CN113736282A - Synthesis and application of indole hemicyanine structure photochromic dye - Google Patents

Synthesis and application of indole hemicyanine structure photochromic dye Download PDF

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CN113736282A
CN113736282A CN202111044380.5A CN202111044380A CN113736282A CN 113736282 A CN113736282 A CN 113736282A CN 202111044380 A CN202111044380 A CN 202111044380A CN 113736282 A CN113736282 A CN 113736282A
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photochromic dye
indole
dye
acetonitrile
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CN113736282B (en
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张诺诺
粟鹏
胡聪
文柳
晏佳莹
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China Three Gorges University CTGU
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    • 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
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    • 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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Abstract

The invention discloses synthesis and application of a photochromic dye with an indole hemicyanine structure. The synthetic method of the water-soluble photochromic dye with the indole hemicyanine structure similar to the spiropyran structure is simple, the reaction condition is easy to control, the photochromic dye has good color changing effect under the irradiation of 365nm ultraviolet light and 254nm visible light, and the material has good water solubility and pH response, thereby being beneficial to analysis and detection and application in organisms.

Description

Synthesis and application of indole hemicyanine structure photochromic dye
Technical Field
The invention discloses an indole hemicyanine structure photochromic dye and related applications thereof, wherein the dye can be widely applied to the fields of environment, biology, material science and the like.
Background
Photochromic materials are widely regarded mainly on the basis of their excellent spectral properties, and are classified into organic and inorganic photochromic materials, such as polyoxometallates, spiropyran compounds, azides, and the like. The phenomenon of photochromism is the reversible conversion of a class of chemical species by the action of electromagnetic radiation that causes two different forms of vibrational absorption spectra to be induced in one or both directions. At present, the research on organic photochromic materials is more important, and particularly, the application of the spiropyran compounds in biological imaging, drug carriers and analysis and detection is mature. The spiropyran structure can perform good reversible transformation when changing the conditions of light, solvent, temperature and pH, and the color of the spiropyran structure can also be correspondingly changed, so that the research on other photochromic materials with similar structures is carried out based on the change characteristics, and the spiropyran structure has important significance for the development of the photochromic materials.
In addition, the photochromic material can fully improve the fluorescent imaging and the molecular construction capability by combining the unique conjugated framework structure and the excellent optical performance of the cyanine-like dye. The cyanine-like structure has high sensitivity to environmental factors, and the change of pH value can cause the spectral property of the structure to generate obvious change, and the characteristic is commonly used for the research of acid-base probes. Moreover, the application of the compound with the cyanine-like structure combined with the photochromic phenomenon is only reported, and the cyanine-like photochromic dye with a reasonable structure has great prospect in the fields of biomedicine, analysis and detection and the like. In addition, many pH probes have only one-way detection of H+Or OH-The functions of the method also comprise the product for simultaneously detecting the pH value, the pH value is difficult to be applied to other fields except the pH value detection, the utilization value of the product is limited, and the purpose of 'one product is multipurpose' cannot be achieved.
Disclosure of Invention
The invention mainly aims to provide a photochromic dye with an indole hemicyanine structure as a pH probe and application of the photochromic dye to ornaments.
The technical scheme of the invention is as follows:
an indole hemicyanine structure photochromic dye, the chemical structural formula of the compound is as follows:
Figure BDA0003250614260000011
the synthesis method of the water-soluble dye with the indole hemicyanine structure comprises the following synthesis paths:
dissolving the compound (1) and the compound (2) in the step in ethanol, heating and refluxing, performing rotary evaporation drying on the mixed solution, and performing silica gel column chromatography separation to obtain a red compound 3, wherein the reaction equation is as follows:
Figure BDA0003250614260000021
in the synthesis step, the feeding molar ratio of the compound 1 to the compound 2 is 1: 1-100. The change of the feeding ratio is beneficial to the purification of the compound 3 and the improvement of the yield of the compound 3.
The reflux temperature in the step (4) is 50-100 ℃, and the reflux is carried out for 0.5-10 hours. This temperature is favorable for the reaction.
The main object of the present invention is to provide two different OH groups-And H+And to a use of the photochromic element in a toy or ornament.
The technical scheme of the invention is the application of indole hemicyanine structure to acid-base detection, specifically to OH respectively by two modes-And H+Detection of (3). The first is that: detection of OH in indole hemicyanine photochromic dye as solvent using acetonitrile in absence of light-(ii) a Secondly, the following steps: detecting H under natural light condition by taking indole hemicyanine photochromic dye as coating and polyvinylpyrrolidone as substrate+. In brief, the response of the indocyanine photochromic dye to acid and alkali can be expressed unidirectionally in two different ways, and the structure of the discoloration phenomenon compound is changed as follows:
Figure BDA0003250614260000022
to OH-The detection steps are as follows:
preparing a compound (1) with a certain concentration, forming a yellow solution after being treated under a non-light condition, dropwise adding alkaline solutions with different equivalents, and researching the selectivity of the compound (1) on pH through an ultraviolet spectrum test.
The concentration of the compound (1) solution in the detection step is 2X 10-5M；
In the detection step, two bases, namely triethylamine and sodium hydroxide are added dropwise, and both organic base and inorganic base can rapidly cause the color change of the solution to be detected.
In the detection step, the dropwise adding amount of the two bases is one equivalent and two equivalents, the ultraviolet absorption coefficient is rapidly reduced by one equivalent of the bases, the ultraviolet absorption coefficient is reduced after two equivalents are dropwise added 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 alkalinity.
To H+The detection steps are as follows:
the method comprises the steps of coating a polyvinylpyrrolidone solution serving as a substrate on the surface of a filter paper strip, coating an indole hemicyanine photochromic dye with a certain concentration serving as a coating on the surface layer of the substrate, wherein the initial color is yellow, the filter paper strip is rapidly changed into colorless under the irradiation of natural light, and finally the filter paper strip is rapidly changed from colorless to yellow through fumigation of an acid solution to achieve H-H+For the purpose of detection.
And in the detection step, the solvent for dissolving the polyvinylpyrrolidone is acetonitrile.
The concentration of the dye in the detection step is 2 x 10-3M-2.5×10-3M, the color change of the filter paper strips 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.
Products of the invention are described in H+The detection test is responsive to various acids, and shows excellent acidity detection capability.
The photochromic phenomenon of the photochromic dye with the indole hemicyanine structure can be used for color-changing jewelry or color-changing toys. The photochromic dye has good water solubility, can be dissolved in various solvents and generates a color change effect, but the color change effects shown by different solvents have certain difference. The photochromic dye is bright yellow after being dissolved in acetonitrile, and has very obvious color change under different illumination conditions, and the structure of the compound with the color change phenomenon is changed as follows:
Figure BDA0003250614260000031
the experimental procedure was as follows:
the solution of the compound (1) with a certain concentration is prepared, the change condition of the color of the solution in the cuvette is observed under the conditions of direct natural light and dark, so that the solution can rapidly change the color, and the compound (1) solution can keep obvious color change effect after the change of multiple times of illumination conditions.
The solvent of the compound (1) in the test step is acetonitrile, and the discoloration effect of the compound (1) dissolved in other solvents is not ideal.
The concentration of compound (1) in the test procedure was 2X 10-5M-2.5×10-5When the concentration of M is higher or lower than this range, the discoloration of the compound (1) in the solvent is deteriorated, and the discoloration effect is not remarkable.
In the test step, two illumination conditions are adopted, namely sunlight and dark and no light conditions, and the sunlight direct irradiating solution is rapidly changed into colorless; in the absence of light, the time for the solution to change from colorless to yellow is relatively long.
The invention is very sensitive to light conditions in a solution state, 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 according to the present invention has an excellent response effect to light conditions and acid-base conditions, and can be applied to a pH probe and a photochromic finishing element of a toy or ornament by cross-coupling the two types of response conditions. The invention introduces ester group on the pyrrole ring, the added electron-withdrawing group reduces the electron cloud density on the pyrrole ring, highlights the ring-forming activity of N on the pyrrole ring in the color-changing process, and compared with the photochromic dye of the same type,the invention has faster color changing process, in addition, the dye has good water solubility and excellent photochromic performance, and presents obvious visual color changing effect in solution, and can be applied to ornaments such as toys and the like to improve the commercial value; the invention combines photochromic effect and acid-base response effect, takes polyvinylpyrrolidone as a substrate to effectively inhibit the color change of the dye under the condition of no light on the filter paper strip, and utilizes the color change effect of the dye under natural light and H response+The positive response of the acid detector can realize the purpose of detecting acidity in one way for multiple times; the invention realizes the application mode of 'one product has multiple purposes', and the product synthesis method has universal applicability.
Drawings
FIG. 1 shows the hydrogen spectrum of compound 3 of the present invention.
FIG. 2 shows the change of photochromic fluorescence intensity of the dye according to the present invention.
FIG. 3 is a graph of an acid-base titration of a photochromic dye of the present invention.
FIG. 4 is a graph of the UV absorption spectrum of the photochromic dye of the present invention reacted with sodium hydroxide.
FIG. 5 is a graph showing the UV absorption spectrum of the photochromic dye according to the present invention in response to triethylamine.
FIG. 6 is a real shot of the photochromic dye of the present invention on a polyvinylpyrrolidone substrate for H + detection.
Figure 7 discoloration of the product of the invention in a fumigated environment at pH 1.
Figure 8 discoloration of the product of the invention in a fumigated environment at pH 2.
Figure 9 discoloration of the product of the invention in a fumigated environment at pH 3.
Figure 10 discoloration of the product of the invention in a fumigated environment at pH 4.
Figure 11 discoloration of the product of the invention in a fumigated environment at pH 5.
Figure 12 discoloration of the product of the invention in a fumigated environment at pH 6.
Figure 13 discoloration of the product of the invention in a fumigated environment at pH 7.
Figure 14 colour change of the product of the invention in a fumigated environment at pH 8.
Figure 15 discoloration of the product of the invention in a fumigated environment at pH 9.
Figure 16 discoloration of the product of the invention in a fumigated environment at pH 10.
Figure 17 discoloration of the product of the invention in a fumigated environment at pH 11.
Figure 18 discoloration of the product of the invention in a fumigated environment at pH 12.
Figure 19 the product of the invention discolors in a fumigated environment at pH 13.
FIG. 20 is a real photograph of the photochromic dye solution of the present invention changing color under outdoor light.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the scope of the examples.
Example 1
Weighing 2,3, 3-trimethyl-N-methylindole iodonium salt (150mg,0.5mmol), taking ethyl 2-formyl-1H-pyrrole-4-carboxylate (84mg,0.5mmol), taking 10ml of ethanol, mixing, dissolving, heating, stirring, refluxing at 80 ℃ for 2 hours, performing column chromatography separation after spin-drying, separating an organic compound by dichloromethane in the column chromatography process, finding more layers when extracting the compound 3 by using methanol, and further obtaining the pure compound 3 through recrystallization.
Example 2
Weighing 2,3, 3-trimethyl-N-methylindole iodonium salt (300mg,1mmol), taking ethyl 2-formyl-1H-pyrrole-4-carboxylate (167mg,1mmol), weighing 10ml ethanol, mixing, dissolving, heating, stirring, refluxing at 80 ℃ for 2 hours, performing column chromatography separation after spinning, and recrystallizing again to obtain a pure compound 3.
Example 3
Weighing 2,3, 3-trimethyl-N-methylindole iodonium salt (300mg,1mmol), taking ethyl 2-formyl-1H-pyrrole-4-carboxylate (334mg,2mmol), weighing 10ml ethanol, mixing, dissolving, heating, stirring, refluxing at 80 ℃ for 2 hours, performing column chromatography separation after spinning, and purifying to obtain a compound 3.
Example 4
Weighing 2,3, 3-trimethyl-N-methylindole iodonium salt (150mg,0.5mmol), taking ethyl 2-formyl-1H-pyrrole-4-carboxylate (334mg,2mmol), measuring 10ml of ethanol, mixing, dissolving, heating, stirring, refluxing at 80 ℃ for 2 hours, performing column chromatography separation after spinning drying, and finally recrystallizing to obtain a pure compound 3, wherein a hydrogen spectrum of the compound is shown in figure 1.
Example 5
Compound 3(0.0045g) obtained in example 4 was weighed out and dissolved in 1mL of acetonitrile to obtain a mother liquor having a concentration of 10-2M, dissolving 12. mu.L of the mother liquor in 3mL of acetonitrile, and preparing the solution with the concentration of 4X 10-5M, immediately testing the fluorescence intensity of the solution, determining the first fluorescence intensity data, placing the solution under natural light for 2 minutes until the solution becomes colorless, testing the fluorescence intensity again, repeating the operation for 5 times or more, taking the operation times as an abscissa and the fluorescence intensity as an abscissa according to the peak value change condition, and drawing a point diagram through Origin, as shown in figure 2, the fluorescence intensity of the colorless solution to be tested after light treatment is obviously reduced, the fluorescence intensity of the yellow solution to be tested after light treatment is increased to a certain extent, and showing that the compound 3 solution with a certain concentration can be reversibly changed by changing the light condition.
Example 6
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, 6. mu.L of the mother liquor was dissolved in 3mL of acetonitrile and prepared to a concentration of 2X 10-5Yellow solution of M (1); 5 mu L of triethylamine is added with 5mL of acetonitrile to prepare the solution with the concentration of 10-2Basic mother liquor (2) of M; 3.8 mu L of trifluoroacetic acid is added with 5mL of acetonitrile to prepare the mixture with the concentration of 10-2An acidic mother liquor (3) of M; measuring the absorption emission spectrogram of the prepared photochromic dye yellow solution (1) in sequence, adding 9 muL of the prepared alkaline mother solution (2) into the solution, measuring the absorption emission spectrum after the absorption peak value is stable, adding 12 muL of the acidic mother solution (3) into the solution, measuring the absorption emission spectrum after the absorption peak value is stableAnd (3) an emission spectrum, namely the cycle of one acid-base titration, and finally repeating the acid-base titration operation five times, wherein the peak forming wavelength of a spectrogram is taken as an X axis, and the corresponding ultraviolet molar absorption coefficient and fluorescence intensity are taken as a Y axis to form a point line graph, as shown in figure 3, the height of the main absorption and emission peak of the dye can be obviously reduced by alkali, the height of the main absorption and emission peak of the dye can be obviously increased by acid, and the reversible change of the dye can be realized by acid and alkali.
Example 7
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, dissolving 6. mu.L of mother liquor in 3mL of acetonitrile, and finally preparing the solution with the concentration of 2X 10-5M is a yellow solution to be detected; weighing 0.0040g of sodium hydroxide solid particles, adding 10ml of deionized water to prepare the solution with the concentration of 10-1M sodium hydroxide mother liquor, adding 6 mul sodium hydroxide mother liquor into 3ml deionized water, and finally preparing into 2X 10-2M aqueous sodium hydroxide solution. Firstly, carrying out ultraviolet test on a yellow solution to be tested, then dropwise adding 6 mu l (one equivalent) of sodium hydroxide aqueous solution into the solution to be tested, carrying out ultraviolet test again, then dropwise adding the sodium hydroxide solution for multiple times, carrying out ultraviolet test once per dropwise adding 6 mu l (one equivalent) each time, and observing: after one equivalent of sodium hydroxide aqueous solution is added, 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, the ultraviolet test of the solution to be tested can not detect a peak, which shows that the inorganic base has strong response capability to the dye of the invention, as shown in figure 4.
Example 8
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, dissolving 6. mu.L of mother liquor in 3mL of acetonitrile, and finally preparing the solution with the concentration of 2X 10-5A yellow solution of M; 5 mul of triethylamine is added with 5ml of acetonitrile to prepare the solution with the concentration of 10-2M triethylamine mother liquor.
Firstly, carrying out ultraviolet test on a yellow solution to be tested, then dropwise adding 6 mu l (one equivalent) of triethylamine solution into the solution to be tested, carrying out ultraviolet test again, and then dropwise adding the triethylamine solution for multiple times, wherein 6 mu l (one equivalent) of triethylamine solution is added once per drop, and the ultraviolet test is carried out once per drop, and the following observation is carried out: after one equivalent of triethylamine solution is added, the ultraviolet absorption coefficient of the solution to be tested is obviously reduced, and when the triethylamine solution is added to two equivalents, the ultraviolet test of the solution to be tested can not detect a peak, which shows that the organic base has strong response capability to the dye of the invention, as shown in fig. 5.
Example 9
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, dissolving 20 μ L of the mother liquor in 40 μ L of acetonitrile, and finally preparing into 2 × 10-3The yellow solution of M was used as a coating. Weighing 0.0100g polyvinylpyrrolidone, dissolving in 60 μ L acetonitrile, coating on the surface of filter paper strip as substrate, oven drying at 50 deg.C for 5min, coating on the surface of substrate, oven drying at 50 deg.C for 5min, and irradiating with sunlight to obtain colorless acidity (H)+) And (5) detecting the product. Then, an acid fumigation test is carried out, 600 microliter 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, and the color of the product is changed from yellow to colorless within 8s after the product is placed in sunlight, and the operation can be repeated for three times or more, which shows that the product of the invention has good response to organic acid, and is shown in fig. 6.
Example 10
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, dissolving 20 μ L of the mother liquor in 40 μ L of acetonitrile, and finally preparing into 2 × 10-3The yellow solution of M was used as a coating. Weighing 0.0100g polyvinylpyrrolidone, dissolving in 60 μ L acetonitrile, coating on the surface of filter paper strip as substrate, oven drying at 50 deg.C for 5min, spreading the coating on the surface of the substrate, oven drying at 50 deg.C for 5min, and irradiating with sunlight to obtain colorless productAcidity (H) in the environment+) And (5) detecting the product. The product is put on pure HCl solution to be fumigated at 50 ℃, the color of the product is rapidly changed from colorless to yellow, but the product can not be changed under natural light, and then the product is put on pure triethylamine to be fumigated at 50 ℃ without obvious color change, which shows the acidity (H) of the invention+) The detection product responds to inorganic acid, but the excessive pH value can cause the product to have poor effect and even destroy the product.
Example 11
Adding 172 mu L of hydrochloric acid into 20ml of deionized water to prepare hydrochloric acid mother liquor with the pH value of 1, and sequentially diluting the hydrochloric acid mother liquor to prepare hydrochloric acid solutions with the pH values of 2,3, 4, 5 and 6 respectively; weighing 200mg of sodium hydroxide, dissolving the sodium hydroxide into 50mL of deionized water to prepare a sodium hydroxide mother liquor with the pH value of 13, and sequentially diluting the sodium hydroxide mother liquor to prepare sodium hydroxide solutions with the pH values of 12, 11, 10, 9 and 8 respectively; a neutralized solution having a pH of 7 was prepared by mixing 10mL of a hydrochloric acid solution having a pH of 6 with 10mL of a sodium hydroxide solution having a pH of 8. The colorless ambient acidity (H) of example 9+) The test product was fumigated to yellow with a solution having a pH of 1 at 50 ℃, followed by irradiation with sunlight to colorless at room temperature, and this operation was repeated 3 times, and then the above test was repeated in each fumigated environment having a pH of 2 to 14. The product of the invention is found to have better color change effect in the environment with pH value of 1-9, as shown in figures 7-16; the product of the invention has no obvious color change in the fumigation environment with the pH value of 10-13, as shown in figures 17-19, which shows that the product of the invention has no obvious color change to H+The excellent detection performance is shown.
Example 12
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, then 6 mul mother liquor is respectively dissolved in 3mL acetonitrile, dimethyl sulfoxide and N, N-dimethylformamide, and finally the concentration is 2 x 10-5Yellow solution of M. 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: the irradiation of 254nm and 365nm ultraviolet lamps, 455-470nm pure blue light, 500-570nm pure green light and 200-5300nm sunlight shows that: through a passage of 254nm andafter the 365nm ultraviolet lamp light source irradiates, the color of the yellow solution with acetonitrile as the solvent changes from yellow to colorless within 1min, and the color of the yellow solution with other two solvents changes from yellow to light yellow within 1 min; after the irradiation of 455-470nm pure blue light, 500-570nm pure green light and 200-5300nm sunlight, the color of the yellow solution prepared by the three solvents can be changed from yellow to colorless within 10 s. The dye can be dissolved in various solvents, has good response to ultraviolet light and visible light, and particularly has the most obvious and rapid color change under the condition of visible light irradiation when acetonitrile is used as the solvent.
Example 12
The mass of the pH probe of the indocyanine structure photochromic dye in the embodiment 4 is 0.0045g, and the dye is dissolved in 1mL of acetonitrile to obtain the mother solution with the concentration of 10-2M, dissolving 12 μ L of the mother liquor in 3mL of acetonitrile, and finally preparing the solution with the concentration of 4 × 10-5Yellow solution of M. After the solution is subjected to direct sunlight treatment, a color change test under dark and dark conditions is carried out, and the result shows that the initial yellow solution becomes a colorless solution within 10 seconds under the irradiation of sunlight, then the color of the solution can be changed from colorless to yellow within 5min by the dark treatment, the process can be repeated for 5 times or more, as shown in figure 20, the illumination and dark conditions are regularly replaced, and the color of the dye forming solution can be reversibly changed.

Claims (7)

1. The photochromic dye with the indole hemicyanine structure is characterized in that the chemical structural formula of the photochromic dye is as follows:
Figure FDA0003250614250000011
2. the method for synthesizing a photochromic dye with an indole hemicyanine structure according to claim 1, wherein the method comprises the following steps:
dissolving 2,3, 3-trimethyl-N-methylindole iodonium salt and 2-formyl-1H-pyrrole-4-ethyl formate in ethanol, heating and refluxing, performing rotary evaporation drying on the mixed solution, and performing chromatographic separation by using a silica gel column to obtain a red compound 3, wherein the reaction equation is as follows:
Figure FDA0003250614250000012
3. the method for synthesizing a photochromic dye with an indole hemicyanine structure according to claim 2, wherein in the synthesis step, the feeding molar ratio of 2,3, 3-trimethyl-N-methylindolyl iodide salt to 2-formyl-1H-pyrrole-4-ethyl formate is 1: 1-10.
4. The method for synthesizing a photochromic dye with an indole hemicyanine structure according to claim 2, wherein the reflux temperature of the synthesis step is 50 ℃ to 100 ℃ and the reflux time is 0.5 to 10 hours.
5. The use of the indocyanine structural photochromic dye in a detection solution according to claim 1, wherein the solution comprises one or more of water, acetonitrile, and alcohol.
6. The application of the indocyanine structure photochromic dye as the pH probe in detecting the pH of a solution according to claim 1, wherein the solution comprises one or more of water, acetonitrile and alcohol.
7. Use of the indocyanine structural photochromic dye according to claim 1 in the detection of light in different wavelength ranges.
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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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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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