. After the filtration membrane is peeled off, a self-supporting layered photochromic film can be obtained.
In one embodiment of the method for preparing a layered photochromic film of the present invention, the method comprises the steps of:
(1) carrying out ion exchange reaction on 0.02-0.4 g of compound 1, 0.02-0.4 g of compound 3 and 0.1-0.5 g of montmorillonite in 5-40mL of water for 1-2 hours, and setting the reaction temperature to be 50-90 ℃, so that the montmorillonite is stripped into a nanosheet structure with photochromic active molecules fixed on the surface;
(2) Naturally cooling the montmorillonite mixed solution after the ion exchange reaction to room temperature, and centrifuging the suspension at the rotating speed of 2000-5000 rpm to obtain light yellow precipitate;
(3) Washing the light yellow precipitate with chloroform/methanol mixed solvent;
(4) Fully stirring and dispersing the light yellow precipitate in chloroform for 24-48 hours;
(5) And (3) carrying out vacuum filtration on the uniformly dispersed mixed solution through a nylon filtering membrane, and then stripping the nylon filtering membrane to obtain the layered photochromic film.
Examples
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The specification and examples are exemplary only.
Example 1
0.4g of montmorillonite was dissolved in 20mL of deionized water at room temperature to give a pale yellow montmorillonite suspension. 0.034g of Compound 1 and 0.306g of Compound 3 were dissolved in 10mL of deionized water. The mixture was transferred to a three-neck flask, and the two were mixed well. The temperature of the three-necked flask was adjusted to 70 ℃ and the mixture was heated and stirred in an oil bath for one hour. After returning to room temperature, the suspension was centrifuged at 2000rpm for 5min to give a pale yellow precipitate. The precipitate was washed with chloroform/methanol at a volume ratio of 1: 1. The washed precipitate was stirred in 25mL of chloroform for 48 hours. Soaking the nylon filtering membrane in chloroform solution to make it completely wet, spreading on the filter, and starting the water pump. And (3) adding 5mL of light yellow suspension to the filter membrane along the wall of the vessel, performing suction filtration for 20min to obtain a compact lamellar membrane, and stripping the lamellar membrane from the filter membrane to obtain the self-supporting lamellar photochromic film 1.
The obtained layered photochromic film 1 was characterized as follows.
(1) TME topography characterization
fig. 1 is a TEM topography of the layered photochromic thin film 1 obtained in example 1, and from fig. 1, it can be clearly seen that the nano-sheet structure of the layered photochromic thin film 1 has a size between tens and hundreds of nanometers, and is larger and can reach several micrometers.
(2) AFM characterization
FIG. 2 is an AFM image obtained by scanning the thickness of the prepared layered photochromic thin film 1 by AFM, and it can be clearly seen from FIG. 2 that the size and thickness of the layered photochromic thin film 1 having a peeled filter film thickness is about 4.5 nm.
(3) SEM topography characterization
Fig. 3 is a view obtained by observing the microscopic morphology of the layered photochromic thin film 1 using SEM. The cross section of the prepared laminated photochromic thin film 1 is observed to have a clear laminated structure.
(4) Photochromic properties of layered photochromic thin films and corresponding ultraviolet reflectance spectra
Figure 4 is a representation of the photochromic properties of the layered photochromic film 1. Firstly, the laminated photochromic film 1 is cut into pieces, and the pieces are attached to an ultraviolet spectrum integrating sphere by using a double-sided adhesive tape for observation. Fig. 4(a) is a color state diagram of the layered photochromic film 1 just prepared (the photochromic active molecules are in an open-loop structure), fig. 4(B) is a color state diagram of the layered photochromic film 1 after being irradiated with visible light (the photochromic active molecules are in a closed-loop structure), and fig. 4(C) is a color state diagram of the layered photochromic film 1 after being irradiated with visible light and being irradiated with ultraviolet light (the photochromic active molecules are in an open-loop structure). The results show that the layered photochromic film 1 has clear photochromic properties, i.e., the color thereof can be restored by ultraviolet light after it is discolored by visible light. Fig. 4(D) is an ultraviolet reflectance spectrum of the layered photochromic thin film 1 in the state corresponding to fig. 4(a), 4(B), and 4 (C).
Example 2
0.2g of montmorillonite was dissolved in 10mL of deionized water at room temperature to give a pale yellow montmorillonite suspension. 0.051g of Compound 1 and 0.119g of Compound 3 were dissolved in 5mL of deionized water. The mixture was transferred to a three-neck flask, and the two were mixed well. The temperature of the three-necked flask was adjusted to 70 ℃ and the mixture was heated and stirred in an oil bath for one hour. After natural cooling and returning to room temperature, the suspension is centrifuged for 5min at 2000rpm of a centrifuge to obtain light yellow precipitate. The precipitate was washed with chloroform/methanol at a volume ratio of 1: 1. The washed precipitate was stirred in 25mL of chloroform for 48 hours. Soaking the nylon filtering membrane in chloroform solution to make it completely wet, spreading on the filter, and starting the water pump. And (3) adding 5mL of light yellow suspension to the filter membrane along the wall of the vessel, performing suction filtration for 20min to obtain a compact layered membrane, and stripping the compact layered membrane from the filter membrane to obtain the photochromic membrane 2.
example 3
0.2g of montmorillonite was dissolved in 10mL of deionized water at room temperature to give a pale yellow montmorillonite suspension. 0.085g of compound 2 and 0.085g of compound 3 were dissolved in 5mL of deionized water. The mixture was transferred to a three-neck flask, and the two were mixed well. The temperature of the three-necked flask was adjusted to 70 ℃ and the mixture was heated and stirred in an oil bath for one hour. After natural cooling and returning to room temperature, the suspension is centrifuged for 5mins at 2000rpm of a centrifuge to obtain light yellow precipitate. The precipitate was washed with chloroform/methanol at a volume ratio of 1: 1. The washed precipitate was stirred in 25mL of chloroform for 48 hours. Soaking the nylon filtering membrane in chloroform solution to make it completely wet, spreading on the filter, and starting the water pump. And (3) adding 5mL of light yellow suspension to the filter membrane along the wall of the vessel, carrying out suction filtration for 20min to obtain a compact laminar membrane, and stripping the laminar membrane from the filter membrane to obtain the photochromic film 3.
Example 4
0.2g of montmorillonite was dissolved in 10mL of deionized water at room temperature to give a pale yellow montmorillonite suspension. 0.119g of Compound 1 and 0.051g of Compound 4 were dissolved in 5mL of deionized water. The mixture was transferred to a three-neck flask, and the two were mixed well. The temperature of the three-necked flask was adjusted to 70 ℃ and the mixture was heated and stirred in an oil bath for one hour. After natural cooling and returning to room temperature, the suspension is centrifuged for 5min at 2000rpm of a centrifuge to obtain a reddish brown precipitate. The precipitate was washed with chloroform/methanol at a volume ratio of 1: 1. The washed precipitate was stirred in 25mL of chloroform for 48 hours. Soaking the nylon filtering membrane in chloroform solution to make it completely wet, spreading on the filter, and starting the water pump. And (3) adding 5mL of light yellow suspension to the filter membrane along the wall of the vessel, carrying out suction filtration for 20min to obtain a compact laminar membrane, and stripping the laminar membrane from the filter membrane to obtain the photochromic film 4.

Claims (9)

1. a layered photochromic film comprising montmorillonite as a host material, cations represented by formula I and quaternary ammonium cations represented by formula II, which is prepared by a process comprising the step of ion-exchanging a precursor of the cation represented by formula I and a precursor of the quaternary ammonium cation represented by formula II with the montmorillonite,
2. The layered photochromic film as claimed in claim 1, wherein the montmorillonite has a nano-platelet structure and the cation represented by formula I is immobilized on the surface thereof.
3. The layered photochromic film of claim 1 wherein the precursor of the cation of formula I comprises Br-And/or Cl-As an anion.
4. The layered photochromic film of claim 1 wherein the precursor of the quaternary ammonium-based cation of formula II comprises Br-and/or Cl-As an anion.
5. the layered photochromic film of any one of claims 1 to 4 which is a self-supporting layered photochromic film.
6. A method for preparing a layered photochromic film according to any one of claims 1 to 5 comprising the following ion exchange steps: performing ion exchange on a precursor of cation shown in the formula I and a precursor of quaternary ammonium cation shown in the formula II and montmorillonite in water,
7. The method of preparing a layered photochromic film of claim 6 further comprising at least one of the following steps:
A centrifugation step: carrying out centrifugal separation on the mixed solution after the ion exchange step, and removing the suspension to obtain a precipitate;
A cleaning step: washing the precipitate with an organic solvent to wash the precipitate;
A dispersing step: stirring and dispersing the precipitate subjected to the cleaning step in chloroform;
A forming step: and (3) carrying out suction filtration on the dispersed precipitate onto a filtering membrane, and then stripping the filtering membrane to obtain the layered photochromic film.
8. The method for preparing a layered photochromic film according to claim 7, wherein the temperature of water during the ion exchange is 50 to 90 ℃, and the mixed solution obtained after the ion exchange needs to be cooled to room temperature before the centrifugal separation.
9. the method of preparing a layered photochromic film according to claim 7, wherein the organic solvent used in the washing step is a chloroform/methanol mixed solvent.
CN201811363901.1A 2018-11-16 2018-11-16 Layered photochromic film and preparation method thereof Active CN109337671B (en)

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