KR101239668B1 - Thioamide compounds having selectivity for Oxone and method for monitoring Oxone using the same - Google Patents

Abstract

The present invention relates to a thioamide compound having an oxone selectivity and an oxone detection method using the same. Significantly increased, it can be used as a turn-on type selective fluorescent sensor.

Description

Thioamide compounds having oxone selectivity and a method for detecting oxone using the same {Thioamide compounds having selectivity for Oxone and method for monitoring Oxone using the same}

The present invention relates to a thioamide compound having an oxone selectivity that can be used as a chemical sensor and a method for detecting oxone using the same.

The search for selective and effective signaling systems for detecting various chemically and biologically related species is an important area of research. In particular, the study of the signaling of a number of biologically significant oxidants, such as hydrogen peroxide, hypochlorous acid, has attracted much interest. However, little research has been done on convenient signaling of more substantial oxidants such as peracids, peroxymonosulfates, and the like.

Among many complex signaling systems, chemical dosimeters have received much attention because of their specificity and weighted signaling effects. There are many useful probe systems for the analysis of metal ions using desulfurization and / or ring forming reactions with metal ions. In particular, desulfurization of thioamides into amide analogues has been used as a signaling means for mercury ions and silver ions.

Potassium peroxymonosulfate (potassium peroxymonosulfate) is known as Oxone (oxone) as a component of the trichloride having the formula 2KHSO ₅ · KHSO ₄ · K ₂ SO ₄ . Oxone is widely used as an oxidant for various consumer applications, such as animal disinfectants, denture cleaners, and non-chlorine oxidants for pool and spa cleanliness. Oxone is also used in industrial applications such as circuit board etching solutions, pulp regeneration, wood cleaning, and oxidation of sulfur and cyanide reduced in wastewater treatment. In synthetic organic chemistry, on the other hand, oxone is a versatile oxidant for converting aldehydes to carboxylic acids or for epoxidation of alkenes. Oxone also oxidizes thioethers to sulfones, pyridines to pyridine-N-oxides, and amines to nitroxides. In particular, oxone has been used as a convenient and inexpensive oxidizing agent for converting thiocarbonyl compounds such as thioamide, thiourea, thioester and the like to the corresponding oxo derivatives.

Measuring the correct concentration of oxone is necessary for accurate monitoring of this oxidant in swimming pools, household products and other industrial processes. In general, oxone can be analyzed using standard iodine metrics or by treatment with excess ammonium sulfate (II) sulfate followed by back titration with a standardized potassium permanganate or cerium sulfate solution.

Although oxone is widely applied, no convenient optical measurement method for detecting it has been reported yet.

It is an object of the present invention to provide a fluorescence signaling detection system using thioamide compounds for simple oxone specific optical measurements.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1)

[Formula 1]

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

The present invention also provides a process for preparing a compound of formula 1 comprising converting an amide compound represented by formula 2 to a thioamide:

[Formula 2]

[Formula 1]

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

In one embodiment, the compound of Formula 2 may be prepared by reacting a compound represented by Formula 3, oxalyl chloride, and a compound represented by Formula 4 under a catalyst:

(3)

R-COOH

[Formula 4]

HNR ₁ R ₂

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

The present invention also provides a sensor for detecting oxone (Oxone) comprising the compound represented by the formula (1):

[Formula 1]

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

The present invention also provides a composition for detecting oxone (Oxone) comprising the compound represented by the formula (1).

The present invention also provides a method for detecting oxone, comprising reacting a sample represented by Chemical Formula 1 with a sample containing Oxone.

The thioamide compound of the present invention is significantly converted into an oxo analogue through selective desulfurization reaction by oxone, and the fluorescence intensity is significantly increased, and the increase in fluorescence may occur without interference of other oxidants, metal ions, and anions. It can be used as an on-type selective fluorescent sensor.

Figure 1 shows the ¹ H NMR and ¹³ C NMR spectrum of the thioamide compound of the present invention.
Figure 2 shows the ¹ H NMR and ¹³ C NMR spectrum of the amide compound of the present invention.
FIG. 3 shows thioamide compound (5.0 × 10 ⁻⁶ M), oxone (5.0 × 10 ⁻⁴ M) of the present invention in acetate buffer (pH = 5.0) / CH ₃ CN (90:10, v / v). The UV-vis spectrum of the thioamide compound and the amide compound (5.0 × 10 ⁻⁶ M) in the presence thereof is shown.
4 shows oxone (5.0 × 10 ⁻⁴ M), hydrogen peroxide (5.0 × 10 ⁻⁴ M), or a mixed solution of acetonitrile and acetate buffer (pH 5.0, 10 mM) (10:90, v / v), or The fluorescence spectrum of the thioamide compound (5.0 × 10 ⁻⁶ M) of the present invention is shown in the presence of hydrogen peroxide and oxone (1 _ex = 340 nm).
Figure 5 shows the effect of pH on the reaction of the thioamide compound (5.0 × 10 ^-6 M) and oxone (5.0 × 10 ^-4 M) of the present invention under water-soluble conditions.
FIG. 6 shows partial ¹³ C NMR spectra of thioamide compounds of the present invention (3.0 × 10 ⁻² M), thioamide compounds upon reaction with oxone, and amide compounds (3.0 × 10 ⁻² M) in deuterated chloroform The spectrum of the thioamide compound in the reaction with oxone is obtained for the purification product of the reaction of 2 equivalents of oxone with the thioamide compound in an acetonitrile aqueous solution.
FIG. 7 shows thioamide compound (5.0 × 10 ⁻⁶ M), oxone (5.0 × 10 ⁻⁴ M) of the present invention in acetate buffer (pH = 5.0) / CH ₃ CN (90:10, v / v). Fluorescence spectra of the thioamide compound and the amide compound (5.0 × 10 ⁻⁶ M) in the presence are shown (λ _ex = 340 nm).
FIG. 8 shows the time-dependent changes in fluorescence intensity of thioamide compounds (5.0 × 10 ⁻⁶ M) of the present invention with or without oxone (5.0 × 10 ⁻⁵ M) in a 10 mM acetate buffered 90% acetonitrile solution. Shown (l _ex = 340 nm).
9 shows fluorescence titration of the thioamide compound (5.0 × 10 ⁻⁶ M) of the present invention using oxone in a mixed solution of acetonitrile and acetate buffer (pH 5.0, 10 mM) (10:90, v / v). Shown (l _ex = 340 nm).
10 is measured at 377 nm in the presence of representative metal ions and anions (5.0 × 10 ⁻⁴ M) in a mixed solution (10:90, v / v) of acetonitrile and acetate buffer (pH 5.0, 10 mM) Fluorescence signaling of oxone (5.0 × 10 ⁻⁵ M) by the thioamide compound (5.0 × 10 ⁻⁶ M) of the present invention is shown (λ _ex = 340 nm).

EMBODIMENT OF THE INVENTION Hereinafter, the structure of this invention is demonstrated concretely.

In order to design a simple oxone specific optical measurement method, the inventors have selected an aromatic moiety as the fluorophore for oxone signaling, and the thioamide derivative having the aromatic moiety is subjected to desulfurization reaction by oxone in the receiving medium. The present invention has been completed by identifying effective and selective fluorescence signaling of oxone.

Accordingly, the present invention relates to a compound represented by the following formula (1) and a method for preparing the same:

[Formula 1]

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

The terms used in the substituent definitions of the compounds of the present invention are as follows.

"Alkyl" refers to straight or branched chain saturated hydrocarbons having 1 to 6 carbon atoms unless otherwise indicated. Examples of C _1-6 alkyl groups include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl and isohexyl Do not.

"Aryl" refers to an aromatic ring compound of 11 to 24 reduction unless otherwise stated. Examples of aryl groups include, but are not limited to, anthracenyl, pyrenyl, and the like.

In addition, the term “pyrene-thioamide or pyrene-amide compound” herein means a thioamide or amide compound containing a pyrene moiety.

Specific examples of the compound of Formula 1

R is pyrenyl,

R ₁ and R ₂ may be each independently hydrogen or a compound representing alkyl having 1 to 4 carbon atoms.

The thioamide compound of Formula 1 may be used as a fluorescence sensor for selectively detecting oxone because the fluorescence intensity increases through a desulfurization reaction in which sulfur atoms are released by oxone.

The method for preparing a thioamide compound of Formula 1 may include converting an amide compound represented by Formula 2 to a thioamide compound:

[Formula 2]

[Formula 1]

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

The compound of Formula 2 may be prepared by reacting a compound represented by Formula 3, oxalyl chloride, and a compound represented by Formula 4 under a catalyst:

(3)

R-COOH

[Formula 4]

HNR ₁ R ₂

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

As the compound of Formula 3, 1-pyrenecarboxylic acid (1-pyrenecarboxylic acid), 1-pyreneacetic acid (1-pyreneacetic acid), 1-pyrenebutyric acid (1-pyrenebutrylic acid) and the like may be used. There is no restriction in particular.

Dimethylamine, Diethylamine, Dipropylamine, Di-iso-propylamine, Dibutylamine, Di-butyl as a compound of Formula 4 -Butylamine (Di-sec-butylamine), di-tert-butylamine (Di-tert-butylamin) and the like can be used, but is not particularly limited thereto.

N, N-dimethylformamide may be used as the catalyst, but is not particularly limited thereto.

The compound of Chemical Formula 2 may be synthesized by dissolving the compound of Chemical Formula 2 in a solvent such as toluene and xylene, followed by reaction with a sulfiding reagent, for example, a Lawesson reagent.

Method for preparing a thioamide compound of formula 1 according to an embodiment of the present invention may be prepared according to the following scheme 1:

[Reaction Scheme 1]

According to Scheme 1, 1-pyrenecarboxylic acid and oxalyl chloride are reacted using N, N-dimethylformamide as a catalyst, and the reactant and diethylamine dissolved in dichloromethane are mixed with diethylamide compound ( Formula 2) is prepared.

In the next step, the diethylamide compound is dissolved in a solvent such as toluene, and then Lawesson reagent is added to synthesize the diethylthioamide compound (Formula 1) in high yield.

The present invention also relates to a sensor for detecting oxone (Oxone) comprising a compound represented by the following formula (1):

[Formula 1]

Where

R is aryl having 11 to 24 carbon atoms,

R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.

Specific examples of the compound of Formula 1

R is pyrenyl,

R ₁ and R ₂ may be each independently hydrogen or a compound representing alkyl having 1 to 4 carbon atoms.

The thioamide compound of Formula 1 may be used as a fluorescence sensor for selectively detecting oxone because the fluorescence intensity increases through a desulfurization reaction in which sulfur atoms are released by oxone.

According to the mechanism of Scheme 2, fluorescence signaling is due to desulfurization by oxone of thioamide. Under aqueous solution, the thioamide compound exhibits very weak fluorescence but is converted to oxoamide with the release of sulfur atoms by oxone, resulting in a turn-on type of fluorescence signaling property that exhibits strong fluorescence:

[Reaction Scheme 2]

The thioamide compound of formula 1 according to the present invention “turn-on” the thioamide compound as it shows a selective increase in fluorescence at 377 nm and 397 nm wavelengths depending on the concentration of oxone in aqueous solution. Oxon can be detected using a type of fluorescent probe.

According to one embodiment of the invention, the thioamide compound of the formula (I) is _{^{F -, Cl -, SO 4}} 2-, HPO 4 -, P 2 O 7 4-, NO 3 -, AcO -, ClO 4 -, or Anion such as HCO ₃ ⁻ does not show a fluorescence change, but when reacted with oxone, it shows a large change in fluorescence in a concentration-dependent manner.

According to one embodiment of the present invention, the thioamide compound of Formula 1 according to the present invention, in addition to oxone, alkali metal ions (Na ⁺ , K ⁺ ), alkaline earth metal ions (Mg ²⁺ , Ca ²⁺ ), etc., are present in the aqueous solution. Even if it reacts selectively with oxone, it shows a big fluorescence change.

According to one embodiment of the present invention, the thioamide compound of formula 1 according to the present invention selectively reacts with oxone even in the presence of other oxidants, for example hydrogen peroxide, in addition to oxone to exhibit a large fluorescence change.

In addition, the thioamide compound of Formula 1 exhibits moderate UV-vis absorption at 334 nm and 349 nm, but shows a significantly increased peak shift to 325 nm and 341 nm in a concentration-dependent manner through selective reaction with oxone. By measuring this, the signal of oxone may be measured.

The sensor for detecting oxone of the present invention may be provided as a conventional kit that can check the presence and concentration of oxone by mixing with a sample solution to detect oxone.

The present invention also relates to an oxone detecting composition comprising the compound represented by Chemical Formula 1.

Oxon detecting composition of the present invention may include a buffer solution in addition to the compound represented by the formula (1). The type and concentration of the buffer solution are not particularly limited, but may be appropriately changed depending on the application of the composition for detecting oxone. More specifically, it may be a buffer solution of pH 3 to 10. Most specifically, an aqueous acetonitrile solution of pH 3 to 10 buffered with acetate buffer may be used.

The present invention also relates to a method for detecting oxone, which comprises reacting a compound represented by Chemical Formula 1 with a sample containing Oxone.

The thioamide compound of formula 1 of the present invention is a "turn-on" type sensor that can detect oxone in an aqueous solution, and the intensity of fluorescence is amplified when oxone is detected in the state of weak fluorescence. This sensor is a sensor type sensor that can detect oxone quickly because of its fast reaction speed. According to one embodiment, the reaction rate can be completed within 10 minutes.

In addition, the detection of oxone by the thioamide compound of the formula (1) can be carried out in an aqueous solution or a mixed aqueous solution containing an organic solvent such as methanol, acetonitrile, tetrahydrofuran, dimethyl sulfoxide, dioxane.

As the aqueous solution, an aqueous solution of pH 3 to 10, more specifically, an acetonitrile aqueous solution of pH 3 to 10 buffered with an acetate buffer may be used, but is not particularly limited thereto.

In addition, the detection of oxone by the thioamide compound of the formula (1) is to measure the change in fluorescence intensity, it can be measured because the fluorescence intensity increases depending on the concentration of oxone.

The detection of oxone can be measured as it shows a significantly increased absorbance at 334 nm and 349 nm in a concentration dependent manner.

Hereinafter, the present invention will be described in more detail through examples according to the present invention, but the scope of the present invention is not limited to the examples given below.

Example 1 Preparation of Pyrene-thioamide Compound

A method for preparing a pyrene-thioamide compound for detecting oxone is briefly shown in Scheme 1 above.

To synthesize the pyrene-amide compound of formula 2 according to Scheme 1, oxalyl chloride (0.11 mL, in a solution of 1-pyrenecarboxylic acid (100 mg, 0.41 mmol) dissolved in CH ₂ Cl ₂ (4 mL) 1.2 mmol) was added. In addition, a drop of N, N-dimethylformamide was injected as a catalyst. The mixture was stirred at rt for 4 h. Pyrene-1-carbonyl chloride was obtained after evaporation of the volatiles. The product was dissolved in a CH ₂ Cl _{2 (2} mL) was, CH ₂ Cl added dropwise to diethyl amine (0.2 mL, 2.0 mmol) dissolved in ₂ (5 mL). The mixed solution was stirred at room temperature for 3 hours. The mixed solution was washed three times with distilled water (75 mL), evaporated and concentrated to yield a pyrene-amide compound as a yellowish product (120 mg, 98%).

¹ H NMR (CDCl ₃ , 300 MHz): δ 8.20-7.91 (m, 9H), 3.92 (dq, J = 6.8 and 6.8 Hz, 1H), 3.65 (dq, J = 6.5 and 6.5 Hz, 1H), 3.11 (dq, J = 6.5 and 6.5 Hz, 2H), 1.45 (t, J = 7.2 Hz, 3H), 0.96 (t, J = 7.2 Hz, 3H).

¹³ C NMR (CDCl ₃ , 600 MHz): δ 170.7, 132.1, 131.4, 131.2, 130.9, 128.6, 128.0, 127.3, 127.2, 126.3, 125.6, 125.5, 124.7, 124.6, 124.5, 124.0, 123.4, 43.3, 39.3 , 14.3, 13.2.

HRMS (DIP) m / z calcd for C ₂₁ H ₁₉ NO [M + H] ⁺ 301.1467; found, 301.1453.

Next, Lawesson's reagent (177 mg, 0.44 mmol) was added to a solution of the pyrene-amide compound (120 mg, 0.40 mmol) dissolved in toluene (5 mL) to synthesize a pyrene-thioamide compound of Formula 1. Then refluxed for overnight. The solvent was evaporated and the crude product was purified by flash column chromatography (silica gel, CH ₂ Cl ₂ / MeOH = 9: 1) to give pyrene-thioamide compound as a yellow solid (101 mg, 78% ).

1 and 2 show ¹ H NMR and ¹³ C NMR spectra of the thioamide compound and the amide compound, respectively.

¹ H NMR (CDCl ₃ , 300 MHz): δ 8.22-7.8 (m, 9H), 4.61 (dq, J = 6.8 alc 13.6 Hz, 1H), 4.10 (dq, J = 6.8 alc 13.5 Hz, 1H), 3.33 (q, J = 7.1 Hz, 2H), 1.60 (t, J = 7.1 Hz, 3H), 1.03 (t, J = 7.1 Hz, 3H).

¹³ C NMR (CDCl ₃ , 600 MHz): δ 199.1, 137.8, 131.3, 130.9, 130.8, 128.6, 127.7, 127.2, 126.3, 125.6, 125.4, 125.2, 124.8, 124.7, 124.6, 123.7, 123.0, 47.9, 45.9 , 13.8, 11.4.

HRMS (DIP) m / z calcd for C ₂₁ H ₁₉ NS [M + H] ⁺ 317.1238; found, 317.1232.

Experimental Example 1 Measurement of UV-vis Spectrum of Pyrene-thioamide Compound by Oxon

The interaction of oxone with pyrene-thioamide compound of formula 1 showed a significant change in UV-vis spectral behavior (FIG. 3). When oxone was treated by the content of the pyrene-thioamide compound of formula 1 in an aqueous solution of acetonitrile (acetate buffered H ₂ O: CH ₃ CN = 9: 1, v / v), the compound of formula 1 at 334 and 349 nm The absorption band of the pyrene-thioamide compound shifted slightly blue at 325 and 341 nm.

Experimental Example 2 Measurement of Fluorescence Spectrum of Pyrene-thioamide Compound by Oxon

The pyrene-thioamide compound of formula 1 exhibited very weak fluorescence emission around 345-510 nm in 90% acetonitrile aqueous solution buffered with acetate buffer at pH 5.0 (FIG. 4). The weak release of thioamide compounds of formula 1 is due to the presence of thiocarbonyl sulfur atoms.

In addition, the pyrene-thioamide compound of formula 1 exhibited a constant fluorescence increase between pH 3 and 10 by oxone (FIG. 5), and the colorless solution appeared light blue when illuminated with a UV lamp.

The I / I _o ratio by oxone, where I and I _o respectively represent the fluorescence intensity after and before the addition of the oxidant, with a fluorescence intensity ratio measured at 377 nm being 281. On the other hand, hydrogen peroxide, another important oxidant, had little effect on the fluorescence of the pyrene-thioamide compound of formula 1, and its fluorescence intensity ratio I / I _o was 1.01.

From the above results, it is believed that the signaling takes place by selective desulfurization of the thioamide of the pyrene-thioamide compound of formula (1) by reaction with oxone (Scheme 2). Chemical modification of the pyrene-thioamide compound of formula 1 to the oxo derivatives is demonstrated by ¹³ C NMR, UV-vis, and fluorescence measurements.

The ¹³ C NMR spectrum of the product obtained by treating two equivalents of oxone with the pyrene-thioamide compound of formula 1 was almost identical to that of the amide compound of formula 2 (FIG. 6).

In addition, the UV-vis and fluorescence spectra of the pyrene-thioamide compound of formula (1) in the presence of oxone were nearly the same as those of the pyrene-amide compound of formula (2) (FIGS. 3 and 7).

The signaling of oxone by the pyrene-thioamide compound of formula 1 was quite fast and showed a constant signal within 10 minutes (FIG. 8). On the other hand, in the absence of oxone, the pyrene-thioamide compound of Formula 1 was stable, and the fluorescence behavior was not detectable until 24 hours after sample preparation.

Fluorescence titration of the pyrene-thioamide compound of formula 1 using oxone yielded a linear calibration curve for oxone up to 2 equivalents (FIG. 9). From this titration curve, the detection limit for oxone analysis was estimated to be 1.9 × 10 ⁻⁶ M (1.2 ppm) in 90% aqueous acetonitrile. This detection limit for the pyrene-thioamide compound of formula 1 is much lower (˜20 ppm) than the oxone concentration used for the non-chlorine oxidant used for swimming pool cleanliness.

Experimental Example 3 Selective Detection of Oxone in the Presence of Other Metal Ions

The possibility of interference in the presence of metal ions and anions commonly found in nature or in tap water in oxone signaling by the pyrene-thioamide compound of formula 1 was investigated (FIG. 10).

For the signaling of oxone by pyrene-thioamide compounds of formula 1 from alkali and alkaline earth metal ions (Na ⁺ , K ⁺ , Mg ²⁺ and Ca ²⁺ ) as well as common anions such as chlorine, nitrate and sulfate Interference was not noticed.

In summary, the present invention provides a new and simple chemical signaling system based on the modification of thioamide to amide for the oxidant, oxone, which is widely used, wherein the pyrene-thioamide derivatives of the present invention are micromolar in aqueous solution. There was clear signaling of oxone in the concentration range. The pyrene-thioamide compounds of the present invention also exhibited effective oxone selective fluorescence signaling behavior without interference in the presence of hydrogen peroxide as well as common metal ions and anions.

Claims (13)

A compound represented by the following formula (1):
[Formula 1]

In this formula,
R is aryl having 11 to 24 carbon atoms,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.
The method of claim 1,
R is pyrenyl,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 4 carbon atoms.
Method for preparing a compound of formula 1 comprising the step of converting an amide compound represented by the formula (2) to a thioamide (thioamide):
(2)

[Formula 1]

In this formula,
R is aryl having 11 to 24 carbon atoms,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.
Sensor for detecting oxone (Oxone) comprising a compound represented by the formula (1):
[Formula 1]

In this formula,
R is aryl having 11 to 24 carbon atoms,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.
5. The method of claim 4,
R is pyrenyl,
R <_1> and R <_2> respectively independently represents hydrogen or the C1-C4 alkyl sensor for oxone detection.
Oxone (Oxone) detection composition comprising a compound represented by the formula (1):
[Formula 1]

In this formula,
R is aryl having 11 to 24 carbon atoms,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.
The method according to claim 6,
R is pyrenyl,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 4 carbon atoms.
A method for detecting oxone comprising reacting a sample represented by Formula 1 with a sample containing oxone:
[Formula 1]

In this formula,
R is aryl having 11 to 24 carbon atoms,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 6 carbon atoms.
9. The method of claim 8,
R is pyrenyl,
R ₁ and R ₂ each independently represent hydrogen or alkyl having 1 to 4 carbon atoms.
9. The method of claim 8,
The method of detecting oxone is carried out under an aqueous solution of pH 3 to 10.
The method of claim 10,
An aqueous solution is a method for detecting oxone, which is an acetonitrile aqueous solution buffered with acetate buffer.
9. The method of claim 8,
The detection method of oxone is to determine the presence of oxone by measuring the increase in fluorescence intensity at 377 nm and 397 nm when measuring the fluorescence spectrum.
9. The method of claim 8,
The detection of oxone is to determine the presence of oxone by measuring the absorbance peaks appearing at 325 nm and 341 nm when UV-vis spectrum measurement.

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