KR20230169741A - Compound for fluorescent detection probe with high selectivity of hypochlorous acid and hypochlorite salt, probe and chemical sensor including the same compound and method of detection of hypochlorous acid or hypochlorite salt - Google Patents

Abstract

The present invention relates to a highly selective fluorescent probe compound for detecting hypochlorous acid or hypochlorite, a probe and chemical sensor containing the same, and a method for detecting hypochlorous acid or hypochlorite using the same. Specifically, it relates to hypochlorous acid (hypochlorous acid) among reactive oxygen species. ) or a fluorescent probe compound that has excellent selectivity for hypochlorite salts and can detect hypochlorite salts non-destructively with high sensitivity and fast response time, a method for detecting hypochlorous acid or hypochlorite using the same, and a method to which the method is applied Concerning probes and chemical sensors.

Description

Compound for fluorescent detection probe with high selectivity of hypochlorous acid and hypochlorite salt, probe and chemical, and method for detecting hypochlorous acid or hypochlorite using the same. sensor including the same compound and method of detection of hypochlorous acid or hypochlorite salt}

The present invention relates to a highly selective fluorescent probe compound for detecting hypochlorous acid and hypochlorite, a probe and chemical sensor containing the same, and a method for detecting hypochlorous acid or hypochlorite using the same. Specifically, it relates to hypochlorous acid (hypochlorous acid) among reactive oxygen species. ) or a fluorescent probe compound that has excellent selectivity for hypochlorite salts and can detect hypochlorite salts non-destructively with high sensitivity and fast response time, a method for detecting hypochlorous acid or hypochlorite using the same, and a method to which the method is applied Concerning probes and chemical sensors.

Reactive oxygen species (ROS) play an important role in various life functions in vivo. Among them, hypochlorous acid (HClO) or hypochlorite salts (ClO ^- ) is produced by the reaction of H ₂ O ₂ and chlorine ions by activated neutrophils within the organism, and is used by pathogens, etc. It is an oxidizing agent that kills. The physiologically relevant level of hypochlorous acid in living organisms is 5 μM to 25 μM. If the content of hypochlorous acid in an organism is excessive, it can react with various biomolecules such as proteins and amino acids, causing various diseases including cardiovascular disease and osteoarthritis, as well as cancer. Therefore, highly sensitive and selective detection is important to observe the abnormal behavior of hypochlorite.

In addition, hypochlorous acid is used in everyday life as a household and industrial disinfectant or bleach, and is widely used to disinfect drinking water and swimming pool water and to control bacteria and odors in the food industry. Chlorine exists in an equilibrium state of hypochlorous acid and hypochlorite in water depending on pH, and is generally used in a concentration range of 10 ^-5 M to 10 ^-2 M to disinfect drinking water. In Korea, residual chlorine in drinking water is less than 4.0 mg/L. At this time, if hypochlorite remains in water in excessive concentration, it poses a risk to human health. Therefore, biologically and environmentally, there is a need for an analytical method that can quantitatively detect hypochlorite (or hypochlorous acid) contained in very small amounts of drinking water.

Chang, et al., “Benzothiazole-based fluorescent sensor for hypochlorite detection and its application for biological imaging”, ELSEVIER, 24. 11. 2016.

The present invention was conceived in consideration of the above-mentioned technical problems, and the problem to be solved by the present invention is the detection of hypochlorous acid and hypochlorite among reactive oxygen species in water quality testing of water (H ₂ O) in contact with the human body, such as drinking water. The object is to provide a fluorescent probe compound for detection with excellent selectivity.

In addition, another problem to be solved by the present invention is to provide a method for detecting hypochlorous acid or hypochlorite in water using the above compound, and a probe and chemical sensor containing the above compound.

In order to solve the above-mentioned technical problems, the present invention provides a fluorescent probe compound for detecting hypochlorite salt or hypochlorous acid with excellent selectivity, represented by the structure of Formula 1 below.

[Formula 1]

In Formula 1, one or both of R ¹ to R ⁴ are functional groups containing a phenothiazine group represented by the following Formula 2,

[Formula 2]

The other has a structure represented by the following formula 3,

[Formula 3]

The remainder is hydrogen or a C ₁ to C ₆ linear or branched alkyl group,

In Formula 2, X ¹ is a single bond, C ₆ to C ₁₄ arylene, or C ₃ to C ₁₂ heteroarylene,

_{In Formula} ³ _{, _} ^{_ _} _{_ _} It is a straight or branched, saturated or unsaturated monovalent hydrocarbon chain.

In a preferred embodiment of the present invention, the fluorescent probe compound may have the structure of Formula 1-1 below.

[Formula 1-1]

In Formula 1-1,

R ³ and R ⁴ are each independently hydrogen or a C ₁ to C ₆ straight or branched alkyl group,

_X ¹ is a _single bond, _a C ₆ to C ₁₄ arylene group or _{a C 3 to C 12 heteroarylene} ^group _,

R ^{`1</sup> and R <sup>`2} are each independently a C ₈ to C ₂₅ straight or branched, saturated or unsaturated monovalent hydrocarbon chain.

In a preferred embodiment of the present invention, the fluorescent probe compound may be a compound represented by the following formula 1-2.

[Formula 1-2]

In Formula 1-2,

R ³ and R ⁴ are each independently hydrogen or a C ₁ to C ₆ straight or branched alkyl group,

R ^{`1</sup> to R <sup>`2} are each independently a C ₈ to C ₂₅ straight or branched saturated or unsaturated monovalent hydrocarbon chain.

The present invention also provides a fluorescent probe for detecting hypochlorous acid or hypochlorite containing the above fluorescent probe compound.

In a preferred embodiment of the present invention, the probe for detecting hypochlorous acid or hypochlorite is a mixed solvent of an organic solvent and water (H ₂ O); and

It may include; the fluorescent probe compound according to claim 1 dissolved in the mixed solvent.

In a preferred embodiment of the present invention, the organic solvent may be one or two or more mixed solvents selected from tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), ethanol, and methanol.

In a preferred embodiment of the present invention, the mixed solvent of the organic solvent and water may have a mixing ratio of the organic solvent of 80 vol% to 95 vol%.

In a preferred embodiment of the present invention, the fluorescent probe compound may be dissolved in the mixed solvent at a concentration of 1.0 μM to 10.0 μM.

The present invention also provides a chemical sensor for detecting hypochlorous acid or hypochlorite including the above fluorescent probe.

In a preferred embodiment of the present invention, the chemical sensor may be a silica gel thin film sensor.

The present invention also includes the steps of: 1) mixing the fluorescent probe with water (H ₂ O) to be tested; and

2) introducing a mixture of the fluorescent probe and the test object onto a silica gel thin film; providing a method for detecting hypochlorous acid or hypochlorite including a step.

The fluorescent probe compound according to the present invention can be synthesized through a simple process, improving the productivity of chemical sensors, and has excellent selectivity for the target hypochlorous acid or hypochlorite even in small amounts, allowing it to precisely select only the relevant active oxygen species. It has the advantage of being detectable.

In addition, the probe and chemical sensor for detecting hypochlorous acid or hypochlorite containing the above fluorescent probe compound according to the present invention have high sensitivity, high selectivity for hypochlorous acid and hypochlorite, fast response time, and non-destructive detection. It is possible to selectively detect hypochlorous acid or hypochlorite among the reactive oxygen species remaining in efficiently purified water.

Figure 1a shows a fluorescent probe in a solution of a probe compound of Formula 4 dissolved in a mixed solvent of THF/H ₂ O (V:V=9:1) at a concentration of 2.5 μM, and 0 to 40 equivalents of the probe compound. This is a comparative graph showing the UV-vis spectrum measured by adding NaClO.
[Formula 4]

Figure 1b is a graph comparing the fluorescence spectrum (λ _ex = 406 nm) when 0 to 40 equivalents of NaClO sample was added to the same fluorescent probe as in Figure 1a.
Figure 2 is a graph comparing the results of a fluorescence reaction by detecting reactive oxygen species in a solution containing 50 equivalents of various reactive oxygen species compared to the probe using the same fluorescent probe as in Figures 1a and 1b.
Figure 3a is a photograph taken after adding 0 and 20 equivalents of NaClO to the same fluorescent probe as in Figure 1a and dropping 1 drop (approximately 10 μl) of the mixed solution on the silica gel thin film before drying.
Figure 3b is a photograph taken after the mixed solution of Figure 3a was dried.
Figures 4 and 5 show ¹ H-NMR spectra of compounds of Formula 5 and Formula 4, respectively.
Figure 6 is a diagram showing the mass spectrometry (MALDI-TOF) spectrum of the compound of Formula 4.

As used herein, “selectivity” means that a chemical reaction occurs more significantly for a specific substance than for other substances. In other words, if a particularly strong chemical reaction occurs for substance A among substances A to Z, the reaction is said to be selective for substance A. Excellent selectivity means that the degree of reaction for substance A (reaction constant, reaction rate, etc.) is significantly different from the degree of reaction for other substances.

Hereinafter, the configuration and effects of the present invention will be described in more detail with reference to the attached drawings and specific embodiments.

Fluorescence imaging technology using fluorescent probes for the detection and detection of reactive oxygen species has high sensitivity, selectivity, fast response time, technical simplicity, and is capable of non-destructive detection, making it suitable for use in environmental and biological systems. has been developed However, due to the nature of the fluorescent probe, which mainly detects target substances by expressing fluorescence through oxidation-reduction reactions, it was difficult to show selectivity for specific reactive oxygen species, which was a difficulty.

Accordingly, in the present invention, a fluorescent probe material for detecting hypochlorous acid or hypochlorite salt with excellent selectivity, represented by the structure represented by the following formula (1), was introduced and included. Using a fluorescent probe and chemical sensor, a technology was developed that can detect hypochlorous acid or hypochlorite with excellent sensitivity due to its high selectivity for these two chemical species compared to other reactive oxygen species.

[Formula 1]

In Formula 1, one or both of R ¹ to R ⁴ are functional groups containing a phenothiazine group represented by the following Formula 2,

[Formula 2]

The other has a structure represented by Formula 3 below,

[Formula 3]

The remainder is hydrogen (H) or a C ₁ to C ₆ linear or branched alkyl group,

In Formula 2, X ¹ is a single bond, C ₆ to C ₁₄ arylene, or C ₃ to C ₁₂ heteroarylene,

_{In Formula} ³ _{, _} ^{_ _} _{_ _} It is a straight or branched, saturated or unsaturated monovalent hydrocarbon chain.

The above compound can be synthesized through a simple process, allowing fluorescent probes and chemical sensors to be obtained in high yield, and exhibits high selectivity for hypochlorous acid and hypochlorite.

Figure 2 is a chemical sensor containing a fluorescent probe compound according to a preferred embodiment of the present invention, comparing the intensity of the fluorescence response for samples (H ₂ O) containing various types of reactive oxygen species substances at the same concentration. This is one graph. Referring to FIG. 2, it can be seen that the chemical sensor according to the present invention shows a significant fluorescence reaction of hypochlorite compared to other reactive oxygen species. In this way, using a chemical sensor using the fluorescent probe compound can be effectively used as a chemical sensor for detecting a specific substance.

The core of the polycyclic structure shown in Formula 1 is a four-dentate chelate compound called porphyrin, which has a strong soret absorption peak, large stokes shift, excellent light stability, and biocompatibility, making it a safe sensor for the human body. You can use it. Porphyrins can emit fluorescence at wavelengths longer than 600 nm, which may minimize light damage and background interference.

The porphyrin ring is characterized by four pyrrole rings connected, and various applications are possible by introducing various functional groups into the meso or beta position of the pyrrole ring through organic reactions.

In the case of the present invention, the selectivity of the fluorescence reaction for hypochlorous acid and hypochlorite among reactive oxygen species is strengthened by introducing a functional group containing at least one phenothiazine functional group at the four reactive positions of the porphyrin. In Formula 2, the sulfur atom of phenothiazine causes an oxidation-reduction reaction with active oxygen species, changing from sulfide to sulfoxide, and has the function of donating electrons toward porphyrin. This is lost, and thus the fluorescence of porphyrin becomes activated compared to before the reaction.

Therefore, after reaction with reactive oxygen species, that is, hypochlorous acid and hypochlorite, the fluorescent probe compound has more distinct fluorescence properties.

Among the substituents R ¹ to R ⁴ around the porphyrin mother nucleus, except for those substituted with Formula 2, one of the remaining substituents may be substituted with a form of Formula 3. This gives hydrophobicity to all fluorescent probe compounds by having a long alkyl, alkenyl, or alka-poly-enyl (i.e., unsaturated hydrocarbon chain with two or more double bonds). and strengthens the affinity with organic solvents.

Among the substituents R ¹ to R ⁴ around the porphyrin mother nucleus, all other substituents other than those substituted in Formulas 2 and 3 are hydrogen (H) or C ₁ to C ₆ straight-chain or branched alkyl groups. Preferably, the remaining substituents may be hydrogen.

The structure represented by Formula 2 and the structure represented by Formula 3 may preferably be arranged in opposite directions around the porphyrin mother nucleus (structure similar to para-substituted benzene). That is, the fluorescent probe compound according to a preferred embodiment of the present invention may be represented by the structure of Formula 1-1 below.

[Formula 1-1]

In Formula 1-1, X ¹ is the same as defined in Formula 2, and X ² is the same as defined in Formula 3,

R ³ and R ⁴ are hydrogen (H) and a C ₁ to C ₆ straight or branched alkyl group.

Preferably, X ¹ may be a single bond or a phenylene group, and X ² may be a trivalent benzene ring.

More preferably, the fluorescent probe compound may be a compound represented by the following formula 1-2.

[Formula 1-2]

In Formula 1-2, R ³ and R ⁴ are each independently hydrogen (H) and a C ₁ to C ₆ straight or branched alkyl group. Preferably, R ³ and R ⁴ may be hydrogen.

In addition, R ^{`1</sup> and R <sup>`2} are each independently a C ₈ to C ₂₅ straight or branched saturated or unsaturated monovalent hydrocarbon chain.

A straight or branched, saturated or unsaturated monovalent hydrocarbon chain means that R ^{`1</sup> and R <sup>`2} are an alkyl group, an alkenyl group, or an alkapolyenyl group, and straight or branched chain means that This means that it is not a cyclic hydrocarbon.

The present invention also provides a fluorescent probe for detecting hypochlorous acid or hypochlorite containing the above fluorescent probe compound. The fluorescent probe according to the present invention has high selectivity for hypochlorous acid and hypochlorite, and the intensity of fluorescence increases proportionally according to the equivalent weight of hypochlorous acid and hypochlorite, which are detection substances, making it easy to quantify detection and is suitable for use as a chemical sensor. do. In addition, since detection is possible even when only a small amount of the fluorescent probe compound is used, it has excellent detection sensitivity. The high selectivity of this fluorescence intensity for hypochlorous acid or hypochlorite is thought to be due to the reduction of the photoinduced electron transfer (PET) effect for porphyrin compounds due to the presence of the phenothiazine group.

A fluorescent probe for detecting hypochlorous acid or hypochlorite according to a preferred embodiment of the present invention may include a mixed solvent and the fluorescent probe compound dissolved in the mixed solvent.

The mixed solvent may preferably be a mixed solvent of an organic solvent and water (H ₂ O). By adjusting the mixing ratio (volume ratio) between organic solvent and water, optimal conditions suitable for the measurement environment (machine used, temperature, etc.) can be achieved. Preferably, the mixing ratio of the organic solvent and water may be 80 vol% to 95 vol%. If the volume ratio of the organic solvent is less than 80 vol%, the polarity of the solvent may be excessive, which may cause a problem in that the detection function, which improves fluorescence due to the stabilizing effect of the solvent, is deteriorated. Additionally, if the volume ratio of the organic solvent exceeds 95 vol%, the polarity of the solvent is too low, which may result in poor compatibility as a chemical sensor for water.

The organic solvent may preferably be one or two or more mixed solvents selected from tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), ethanol, and methanol, and more preferably tetrahydrofuran, but must be It is not limited to the solvents listed above, and may be a solvent that is compatible with porphyrin-based compounds and does not have any separate chemical or physical interaction with hypochlorous acid or hypochlorite.

Additionally, in a preferred embodiment of the present invention, the fluorescent probe compound may be dissolved in the mixed solvent at a concentration of 1.0 μM to 10.0 μM. More preferably, the fluorescent probe compound may be dissolved in the mixed solvent at a concentration of 1.0 μM to 4.0 μM.

If the fluorescent probe compound is dissolved in a mixed solvent at a content of less than 1.0 μM, the sensitivity of detection is weakened and it is difficult to function as a sensor, and if it exceeds 10.0 μM, the excitation energy decreases due to collisions between molecules as the concentration increases. Self-quenching may occur, reducing fluorescence intensity and making accurate detection difficult.

The present invention also provides a chemical sensor for detecting hypochlorous acid or hypochlorite including the fluorescent probe. This sensor may preferably be a silica gel thin film sensor.

Specifically, the silica gel thin film sensor may be in the form of a thin film coated with silica gel containing the fluorescent probe on an aluminum substrate.

The silica gel thin film sensor can analyze many samples simultaneously under the same conditions and is suitable for use as a detection sensor for substances such as the present invention due to the characteristic of being able to observe the results with the naked eye using UV light.

The present invention also provides a detection method for detecting hypochlorous acid or hypochlorite remaining in water (H ₂ O) using the fluorescent probe and fluorescent sensor. The method includes 1) mixing the fluorescent probe according to a preferred embodiment of the present invention described above with water (H ₂ O) to be tested (hypochlorous acid or hypochlorite is thought to be contained); and 2) introducing and detecting the mixture of the fluorescent probe and the test object into a silica gel thin film sensor.

Hereinafter, the effects of the present invention will be described in detail through specific examples. However, the following examples do not limit the scope of the present invention. The present invention can be implemented by adding, deleting, or changing non-essential elements within the scope of the technical idea including the components described in the embodiments, and it is a skill of those skilled in the art to implement it by adding, deleting, or changing such elements. It should be understood that all such embodiments are within the scope of the present invention as it is generally accomplished within the scope of the present invention.

[Example]

Example 1: Fabrication of a silica gel thin film sensor containing a fluorescent probe and fluorescence reaction experiment

1) The compound of formula 4 was synthesized in the same manner as described below.

[Formula 4]

Specifically, the phenothiazine aldehyde compound of Formula 5-1 below is reacted with the dipyrromethene compound of Formula 5-2 and the aldehyde compound of Formula 5-3.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

2) A solution of the compound of Chemical Formula 4 synthesized as described above was dissolved at a concentration of about 2.5 μM in a mixed solvent containing tetrahydrofuran (THF) and water (H ₂ O) at a volume ratio (v/v) of 9:1. Manufactured. This solution was used as a fluorescent probe for detecting hypochlorous acid or hypochlorite.

3) The probe compound in the fluorescent probe solution was mixed with water (H ₂ O) containing 0, 5, 10, 15, 20, 25, 30, 35, and 40 equivalents of NaClO, and the UV-vis spectrum was obtained. The measurements are shown in Figure 1a. Referring to Figure 1a, it was confirmed that the UV-vis peak appeared the same at all concentrations. This is a characteristic peak of porphyrin, meaning that even if it reacted with hypochlorite, the chemical structure of the porphyrin main body was not affected. In addition, Figures 3a and 3b show the fluorescence that appears after dropping a drop of the mixture for 0 and 20 equivalents on a silica gel thin film i) before drying (Figure 3a, 0 equivalents on the left, 20 equivalents on the right). , ii) Pictures taken after drying (Figure 3b, 0 equivalent on the left, 20 equivalent on the right).

4) Additionally, the same fluorescent probe solution was mixed with water (H ₂ O) containing 0, 5, 10, 15, 20, 25, 30, 35, and 40 equivalents of NaClO, and the fluorescence of the mixture was The spectrum was measured and shown in Figure 1b. Referring to Figure 1b, it was confirmed that depending on the equivalent weight, the fluorescence intensity (FL on the vertical axis) appeared in proportion to the equivalent weight of NaClO, the substance to be detected. Accordingly, it was confirmed that the fluorescent probe material and the chemical sensor containing the same according to the present invention have the advantage of being able to detect substances quantitatively.

5) In addition, the same fluorescence probe solution was reacted with 50 equivalents of water (H ₂ O) containing various active oxygen species, and the intensity of the fluorescence reaction at the fluorescence peak was detected for comparison. Active oxygen species include superoxide anion (O ₂ ^- ), hydroxyl radical (·OH), singlet oxygen ( ¹ O ₂ ), hydrogen peroxide (H ₂ O ₂ ), and nitrogen monoxide (NO), but they are active nitrogen species. (experiment together for), peroxynitride (ONOO ^- ), tert -butyl hydroperoxide ( tert -butyl hydroperoxide), TBO, blank and NaClO (ClO ^- )

Example 2: Fabrication of a silica gel thin film sensor containing a fluorescent probe and fluorescence reaction experiment

The same procedure as in Example 1 was carried out, except that the fluorescent probe was prepared using a mixture of THF and water (H ₂ O) at a volume ratio of 7:3 as a solvent.

Example 3: Fabrication of a silica gel thin film sensor containing a fluorescent probe and fluorescence reaction experiment

The same procedure as in Example 1 was carried out, except that the fluorescent probe was prepared using a solvent containing 100% THF.

Example 4: Fabrication of a silica gel thin film sensor containing a fluorescent probe and fluorescence reaction experiment

The same procedure as Example 1 was performed, except that the concentration of the fluorescent probe compound was adjusted to 0.5 μM in the mixed solution.

Example 5: Fabrication of a silica gel thin film sensor containing a fluorescent probe and fluorescence reaction experiment

The same procedure as Example 1 was performed, except that the concentration of the fluorescent probe compound was adjusted to 10.0 μM in the mixed solution.

Comparative Example 1: Fabrication of a silica gel thin film sensor containing a fluorescent probe and fluorescence reaction experiment

The same procedure as in Example 1 was performed except that a porphyrin probe without a phenothiazine group was used as the fluorescent probe compound.

Fluorescent reactions were observed for the fluorescent probe solutions prepared according to Examples 2 to 5 and Comparative Example 1 to 50 equivalents of various reactive oxygen species in the same manner as in Example 1.

When the results in Example 1 were set to 100, the relative values of other values are shown in Table 1 below. In addition, the ratio of the fluorescence response intensity for OCl ^- and the fluorescence response intensity for O ₂ ^- expressed as a percentage (related to selectivity) was compared by showing in the rightmost column.

ROS O ₂ ^{- 1} O ₂ H ₂ O ₂ ^ONOO- TBHP TBO OCl ^- O ₂ ^- /OCl ^- Example 1 100 100 100 100 100 100 100 15.6% Example 2 73 75 77 80 72 75 77 14.8% Example 3 137 140 144 148 142 140 116 18.4% Example 4 81 79 84 80 74 78 83 15.2% Example 5 179 180 187 171 188 164 133 21.0% Comparative Example 1 495 586 395 517 588 530 129 59.9%

Referring to Table 1, in Example 2 where the THF mixing ratio was less than 80 vol% and Example 4 where the fluorescent probe compound concentration was less than 1.0 μM, the fluorescence response was small for all reactive oxygen species, and on the contrary, the mixed solvent was THF 100%. %, it was confirmed that in Example 3, the fluorescence response to all reactive oxygen species was greater than that in Example 1. In Example 5, where the concentration of the fluorescent probe compound exceeds 4.0 μM, all reactive oxygen species appear significantly, but the degree is irregular.

In the case of Comparative Example 1, regardless of the size of the fluorescence response for OCl ^- , other chemical species were also measured to have similar sizes, so it was confirmed that the selectivity was significantly low and did not meet the purpose of the present invention.

Claims (11)

A fluorescent probe compound for detecting hypochlorous acid or hypochlorite salt with excellent selectivity, represented by the structure represented by the following formula (1):
[Formula 1]

In Formula 1, one or both of R ¹ to R ⁴ are functional groups containing a phenothiazine group represented by the following Formula 2,
[Formula 2]

The other has a structure represented by Formula 3 below,
[Formula 3]

The remainder is hydrogen (H) or a C ₁ to C ₆ linear or branched alkyl group,
In Formula 2, X ¹ is a single bond, C ₆ to C ₁₄ arylene, or C ₃ to C ₁₂ heteroarylene,
_{In Formula} ³ _{, _} ^{_ _} _{_ _} It is a straight or branched, saturated or unsaturated monovalent hydrocarbon chain.
According to paragraph 1,
The fluorescent probe compound is a fluorescent probe compound for detecting hypochlorous acid or hypochlorite with excellent selectivity, characterized in that it has the structure of the following formula 1-1:
[Formula 1-1]

In Formula 1-1,
R ³ and R ⁴ are each independently hydrogen (H) or a C ₁ to C ₆ straight or branched alkyl group,
_X ¹ is a _single bond, _a C ₆ to C ₁₄ arylene group or _{a C 3 to C 12 heteroarylene} ^group _,
R ^{`1</sup> and R <sup>`2} are each independently a C ₈ to C ₂₅ straight or branched, saturated or unsaturated monovalent hydrocarbon chain.
According to paragraph 1,
The fluorescent probe compound is a fluorescent probe compound for detecting hypochlorous acid or hypochlorite with excellent selectivity, characterized in that it is a compound represented by the following formula 1-2:
[Formula 1-2]

In Formula 1-2,
R ³ and R ⁴ are each independently hydrogen (H) or a C ₁ to C ₆ straight or branched alkyl group,
R ^{`1</sup> to R <sup>`2} are each independently a C ₈ to C ₂₅ straight or branched saturated or unsaturated monovalent hydrocarbon chain.
A fluorescent probe for detecting hypochlorous acid or hypochlorite comprising the fluorescent probe compound according to claim 1.
According to paragraph 4,
The probe for detecting hypochlorous acid or hypochlorite is a mixed solvent of an organic solvent and water (H ₂ O); and
A fluorescent probe for detecting hypochlorous acid or hypochlorite, comprising: a fluorescent probe compound according to claim 1 dissolved in the mixed solvent.
According to clause 5,
A fluorescent probe for detecting hypochlorous acid or hypochlorite, wherein the organic solvent is one or two or more mixed solvents selected from tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), ethanol, and methanol.
According to clause 5,
The mixed solvent of the organic solvent and water is a fluorescent probe for detecting hypochlorous acid or hypochlorite, characterized in that the mixing ratio of the organic solvent is 80 vol% to 95 vol%.
According to clause 5,
A probe for detecting hypochlorous acid or hypochlorite, wherein the fluorescent probe compound is dissolved in the mixed solvent at a concentration of 1.0 μM to 10.0 μM.
A chemical sensor for detecting hypochlorous acid or hypochlorite comprising the fluorescent probe according to any one of claims 4 to 8.
According to clause 9,
The chemical sensor is a chemical sensor for detecting hypochlorous acid or hypochlorite, characterized in that the chemical sensor is a silica gel thin film sensor.
1) Mixing the fluorescent probe according to any one of claims 4 to 8 with water (H ₂ O) to be tested; and
2) A method for detecting hypochlorous acid or hypochlorite comprising the step of introducing a mixture of the fluorescent probe and the test object onto a silica gel thin film.