CN113736282B - Synthesis and application of indole hemicyanine structure photochromic dye - Google Patents
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention discloses synthesis and application of an indole half-cyanine structural photochromic dye, wherein the synthesis method is to use 2, 3-trimethyl indole derivatives and 2-formyl-1H-pyrrole-4-ethyl formate as raw materials to synthesize the indole half-cyanine structural water-soluble photochromic dye through a single condensation reaction. The synthesis method of the spiropyran-like indole hemicyanine structure water-soluble photochromic dye is simple, the reaction conditions are easy to control, the material has good color-changing effect when irradiated by ultraviolet light and visible light at 365nm and 254nm, and the material has good water solubility and pH response, thereby being beneficial to analysis and detection and application in organisms.
Description
Technical Field
The invention discloses an indole hemicyanine structure photochromic dye and related application thereof, and the dye can be widely applied to the fields of environment, biology, material science and the like.
Background
Photochromic materials are widely appreciated based on their excellent spectral properties, and are classified into organic and inorganic photochromic materials such as polymetal oxide salts, spiropyran compounds, azides, and the like. Photochromic phenomena are reversible transformations of a class of chemical substances that induce two different forms of vibrational absorption spectra in one or both directions by the action of electromagnetic radiation. At present, the research on organic photochromic materials is important, and particularly, the application of the spiropyran compounds in biological imaging, drug carriers and analysis and detection is mature. The spiropyran structure can be well and reversibly converted when light, solvent, temperature and pH conditions are changed, and the color of the spiropyran structure can be correspondingly changed, so that the spiropyran structure is used for researching other photochromic materials with similar structures based on the change characteristic, and has great significance for development of the photochromic materials.
In addition, the fluorescence imaging and molecular constructing capacity of the photochromic material can be fully improved by combining the unique conjugated skeleton structure and excellent optical performance of the cyanine-like dye. The cyanine-like structure has higher sensitivity to environmental factors, and the spectral properties of the structure can be obviously changed by changing the pH value, and the characteristic is commonly used for researching acid-base probes. And, flower-likeThe application of the compound with the cyanine structure combined with the photochromic phenomenon is rarely reported, and the cyanine-like photochromic dye with reasonable design structure has great prospect in the fields of biological medicine, analysis and detection and the like. In addition, many pH probes have only one-way detection of H + Or OH (OH) - The function of the product is also included, the product is difficult to apply to other fields except for detecting the pH value, the utilization value of the product is limited, and the purpose of 'one product for multiple purposes' cannot be achieved.
Disclosure of Invention
The invention mainly aims to provide an indole hemicyanine structure photochromic dye which is used as a pH probe and applied to decorations.
The technical scheme of the invention is as follows:
an indole hemicyanine structure photochromic dye, wherein the chemical structural formula of the compound is as follows:
the synthesis method for synthesizing the indole hemicyanine structure water-soluble dye comprises the following synthesis paths:
dissolving the compound (1) and the compound (2) in ethanol, heating and refluxing, performing rotary evaporation and drying on the mixed solution, and separating by silica gel column chromatography to obtain a red compound 3, wherein the reaction equation is as follows:
in the synthesis step, the feeding molar ratio of the compound 1 to the compound 2 is 1:1-100. The material ratio is changed, which is beneficial to the purification of the compound 3 and the improvement of the yield of the compound 3.
The reflux temperature of the step (4) is 50-100 ℃ and the reflux time is 0.5-10 hours. This temperature favors the reaction.
The main purpose of the present invention is to provide two different OH groups - And H + And a method for detecting the same on a toy or ornamentUse of a photochromic element.
The technical scheme of the invention is that the indole hemicyanine structure is applied to acid and alkali detection, and in particular OH is respectively detected in two ways - And H + Is detected. Firstly, it is: indole hemicyanine photochromic dye used as solvent for detecting OH under dark condition in acetonitrile - The method comprises the steps of carrying out a first treatment on the surface of the Secondly, it is: indole hemicyanine photochromic dye as paint, polyvinylpyrrolidone as substrate, and detecting H under natural light condition + . In short, the response of the indole hemicyanine photochromic dye to acid and alkali can be expressed in one way in two different modes, and the structure of the photochromic compound is changed as follows:
for OH - The detection steps are as follows:
compound (1) is prepared into yellow solution after being treated under the dark condition, alkaline solution with different equivalent weights is dripped, and the selectivity of the compound to pH is studied through ultraviolet spectrum test.
The concentration of the solution of the compound (1) in the detection step is 2X 10 -5 M；
In the detection step, two kinds of alkali, namely triethylamine and sodium hydroxide, are dripped, and both organic alkali and inorganic alkali can rapidly cause the color change of the solution to be detected.
In the detection step, the dropping amount of the two kinds of alkali is one equivalent and two equivalents, the ultraviolet absorption coefficient is rapidly reduced by one equivalent of alkali, the ultraviolet absorption coefficient is reduced after the two equivalents are dropped again, the reduction degree is not obvious, and the obvious reduction of the ultraviolet absorption coefficient shows that the product has a strong response effect on the alkali.
For H + The detection steps are as follows:
the method comprises the steps of coating the surface of a filter paper strip with polyvinylpyrrolidone solution as a substrate, coating the surface layer of the substrate with indole hemicyanine photochromic dye with a certain concentration as a coating, and rapidly changing under natural light irradiation, wherein the initial color is yellowColorless, and finally fumigating with acidic solution to change the filter paper strip from colorless to yellow rapidly to obtain a product for H + For detection purposes of (a).
The solvent for dissolving polyvinylpyrrolidone in the detection step is acetonitrile.
The dye concentration in the detection step is 2×10 -3 M-2.5×10 -3 M, the color change of the filter paper strip is not obvious when the concentration is higher or lower than the range.
The acids used in the detection step are trifluoroacetic acid and hydrochloric acid, both of which are responsive thereto.
The product of the invention is shown in H + The test of the detection is responsive to various acids, and shows excellent acidity detection capability.
The photochromic phenomenon of the photochromic dye with the indole-half cyanine structure can be used for a color-changing jewelry or a color-changing toy. The photochromic dye provided by the invention has good water solubility, can be dissolved in various solvents and has a color-changing effect, but different solvents have a certain difference in the color-changing effect. The photochromic dye presents bright yellow after being dissolved in acetonitrile, has obvious color change under different illumination conditions, and the structure of the photochromic compound is changed as follows:
the experimental procedure was as follows:
the solution of the compound (1) with a certain concentration is prepared, the color change condition of the solution in the cuvette is observed under the direct irradiation of natural light and the dark condition of no light respectively, the solution can be found to be capable of rapidly changing color, and the solution of the compound (1) can also keep obvious color change effect after the change of multiple illumination conditions.
In the test step, the solvent of the compound (1) is acetonitrile, and the color-changing effect of the compound (1) dissolved by other solvents is not ideal.
The concentration of compound (1) in the test step was 2X 10 -5 M-2.5×10 -5 M, concentration is higher or lower than this rangeIn this case, the discoloration of the compound (1) in the solvent is poor, and the discoloration effect is not remarkable.
The two illumination conditions in the test step are sunlight and dark conditions respectively, and the direct sunlight solution rapidly becomes colorless; in the absence of light, the time for the solution to change from colorless to yellow is relatively long.
The present invention is very sensitive to light conditions in the state of a solution, and particularly shows a rapid color change phenomenon from a yellow solution to a colorless solution under natural light.
The invention has the following beneficial effects:
the photochromic dye provided by the invention has excellent response effects on light conditions and acid-base conditions, and can be applied to pH probes and photochromic modification elements of toys or ornaments by combining the two response conditions. According to the invention, the ester group is introduced into the pyrrole ring, the electron cloud density on the pyrrole ring is reduced by the added electron withdrawing group, the ring forming activity of N on the pyrrole ring in the color change process is highlighted, compared with the photochromic dye of the same type, the dye has a faster color change process, in addition, the dye has good water solubility and excellent photochromic performance, and a remarkable visual color change effect is presented in the solution, so that the dye can be applied to decorations such as toys and the like to improve the commercial value; the invention combines photochromic and acid-base response effects, takes polyvinylpyrrolidone as a substrate to effectively inhibit the color change of the dye under the condition of no light on a filter paper strip, and utilizes the color change effect of the dye under natural light and H-resistance + The aim of unidirectional multiple detection of acidity can be fulfilled; the invention realizes the application mode of 'one product multipurpose', and the product synthesis method has universal applicability.
Drawings
FIG. 1 shows a hydrogen profile of compound 3 of the present invention.
FIG. 2 shows the change in the photochromic fluorescence intensity of the dye of the present invention.
FIG. 3 shows an acid-base titration diagram for a photochromic dye of the present invention.
FIG. 4 is a graph showing the ultraviolet absorption spectrum of the effect of the photochromic dye of the present invention on sodium hydroxide.
FIG. 5 is a graph showing the ultraviolet absorption spectrum of the effect of the photochromic dye of the present invention on triethylamine.
FIG. 6 is a real photograph of the detection of H+ by the photochromic dyes of the present invention on a polyvinylpyrrolidone substrate.
Fig. 7 discoloration of the product of the present invention in a fumigated environment at ph=1.
Fig. 8 discoloration of the product of the present invention in a fumigated environment at ph=2.
Fig. 9 discoloration of the product of the present invention in a fumigated environment at ph=3.
Fig. 10 color change of the product of the present invention in a fumigated environment at ph=4.
Fig. 11 discoloration of the product of the present invention in a fumigated environment at ph=5.
Fig. 12 discoloration of the product of the present invention in a fumigated environment at ph=6.
Fig. 13 color change of the product of the present invention in a fumigated environment at ph=7.
Fig. 14 discoloration of the inventive product in a fumigated environment at ph=8.
Fig. 15 discoloration of the product of the present invention in a fumigated environment at ph=9.
Fig. 16 discoloration of the product of the present invention in a fumigated environment at ph=10.
Fig. 17 discoloration of the product of the present invention in a fumigated environment at ph=11.
Fig. 18 discoloration of the product of the present invention in a fumigated environment at ph=12.
Fig. 19 discoloration of the product of the present invention in a fumigated environment at ph=13.
FIG. 20 is a photograph showing the color change of the photochromic dye solution of the present invention under outdoor light.
Detailed Description
The present invention will be further illustrated by the following examples, but the scope of the invention is not limited to the examples.
Example 1
2, 3-trimethyl-N-methylindole iodide (150 mg,0.5 mmol) was weighed, ethyl 2-formyl-1H-pyrrole-4-carboxylate (84 mg,0.5 mmol) was weighed, 10ml of ethanol was measured, mixed and dissolved, heated and stirred, refluxed at 80℃for 2 hours, dried by spinning, and then subjected to column chromatography separation, after which the organic compound was separated by methylene chloride, more delamination was found when the compound 3 was extracted with methanol, and further pure compound 3 could not be obtained by recrystallization.
Example 2
2, 3-trimethyl-N-methylindole iodide (300 mg,1 mmol) was weighed, ethyl 2-formyl-1H-pyrrole-4-carboxylate (167 mg,1 mmol) was weighed, 10ml of ethanol was measured, mixed and dissolved, heated and stirred, refluxed for 2 hours at 80 ℃, dried by spin, separated by column chromatography, and recrystallized again to obtain purer compound 3.
Example 3
2, 3-trimethyl-N-methylindole iodide (300 mg,1 mmol) was weighed, ethyl 2-formyl-1H-pyrrole-4-carboxylate (334 mg,2 mmol) was weighed, 10ml of ethanol was measured, mixed and dissolved, heated and stirred, refluxed for 2 hours at 80 ℃, subjected to column chromatography separation after spin-drying, and impurities remained after recrystallization, and purification could not be performed well to obtain compound 3.
Example 4
2, 3-trimethyl-N-methylindole iodide (150 mg,0.5 mmol) was weighed, ethyl 2-formyl-1H-pyrrole-4-carboxylate (334 mg,2 mmol) was weighed, 10ml of ethanol was measured, the mixture was dissolved, heated and stirred, refluxed at 80 ℃ for 2 hours, dried by spin-drying, and then subjected to column chromatography separation, and finally recrystallized to obtain pure compound 3, the hydrogen spectrum of which is shown in figure 1.
Example 5
Compound 3 (0.0045 g) obtained in example 4 was weighed and dissolved in 1mL of acetonitrile to obtain a mother liquor concentration of 10 -2 M, 12 mu L of mother solution is dissolved in 3mL of acetonitrile to prepare the solution with the concentration of 4 multiplied by 10 -5 M yellow solution, immediately testing the fluorescence intensity of the solution, after determining the first fluorescence intensity data, exposing the solution to natural light for 2 minutes until the color of the solution becomes colorless, testing the fluorescence intensity again, repeating the operation 5 times or more, taking the operation times as the abscissa and the fluorescence intensity as the abscissa according to the peak change condition, and taking the point diagram through Origin as shown in figure 2, wherein the point diagram is obtained through lightThe fluorescence intensity of the colorless to-be-measured solution after the treatment is obviously reduced, and the fluorescence intensity of the yellow to-be-measured solution after the no-light treatment is raised to a certain extent, which indicates that the compound 3 solution with a certain concentration can be reversibly changed by changing the illumination condition.
Example 6
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, 6 mu L of mother solution is dissolved in 3mL of acetonitrile to prepare the solution with the concentration of 2 multiplied by 10 -5 Yellow solution of M (1); 5 mu L of triethylamine is added with 5mL of acetonitrile to prepare the concentration of 10 -2 Alkaline mother liquor (2) of M; 3.8 mu L of trifluoroacetic acid is added with 5mL of acetonitrile to prepare the concentration of 10 -2 An acidic mother liquor (3) of M; the prepared photochromic dye yellow solution (1) is sequentially measured for an absorption and emission spectrum, then 9 mu L of prepared alkaline mother solution (2) is added into the solution, after an absorption peak value is stable, the absorption and emission spectrum is measured, then 12 mu L of acid mother solution (3) is added into the solution, after the absorption peak value is stable, the absorption and emission spectrum is measured, so that the acid-base titration operation is repeated for five times, the peak wavelength of the spectrogram is taken as an X axis, the corresponding ultraviolet molar absorption coefficient and the fluorescence intensity are taken as a point line graph, as shown in figure 3, the absorption and emission main peak height of the dye can be obviously reduced by alkali, and the absorption and emission main peak height of the dye can be obviously increased by acid, so that the dye can be reversibly changed by acid and alkali.
Example 7
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, dissolving 6 μl of mother liquor in 3mL of acetonitrile, and preparing into 2×10 concentration -5 Yellow test solution of M; weighing sodium hydroxide solid particles 0.0040g, adding 10ml deionized water to obtain a concentration of 10 -1 M sodium hydroxide mother liquor, adding 6 μl sodium hydroxide mother liquor into 3ml deionized water, and preparing into 2×10 concentration -2 M aqueous sodium hydroxide solution. Firstly, carrying out ultraviolet test on a yellow solution to be tested, and then dissolving the yellow solution to be tested in the solution to be testedAfter dropping 6. Mu.l (one equivalent) of an aqueous sodium hydroxide solution, the ultraviolet test was again performed, and then, dropping 6. Mu.l (one equivalent) of the sodium hydroxide solution each time, and performing the ultraviolet test once each time, it was observed that: after one equivalent of sodium hydroxide aqueous solution is added, the ultraviolet absorption coefficient of the solution to be measured is obviously reduced, and when the solution to be measured is added to two equivalents, no peak is detected in the ultraviolet test of the solution to be measured, which indicates that the inorganic base has strong response capability to the dye of the invention, as shown in fig. 4.
Example 8
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, dissolving 6 μl of mother liquor in 3mL of acetonitrile, and preparing into 2×10 concentration -5 Yellow solution of M; 5 mu l of triethylamine is added with 5ml of acetonitrile to prepare the concentration of 10 -2 M triethylamine mother liquor.
Firstly, carrying out ultraviolet test on a yellow solution to be tested, then, dripping 6 mu l (one equivalent) of triethylamine solution into the solution to be tested, carrying out ultraviolet test again, and then, dripping 6 mu l (one equivalent) of triethylamine solution each time, and carrying out ultraviolet test once every time, wherein the observation is that: after adding one equivalent of triethylamine solution, the ultraviolet absorption coefficient of the solution to be tested is obviously reduced, and when the solution to be tested is added to two equivalents, no peak is detected in the ultraviolet test of the solution to be tested, which indicates that the organic base has strong response capability to the dye of the invention, as shown in figure 5.
Example 9
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, dissolving 20 μl of mother liquor in 40 μl acetonitrile, and preparing into 2×10 concentration -3 The yellow solution of M was used as a coating. Weighing 0.0100g polyvinylpyrrolidone, dissolving in 60 μl acetonitrile, coating on the surface of filter paper strip as substrate, drying in oven at 50deg.C for 5min, coating on the surface of substrate, drying in oven at 50deg.C for 5min to completely dry, and irradiating with sunlight to obtain colorless acidity (H) + ) Detecting the product.Then, an acid fumigation test is carried out, 600 mu L of trifluoroacetic acid is dissolved in 19.4mL of acetonitrile to prepare 30000ppm of acid solution, and the product is fumigated at 50 ℃, so that the color of the product is changed from colorless to yellow within 5s, the color of the product is changed from yellow to colorless within 8s after the product is placed under sunlight, the operation can be repeated three times or more, and the good response of the product to organic acid is shown in a figure 6.
Example 10
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, dissolving 20 μl of mother liquor in 40 μl acetonitrile, and preparing into 2×10 concentration -3 The yellow solution of M was used as a coating. Weighing 0.0100g polyvinylpyrrolidone, dissolving in 60 μl acetonitrile, coating on the surface of filter paper strip as substrate, drying in oven at 50deg.C for 5min, spreading the coating on the surface of substrate, drying in oven at 50deg.C for 5min to completely dry, and irradiating with sunlight to obtain colorless acidity (H) + ) Detecting the product. The product is fumigated on pure HCl solution at 50 ℃, the color of the product is changed from colorless to yellow rapidly, but the product cannot be changed in color under natural light, and then fumigated on pure triethylamine at 50 ℃ without obvious color change, which indicates the acidity (H) + ) The detection product is responsive to inorganic acids, but too high a pH can result in poor product results or even damage to the product itself.
Example 11
Adding 172 mu L of hydrochloric acid into 20ml of deionized water to prepare hydrochloric acid mother solution with pH=1, and sequentially diluting the hydrochloric acid mother solution to prepare hydrochloric acid solutions with pH of 2,3, 4, 5 and 6 respectively; 200mg of sodium hydroxide is weighed and dissolved in 50mL of deionized water to prepare sodium hydroxide mother solution with pH value of 13, and the sodium hydroxide mother solution is diluted in sequence to prepare sodium hydroxide solutions with pH values of 12, 11, 10, 9 and 8 respectively; a neutralization solution of ph=7 was prepared by mixing 10mL of a ph=6 hydrochloric acid solution and 10mL of a ph=8 sodium hydroxide solution. Colorless ambient acidity (H) in example 9 + ) The test product was fumigated to yellow with a ph=1 solution at 50 ℃ and then at normal temperatureUnder warm conditions, the procedure was repeated 3 times after irradiation with sunlight to colorless, and then the above experiment was repeated in a fumigated environment at ph=2-14, respectively. The product of the invention has better color-changing effect in the environment with pH=1-9, as shown in figures 7-16; discoloration of the product of the present invention was not evident in the fumigating environment at ph=10-13, as illustrated in fig. 17-19, indicating that the product of the present invention was resistant to H + Exhibits excellent detection performance.
Example 12
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, dissolving 6 μl of mother liquor in 3mL of acetonitrile, dimethyl sulfoxide and N, N-dimethylformamide respectively, and making into final product with concentration of 2×10 -5 Yellow solution of M. The three groups of solutions with the same concentration and different solvents are respectively irradiated by 5 light sources with different wavelengths, and the five light sources are respectively: 254nm, 365nm ultraviolet lamp irradiation, 455-470nm pure blue light, 500-570nm pure green light, and 200-5300nm sunlight, found: after being irradiated by ultraviolet lamp light sources of 254nm and 365nm, the yellow solution taking acetonitrile as a solvent changes from yellow to colorless within 1min, and the yellow solution of the other two solvents changes from yellow to light yellow within 1 min; after 455-470nm of pure blue light, 500-570nm of pure green light and 200-5300nm of sunlight are irradiated, the color of the yellow solution prepared by the three solvents can be changed from yellow to colorless within 10 seconds. The dye disclosed by the invention can be compatible with various solvents, has good response to ultraviolet light and visible light, and particularly has the most obvious and most rapid color change under the condition of irradiation of visible light when acetonitrile is taken as a solvent.
Example 12
The pH probe mass of the indole hemicyanine structure photochromic dye of example 4 was weighed to be 0.0045g, and dissolved in 1mL acetonitrile to obtain a mother liquor concentration of 10 -2 M, dissolving 12 μl of mother liquor in 3mL of acetonitrile, and preparing into 4×10 concentration -5 Yellow solution of M. The solution is subjected to direct sunlight treatment and then is subjected to a color-changing test under dark condition, and the initial yellow solution is found to be colorless within 10 seconds under sunlight irradiationThe color of the solution can be changed from colorless to yellow within 5min after the solution is subjected to no light treatment, the process can be repeated for 5 times or more, as shown in figure 20, the illumination and no light conditions are replaced regularly, and the color of the solution formed by the dye can be changed reversibly.
Claims (5)
1. The application of the indole hemicyanine structure photochromic dye in detecting hydrogen ions in a solution in visible light, wherein the solution is acetonitrile, and the chemical structural formula of the dye is as follows:
2. the use according to claim 1, characterized in that the preparation method of the photochromic dye of the indocyanine structure comprises the following steps:
dissolving 2, 3-trimethyl-N-methylindole iodide and 2-formyl-1H-pyrrole-4-ethyl formate in ethanol, heating for reflux, performing rotary evaporation drying on the mixed solution, and separating by silica gel column chromatography to obtain the indole hemicyanine structure photochromic dye, wherein the reaction equation is as follows:
3. the use according to claim 2, wherein in the preparation method, the molar ratio of 2, 3-trimethyl-N-methylindole iodide to ethyl 2-formyl-1H-pyrrole-4-carboxylate is 1:1-10.
4. Use according to claim 2, characterized in that the reflux temperature in the preparation process is 50-100 ℃ and the reflux time is 0.5-10 hours.
5. The application of the photochromic dye with the indole hemicyanine structure as a pH probe in detecting hydrogen ions in a solution in visible light, wherein the solution is acetonitrile, and the chemical structural formula of the photochromic dye is as follows:
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| CN105693591A (en) * | 2016-03-14 | 2016-06-22 | 上海师范大学 | Ratiometric pH fluorescent probe as well as preparation method and application thereof |
| CN108976242A (en) * | 2018-08-02 | 2018-12-11 | 南京大学 | Synthesis a kind of while that there is photochromic and ion detection function Indoline spiropyran derivative |
| CN110387137A (en) * | 2019-07-19 | 2019-10-29 | 三峡大学 | A kind of water-soluble dye and its synthetic method of half flower cyanines structure of indoles |
| CN111100474A (en) * | 2019-12-09 | 2020-05-05 | 三峡大学 | Synthetic method of cyanine dye and application of cyanine dye as acid-base response fluorescent reagent |
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