阅读说明：本技术 一种基于萘酰亚胺的次氯酸荧光探针及其制备方法 (Naphthalimide-based hypochloric acid fluorescent probe and preparation method thereof ) 是由 段洪东 雷绍玉 于 2020-11-30 设计创作，主要内容包括：本申请属于荧光探针领域,具体涉及一种能够探测次氯酸的荧光探针及其制备方法。该荧光探针为萘酰亚胺衍生物,该化合物具有易被次氯酸特异性裂解的亚胺键,特殊的共轭结构和良好的化学反应性能使探针分子能够在复杂体系中准确地识别出次氯酸。探针溶液在加入次氯酸溶液后探针的亚胺键断裂释放出具有醛基的萘酰亚胺荧光团,出现肉眼可见的颜色变化,且其紫外可见吸收光谱出现较强的吸收峰,荧光光谱也出现显著的发射峰。因此,是一种理想的次氯酸荧光探针。另外,该合成工艺具有操作简单、产率高、成本低、检测快速等优点。(The application belongs to the field of fluorescent probes, and particularly relates to a fluorescent probe capable of detecting hypochlorous acid and a preparation method thereof. The fluorescent probe is a naphthalimide derivative, and the compound has an imine bond which is easy to be specifically cracked by hypochlorous acid, and has a special conjugated structure and good chemical reaction performance, so that probe molecules can accurately identify the hypochlorous acid in a complex system. After the probe solution is added with the hypochlorous acid solution, the imine bond of the probe is broken to release a naphthalimide fluorophore with aldehyde group, macroscopic color change occurs, the ultraviolet visible absorption spectrum of the naphthalimide fluorophore has a strong absorption peak, and the fluorescence spectrum also has a remarkable emission peak. Therefore, the fluorescent probe is an ideal hypochlorous acid fluorescent probe. In addition, the synthesis process has the advantages of simple operation, high yield, low cost, quick detection and the like.)

1. A hypochlorous acid fluorescent probe based on naphthalimide is characterized in that: the structural formula is as follows:

2. the method for preparing the naphthalimide-based hypochlorous acid fluorescent probe as claimed in claim 1, which is characterized by comprising the following steps:

3. the use of a naphthalimide-based hypochlorous acid fluorescent probe according to claim 1, wherein: the application in hypochlorous acid detection.

4. The method for preparing a hypochlorous acid fluorescent probe based on naphthalimide as claimed in claim 2, wherein: the method comprises the following specific steps:

1) weighing 4-bromo-1, 8-naphthalic anhydride and n-butylamine, dissolving in a solvent, reacting for 10h at constant temperature of 85 ℃ under stirring, cooling to room temperature, standing the solution to precipitate a solid, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain a compound 1;

2) weighing CH₃ONa、CuSO₄·5H₂Dissolving O and the compound 1 obtained in the step 1) in a solvent, reacting for 8 hours at a constant temperature of 85 ℃, cooling to room temperature, standing the solution to precipitate white crystals, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain a compound 2;

3) weighing the compound 2 obtained in the step 2), dissolving in a solvent, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting the pH value of the solution to be neutral by using a 50% sodium hydroxide solution, extracting with ethyl acetate, drying, separating by using column chromatography, and drying in vacuum to obtain a compound 3;

4) weighing urotropine and the compound 3 obtained in the step 3), dissolving in a solvent, reacting at a constant temperature of 90 ℃ for 21h, cooling to room temperature, adjusting the pH value of the solution to be neutral by using a 50% sodium hydroxide solution, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain a compound 4;

5) weighing 1, 8-diaminonaphthalene and the compound 4 obtained in the step 4), dissolving in a solvent, reacting at the constant temperature of 80 ℃ for 8 hours, cooling to room temperature, carrying out suction filtration, carrying out column chromatography separation, and carrying out vacuum drying to obtain the probe NADN.

5. The method for preparing the naphthalimide-based hypochlorous acid fluorescent probe of claim 4, wherein the solvent used in step 1) is methanol; the solvent in the step 2) is methanol; the solvent in the step 3) is a 55% HI solution; the solvent in the step 4) is trifluoroacetic acid; the solvent in the step 5) is ethanol.

6. The method for preparing the naphthalimide-based hypochlorous acid fluorescent probe according to claim 4, wherein the molar ratio of the 4-bromo-1, 8-naphthalic anhydride to n-butylamine in step 1) is 1:5 to 1: 10; the molar ratio of the 4-bromo-1, 8-naphthalic anhydride to the solvent is 1: 20-1: 50.

7. The method for preparing the naphthalimide-based hypochlorous acid fluorescent probe according to claim 4, wherein the molar ratio of the compound 1 to sodium methoxide in the step 2) is 1:3 to 1: 6; the compound 1 and CuSO₄·5H₂The molar ratio of O is 1: 0.1-1: 0.3; the molar ratio of the compound 1 to the solvent is 1: 20-1: 50.

8. The method for preparing the naphthalimide-based hypochlorous acid fluorescent probe according to claim 4, wherein the molar ratio of the compound 2 to the solvent in the step 3) is 1:5 to 1: 50.

9. The method for preparing the naphthalimide-based hypochlorous acid fluorescent probe according to claim 4, wherein the molar ratio of the compound 3 to the urotropine in the step 4) is 1:3 to 1: 10; the molar ratio of the compound 3 to the solvent is 1: 10-1: 20.

10. The method for preparing the naphthalimide-based hypochlorous acid fluorescent probe according to claim 4, wherein the molar ratio of the compound 4 to the 1, 8-diaminonaphthalene in the step 5) is 1:1 to 1: 3; the molar ratio of the compound 4 to the solvent is 1: 10-1: 50.

Technical Field

The application belongs to the field of fluorescent probes, and particularly relates to a fluorescent probe capable of detecting hypochlorous acid and a preparation method thereof.

Background

Hypochlorous acid is widely used as a strong oxidant, is often used as a bleaching agent, a disinfectant and a deodorant in life, and the chlorination method adopted for disinfecting tap water also utilizes hypochlorous acid generated by dissolving chlorine in water to oxidize and inactivate odor inorganic substances and natural substances in the water so as to achieve the sterilization effect. Hypochlorous acid also plays an important role in human body, and the abnormal level of the hypochlorite in the organism has important relationship with diseases such as tissue injury, neuron degeneration, cancer, cardiovascular diseases, arthritis and the like. Therefore, it is important to find a method for detecting hypochlorous acid with high efficiency, sensitivity and specificity. Compared with the traditional detection method, the fluorescent marker as a new detection technology has the advantages of low cost, high sensitivity, simple and convenient operation and the like.

The naphthalimide molecules have the characteristics of rigidity and coplanarity, the stronger the rigidity and the coplanarity of the fluorescent substance, the less the interaction between the molecules and the solvent or other solute molecules, the less the external transfer energy loss, and the emission of fluorescence is facilitated. In addition, the naphthalimide molecules have a large conjugated system, so that delocalized pi electrons are easy to excite, and therefore fluorescence is easy to generate, and a push-pull electron system is arranged in the molecular structure of the naphthalimide molecules, and electrons in the system are easy to be excited by external light or electric field to generate transition, so that fluorescence is generated. The invention takes naphthalimide with large Stokes displacement and high fluorescence quantum yield as a fluorophore, and obtains a compound containing an imine bond by synthesizing the naphthalimide fluorophore with aldehyde group and carrying out condensation reaction with 1, 8-diaminonaphthalene, thereby forming the hypochlorous acid fluorescent probe with high sensitivity by taking the 1, 8-diaminonaphthalene derived imine bond as an identification position. The probe obtained in the patent has good selectivity for hypochlorous acid, and can accurately identify the hypochlorous acid in a complex system.

The invention content is as follows:

the invention provides a novel naphthalimide-based hypochloric acid fluorescent probe. The fluorescent probe is a naphthalimide derivative, and the compound has an imine bond which is easy to be specifically cracked by hypochlorous acid, and has a special conjugated structure and good chemical reaction performance, so that probe molecules can accurately identify the hypochlorous acid in a complex system. After the probe solution is added with the hypochlorous acid solution, the imine bond of the probe is broken to release a naphthalimide fluorophore with aldehyde group, macroscopic color change occurs, the ultraviolet visible absorption spectrum of the naphthalimide fluorophore has a strong absorption peak, and the fluorescence spectrum also has a remarkable emission peak. Therefore, the fluorescent probe is an ideal hypochlorous acid fluorescent probe. In addition, the synthesis process has the advantages of simple operation, high yield, low cost, quick detection and the like.

In order to achieve the above object, the solution adopted by the present application is as follows:

a hypochlorous acid fluorescent probe based on naphthalimide has the following specific structure:

the specific route of the method for preparing the naphthalimide-based hypochloric acid fluorescent probe is as follows:

the application of the hypochlorous acid fluorescent probe based on the naphthalimide is application in the aspect of hypochlorous acid detection.

The preparation method of the hypochlorous acid fluorescent probe based on the naphthalimide comprises the following specific steps:

1) weighing 4-bromo-1, 8-naphthalic anhydride and n-butylamine, dissolving in a solvent, reacting for 10h at constant temperature of 85 ℃ under stirring, cooling to room temperature, standing the solution to precipitate a solid, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain a compound 1;

2) weighing CH₃ONa、CuSO₄·5H₂Dissolving O and the compound 1 obtained in the step 1) in a solvent, reacting for 8 hours at a constant temperature of 85 ℃, cooling to room temperature, standing the solution to precipitate white crystals, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain a compound 2;

3) weighing the compound 2 obtained in the step 2), dissolving in a solvent, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting the pH value of the solution to be neutral by using a 50% sodium hydroxide solution, extracting with ethyl acetate, drying, separating by using column chromatography, and drying in vacuum to obtain a compound 3;

4) weighing urotropine and the compound 3 obtained in the step 3), dissolving in a solvent, reacting at a constant temperature of 90 ℃ for 21h, cooling to room temperature, adjusting the pH value of the solution to be neutral by using a 50% sodium hydroxide solution, carrying out suction filtration, carrying out column chromatography separation, and carrying out vacuum drying to obtain a compound 4;

5) weighing 1, 8-diaminonaphthalene and the compound 4 obtained in the step 4), dissolving in a solvent, reacting at the constant temperature of 80 ℃ for 8 hours, cooling to room temperature, carrying out suction filtration, carrying out column chromatography separation, and carrying out vacuum drying to obtain the probe NADN.

Preferably, the molar ratio of the 4-bromo-1, 8-naphthalic anhydride to n-butylamine in step 1) is 1:5 to 1: 10; the molar ratio of the 4-bromo-1, 8-naphthalic anhydride to the solvent is 1: 20-1: 50; the molar ratio of the n-butylamine to the solvent is 1: 5-1: 10;

preferably, the molar ratio of the compound 1 to sodium methoxide in the step 2) is 1: 3-1: 6; the compound 1 is mixed with CuSO4 & 5H₂The molar ratio of O is 1: 0.1-1: 0.3; the molar ratio of the compound 1 to the solvent is 1: 20-1: 50;

preferably, the molar ratio of the compound 2 to the solvent in the step 3) is 1: 5-1: 50;

preferably, the molar ratio of the compound 3 to the urotropine in the step 4) is 1: 3-1: 10; the molar ratio of the compound 3 to the solvent is 1: 10-1: 20; the mol ratio of the urotropine to the solvent is 1: 10-1: 20;

preferably, the molar ratio of the compound 4 to the 1, 8-diaminonaphthalene in the step 5) is 1: 1-1: 3; the molar ratio of the compound 4 to the solvent is 1: 10-1: 50; the molar ratio of the 1, 8-diaminonaphthalene to the solvent is 1: 10-1: 50;

preferably, the solvent in step 1) is methanol;

preferably, the solvent in step 2) is methanol;

preferably, the solvent described in step 3) is a 55% HI solution;

preferably, the solvent in step 4) is trifluoroacetic acid;

preferably, the solvent in the step 5) is ethanol;

in the probe NADN, the aldehyde group in naphthalimide with aldehyde group and the amino group of 1, 8-diaminonaphthalene are subjected to condensation reaction to generate imine bond, and the imine bond and hypochlorous acid are subjected to specific reaction to release a fluorophore so as to achieve the specific recognition of the hypochlorous acid.

The novel compound can be used as a probe to be applied to the field of hypochlorous acid detection. The compound has good specific selectivity on hypochlorous acid, and can identify the hypochlorous acid in a complex system.

Description of the drawings:

(1) FIG. 1 is a NMR spectrum of probe NADN.

(2) FIG. 2 is a graph of the UV-VIS absorption spectrum of probe NADN selective for hypochlorous acid (excitation wavelength on the abscissa and absorbance on the ordinate).

(3) FIG. 3 is a fluorescence spectrum of probe NADN on hypochlorous acid selectivity (emission wavelength on abscissa and fluorescence intensity on ordinate).

The specific implementation mode is as follows:

in order to better understand the technical solution of the present invention, the following detailed description is given by specific examples.

Example 1

Weighing 1.385g (5mmol) of 4-bromo-1, 8-naphthalic anhydride and 0.5mL (25mmol) of n-butylamine, dissolving in 30mL of methanol, reacting for 10h at 85 ℃ under constant temperature stirring, cooling to room temperature, standing the solution to precipitate a white solid, performing suction filtration, and performing vacuum drying to obtain the compound 1.

Weighing 1.32g (4mmol) of compound 1, 0.64g (12mmol) of sodium methoxide and 0.2o0.2g (0.8mmol) of CuSO 4.5H 2O, dissolving in 50mL of methanol, reacting at constant temperature of 85 ℃ for 8h, cooling to room temperature, standing to separate out white solid, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain compound 2.

Weighing 0.283g (1mmol) of compound 2, dissolving in 25mL of HI (55%) solution, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting pH to neutral with 50% NaOH solution, extracting with ethyl acetate, drying, separating by column chromatography, and vacuum drying to obtain compound 3.

0.269g (1mmol) of compound 3 and 0.42g (3mmol) of urotropine are weighed and dissolved in 20mL of trifluoroacetic acid, the mixture reacts for 21h at a constant temperature of 90 ℃, the reaction product is cooled to room temperature, the pH value is adjusted to be neutral by using a 50% NaOH solution, and the compound 4 is obtained after suction filtration, column chromatographic separation and vacuum drying.

0.297g (1mmol) of the compound 4 and 0.158g (1mmol) of 1, 8-diaminonaphthalene are weighed and dissolved in 25mL of ethanol, and after the reaction is carried out at the constant temperature of 80 ℃ for 8h, the solution is cooled to the room temperature, filtered by suction, separated by column chromatography and dried in vacuum, and the probe NADN is obtained.

Example 2

Weighing 1.385g (5mmol) of 4-bromo-1, 8-naphthalic anhydride and 0.6mL (30mmol) of n-butylamine, dissolving in 25mL of methanol, reacting for 10h at 85 ℃ under constant temperature stirring, cooling to room temperature, standing the solution to precipitate a white solid, performing suction filtration, and performing vacuum drying to obtain the compound 1.

Weighing 1.32g (4mmol) of compound 1, 0.852g (16mmol) of sodium methoxide and 0.1g (0.4mmol) of CuSO 4.5H 2O0, dissolving in 45mL of methanol, reacting at constant temperature of 85 ℃ for 8h, cooling to room temperature, standing to separate out a white solid, carrying out suction filtration, carrying out column chromatography separation, and carrying out vacuum drying to obtain the compound 2.

Weighing 0.283g (1mmol) of compound 2, dissolving in 20mL of HI (55%) solution, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting pH to neutral with 50% NaOH solution, extracting with ethyl acetate, drying, separating by column chromatography, and vacuum drying to obtain compound 3.

0.269g (1mmol) of compound 3 and 0.56g (4mmol) of urotropine are weighed and dissolved in 10mL of trifluoroacetic acid, the mixture reacts for 21h at a constant temperature of 90 ℃, the reaction product is cooled to room temperature, the pH value is adjusted to be neutral by using a 50% NaOH solution, and the compound 4 is obtained after suction filtration, column chromatographic separation and vacuum drying.

0.297g (1mmol) of the compound 4 and 0.158g (1mmol) of 1, 8-diaminonaphthalene are weighed and dissolved in 20mL of ethanol, and after the reaction is carried out at the constant temperature of 80 ℃ for 8h, the solution is cooled to the room temperature, filtered by suction, separated by column chromatography and dried in vacuum, and the probe NADN is obtained.

Example 3

Weighing 1.385g (5mmol) of 4-bromo-1, 8-naphthalic anhydride and 0.7mL (35mmol) of n-butylamine, dissolving in 35mL of methanol, reacting for 10h at 85 ℃ under constant temperature stirring, cooling to room temperature, standing the solution to precipitate a white solid, performing suction filtration, and performing vacuum drying to obtain the compound 1.

Weighing 1.32g (4mmol) of compound 1, 1.065g (20mmol) of sodium methoxide and 1.3 g (1.2mmol) of CuSO 4.5 H2O0.3g (40 mL) of methanol, reacting at constant temperature of 85 ℃ for 8h, cooling to room temperature, standing to separate out white solid, performing suction filtration, performing column chromatography separation, and performing vacuum drying to obtain compound 2.

Weighing 0.283g (1mmol) of compound 2, dissolving in 20mL of HI (55%) solution, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting pH to neutral with 50% NaOH solution, extracting with ethyl acetate, drying, separating by column chromatography, and vacuum drying to obtain compound 3.

0.269g (1mmol) of compound 3 and 0.7g (5mmol) of urotropine are weighed and dissolved in 15mL of trifluoroacetic acid, the mixture reacts for 21h at a constant temperature of 90 ℃, the reaction product is cooled to room temperature, the pH value is adjusted to be neutral by using a 50% NaOH solution, and the compound 4 is obtained after suction filtration, column chromatographic separation and vacuum drying.

Weighing 0.297g (1mmol) of compound 4 and 0.474(3 mmol) of 1, 8-diaminonaphthalene, dissolving in 30mL of ethanol, reacting at 80 ℃ for 8h, cooling to room temperature, performing suction filtration, performing column chromatography separation, and drying in vacuum to obtain the probe NADN.

Example 4

Weighing 1.385g (5mmol) of 4-bromo-1, 8-naphthalic anhydride and 0.8mL (40mmol) of n-butylamine, dissolving in 40mL of methanol, reacting for 10h at 85 ℃ under constant temperature stirring, cooling to room temperature, standing the solution to precipitate a white solid, performing suction filtration, and performing vacuum drying to obtain the compound 1.

Weighing 1.32g (4mmol) of compound 1, 1.278g (24mmol) of sodium methoxide and 0.2o0.2g (0.8mmol) of CuSO 4.5H 2O, dissolving in 50mL of methanol, reacting at constant temperature of 85 ℃ for 8h, cooling to room temperature, standing to separate out a white solid, carrying out suction filtration, carrying out column chromatography separation, and carrying out vacuum drying to obtain a compound 2.

Weighing 0.141g (0.5mmol) of compound 2, dissolving in 30mL of HI (55%) solution, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting pH to neutral with 50% NaOH solution, extracting with ethyl acetate, drying, separating by column chromatography, and vacuum drying to obtain compound 3.

0.269g (1mmol) of compound 3 and 0.84g (6mmol) of urotropine are weighed and dissolved in 10mL of trifluoroacetic acid, the mixture reacts for 21h at a constant temperature of 90 ℃, the reaction product is cooled to room temperature, the pH value is adjusted to be neutral by using a 50% NaOH solution, and the compound 4 is obtained after suction filtration, column chromatographic separation and vacuum drying.

0.297g (1mmol) of compound 4 and 0.316g (2mmol) of 1, 8-diaminonaphthalene are weighed and dissolved in 50mL of ethanol, and after the reaction is carried out at the constant temperature of 80 ℃ for 8h, the solution is cooled to the room temperature, and then is filtered, separated by column chromatography and dried in vacuum, thus obtaining the probe NADN.

Example 5

Weighing 1.385g (5mmol) of 4-bromo-1, 8-naphthalic anhydride and 0.6mL (30mmol) of n-butylamine, dissolving in 45mL of methanol, reacting for 10h at 85 ℃ under constant temperature stirring, cooling to room temperature, standing the solution to precipitate a white solid, performing suction filtration, and performing vacuum drying to obtain the compound 1.

0.66g (2mmol) of compound 1, 0.64g (12mmol) of sodium methoxide and 0.1g (0.4mmol) of CuSO 4.5H 2O0 are weighed, dissolved in 35mL of methanol, reacted at constant temperature of 85 ℃ for 8h, cooled to room temperature, and the solution is kept still to precipitate white solid, filtered, separated by column chromatography and dried in vacuum, thus obtaining the compound 2.

Weighing 0.283g (1mmol) of compound 2, dissolving in 40mL of HI (55%) solution, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting pH to neutral with 50% NaOH solution, extracting with ethyl acetate, drying, separating by column chromatography, and vacuum drying to obtain compound 3.

0.269g (1mmol) of compound 3 and 0.96g (7mmol) of urotropine are weighed and dissolved in 20mL of trifluoroacetic acid, the mixture reacts for 21h at a constant temperature of 90 ℃, the reaction product is cooled to room temperature, the pH value is adjusted to be neutral by using a 50% NaOH solution, and the compound 4 is obtained after suction filtration, column chromatographic separation and vacuum drying.

0.297g (1mmol) of compound 4 and 0.474g (3mmol) of 1, 8-diaminonaphthalene are weighed and dissolved in 40mL of ethanol, and after the mixture reacts for 8 hours at a constant temperature of 80 ℃, the mixture is cooled to room temperature, filtered, separated by column chromatography and dried in vacuum, and the probe NADN is obtained.

Example 6

Weighing 1.385g (5mmol) of 4-bromo-1, 8-naphthalic anhydride and 0.5mL (25mmol) of n-butylamine, dissolving in 50mL of methanol, reacting for 10h at 85 ℃ under constant temperature stirring, cooling to room temperature, standing the solution to precipitate a white solid, performing suction filtration, and performing vacuum drying to obtain the compound 1.

0.66g (4mmol) of compound 1, 0.64g (12mmol) of sodium methoxide and 0.15g (0.6mmol) of CuSO 4.5H 2O0.15g are weighed, dissolved in 30mL of methanol, reacted at constant temperature of 85 ℃ for 8h, cooled to room temperature, the solution is kept still to precipitate white solid, filtered by suction, separated by column chromatography and dried in vacuum, and the compound 2 is obtained.

Weighing 0.424g (1.5mmol) of compound 2, dissolving in 50mL of HI (55%) solution, reacting at 140 ℃ for 12h, cooling to room temperature, adjusting pH to neutral with 50% NaOH solution, extracting with ethyl acetate, drying, separating by column chromatography, and vacuum drying to obtain compound 3.

0.269g (1mmol) of compound 3 and 1.12g (8mmol) of urotropine are weighed and dissolved in 20mL of trifluoroacetic acid, the mixture reacts for 21h at a constant temperature of 90 ℃, the reaction product is cooled to room temperature, the pH value is adjusted to be neutral by using a 50% NaOH solution, and the compound 4 is obtained after suction filtration, column chromatographic separation and vacuum drying.

0.297g (1mmol) of compound 4 and 0.474g (3mmol) of 1, 8-diaminonaphthalene are weighed and dissolved in 30mL of ethanol, and after the mixture reacts for 8 hours at a constant temperature of 80 ℃, the mixture is cooled to room temperature, filtered, separated by column chromatography and dried in vacuum, and the probe NADN is obtained.

Nuclear magnetic analysis (nuclear magnetic spectrum is shown in figure 1) of the compound of the final product:

table 1 was obtained by analyzing the structural formula of the probe NADN and the NMR spectrum. The compound has 12 hydrogen atoms. Wherein the signal peak appearing around 0.98ppm is the signal peak of hydrogen on carbon 17, and the peak area thereof is 3.22; the signal peak appearing around 1.45ppm was that of hydrogen on carbon 16, and its peak area was 2.36; the signal peak appearing around 1.71ppm was the signal peak of hydrogen on carbon 15, whose peak area was 2.31; the signal peak appearing around 4.17ppm was the signal peak for hydrogen on carbon 14, whose peak area was 2.33; the signal peak appearing in the vicinity of 4.88ppm was that of hydrogen on nitrogen 22 and 26, and its peak area was 2.02; the signal peak appearing around 5.81ppm was the signal peak of hydrogen on carbon 21, whose peak area was 1.15; the signal peak appearing around 6.74ppm was that of hydrogen on carbons 30 and 31, whose peak area was 2.19; the signal peaks appearing around 7.39ppm were the signal peaks for hydrogen on carbons 28, 29, 32 and 33, whose peak area was 4.40; the signal peak appearing around 7.72ppm was that of hydrogen on carbon 8, and its peak area was 1.14; the signal peak appearing around 8.43ppm was the signal peak of hydrogen on carbon 9, and its peak area was 1.10; the signal peak appearing around 8.61ppm was that of hydrogen on carbons 7 and 13, and its peak area was 2.16; the signal peak appearing in the vicinity of 10.56ppm was that of hydrogen on oxygen 20, and its peak area was 1.00. Therefore, the nuclear magnetic resonance hydrogen spectrum of the compound well accords with the structure of the compound, namely NDAN.

Of the compounds of Table 1¹Chemical shift and peak assignment for HNMR

Application of hypochlorous acid fluorescent probe

Experimental example 1

A naphthalimide-based hypochlorous acid fluorescent probe prepared in example 1 was dissolved in DMSO and diluted to 1.0X 10^-5mol/L of sample solution. Measuring pure probe solution and probe solution in the presence of different interference substances F with equivalent weight by using UV-2600PC ultraviolet-visible absorption spectrometer and F-7000 fluorescence spectrophotometer^-、Cl^-、CO₃ ^2-、H₂PO₄ ^-、HPO₄ ^2-、S^2-、S₂O₃ ^2-、SO₃ ^2-、SO₄ ^2-、CH₃CH₂O^-The uv-vis absorption spectrum (as shown in fig. 2) and the fluorescence emission spectrum (as shown in fig. 3) after Glu, Gly, Cys, it can be seen from fig. 2 and 3 that only hypochlorous acid among many substances can cause the probe solution to show a significant color change, and the absorption peaks and emission peaks of the probe solution containing hypochlorous acid are significantly different from those of the probe solution containing other ions and the pure probe solution, which all indicate that the probe has a good selectivity for hypochlorous acid.