Acid-responsive fluorescent sensing material, preparation method and application thereof

Abstract

The application discloses an acid-responsive fluorescent sensing material and a preparation method and application thereof. The acid-responsive fluorescent sensing material can detect strong acid in a liquid environment. The structure of the acid-responsive fluorescent sensing material is as follows: the group responding to acid of the material is a hydroxyl group of a tertiary alcohol, and the hydroxyl group is removed under the action of acid to change the fluorescence intensity. Different molar amounts of strong acid can be distinguished by different fluorescence intensities in various liquid environments. The fluorescent sensing material prepared by the application can detect acid. After the fluorescent sensing material is mixed with acid, the color of the solution can be obviously observed to change. The change of the fluorescence signal under an ultraviolet lamp can be observed by naked eyes. The visual detection of strong acid is realized. The response speed and accuracy of the acid are improved. The fluorescent sensing material has good reusability. The acid-responsive fluorescent sensing material has the advantages of simple synthesis method, convenient separation and purification, high yield and good stability, and therefore has certain application value in the field of intelligent sensors.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of chemical fluorescent sensing materials, and relates to an acid-responsive fluorescent sensing material as well as a preparation method and application thereof. BACKGROUND

[0002] Acid-responsive materials are materials that undergo physical or chemical changes in an acidic environment. Most acid-responsive compounds have groups in their structure that can interact with acids, such as carboxyl groups (-COOH), amine groups (-NH2), pyridine groups (-py), hydroxyl groups (-OH), and Schiff base structures (-CN-), etc. These materials can change their properties or functions by absorbing or releasing acidic substances. Acid-responsive materials have a wide range of applications in many fields, including drug delivery, intelligent sensors, intelligent coatings, etc. In the field of drug delivery, acid-responsive materials are often used to control the release rate and location of drugs. When an acidic environment contacts the acid-responsive material, the material will swell or dissolve, releasing the drug. This property can be used to control the release of drugs at specific sites, improving drug efficacy and reducing side effects. In the field of intelligent sensors, acid-responsive materials can be used to detect the presence and concentration changes of acidic substances. When acidic substances contact acid-responsive materials, the resistance, optical properties, or electrochemical properties of the materials change, allowing the presence and concentration of acidic substances to be detected by measuring these changes. In the field of intelligent coatings, acid-responsive materials can be used to prepare coatings with variable color or transparency. When an acidic environment contacts the coating, the color or transparency of the coating changes, allowing for controlled adjustment of color or transparency. In summary, acid-responsive materials have broad application prospects and can play an important role in the fields of medicine, sensors, and coatings.

[0003] Trifluoromethanesulfonic acid is one of the strongest organic acids, and contact with the eyes will cause severe eye burns and possible blindness. Contact with the skin will cause severe chemical burns and delayed severe tissue damage. Inhaling vapors will cause severe convulsive reactions, inflammation, and edema. Ingestion will cause severe digestive tract burns. Trifluoroacetic acid can be in contact with high-temperature surfaces or flames, decompose, and generate toxic fumes. It is a medium-strong acid that reacts violently with strong bases, reducing agents, and oxidizing agents to generate toxic, corrosive fumes containing hydrogen fluoride. Trifluoroacetic acid is corrosive to the eyes, skin, and respiratory tract. Methyl sulfonic acid has strong irritant properties to mucous membranes, the upper respiratory tract, the eyes, and the skin. After inhalation, it can cause death due to laryngeal and bronchial spasm, inflammation, edema, chemical pneumonia, or pulmonary edema. After contact, burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting can occur, which can cause burns. It is harmful to the environment and can pollute water bodies and the atmosphere.

[0004] The visual detection of acid has the following important roles: 1. Determining the presence or absence: visual detection can help determine whether acid is present in the sample. By observing the color change of a certain indicator or reagent after reacting with acid, it can be quickly judged whether the sample contains acid. 2. Determine the concentration: visual detection can provide a simple method to estimate the concentration of acid. According to the degree of color change, the concentration of acid can be roughly judged. This is of great significance for quantitative analysis or control of reaction conditions. 3. Real-time monitoring: visual detection can achieve real-time monitoring of acid. By using a certain indicator or reagent, color changes can be observed at any time during the reaction, so that the generation or consumption of acid can be known. This is very important for real-time regulation of the reaction process or control of the continuity and stability of the reaction. 4. Environmental safety: visual detection can help monitor and control the use and discharge of acid, thereby ensuring environmental safety in practical applications. By timely detection and monitoring, excessive use or leakage of acid can be avoided, reducing potential harm to the environment and human body. In summary, visual detection of acid plays an important role in determining the presence or absence, determining the concentration, real-time monitoring, and environmental safety, and has practicality and significance for practical applications and control.

[0005] The existing acid-responsive materials have the following shortcomings: low selectivity, current acid-responsive materials usually respond to multiple acidic substances, but lack high selectivity to specific acidic substances, which may lead to inaccurate detection or control of target acidic substances in complex acidic environments; slow response speed, some acid-responsive materials have slow response speed, which requires a long time to complete the response, which may limit certain applications that require fast response, such as real-time monitoring or control; poor stability, some acid-responsive materials may experience performance degradation or failure when used for a long time or exposed to extreme environments (such as high temperature, high humidity, etc.), which limits the reliability and durability of these materials in certain applications; lack of reusability, some acid-responsive materials are difficult or impossible to reverse to the original state after changing in acidic environments, resulting in poor reusability of the materials, which may limit certain applications that require multiple uses, such as intelligent sensors or drug delivery systems; lack of adaptability to different acidic environments, current acid-responsive materials usually have good response to specific acidic environments, but poor response to other acidic environments, which may limit the adaptability and widespread application of these materials in different application environments.

[0006] Therefore, it is necessary to provide a detection method that is simple to operate, rapid to detect, stable, highly reusable, highly sensitive to acid identification, and has naked-eye identification. SUMMARY

[0007] The purpose of this invention is to address the shortcomings of existing technologies by providing an acid-responsive fluorescent sensing material, thereby solving the problems of slow response speed, poor stability, and low reusability of existing acid-responsive materials.

[0008] To achieve the above objectives, the present invention provides an acid-responsive fluorescent sensing material, wherein the general formula of the compound structure of the acid-responsive fluorescent sensing material is as follows:

[0009]

[0010] In the formula It is a benzene derivative. It is an aromatic compound.

[0011] As a further improvement of the present invention, the It is one of the following structures:

[0012]

[0013]

[0014] Where R is an alkyl chain and the number of C atoms does not exceed 5.

[0015] As a further improvement of the present invention, the It is one of the following structures:

[0016]

[0017] R1 is an alkyl chain or a halogen atom.

[0018] This invention also provides a method for preparing an acid-responsive fluorescent sensing material, comprising the following steps:

[0019] Step 1: Dibromobenzene or its derivatives, magnesium and iodine are added to reactor A. Dry tetrahydrofuran is slowly added under inert gas protection. The mixture is heated and stirred until the reaction is complete to synthesize the Grignard reagent.

[0020] Step 2: Under inert gas protection, add Grignard reagent, aromatic ketone or its derivative and dry tetrahydrofuran to reactor B, heat and stir until the reaction is complete, and obtain the product acid-responsive fluorescent sensing material containing ditertiary alcohol after post-processing.

[0021] The application further discloses an application of the acid-responsive fluorescent sensing material, and specifically, the acid-responsive fluorescent sensing material containing a di-tert-butyl alcohol structure is dissolved in an organic solvent, and a to-be-detected acid solution is added; if color change occurs in the solution, that is, fluorescence is generated under irradiation of a 365nm ultraviolet lamp, the to-be-detected solution contains a strong acid; if no color change occurs in the solution, the to-be-detected solution does not contain a strong acid.

[0022] As a further improvement of the application, the feature dimension is 256.

[0023] As a further improvement of the application, the to-be-detected solution is triflic acid, trifluoroacetic acid or methyl sulfonic acid.

[0024] As a further improvement of the application, the organic solvent is one or more of dichloromethane, tetrahydrofuran, toluene, chloroform, 1,4-dioxane and 1,2-dichloroethane.

[0025] The application has the following advantages: the system for preparing the material is simple, the reaction condition is mild and easy to control, the post-processing process is convenient, the product is simple to purify and has high purity, and the product is stable in air; the acid is detected by the fluorescent sensing material containing a di-tert-butyl alcohol structure; after the fluorescent material is mixed with the acid, the color of the dehydroxyl solution changes from colorless and transparent to yellow under the action of the acid, and yellow precipitate is generated in the solution; under irradiation of a 365nm ultraviolet lamp, strong yellow fluorescence is generated, visual detection of the acid is realized, the response time is fast, the accuracy is high, the operation is simple, and the material has good reusability, thereby providing a reference for application of the material in the field of chemical sensors. BRIEF DESCRIPTION OF DRAWINGS

[0026] Figure 1 It is a nuclear magnetic hydrogen spectrum of a compound I (Compound-1) obtained in Example 1.

[0027] Figure 2 It is a nuclear magnetic hydrogen spectrum of a compound II (Compound-2) obtained in Example 2.

[0028] Figure 3 It is a nuclear magnetic hydrogen spectrum of a compound III (Compound-3) obtained in Example 3.

[0029] Figure 4 It is an absorption spectrum of the compound I (Compound-1) obtained in Application Example 1 in a dichloromethane solution for different acids.

[0030] Figure 5 It is an emission spectrum of the compound I (Compound-1) obtained in Application Example 1 in a dichloromethane solution for different acids.

[0031] Figure 6is the absorption spectrum of Compound-2 (Compound-2) obtained in Example 2 in dichloromethane solution against different acids.

[0032] Figure 7 is the emission spectrum of Compound-2 (Compound-2) obtained in Example 2 in dichloromethane solution against different acids.

[0033] Figure 8 is the absorption spectrum of Compound-3 (Compound-3) obtained in Example 3 in dichloromethane solution against different acids.

[0034] Figure 9 is the emission spectrum of Compound-3 (Compound-3) obtained in Example 3 in dichloromethane solution against different acids.

[0035] Figure 10 is the visual detection spectrum of Compound-1 (Compound-1) obtained in Example 1 in dichloromethane solution against different acids.

[0036] Figure 11 is the visual detection spectrum of Compound-2 (Compound-2) obtained in Example 2 in dichloromethane solution against different acids.

[0037] Figure 12 is the visual detection spectrum of Compound-3 (Compound-3) obtained in Example 3 in dichloromethane solution against different acids. DETAILED DESCRIPTION

[0038] In order to make the purpose, technical solutions and advantages of the present application more clear, the present application is further described in detail in combination with the following specific examples and with reference to the accompanying drawings, but not used to limit the scope of the present application.

[0039] Example 1

[0040] Step 1: 1,4-dibromobenzene, magnesium (Mg) and iodine (I) were added to reactor A, and dry tetrahydrofuran (THF) was slowly added under nitrogen protection, heated and stirred until the reaction was completed.

[0041] Specifically, after the glass instrument of reactor A was assembled, 1,4-dibromobenzene (5 g, 1 eq), Mg (2.54 g, 5 eq) and iodine (20 mg) were added to reactor A and sealed by vacuum grease and sealing tape, reactor A was vacuumed and inert gas was filled, the operation was repeated three times, and the balloon filled with inert gas was assembled for protection.

[0042] A 50 ml syringe was used to take 30 ml of dry tetrahydrofuran, a small amount of dry tetrahydrofuran was injected into reactor A through the syringe, the stirring was turned on, and the reactor A was heated with the hot air blown by the heating gun to initiate the reaction of the raw materials in the reactor A. The solution in the reactor A changed as follows: it initially presented a yellow-brown color, and then the color faded to colorless, indicating that the reaction was successfully initiated. Then the remaining dry tetrahydrofuran was slowly added through the syringe.

[0043] Step 2: Under inert gas protection, xanthone (5 eq) and dry tetrahydrofuran were added to reactor B, then the reaction solution obtained in step 1 was added, heated to 85°C and stirred until the reaction was complete. After treatment, white compound I (Compound-1) was obtained.

[0044]

[0045] Example 2

[0046] Step 1: 1,4-dibromobenzene, magnesium (Mg) and iodine (I) were added to reactor A, and dry tetrahydrofuran (THF) was slowly added under nitrogen protection. The reactor A was heated and stirred until the reaction was complete.

[0047] Specifically, after the glassware of reactor A was assembled, 1,4-dibromobenzene (5 g, 1 eq), Mg (2.54 g, 5 eq) and iodine (20 mg) were added to reactor A and sealed by vacuum grease and sealing tape. The reactor A was vacuumed and filled with inert gas, and the operation was repeated three times. An inert gas balloon was assembled for protection.

[0048] A 50 ml syringe was used to take 30 ml of dry tetrahydrofuran, a small amount of dry tetrahydrofuran was injected into reactor A through the syringe, the stirring was turned on, and the reactor A was heated with the hot air blown by the heating gun to initiate the reaction of the raw materials in the reactor A. The solution in the reactor A changed as follows: it initially presented a yellow-brown color, and then the color faded to colorless, indicating that the reaction was successfully initiated. Then the remaining dry tetrahydrofuran (30 ml) was slowly added through the syringe.

[0049] Step 2: Under inert gas protection, xanthone (5 eq) and dry tetrahydrofuran were added to reactor B, then the reaction solution obtained in step 1 was added, heated to 85°C and stirred until the reaction was complete. After treatment, white compound I (Compound-1) was obtained.

[0050]

[0051] Example 3

[0052] Step 1: Add 1,4-dibromobenzene, magnesium (Mg) and iodine (I) into reactor A, slowly add dry tetrahydrofuran (THF) under nitrogen protection, heat and stir until the reaction is complete.

[0053] Specifically, after the glassware of reactor A is assembled, 1,4-dibromobenzene (5 g, 1 eq), Mg (2.54 g, 5 eq) and iodine (20 mg) are added into reactor A and sealed by vacuum grease and sealing tape, reactor A is vacuumed and filled with inert gas, the operation is repeated three times, and a balloon filled with inert gas is assembled for protection.

[0054] A 50 ml syringe is used to suck 30 ml of dry tetrahydrofuran, a small amount of dry tetrahydrofuran is injected into reactor A through the syringe, the stirring is turned on, and the hot air blown by the heating gun is used to heat reactor A to initiate the reaction of the raw materials in reactor A. The change of the solution in reactor A is that it starts to present yellow-brown color, then the color fades to colorless, indicating that the reaction is successfully initiated, then the remaining dry tetrahydrofuran (30 ml) is slowly added through the syringe.

[0055] Step 2: Add fluorenone (5 eq) and dry tetrahydrofuran into reactor B under inert gas protection, then add the reaction solution obtained in step 1, heat to 85°C and stir until the reaction is complete, and obtain white compound III (Compound-3) after post-treatment;

[0056]

[0057] Application Example 1

[0058] Please refer to Figure 1 and combine Figure 4 , Figure 5 , Figure 10 as shown.

[0059] 1) Compound I (Compound-1) is weighed and dissolved in an organic solvent to prepare solution A with a concentration of 10 -4 orders of magnitude mol / L, and solution A is equally divided into multiple groups;

[0060] 2) Different kinds of acids are dissolved in an organic solvent to prepare solution B with a concentration of 10 -3 orders of magnitude mol / L 1-4 , wherein the equivalent ratio of acid to compound I (Compound-1) is 10:1;

[0061] 3) Equal amounts of solution B 1-4Mix equal amount of solution A with blank solvent (the equivalent ratio of blank solvent to Compound-1 solution is 8:1), and add the blank solvent to the mixed solution respectively to dilute the mixed solution into solution C 1-4 Mix equal amount of solution A with blank solvent (the equivalent ratio of blank solvent to Compound-1 solution is 9:1) to dilute into solution C5;

[0062] 4) Measure the absorption spectrum and emission spectrum of the mixed solution C of different kinds of acid and Compound-1 (Compound-1) respectively, and draw the wavelength-absorption and wavelength-fluorescence intensity curves. 1-5

[0063] In the present application, the organic solvent is one or more of dichloromethane, tetrahydrofuran, toluene, chloroform, 1,4-dioxane, 1,2-dichloroethane, etc.

[0064] The results of whether Compound-1 (Compound-1) has acid response are shown by absorption spectrum and fluorescence spectrum, which are as follows:

[0065] Dissolve Compound-1 (Compound-1) in dichloromethane to prepare solution B with a concentration of 1×10 -4 mol / L, and dissolve triflic acid, trifluoroacetic acid, methylsulfonic acid and acetic acid in dichloromethane to prepare solution D with a concentration of 1×10 -3 mol / L respectively. Add different acid solutions to solution B to make the acid solution mix uniformly with Compound-1 (Compound-1), and measure the absorption spectrum and fluorescence spectrum of each mixed solution.

[0066] When the equivalent ratio of added triflic acid, trifluoroacetic acid and methylsulfonic acid solution to Compound-1 (Compound-1) is 10:1, new absorption peaks at 262nm and 380nm are observed in the absorption spectrum, indicating the generation of new substances, which can indicate that Compound-1 (Compound-1) can respond to acid in dichloromethane solvent. At the same time, the fluorescence emission spectrum of the probe solution mixed with triflic acid, trifluoroacetic acid and methylsulfonic acid shows obvious fluorescence enhancement, while the fluorescence emission spectrum of the Compound-1 (Compound-1) solution containing acetic acid does not change significantly, further indicating that Compound-1 (Compound-1) responds to triflic acid, trifluoroacetic acid and methylsulfonic acid.

[0067] Please refer to Figure 4 As can be seen from the figure, new absorption peaks appear at about 262nm and 380nm when triflic acid, trifluoroacetic acid and methylsulfonic acid solutions are added. Please refer to Figure 5 ​As shown in the figure, it can be seen that the emission intensity of the solution containing trifluoromethanesulfonic acid, trifluoroacetic acid and methyl sulfonic acid is obviously quenched at about 295 nm and the emission intensity at about 540 nm is obviously enhanced.

[0068] The result of whether the fluorescent probe can detect acid can be shown by observing the color of the solution, which is:

[0069] Compound I (Compound-1) is dissolved in an organic solvent, and an acid solution is added, and then the color of the reaction solution changes from colorless to yellow.

[0070] Specifically, Compound I (Compound-1) is dissolved in dichloromethane to prepare a solution A with a concentration of 5×10-4mol / L, and the solution A is divided into several equal parts, and different acids are weighed 5×10 -3 mol respectively into solution A, please refer to Figure 10 As shown in the figure, it can be seen that the solution containing trifluoromethanesulfonic acid, trifluoroacetic acid and methyl sulfonic acid is found to have color change, and the solution has yellow fluorescence under 365nm ultraviolet lamp, and the solution containing acetic acid is still colorless and transparent, which shows that Compound I (Compound-1) has certain visual detection ability for acid, that is, the operator can quickly judge whether the solution contains strong acid.

[0071] Application Example 2

[0072] Please refer to Figure 2 and in combination with Figure 6 , Figure 7 , Figure 11 shown.

[0073] 1) Compound II (Compound-2) is weighed and dissolved in an organic solvent to prepare a solution A with a concentration of 10 -4 orders of magnitude mol / L, and the solution A is divided into multiple groups in equal amounts;

[0074] 2) Different kinds of acids are dissolved in an organic solvent to prepare solution B with a concentration of 10 -3 orders of magnitude mol / L 1-4 , wherein the equivalent ratio of acid to Compound II (Compound-2) is 10:1;

[0075] 3) Equal amounts of solution B1-4 and equal amounts of solution A are mixed, and a blank solvent (the equivalent ratio of this blank solvent to Compound II (Compound-2) solution is 8:1) is added to the mixed solution to dilute the mixed solution into solution C 1-4 , and equal amounts of solution A and a blank solvent (the equivalent ratio of this blank solvent to Compound II (Compound-2) solution is 9:1) are mixed to dilute into solution C5;

[0076] 4) Respectively determine the absorption spectrum, the emission spectrum with the excitation wavelength of 260nm of the mixed solution C of different kinds of acid and Compound-2, and draw the wavelength-absorption and wavelength-fluorescence intensity curves. 1-5 The absorption spectrum, the emission spectrum with the excitation wavelength of 260nm of the mixed solution C of different kinds of acid and Compound-2, and draw the wavelength-absorption and wavelength-fluorescence intensity curves.

[0077] In the present application, the organic solvent is one or more of dichloromethane, tetrahydrofuran, toluene, chloroform, 1,4-dioxane, 1,2-dichloroethane, etc.

[0078] The results of whether Compound-2 has acid response are shown by the absorption spectrum and fluorescence spectrum, which are as follows:

[0079] Compound-2 is dissolved in dichloromethane to prepare a solution B with a concentration of 1×10 -4 mol / L, trifluoromethanesulfonic acid, trifluoroacetic acid, methylsulfonic acid and acetic acid are dissolved in dichloromethane to prepare solutions D with a concentration of 1×10 -3 mol / L. Different acid solutions are added to solution B to make the acid solution and Compound-2 mixed uniformly, and the absorption spectrum and fluorescence spectrum of each mixed solution are measured.

[0080] When the equivalent ratio of the added trifluoromethanesulfonic acid and methylsulfonic acid solution to Compound-2 is 10:1, new absorption peaks at 420nm and 460nm are observed in the absorption spectrum, indicating the generation of new substances, which can indicate that Compound-2 can respond to acid in dichloromethane solvent. At the same time, the fluorescence emission spectrum of the solution mixed with trifluoromethanesulfonic acid and methylsulfonic acid is obviously quenched, while the Compound-2 solution containing trifluoroacetic acid and acetic acid does not have obvious quenching effect, further indicating that Compound-2 responds to trifluoromethanesulfonic acid and methylsulfonic acid.

[0081] Please refer to Figure 6 As can be seen from the figure, the solution added with trifluoromethanesulfonic acid and methylsulfonic acid appears new absorption peaks at about 420nm and 460nm. Figure 7 Please refer to

[0082] The results of whether the fluorescence probe can detect acid can be shown by observing the color of the solution, which are as follows:

[0083] Compound-2) was dissolved in an organic solvent, and an acid solution was added, and the color of the reaction solution immediately changed from colorless to yellow.

[0084] Specifically, Compound-2 was dissolved in dichloromethane to prepare a solution A with a concentration of 5 x 10-4 mol / L, and the solution A was divided into several equal parts, and different amounts of acids were weighed into each part. -3 Please refer to Figure 11 As can be seen from the figure, the solutions containing triflic acid and methyl sulfonic acid changed color, and the solutions had fluorescence under irradiation of a 365 nm ultraviolet lamp, and the solutions containing trifluoroacetic acid and acetic acid remained colorless and transparent, which indicated that Compound-2 had certain visual detection ability for acids, i.e., an operator could quickly determine whether a solution contained a strong acid.

[0085] Application Example 3

[0086] Please refer to Figure 3 and in combination with Figure 8 , Figure 9 , Figure 12 as shown.

[0087] 1) Compound-3 was weighed and dissolved in an organic solvent to prepare a solution A with a concentration of 10 -4 orders of magnitude mol / L, and the solution A was divided into multiple groups in equal amounts;

[0088] 2) Different types of acids were dissolved in an organic solvent to prepare solution B with a concentration of 10 -3 orders of magnitude mol / L 1-4 , wherein the equivalent ratio of the acid to Compound-3 was 10:1;

[0089] 3) Equal amounts of solution B 1-4 and equal amounts of solution A were mixed, and a blank solvent (the equivalent ratio of the blank solvent to the Compound-3 solution was 8:1) was added to the mixed solution to dilute the mixed solution into solution C 1-4 , and equal amounts of solution A and a blank solvent (the equivalent ratio of the blank solvent to the Compound-3 solution was 9:1) were mixed to dilute into solution C5;

[0090] 4) The absorption spectrum and the emission spectrum with an excitation wavelength of 260 nm of the mixed solution C 1-5 of different types of acids and Compound-3 were measured, and the wavelength-absorption and wavelength-fluorescence intensity curves were drawn.

[0091] The organic solvent in the present application is one or more of dichloromethane, tetrahydrofuran, toluene, chloroform, 1,4-dioxane, 1,2-dichloroethane, etc.

[0092] The results of whether the compound III (Compound-3) has an acid response are shown by absorption spectrum and fluorescence spectrum, and specifically are as follows:

[0093] The compound III (Compound-3) is dissolved in dichloromethane to prepare a solution B with a concentration of 1×10 -4 mol / L, and triflic acid, trifluoroacetic acid, methyl sulfonic acid and acetic acid are dissolved in dichloromethane to prepare solutions D with a concentration of 1×10 -3 mol / L respectively. Different acid solutions are added to the solution B to make the acid solution and the compound III (Compound-3) mixed uniformly, and the absorption spectrum and fluorescence spectrum of each mixed solution are measured respectively.

[0094] When the equivalent ratio of the added triflic acid and methyl sulfonic acid to the compound III (Compound-3) is 10:1, a new absorption peak at 260 nm is observed in the absorption spectrum, indicating the generation of a new substance, which can indicate that the compound III (Compound-3) can respond to acid in dichloromethane solvent. At the same time, a new emission spectrum appears in the solution mixed with triflic acid and methyl sulfonic acid, while the compound III (Compound-3) solution containing trifluoroacetic acid and acetic acid does not have obvious emission peaks, further indicating that the compound III (Compound-3) responds to triflic acid and methyl sulfonic acid.

[0095] Please refer to Figure 8 It can be seen from the figure that a new absorption peak appears at about 260 nm in the solution added with triflic acid. Please refer to Figure 9 It can be seen from the figure that new emission peaks appear at about 310 nm and 620 nm in the solution added with triflic acid and methyl sulfonic acid.

[0096] The results of whether the fluorescence probe can detect acid can be shown by observing the color of the solution, and specifically are as follows:

[0097] The compound III (Compound-3) is dissolved in an organic solvent, and an acid solution is added, and then the color of the reaction solution changes from colorless to purple immediately.

[0098] Specifically, the compound III (Compound-3) is dissolved in dichloromethane to prepare a solution A with a concentration of 5×10-4mol / L, and the solution A is divided into several equal parts, and different amounts of acids are weighed and added to the solution A respectively, each 5×10 -3 mol, please refer to Figure 12As shown, it can be seen from the figure that the solution containing triflic acid and methyl sulfonic acid is discolored, the solution has fluorescence under the irradiation of a 365 nm ultraviolet lamp, and the solution containing trifluoroacetic acid and acetic acid is still colorless and transparent, which indicates that the compound III (Compound-3) has certain visual detection capability for acid, that is, an operator can quickly judge whether the solution contains strong acid.

[0099] In conclusion, the acid is detected by the fluorescent sensing material, the solution color can be obviously observed to be discolored after the fluorescent sensing material is mixed with the acid, the change of the fluorescence signal is visible to the naked eye under the ultraviolet lamp, the visual detection of the acid is realized, and the response speed and accuracy of the acid are improved, and the fluorescent sensing material has good reusability.

[0100] The above examples are only used to illustrate the technical solutions of the present application, but not limit the present application; any equivalent replacement or change according to the technical solutions and the inventive concept of the present application within the technical scope disclosed by the present application should be covered within the protection scope of the present application.

Claims

1. Use of an acid-responsive fluorescent sensing material, characterized in that: The acid-responsive fluorescent sensing material is used, specifically, the acid-responsive fluorescent sensing material containing a di-tert-butyl alcohol structure is dissolved in an organic solvent, and a to-be-measured acid solution is added; if a color change occurs in the solution, that is, fluorescence is generated under irradiation of a 365 nm ultraviolet lamp, then the to-be-measured solution contains a strong acid; if no change occurs in the solution, then the to-be-measured solution does not contain a strong acid. The compound structure of the acid-responsive fluorescent sensing material is as follows: wherein is a benzene derivative, is an aromatic compound; The is one of the following structures: wherein R is an alkyl chain, and the number of C atoms is not more than 5; The is one of the following structures:

2. The use of the acid-responsive fluorescent sensing material according to claim 1, characterized in that; The to-be-measured acid solution is triflic acid, trifluoroacetic acid or methyl sulfonic acid.

3. The use of the acid-responsive fluorescent sensing material according to claim 1, characterized in that; The organic solvent is one or more of dichloromethane, tetrahydrofuran, toluene, chloroform, 1,4-dioxane, 1,2-dichloroethane.

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