CN115304552B

CN115304552B - Dihydroxyl functional monomer capable of reversible photochromism, and preparation method and application thereof

Info

Publication number: CN115304552B
Application number: CN202210928217.3A
Authority: CN
Inventors: 陈旭东; 郭�旗; 黄珍杰; 钟世龙
Original assignee: Sun Yat Sen University
Current assignee: Sun Yat Sen University
Priority date: 2022-08-03
Filing date: 2022-08-03
Publication date: 2023-08-29
Anticipated expiration: 2042-08-03
Also published as: CN115304552A

Abstract

The invention discloses a reversible photochromic dihydroxyl functional monomer and a preparation method and application thereof, belonging to the technical field of organic synthesis. The preparation method of the reversible photochromic dihydroxy functional monomer is simple and convenient, low in production cost, high in output efficiency, mild in reaction condition and stable in intermediate product. The dihydroxyl functional monomer with the reversible photochromism prepared by the preparation method has strong stability, contains two long-chain alkyl alcohols, and can be used as the functional monomer to participate in polymerization reaction when being applied to photochromic materials, thereby avoiding the problems of uneven distribution and small molecular precipitation caused by direct doping.

Description

Dihydroxyl functional monomer capable of reversible photochromism, and preparation method and application thereof

Technical Field

The invention belongs to the technical field of organic synthesis, and particularly relates to a reversible photochromic dihydroxyl functional monomer, and a preparation method and application thereof.

Background

Polymers containing photochromic dyes have been used in research as a variety of materials ranging from optical data storage to sensors, drives, biomedical devices, nonlinear optical elements, and the like. Thus, improving the photoelectric conversion capability and efficiency of photochromic materials in a polymeric matrix is of great importance for further advancing their application and successfully utilizing them as translators of light stimuli to trigger macroscopic property changes of the material. However, achieving efficient and reversible photoelectric conversion in a polymer matrix has been a continuing challenge, as photochemically reactive kinetics and other properties of the photochromic are often strongly affected by the properties of the matrix environment, particularly rigidity, free volume and polarity.

Conventional photochromic dyes generally exist in a colorless state until activated by ultraviolet light in the 300-400 nm range, causing electronic and conformational changes to stain. Such coloring conditions are often difficult to achieve quickly in daily life by means of ultraviolet light in sunlight alone. Donor-acceptor Stanhaus adducts (DASA) are a novel class of T-type negative photochromic dyes that reversibly transition from an energy-favored colored state to a colorless state in response to visible light, and revert to the colored state in a dark or hot environment.

DASA optical switches have been widely used in the fields of sensors, molecular machines, smart materials, and drug delivery since DASA development in 2014. However, the conventional DASA polymer-based material is usually formed by modification reaction or direct doping of a polymer main chain, and the combination mode can influence the uniform distribution of DASA in the polymer, and meanwhile, the problems of low grafting rate, dopant precipitation and the like are also caused. Meanwhile, the preparation efficiency of the DASA functional monomer which can be directly copolymerized with the polymer is low and the steps are complex in the prior art, so that the skilled person is still dedicated to researching the DASA reversible photochromic functional monomer which has high preparation efficiency and simple steps and can be copolymerized with more various polymers.

Disclosure of Invention

Aiming at the defects of the prior art, the invention provides a dihydroxy functional monomer capable of reversible photochromic, and a preparation method and application thereof.

In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: a preparation method of a reversible photochromic dihydroxyl functional monomer comprises the following steps:

s1, uniformly mixing haloalkyl alcohol and aromatic amine, and adding Lewis base, an iodine catalyst and a phase transfer catalyst for nucleophilic substitution reaction to prepare a compound A; one end of the haloalkyl alcohol is halogen, and the other end of the haloalkyl alcohol is hydroxyl; the structural formula of the aromatic amine is shown as the formula (I):

wherein R is ₁ 、R ₂ 、R ₃ 、R ₄ 、R ₅ Is hydrogen, C _1～20 Aryl, C _1～20 Heteroaryl, C _1～20 Alkyl, C _1～20 Acyl, C _1～20 Ester group, C _1～20 Keto, C _1～20 Aldehyde group, C _1～20 Alkoxy, C _1～20 Any one of aryloxy groups, and R ₁ 、R ₂ 、R ₃ 、R ₄ 、R ₅ Contains at least one hydroxyl group;

s2, carrying out nucleophilic substitution reaction on the 2-furaldehyde compound and a receptor compound to generate a compound B;

s3, performing electrophilic addition reaction on the compound A and the compound B to obtain the reversible photochromic dihydroxyl functional monomer.

Preferably, the compound A is further subjected to ethyl acetate recrystallization purification treatment; the compound B is also subjected to filtering and water washing treatment; the dihydroxyl functional monomer with reversible photochromism is also subjected to suction filtration and washing treatment; in the step S1, the nucleophilic substitution reaction temperature is 20-100 ℃, and the reaction process is carried out in a solvent; in the step S2, the nucleophilic substitution reaction temperature is 0-100 ℃, and the reaction process is carried out in a solvent; in the step S3, the temperature of the electrophilic addition reaction is 0-80 ℃, and the reaction process is carried out in a solvent.

Under the action of Lewis base, iodine catalyst and phase transfer catalyst, the halogen at one end of haloalkyl alcohol reacts with amino group on aromatic amine to generate secondary amine.

Preferably, the structural formula of the 2-furaldehyde compound is shown as a formula (II):

wherein R is ₁ 、R ₂ 、R ₃ Is hydrogen, halogen or C _1～20 Aryl, C _1～20 Heteroaryl, C _1～20 Alkyl, C _1～20 Acyl, C _1～20 Ester group, C _1～20 Keto, C _1～20 Aldehyde group, C _1～20 Alkoxy, C _1～20 Any one of the aryloxy groups.

Preferably, the receptor compound is any one of the following a to h:

preferably, in the step S1, the lewis base is at least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, beryllium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, sodium hydride, and calcium hydride; the iodine catalyst is at least one of sodium iodide, potassium iodide, ammonium iodide, copper iodide, cuprous iodide, zinc iodide and cesium iodide; the phase transfer catalyst is at least one of tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium bisulfate, benzyl triethyl ammonium chloride, trioctyl methyl ammonium chloride, dodecyl trimethyl ammonium chloride, tetradecyl trimethyl ammonium chloride, polyethylene glycol and polyethylene glycol dialkyl ether.

Preferably, the solvent is at least one of water, methanol, ethanol, acetonitrile, tetrahydrofuran, acetone, cyclopentanone, cyclohexanone, dichloromethane, chloroform, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, dioxane, hexafluoroisopropanol, sulfolane, N-methyl-2-pyrrolidone, m-cresol, xylenol, benzene, toluene, xylene, N-vinyl-2-pyrrolidone, butyrolactone, butyl acetate.

In addition, the invention provides a reversible photochromic dihydroxy functional monomer prepared by the preparation method.

Preferably, the wavelength range of the reversible photochromic dihydroxyl functional monomer for absorbing ultraviolet-visible light is 400-800 nm.

Further, the invention provides application of the reversible photochromic dihydroxy functional monomer in preparing a photochromic material; preferably, the photochromic material is combined with a carrier at the time of preparation; the carrier includes a solvent, a polymer, and paper.

Compared with the prior art, the invention has the beneficial effects that:

(1) The preparation method can prepare the reversible photochromic dihydroxyl functional monomer in three steps, and has the characteristics of simplicity, convenience, low production cost and high output efficiency. The synthesis process has mild reaction condition, stable intermediate product, simple purification, no need of column chromatography, low equipment and instrument dependence, high safety in production process, and high stability and economic value of the prepared reversible photochromic dihydroxyl functional monomer.

(2) The prepared reversible photochromic dihydroxyl functional monomer introduces two long-chain alkyl alcohols, and when the reversible photochromic dihydroxyl functional monomer is applied to a photochromic material, the dihydroxyl functional monomer can be used as a functional monomer to participate in a polymerization reaction, so that a photochromic molecule is combined with a polymer in a covalent bond combination mode, and the problems of uneven distribution and precipitation of small molecules caused by direct doping are avoided.

Drawings

FIG. 1 is a diagram showing the synthetic route of a reversibly photochromic dihydroxyl functional monomer according to example 1 of the present invention.

FIG. 2 is a diagram showing the synthetic route of the reversibly photochromic dihydroxyl functional monomer according to example 2 of the present invention.

FIG. 3 is a diagram showing the synthetic route of the reversibly photochromic dihydroxyl functional monomer according to example 3 of the present invention.

FIG. 4 is a synthetic route diagram of the reversibly photochromic, dihydroxyl functional monomer of example 4 of the present invention.

FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the compound A in example 1 of the present invention.

FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the compound B in example 1 of the present invention.

FIG. 7 is a nuclear magnetic resonance spectrum of the final product of example 1 of the present invention.

FIG. 8 is a graph showing the UV-visible absorption spectrum of the final product of example 1 of the present invention.

FIG. 9 is a nuclear magnetic resonance hydrogen spectrum of the compound B in example 2 of the present invention.

FIG. 10 is a nuclear magnetic resonance spectrum of the final product in example 2 of the present invention.

FIG. 11 is a graph showing the UV-visible absorption spectrum of the final product in example 2 of the present invention.

FIG. 12 is a mask exposure of the final product of example 1 of the present invention in a polymer substrate.

FIG. 13 is a graph of the time resolved pump-probe UV-visible absorption spectra in a polymer substrate of the final product of example 1 of the present invention.

Detailed Description

For better illustrating the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to specific examples, but the scope and embodiments of the present invention are not limited thereto.

The test methods used in the following examples are conventional methods unless otherwise specified; the materials, reagents and the like used, unless otherwise specified, are those commercially available.

Example 1

The synthetic route of the dihydroxyl functional monomer reversibly photochromic in this example is shown in FIG. 1.

The preparation method comprises the following steps:

s1, synthesis of compound A

S1-1, adding 6.5g of 4-hydroxyethyl aniline into a double-mouth bottle provided with a reflux condenser and a constant pressure dropping funnel, simultaneously adding 100ml of absolute ethyl alcohol, and adding 10g of absolute potassium carbonate, 0.6g of potassium iodide and 1.6g of tetrabutylammonium bromide under magnetic stirring;

s1-2, magnetically stirring the solution under the protection of nitrogen, heating to reflux, dropwise adding 6g of mixed solution of 2-bromoethanol and 50ml of absolute ethanol through a constant pressure dropping funnel at the dropping speed of 2 drops/S, magnetically stirring and refluxing for reaction for 12 hours after the dropwise adding is finished;

s1-3. After the reaction, the temperature of the reaction solution was lowered to room temperature, the filtrate was dried by spin-drying, and compound A (N- (4-hydroxyethyl phenyl) -ethanolamine) was obtained as a white powder by recrystallization from ethyl acetate, and the yield was found to be 91.1%. The nuclear magnetic characterization was performed and the results are shown in fig. 5.

S2 Synthesis of Compound B

S2-1, adding 7.8g of N, N-dimethylbarbituric acid and 200ml of deionized water into a beaker, and magnetically stirring for dissolution;

s2-2, slowly adding 6ml of 2-furaldehyde into the dimethylbarbituric acid solution, and magnetically stirring at room temperature for 1h after the addition is finished;

s2-3, after the reaction is finished, filtering to obtain filter residues, and washing with water for many times to obtain a compound B of yellow powder, wherein the yield of the compound B is 98.9 percent respectively. The nuclear magnetic characterization was performed and the results are shown in fig. 6.

S3, synthesis of dihydroxyl functional monomer capable of reversible photochromism

S3-1, adding 2.3g of compound B and 20ml of dichloromethane into a single-mouth bottle, and magnetically stirring for dissolution;

s3-2, adding 2g of compound A into the solution, and magnetically stirring the solution to react for 12 hours at room temperature;

s3-3, after the reaction is finished, rotary evaporation and concentration are carried out, a small amount of tetrahydrofuran is redissolved, then the solution is dripped into n-hexane with the volume of 50 times, suction filtration is carried out, filter residues are washed by tetrahydrofuran, deionized water and diethyl ether in sequence, and the deep blue reversible photochromic dihydroxyl functional monomer is obtained, and the yield is measured to be 72.5%. The nuclear magnetic characterization was performed and the results are shown in fig. 7. The absorption spectrum is shown in FIG. 8.

Example 2

The synthetic route of the dihydroxyl functional monomer reversibly photochromic in this example is shown in FIG. 2.

The preparation method comprises the following steps:

s1, synthesis of compound A

S1-1, adding 6.5g of 4-hydroxyethyl aniline into a double-mouth bottle provided with a reflux condenser and a constant pressure dropping funnel, simultaneously adding 100ml of acetonitrile, and adding 8g of anhydrous sodium carbonate, 0.75g of sodium iodide and 1.8g of tetrabutylammonium iodide under magnetic stirring;

s1-2, magnetically stirring the solution under the protection of nitrogen, heating to reflux, dropwise adding a mixed solution of 8.2g of 2-iodoethanol and 50ml of acetonitrile through a constant pressure dropping funnel at a dropping speed of 1 drop/S, magnetically stirring and refluxing for reaction for 12 hours after the dropwise adding is finished;

s1-3. After the reaction, the temperature of the reaction solution was lowered to room temperature, the filtrate was dried by spin-drying after suction filtration, and compound A (N- (4-hydroxyethyl phenyl) -ethanolamine) was obtained as a white powder by recrystallization from ethyl acetate, and the yield was found to be 95.1%.

S2 Synthesis of Compound B

S2-1, adding 8.9g of 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone and 200ml of deionized water into a beaker, and magnetically stirring for dissolution;

s2-2, slowly adding 6ml of 2-furaldehyde into a 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone solution, and magnetically stirring to react for 1h at 40 ℃ after the addition is finished;

s2-3, after the reaction is finished, filtering to obtain filter residues, and washing with water for many times to obtain compound B of brown powder, wherein the yields are 87.1% respectively. The nuclear magnetic characterization was performed and the results are shown in fig. 9.

S3-1, adding 2.6g of a compound B and 20ml of hexafluoroisopropanol into a single-mouth bottle, and magnetically stirring for dissolution;

s3-2, adding 2g of compound A into the solution, and magnetically stirring and reacting for 12 hours at room temperature;

s3-3, after the reaction is finished, rotary evaporation and concentration are carried out, a small amount of tetrahydrofuran is added, suction filtration is carried out after ultrasonic treatment is carried out for 1 minute, filter residues are washed by tetrahydrofuran, deionized water and diethyl ether in sequence, and the grey blue reversible photochromic dihydroxyl functional monomer is obtained, and the yield is measured to be 90.5%. The nuclear magnetic characterization was performed and the results are shown in fig. 10. The absorption spectrum is shown in FIG. 11.

Example 3

The synthetic route of the dihydroxyl functional monomer reversibly photochromic in this example is shown in FIG. 3.

The preparation method comprises the following steps:

s1, synthesis of compound A

S1-1, adding 6.2g of 4-hydroxymethyl aniline into a double-mouth bottle provided with a reflux condenser and a constant pressure dropping funnel, simultaneously adding 100ml of N, N-dimethylformamide, and adding 16g of anhydrous cesium carbonate, 1.3g of cesium iodide and 1.4g of tetrabutylammonium chloride under magnetic stirring;

s1-2, dropwise adding a mixed solution of 4.5g of 2-chloroethanol and 50ml of N, N-dimethylformamide at a dropping speed of 2 drops/S through a constant pressure dropping funnel under the protection of nitrogen, magnetically stirring after the dropwise adding is finished, and reacting for 12 hours at 100 ℃;

s1-3, after the reaction is finished, the temperature of the reaction solution is reduced to room temperature, the reaction solution is dripped into deionized water with the volume of 10 times, filter residues are recrystallized through ethyl acetate after suction filtration to obtain a white powder compound A (namely N- (4-hydroxymethyl phenyl) -ethanolamine), and the yield is measured to be 86.4%.

S2 Synthesis of Compound B

S2-1, adding 7.4g of 1, 3-indandione and 200ml of deionized water into a beaker, and magnetically stirring for dissolution;

s2-2, slowly adding 6ml of 2-furaldehyde into the 1, 3-indandione solution, and magnetically stirring to react for 1h at room temperature after the addition is finished;

s2-3, after the reaction is finished, filtering to obtain filter residues, and washing with water for multiple times to obtain a compound B of yellow powder, wherein the yields are respectively 94.8 percent.

S3-1, adding 2.2g of compound B and 20ml of acetonitrile into a single-mouth bottle, and magnetically stirring for dissolution;

s3-2, adding 3.6g of compound A into the solution, and magnetically stirring the solution to react for 12 hours at room temperature;

s3-3, after the reaction is finished, rotary evaporation and concentration are carried out, a small amount of tetrahydrofuran is added, suction filtration is carried out after ultrasonic treatment is carried out for 1 minute, deionized water and diethyl ether are sequentially used for washing filter residues, and the blue reversible photochromic dihydroxyl functional monomer is obtained, and the yield is measured to be 81.4%.

Example 4

The synthetic route of the dihydroxyl functional monomer reversibly photochromic in this example is shown in FIG. 4.

The preparation method comprises the following steps:

s1, synthesis of compound A

S1-1, adding 3.1g of 4-hydroxymethyl aniline into a double-mouth bottle provided with a reflux condenser and a constant pressure dropping funnel, simultaneously adding 50ml of toluene, and adding 0.6g of sodium hydride, 0.3g of sodium iodide and 0.6g of benzyl triethyl ammonium chloride under magnetic stirring;

s1-2, dropwise adding a mixed solution of 4g of 2-bromoethanol and 20ml of toluene through a constant pressure dropping funnel at a dropping speed of 1 drop/S under the protection of nitrogen, magnetically stirring after the dropwise adding is finished, and reacting at 100 ℃ for 12 hours;

s1-3, after the reaction, the temperature of the reaction solution is reduced to room temperature, the filtrate is dried by spin-drying after suction filtration, and the compound A (namely N- (4-hydroxymethyl phenyl) -ethanolamine) of white powder is obtained through recrystallization of ethyl acetate, and the yield is measured to be 95.1%.

S2 Synthesis of Compound B

S2-1, adding 8.9g of cyclopropylene malonate and 200ml of deionized water into a beaker, and magnetically stirring for dissolution;

s2-2, slowly adding 6ml of 2-furaldehyde into the cyclopropylene malonate solution, and magnetically stirring for reaction for 1h at 50 ℃ after the addition is finished;

s2-3, after the reaction is finished, filtering to obtain filter residues, washing with water for many times to obtain a compound B of yellow powder, wherein the yields are respectively 99.2 percent.

S3-1, adding 2.5g of compound B and 20ml of tetrahydrofuran into a single-mouth bottle, and magnetically stirring for dissolution;

s3-2, adding 4g of compound A into the solution, and magnetically stirring and reacting for 12 hours at room temperature;

s3-3, after the reaction is finished, dripping the reaction liquid into 500ml of normal hexane, carrying out suction filtration, washing filter residues with tetrahydrofuran, water and diethyl ether in sequence, and obtaining the black reversible photochromic dihydroxyl functional monomer, wherein the yield is 83.7 percent.

Example 5 application of a reversible photochromic dihydroxy functional monomer in the preparation of photochromic Material

The reversibly photochromic functional monomer (DASA) prepared in example 1 was 0.48g, hexamethylene Diisocyanate (HDI) 3.4g, polytetrahydrofuran (PTMG, M) _n =2000) 20g and 220g of N, N-Dimethylformamide (DMF), were added to a three-necked round bottom flask equipped with a thermometer and a stirrer, stirred for 2h at 80 ℃, followed by one-time addition of 0.8g of 1, 4-Butanediol (BDO), the mass ratio of each reactant being HDI: PTMG: (bdo+dasa) =2:1:1, the weight percentage concentration of the reaction system is about 10%, the reaction is continuously stirred, the residual amount of isocyanate is monitored by infrared, and the reaction is stopped when the infrared characteristic peak of the isocyanate disappears, so that polyurethane with the number average molecular weight of 20000-80000 is obtained.

And (3) coating the obtained polyurethane solution on a clean glass sheet, transferring to a blast oven at 60 ℃, drying for 2 hours, transferring to a vacuum drying oven at 70 ℃, vacuum drying for 24 hours, and removing the film from the substrate glass to obtain the polyurethane film with reversible photochromism. The thickness of the film is 10-100 mu m, and the glass transition temperature of the film is-70 to-40 ℃. The method is characterized by taking visible light as a light source to perform photochromic performance, wherein a mask exposure diagram is shown in fig. 12, and a time-resolved pump-probe ultraviolet-visible absorption spectrum diagram is shown in fig. 13. The prepared photochromic material gradually reduces the absorbance under the irradiation of visible light, the material changes from blue-violet to colorless, the material is placed in a dark place, the absorbance slowly rises and recovers, and the material has the characteristic of reversible photochromism.

Finally, it should be noted that the foregoing embodiments are merely illustrative of the technical solutions of the present invention, and not limiting the scope of the present invention, and that other variations and modifications in light of the above description and thought may be made by those skilled in the art, and it is not necessary or impossible to make an exhaustive list of all embodiments, and any modifications, equivalents, improvements, etc. that fall within the spirit and principles of the present invention are intended to be included within the scope of the claims of the present invention.

Claims

1. The structural formula of the reversible photochromic dihydroxyl functional monomer is any one of formulas (1), (2), (3) and (4):

formula (1); />Formula (2);

formula (3); />Formula (4).

2. The reversible photochromic dihydroxy functional monomer of claim 1, wherein the reversible photochromic dihydroxy functional monomer absorbs ultraviolet-visible light in a wavelength range of 400 to 800nm.

3. The method for preparing the reversible photochromic dihydroxy functional monomer of claim 1, comprising the steps of:

s1, uniformly mixing haloalkyl alcohol and aromatic amine, and adding Lewis base, an iodine catalyst and a phase transfer catalyst for nucleophilic substitution reaction to prepare a compound A; one end of the haloalkyl alcohol is halogen, and the other end of the haloalkyl alcohol is hydroxyl; the structural formula of the aromatic amine is shown as a formula (I) or a formula (II), and the structural formula of the compound A is shown as a formula (III) or a formula (IV):

formula (I),>formula (II);

formula (III),>formula (IV);

the structural formula of the 2-furaldehyde compound is shown as a formula (V), the receptor compound is any one of the following a-d, and the structural formula of the compound B is any one of the following e-h:

formula (V); />；

；

S3, performing electrophilic addition reaction on a compound A shown in a formula (III) and a compound B shown in a formula (e) to prepare the reversible photochromic dihydroxy functional monomer shown in the formula (1);

performing electrophilic addition reaction on a compound A shown in a formula (III) and a compound B shown in a formula f to prepare a dihydroxyl functional monomer with reversible photochromism shown in the formula (2);

performing electrophilic addition reaction on a compound A shown in a formula (IV) and a compound B shown in a formula g to prepare a dihydroxyl functional monomer with reversible photochromism shown in the formula (3);

and (3) performing electrophilic addition reaction on a compound A shown in the formula (IV) and a compound B shown in the formula (h) to obtain the reversible photochromic dihydroxy functional monomer shown in the formula (4).

4. A method of preparing a reversibly photochromic, dihydroxyl functional monomer according to claim 3, comprising at least one of the following a-F:

A. the compound A is subjected to recrystallization and purification treatment by ethyl acetate;

B. the compound B is also subjected to filtering and water washing treatment;

C. the dihydroxyl functional monomer with reversible photochromism is also subjected to suction filtration and washing treatment;

D. in the step S1, the temperature of the nucleophilic substitution reaction is 20-100 ℃, and the reaction process is carried out in a solvent;

E. in the step S2, the temperature of the nucleophilic substitution reaction is 0-100 ℃, and the reaction process is carried out in a solvent;

F. in the step S3, the temperature of the electrophilic addition reaction is 0-80 ℃, and the reaction process is carried out in a solvent.

5. The method for preparing a reversible photochromic dihydroxy functional monomer according to any one of claims 3 to 4, wherein in step S1, the lewis base is at least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, beryllium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, sodium hydride, and calcium hydride; the iodine catalyst is at least one of sodium iodide, potassium iodide, ammonium iodide, copper iodide, cuprous iodide, zinc iodide and cesium iodide.

6. The method for preparing a reversible photochromic dihydroxy functional monomer according to any one of claims 3 to 4, wherein in the step S1, the phase transfer catalyst is at least one of tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium bisulfate, benzyltriethylammonium chloride, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, tetradecyltrimethylammonium chloride, polyethylene glycol, and polyethylene glycol dialkyl ether.

7. Use of a reversibly photochromic dihydroxyl functional monomer according to any one of claims 1 to 2 in the preparation of photochromic materials.

8. The use according to claim 7, wherein the photochromic material is incorporated in the carrier at the time of preparation; the carrier is selected from the group consisting of solvents, polymers, and paper.