KR20160015725A - A Nobel Julolidine Based Compounds, Agent Selecting Aluminum Ion Or Cyanide Ion Using The Same, Detecting Method And Detecting Device Thereof - Google Patents

Abstract

The present invention relates to: a novel julolidine-based compound; a detecting agent for aluminum ions or cyanide ions using the same; a detection method using the same; and a detection device using the same. More particularly, the present invention relates to: a julolidine-based compound which has a specific selectivity to aluminum ions (Al^+3) or cyanide ions (CN^-); a detecting agent for aluminum ions (Al^+3) or cyanide ions (CN^-) using the same; a detection method using the same; and a detection device using the same. The julolidine-based compound of the present invention is represented by chemical formula 1.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel choloridine-based compound, an aluminum ion or a cyanide ion detector using the same, a detection method, and a detection device using the same.

The present invention relates to novel Raleigh dingye compound, which by aluminum ions (Al ^{3 +)} or cyanide ion (CN ^-) detection agent, relates to a detection method and a detection apparatus, and more particularly, aluminum ions (Al ^{3 +)} or cyanide ion (CN ^{-) -} relates to the detection, the detection method and detection apparatus Raleigh dingye compound, this aluminum ions (Al ^{+ 3)} or a cyanide ion (CN) with which a specific selectivity to the.

Aluminum is the most common metal and is the next richest component of oxygen and silicon on the surface. However, excessive aluminum can cause damage to human tissues and cells, causing diseases such as Alzheimer's disease and Parkinson's disease. WHO therefore defined excess aluminum as one of the food sources and limited the aluminum concentration of drinking water to 200 μg / L (7.41 μM). In addition, the solubility of aluminum in the mineral water is increased under acidic conditions, and this increase of the aluminum ions (Al ^{+ 3)} is a fatal to plants and fish. Accordingly, it is the WHO development of which can detect an aluminum ion at a concentration below the recommended limit (Al ^{3 +)} sensitive and select sensor is very important in a wide pH range.

Cyanide anion (CN ^{-) -} toxicity is to be due to a tendency to combine with iron ions of cytochrome c oxidase, when combined with the iron ion-cyanide anion (CN ^-) of the is known as a poison to most fast acting, cyanide anion (CN) Interferes with electron transfer and causes hypoxemia. In addition, some studies have reported that cyanide anion (CN ^- ) is an important factor in many fire - related deaths. However cyanide anion (CN ^-), despite the cyanide anion to the fiber and resin, the starting materials for synthesis and the gold recovery of herbicide (CN ^-) use of toxicity is necessary. Therefore, there is a need for a reliable and effective method for detecting cyanide anion (CN ^- ).

Recent researches on the development of chemical sensors for the detection of cyanide anions (CN ^- ) have been carried out, and a study to develop a cyanide anion (CN ^- ) receptor which can be identified by simple color change without interfering with other elements It is progressing. However, many cyanide anion (CN ^- ) receptors have limitations such as the detection of fluoride and acetate ions, the use of expensive equipment, the complexity of the synthesis process, and detection only in organic solvents. Therefore, the selective detection of cyanide anions in aqueous solution remains a major challenge.

The development of chemical sensors capable of simultaneously detecting metal ions and anions is one of the most important tasks because of its potential applications in biological industries and environmental processes. In addition, one receptor that can detect multiple ions is more effective and can attract more attention because it can save money over a single detector receptor. Of the various methods of detecting both metal ions and anions, fluorescence and color change detection methods are more popular with their high sensitivity and ease of manipulation, fast response, and low cost.

Therefore, research and development of a chemical sensor capable of simultaneously detecting a metal ion and an anion in an aqueous solution are required.

Soojin Kim, Jin Young Noh, Sol Ji Park, Yu Jeong Na, In Hong Hwang, Jisook Min, Cheal Kim, Jinheung Kim. RSC Advances. 4 (2014) 18094-18099

That in combination with the optional to provide a novel Raleigh dingye compound showing a color change ^- the present invention in combination with selective with aluminum ions (Al ^{3 +)} from the metal ion emits fluorescence, and in the anion cyanide ion (CN) The purpose.

In addition, the present invention is the novel Raleigh Dean aluminum ions using the compound (Al ^{+ 3)} or a cyanide ion (CN ^-) is an object of the present invention to provide a detection agent, a detection method and a detection device.

In order to achieve the above object,

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

The present invention also provides a process for preparing the above-mentioned formula (1), which comprises reacting 8-hydroxyquinalrrolidine-9-carboxaldehyde and benzhydrazide.

The invention also aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) containing the compound of formula (I) provides a detection agent.

The invention also aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) using a compound of formula (I) provides a detection method.

The invention also aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^{-) -} provides a detection apparatus aluminum ions (Al ^{+ 3)} or a cyanide ion (CN) comprising a detection agent.

The novel rorolide compound of the present invention can be prepared at room temperature, which is advantageous in that it can be easily produced.

In addition, the novel Raleigh dingye compounds of the invention may form a complex combines metal ion and coordinated, when combined with the particular aluminum ions (Al ^{3 +)} is the fluorescence emission of aluminum ions (Al ^{3 +)} selective It can be detected, and aluminum ions (Al ^{+ 3)} in the cell as can be detected.

In addition, the novel compounds of the present invention Raleigh dingye cyanide ion (CN ^-), when combined with the color change is observed cyanide ion (CN ^-) it can be selectively detected in the.

Figure 1 of the formula I compounds of the present invention showing the structure in combination with aluminum ions (Al ^{+ 3).}
FIG. 2 is a graph showing fluorescence intensities when various metals are added to the compound of Formula 1 of the present invention. FIG.
3 is a graph showing the intensity of fluorescence when the compound of Formula 1 of the present invention is added while increasing the concentration of aluminum ion (Al ^{3 +} ).
4 is a graph showing the intensity of fluorescence measured at 488 nm when the compound of Formula 1 of the present invention is added while increasing the concentration of aluminum ion (Al ^{3 +} ).
5 is a graph of Job's plot showing the bonding ratio between the compound of formula (I) of the present invention and aluminum ion (Al ^{3 +} ).
Figure 6 is the first compound and the aluminum ions in the general formula (I) of the present invention (Al ^{3 +):} ESI-MS spectrum is shown to bond to one.
FIG. 7 is a graph showing the intensity of fluorescence when the compound of formula (I) of the present invention is disturbed from various metal ions when detecting aluminum ion (Al ^{3 +} ).
Figure 8 is a graph measuring the fluorescence intensity of the compound of general formula (I) of the present invention for the presence of aluminum ions (Al ^{+ 3)} at pH 2 to 12.
Of Figure 9 A, B, C, D, E, F and G of the addition of the aluminum ions (Al ^{3 +)} of 0, 10, 20, 40, 70, 90 and 100μM on human skin fibroblasts , And H, I, J, K, L, M, and N are fluorescence expression images when 20 μM of the compound of the present invention is added to the above A, B, C, D, E, .
10 is a graph of absorbance when various anions are added to the compound of Formula 1 of the present invention.
11 is a photograph showing the color change when various anions are added to the compound of Chemical Formula 1 of the present invention.
12 is a cyanide ion (CN ^-) to a compound of general formula (I) of the present invention in 30% aqueous methanol solution is the absorbance graph of the increase from 10 to 200 equivalents of the concentration.
13 is a graph showing absorbance at 450 nm when the concentration of cyanide ions (CN ^- ) is increased by 10 to 200 equivalents in a 30% aqueous methanol solution of the compound of the present invention.
14 is a cyanide ion (CN ^-) to a compound of general formula (I) of the present invention in 30% aqueous methanol solution is the absorbance graph of the increase from 10 to 40 equivalents of the concentration.
15 is a graph of absorbance when the concentration of cyanide ion (CN ^- ) is increased by 40 to 200 equivalents in a 30% aqueous methanol solution of the compound of the present invention.
FIG. 16 is a graph of absorbance observed when the compound of Chemical Formula 1 of the present invention is disturbed by various anions when cyanide ion (CN ^- ) is detected.
17 is a photograph of color change observed when the compound of Chemical Formula 1 of the present invention is observed to be interfered with various anions when cyanide ion (CN ^- ) is detected.
18 is a ¹ H-NMR chart when the concentration of cyanide ions (CN ^- ) is increased in the compound of formula (I) of the present invention in a 30% methanol aqueous solution.

Hereinafter, the present invention will be described in more detail.

The present invention relates to a compound represented by the following general formula (1).

[Chemical Formula 1]

The 8-hydroxyquinoloridine-9-carboxaldehyde, which contains a major lauridin structure used as a chemical sensor, is a well-known chromophore and is well soluble in water. In addition, a structure including a benzhydrazide or an amide group can detect anions through anions and hydrogen bonds.

Accordingly, it is an object of the present invention to provide a compound capable of detecting both a metal ion and an anion by synthesizing a structure including a chromolanyl group-containing chololide compound and a benzhydrazide group capable of detecting a metal ion and an anion in water, In the present invention, the compound of Formula 1 was prepared.

The compound of Formula 1 has the main pyrrolidine structure and benz high because it contains the drive Zaid can detect a metal ion and an anion, and in more particularly, the metal ions are detected with aluminum ions (Al ^{3 +),} negative ions during the cyanide Ions (CN < ^- >) can be selectively detected.

The compound of Formula 1 of the present invention is prepared through the reaction of 8-hydroxyralin-9-carboxaldehyde and benzhydrazide, and can be easily reacted at room temperature.

The invention also aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) containing the compound of formula (I) relates to a detection agent.

The compound of Formula 1 has a variety of metal ions ^{(e.g., Mn 2 +, Fe 2 +} , Fe 3 +, Co 2+, Ni 2 +, Cu 2 +, Zn 2 +, Cd 2 +, Hg 2 +, Na + ^{, K +, Mg 2 +,} Ca 2 +, Al 3 +, Pb 2 +, Cr 3 +, Ga 3 +, in 3 +) is the fluorescence intensity increased significantly when combined with aluminum ions (Al ^{3 +),} among do. In addition, the compound of formula (1) is bonded to cyanide ion (CN ^- ) among various anions (for example, CN ^- , F ^- , Cl ^- , Br ^- , I ^- , OAc ^- , SO ₄ ^{2 -} , N ₃ ^- Color change is observed.

Accordingly, the compounds of the formula (1) cyanide ion (CN ^-) from the aluminum ion (Al ^{3 +),} negative ions from the metal ion can be seen that the selectivity to, by using the properties of aluminum ions (Al ^{3 +)} or cyanide (CN < ^- >).

In addition, aluminum ions (Al ^{+ 3)} detection of the present invention may comprise a further solvent, the solvent is preferably one that the distilled water, and the like. The cyanide ion (CN ^- ) detecting agent of the present invention may further comprise a solvent, wherein the solvent is at least one selected from the group consisting of distilled water and methanol, and distilled water and methanol are used at a ratio of 0:10 to 8: 2, but is not limited thereto.

The invention aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) using a compound of formula (I) provides a detection method. More specifically the compound of formula (I) and the change in fluorescence intensity in combination with aluminum ions (Al ^{+ 3),} cyanide ion (CN ^-) in combination with providing a method of detecting a color change appears.

In addition, the present invention is the aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) it provides a detection apparatus comprising a detection agent. The detection device is aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) through a fluorescent or color change can be detected, the detection device is preferably a probe (probe).

Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples. These Examples and Experimental Examples are only for illustrating the present invention, and the scope of the present invention is not limited to these Examples and Experimental Examples.

Example  1. Preparation of compound of formula (1)

Benzhydrazide (0.14 g, 1 mmol) was dissolved in ethanol (3 mL), and then 0.23 g (1 mmol) of 8-hydroxyquinoloridine-9-carboxaldehyde was added to the solution. Then, 2 drops of hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The yellow precipitate was filtered off several times with cold ethanol and dried under vacuum to give the compound.

[Reaction Scheme 1]

Further, the structure of the compound was confirmed by ¹ H-NMR, ¹³ C-NMR, HRMS and EA analysis.

Yield: 0.17 mg (51%).

^{1 H-NMR (DMSO-d} 6, 400 MHz): δ 11.79 (s, 1H), 11.78 (s, 1H), 8.31 (s, 1H), 7.91 (d, 2H), 7.59 (t, 1H), 2H), 6.72 (s, 1H), 3.18 (m, 4H), 2.62 (m, 4H), 1.86 (m, 4H).

¹³ C-NMR (DMSO-d ₆ , 400 MHz): 162.78, 155.37, 151.58, 145.90, 133.83, 132.31,129.14,128.96,128.15,119.10,106.96,106.45,50.00,49.54,27.21,22.20,21.38,20.91 ppm .

HRMS (ESI): [M + H ^& lt ^{; +} & gt ^; ]: calcd, 335.16, found, 335.23.

EA: Anal. Calcd for C ₂₀ H ₂₁ N ₃ O ₂ (335.41): C 71.62, H 6.31, N 12.53%

Found: C 71.45, H 6.45, N 12.39%.

Through the above analysis, it was confirmed that the compound prepared in Example 1 had the structure of Formula 1 of the present invention.

Experimental Example  1. Fluorescence analysis of compounds of formula (I) for various metal ions

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol and 10 μL (3 mM) was taken and diluted in 2.99 mL of water to prepare a final concentration of 10 μM. Various metal ions of 19 equivalents to the solution ^{(Mn 2 +, Fe 2 +} , Fe 3 +, Co 2 +, Ni 2+, Cu 2 +, Zn 2 +, Cd 2 +, Hg 2 +, Na +, K ^{+, Mg 2 +, Ca 2} +, Al 3 +, Pb 2 +, Cr 3 +, to put the Ga ^{3 +,} in ^{3 +)} solution, respectively, using fluorescence (fluorescence) device to measure the respective fluorescence intensity ( lt; / RTI > = 410 nm). All of the metal ion solutions used were nitrate salts and distilled water was used as a solvent.

As a result, ^{Mn 2 +, Fe 2 +,} Fe 3 +, Co 2 +, Ni 2 +, Cu 2 +, Zn 2 +, Cd 2 +, Hg 2 +, Na +, K +, Mg 2 +, Ca 2 Metal ions such as ⁺ , Pb ^{2 +} , Cr ^{3 +} , Ga ^{3 +} and In ^{3 +} did not increase fluorescence intensity and showed no change in fluorescence. On the other hand, aluminum ion (Al ^{3 +} ) showed a strong increase in fluorescence intensity (FIG. 2).

Accordingly, the compounds of general formula (I) of the present invention it was found that by combining (1) and the aluminum ions (Al ^{+ 3),} because the fluorescence emission, and optionally detected with the aluminum ions (Al ^{+ 3).}

Experimental Example  2. Aluminum ion ( Al ^{3 +} ) ≪ / RTI > of the compound of formula (1)

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol, and then 10 μL (3 mM) was taken and diluted in 2.99 mL of water to prepare a final concentration of 10 μM. Fluorescence intensity was measured using a fluorescence instrument while increasing the concentration of aluminum ion (Al ^{3 +} ) to 1 to 19 equivalents per equivalent of the solution (FIG. 3).

The intensity of fluorescence increased as the equivalent of aluminum ion (Al ^{3 +} ) increased. More specifically, since 10 equivalents, the intensity of fluorescence gradually increased, the intensity of fluorescence increased to 19 equivalents, and no change thereafter (FIG. 4). Further, it was found through the Job's plot that the coupling ratio of the compound of formula (1) and aluminum ion (Al ^{3 +} ) was one to one (FIG. 5).

The ESI-MS experiment was conducted to investigate the binding ratio between the compound of formula (1) prepared in Example 1 and aluminum ion (Al ^{3 +} ). As a result, a single aluminum ion (Al ^{3 +)} and a value when the combination of two compounds of the formula: is measured with the highest values in (m / z = 423.60, the theoretical 423.125), and of a compound of formula It was found that the aluminum ion (Al ^{3 +} ) was 1: 1 bonded (FIG. 6).

Experimental Example  3. Other metal ions and pH Is an aluminum ion ( Al ^{3 +} ) And the fluorescence intensity of the compound of formula (1)

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol, and then 10 μL (3 mM) was taken and diluted in 2.99 mL of water to prepare a final concentration of 10 μM. Formula other metal ions in the solution of compound ^{1 (Mn 2 +, Fe 2} +, Fe 3 +, Co 2+, Ni 2 +, Cu 2 +, Zn 2 +, Cd 2 +, Hg 2 +, Na +, ^{K +, Mg 2 +, Ca} 2 +, Pb 2 +, Cr 3 +, Ga 3 +, In 3 +) , respectively, insert by 19 equivalents, aluminum ions (Al ^{3 +)} also put 19 eq measuring fluorescence Respectively.

As a ^{result, Mn 2 +, Co 2 +} , Ni 2 +, Zn 2 +, Cd 2 +, Hg 2 +, Na +, K +, Mg 2 +, Ca 2 +, Pb 2 +, Ga 3 +, In ³⁺ did not interfere with the fluorescence intensity of the metal ions such as aluminum ions are compounds of formula ^{1 (Al 3 +), Fe} 2 +, Fe 3 +, Cu 2 +, Cr 3 + metal ions such as are of the formula And interferes somewhat with the interaction of the compound with aluminum ions (Al ^< ^{3 + &} gt ^; ) (Fig. 7).

In addition, the aluminum ion is a compound of formula (1) prepared in Example 1 in combination with (Al ^{+ 3)} was observed how the fluorescent intensity varies with the pH (Fig. 8).

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol, and then 10 μL (3 mM) was taken and diluted in 2.99 mL of water to prepare a final concentration of 10 μM. 30 mM of aluminum ion (Al ^{3 +} ) was added to the compound of formula (1), and the solutions of pH 2 to 12 were measured with a fluorescence instrument. showed fluorescence sensitivity at pH 3 to 11, and excellent fluorescence sensitivity at pH 4 to 10. If the pH range outside of the above range, has about the fluorescence intensity, when aluminum ions (Al ^{+ 3)} does not have the fluorescence intensity was not observed.

Experimental Example  4. Compounds of formula (I) and aluminum ions Al ^{3 +} ) In the cell

Intracellular experiments were carried out to examine the fluorescence ability of the compound of Formula 1 prepared in Example 1 in the presence of aluminum ion (Al ^{3 +} ).

To aluminum ions (Al ^{+ 3)} of human skin fibroblasts (dermal fibroblast), respectively 0, 10, 20, 40, 70, 90 and 100μM (A to G in Fig. 9) were exposed for four hours. The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol and then 20 μL (2 mM) was taken and diluted in 2.98 mL of water to prepare a final concentration of 20 μM 1 for 30 minutes, and a fluorescence image was observed (H to N in FIG. 9).

Human skin fibroblasts aluminum ions (Al ^{3 +)} is not present, thus as is the absence of a compound of formula 1 did not show fluorescence, the fluorescence intensity in the cells is increased the concentration of the aluminum ions (Al ^{3 +)} Respectively.

Thus, a compound of formula (1) prepared in Example 1 may detect the aluminum ions (Al ^{+ 3)} in the cells by fluorescence.

Experimental Example  5. Absorbance analysis of compounds of formula (1) for various anions

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol, and then 30 μL (3 mM) was taken and diluted in 2.97 mL of 30% aqueous methanol to obtain a final concentration of 30 μM. Was prepared. The color change was observed by adding 200 equivalents of various anions (CN ^- , F ^- , Cl ^- , Br ^- , I ^- , OAc ^- , SO ₄ ^{2 -} , N ₃ ^- ) to the solution. All of the anion solutions used were tetraethylammonium salt and water was used as the solvent.

The cyanide anion (CN ^- ) changed color from colorless to yellow and no color change was observed for other anions (Fig. 11). Further, 200 equivalents of various anions (CN ^- , F ^- , Cl ^- , Br ^- , I ^- , OAc ^- , SO ₄ ^{2 -} , N ₃ ^- ) were added to the compound of Formula 1 having a concentration of 30 μM As a result of observation with UV-vis, it was confirmed that there was almost no difference in spectrum between the compound of formula (1) and other anions, and the wavelength was changed in the case of cyanide anion (CN ^- ) (FIG.

Accordingly, it was found that the compound of formula (I) of the present invention selectively detects cyanide anion (CN ^- ).

Experimental Example  6. Cyanide ion ( CN ^- ) ≪ / RTI > of the compound of formula (I)

UV titration experiments were carried out to examine the binding properties of the compound of formula (1) prepared in Example 1 and the cyanide anion (CN ^- ).

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol, and then 30 μL (3 mM) was taken and diluted in 2.97 mL of 30% aqueous methanol to obtain a final concentration of 30 μM. Was prepared. Absorbance was measured using a UV-vis instrument while gradually increasing the concentration of the cyanide anion (CN ^- ) by 10 to 200 equivalents in 10 equivalents (FIG. 12). As the concentration of cyanide ion (CN ^- ) increases, the absorbance increases at 450 nm (FIG. 13).

More specifically, the result of the absorbance according to the concentration of cyanide ion (CN ^- ) was divided into two steps. As the first step, the absorbance at 478 nm decreased as the concentration of cyanide anion (CN ^- , And a new absorption wavelength was generated at 350 nm and 400 nm (Fig. 14). Also, an isosbestic point was observed at 337 nm and 408 nm.

As a second step, it was confirmed that as the concentration of cyanide anion (CN ^- ) increased from 40 equivalents to 200 equivalents, the absorbance decreased at 370 nm and a new absorption wavelength was generated at 290 nm and 450 nm. An isosbestic point was also observed at 324 nm and 403 nm (Fig. 15).

As a result of the above two steps, it was confirmed that hydrogen was separated from -OH of phenol and -NH 2 of amide. In addition, bathochromic shift of the absorption wavelength revealed that the deprotonation of the chemical sensor by the cyanide anion (CN ^- ) caused intramolecular charge transfer (ICT).

Experimental Example  7. Other anions are cyanide ions ( CN ^- ) And the effect of the compound of formula (1) on the absorbance

The effect of different anions on the absorbance of the compound of formula (1) prepared in Example 1 and the cyanide ion (CN ^- ) was observed.

The compound of Formula 1 (1.01 mg, 0.003 mmol) prepared in Example 1 was dissolved in 1 mL of methanol, and then 30 μL (3 mM) was taken and diluted in 2.97 mL of 30% aqueous methanol to obtain a final concentration of 30 μM. Was prepared. Other anions to the solution ^{(F -, Cl -, Br} -, I -, OAc -, SO 4 2 -, N 3 -) , respectively, insert by 200 equivalents of cyanide ion (CN ^-) is also put in the absorption of 200 eq. (Fig. 16).

Other anion ^{(F -, Cl -, Br} -, I -, OAc -, SO 4 2 -, N 3 -) is a compound with cyanide anion (CN ^-) of formula (1) did not interfere with the absorbance, a color shift (Fig. 17).

Therefore, it has been found that the compound of formula (1) has high selectivity for cyanide ion (CN ^- ) even in the presence of other anions, and thus can be used as an effective detecting agent capable of detecting cyanide ions (CN ^- ).

Experimental Example  8. Cyanide ion ( CN ^- ) And a proton for the compound of formula (I) Nuclear magnetic  resonance( ^One H- NMR ) Titration experiment

¹ H-NMR titration in DMSO- d ₆ was carried out to investigate the deprotonation reaction of the compound of Formula 1 prepared in Example 1 with cyanide ion (CN ^- ).

Example 1 The compound of formula (1) prepared in (3.35 mg, 0.01 mmol) was dissolved in DMSO- d ₆ in 700 μL, cyanide ion (CN ^-) in the solution of 0, 0.5, 1.0, 2.0, 5.0 ¹ H-NMR was measured (Fig. 18).

When two equivalents of cyanide ions (CN < ">) are added, the hydroxyl group of the compound of formula The H of the cation and amide groups The cation peak completely disappeared. The above results indicate that the addition of cyanide ion (CN < ^- >) caused a deprotonation reaction between the hydroxyl group and the amide group.

Claims (11)

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

8-hydroxyquinoloridine-9-carboxaldehyde and benzhydrazide are reacted in the presence of a base. (Al ^< ^{3 + &} gt ^; ) or a cyanide ion (CN < ^- >) detecting agent comprising the compound of Chemical Formula 1 of claim 1. The method according to claim 3, wherein the aluminum ions (Al ^{+ 3)} is the detected first detected, characterized in that that may include a solvent in addition. 5. The detection agent according to claim 4, wherein the solvent is distilled water. The detecting agent according to claim 3, wherein the cyanide ion (CN ^- ) detecting agent can further comprise a solvent. 7. The detection agent according to claim 6, wherein the solvent is at least one selected from the group consisting of distilled water and methanol. 8. The detection agent according to claim 7, wherein the distilled water and methanol are mixed at a volume ratio of 0:10 to 8: 2. Aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) using a compound of general formula (I) of claim 1 detection method. Of claim 3 aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) containing the detection agent detector. The method according to claim 10, wherein the aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-) detection apparatus aluminum ions (Al ^{+ 3)} or a cyanide ion (CN ^-), characterized in that the probe (probe) detection apparatus.

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