KR101638682B1 - Quinoline compounds, agent selecting zinc ion, cadmium ion and copper ion using the same, detecting method and detecting device thereof - Google Patents

Quinoline compounds, agent selecting zinc ion, cadmium ion and copper ion using the same, detecting method and detecting device thereof Download PDF

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KR101638682B1
KR101638682B1 KR1020140093025A KR20140093025A KR101638682B1 KR 101638682 B1 KR101638682 B1 KR 101638682B1 KR 1020140093025 A KR1020140093025 A KR 1020140093025A KR 20140093025 A KR20140093025 A KR 20140093025A KR 101638682 B1 KR101638682 B1 KR 101638682B1
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김철
송은주
강주혜
유가림
이명미
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서울과학기술대학교 산학협력단
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Abstract

The invention quinoline compound, the compound of zinc ions (Zn + 2), the colorimetric detection agent, with a cadmium ion selective in (Cd 2 +) fluorescence detection and the cobalt ion (Co 2+) with a selectivity for containing them And a detection method using the same.

Description

TECHNICAL FIELD The present invention relates to a quinoline compound, a zinc ion, a cadmium ion, and a cobalt ion detector using the same, a detection method and a detection device using the same,

The invention comprises a novel quinoline compound, the compound of zinc ions (Zn + 2), cadmium ion (Cd + 2) and cobalt ion detection agent, a detection method using the same that is less selective to specific to the (Co 2+) And a detection device.

The development of metal ion detection methods is a very important field of study both environmentally and biologically. Efforts have been made to synthesize a single compound capable of detecting one or more metal ions and development of a device capable of detecting metal ions by other detection methods such as fluorescence or color change has been extensively studied.

Detection of zinc ions among metal ions is biologically important. Zinc is a zinc group element belonging to the 4th cycle of Group 12 of the Periodic Table. It exists in the organism as a divalent cation and plays an important role in various biological processes such as neurotransmission, signal transduction and gene expression. It is an inorganic material and a major element of the crust. However, excessive intake of zinc may cause mineral imbalance, which is a target item for water quality management that can be harmful to human beings. In terms of water quality, zinc concentration is an important management target item.

Cadmium has been widely used in the fields of nickel-cadmium batteries, phosphate fertilizers, pigments and semiconductor quantum dots and roads. However, the harmful effects of cadmium on human health are increasingly recognized by people, and long-term exposure to cadmium is associated with an increased incidence of certain cancers that can be caused by kidney dysfunction, calcium metabolic disease, It is known that it can bring about.

As a transition metal, cobalt plays an important role in the synthesis of hemoglobin and in the metabolism of iron and is important for organic organisms as an important component of vitamin B 12 and other biological compounds. However, excess cobalt due to overexposure to cobalt ions adversely affects humans and animals and causes a variety of diseases and disorders such as heart disease, lung disease, dermatitis, vasodilatation, such as asthma, decreased cardiac output and cardiac enlargement. Therefore, it is important to detect trace amounts of cobalt ions in biological and environmental materials.

Therefore, a method for detecting metal ions using an analytical reagent having selectivity for an environmentally and biologically important metal ion has been demanded. In addition to the emergence of supramolecular chemistry, the invention of a photochemical chemical sensor for detecting a specific metal ion and its synthesis Have been studied. Although it is very important to develop a probe capable of selectively detecting metal ions, many studies have been made, but it is very difficult to develop and is not known in practice.

 Jin Hoon Kim; In Hong Hwang; Seung Pyo Jang; Juhye Kang; Sumi Kim; Insup Noh; Youngmee Kim; Cheal Kim; Roger G. Harrison; Dalton Transactions, 2013, 42, 5500-5507.

The present invention been made in view of solving the problems of the prior art, zinc ions (Zn + 2), cadmium ion (Cd 2 +) or cobalt ions in combination with (Co 2+) and, optionally, a change in fluorescence or color Or a quinoline compound.

Another object of the present invention is to provide a detection agent, detection methods and detection apparatus of the zinc ions (Zn + 2) using the quinoline compounds, cadmium ion (Cd + 2), or a cobalt ion (Co 2+) .

In order to achieve the above object,

The present invention provides a quinoline compound (2 - (2-hydroxybenzyl) (pyridin-2-ylmethyl) amino) -N- (quinolin-8-yl) acetamide.

 [Chemical Formula 1]

Figure 112014069152552-pat00001

The present invention also relates to a process for the preparation of 2 - ((pyridin-2-yl) methylamino) methyl) phenol and N, N-diisopropylethylamine (DIPEA ) Of the compound of formula (1).

The present invention also provides zinc ion (Zn 2 + ), cadmium ion (Cd 2 + ) or cobalt ion (Co 2 + ) detecting agent containing the compound of formula (1).

In addition, the present invention the zinc ion (Zn 2 +), cadmium ion (Cd 2 +) or cobalt ions (Co 2 +) zinc ion containing the detection agent (Zn 2 +), cadmium ion (Cd 2 +) or It provides a cobalt ion (Co + 2) detecting device.

Quinoline compounds of formula (I) of the present invention may form a complex combination of metal ion and the coordination, and the change in fluorescence intensity when combined with inter alia zinc ions (Zn + 2) or cadmium ion (Cd 2+), cobalt ions may be selectively detected in the (Co + 2) and a color change when combined up and zinc ions (Zn + 2), cadmium ion (Cd + 2), or a cobalt ion (Co 2+). Further, a zinc ion, a cadmium ion or a cobalt ion detecting agent, a detecting method and a detecting apparatus using the quinoline compound can be provided.

1 is a graph showing fluorescence intensities measured by adding various metal ions to the compound of Chemical Formula 1 in an acetonitrile solvent.
Fig. 2 shows the color change when various metal ions are added to the compound of formula (1) in an acetonitrile solvent.
FIG. 3 is a graph showing fluorescence intensities measured by adding various metal ions to the compound of Chemical Formula 1 in an acetonitrile aqueous solution. FIG.
FIG. 4 is a graph showing the intensity of fluorescence while gradually increasing the amount of zinc ions (Zn 2+ ) in the compound of Formula 1. FIG.
FIG. 5 is a graph showing the change in absorbance when the concentration of zinc ion (Zn 2+ ) is gradually increased in the compound of formula (1).
6 is a Job's Plot for determining the binding ratio between the compound of Formula 1 and zinc ion (Zn 2+ ).
FIG. 7 is a bar graph showing the fluorescence intensity experiment results to confirm that the compound of formula (I) is interfered with the detection of zinc ion (Zn 2+ ) when various metal ions are present.
8 is a graph showing the intensity of fluorescence while gradually increasing the concentration of cadmium ion (Cd 2+ ) in the compound of formula (I).
9 is a Job's Plot for determining the binding ratio between the compound of Chemical Formula 1 and cadmium ion (Cd 2+ ).
FIG. 10 is a bar graph showing the fluorescence intensity experiment results to confirm whether the compound of Chemical Formula 1 is interfered with the detection of cadmium ion (Cd 2+ ) when various metal ions are present.
11 shows the crystal structure of the compound of formula (1) and the cadmium ion (Cd 2 + ) complex.
12 is a graph showing the change of absorbance when the concentration of cobalt ion (Co 2+ ) is gradually increased in the compound of formula (1).
13 is an ESI-MS result for examining the bond form of the compound of formula (I) and cobalt ion (Co 2 + ).
FIG. 14 is a Job's Plot for determining the bonding ratio between the compound of Formula 1 and cobalt ions (Co 2+ ).
FIG. 15 shows a color change experiment result to confirm whether the compound of Chemical Formula 1 is interfered with the detection of cobalt ion (Co 2+ ) when various metal ions are present.

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

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

[Chemical Formula 1]

Figure 112014069152552-pat00002

Compound of Formula 1 by zinc ions (Zn + 2) and selectively detects the cadmium ion (Cd + 2) Of the various metal ion represents a change in fluorescence, color cobalt ion is selectively recognized by a (Co 2+) by indicating a change, it is possible to detect zinc ions (Zn + 2), cadmium ion (Cd 2 +) ions, and cobalt (Co + 2).

The quinoline compound of formula (I) of the present invention may be prepared by reacting 2-chloro-N- (quinolin-8-yl) acetamide, 2- Lt; / RTI > and reacting it with propylethylamine. The above reaction is shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

Figure 112014069152552-pat00003

The compound of Formula 1 forms a complex to detect zinc ions (Zn 2 + ), cadmium ions (Cd 2 + ), and cobalt ions (Co 2 + ).

The compounds of general formula (I) of the present invention Na +, K +, Mg 2 +, Cd 2 +, Co 2 +, Ca 2 +, Al 3 +, Ga 3 +, In 3+, Pb 2 +, Hg 2 +, Cr 3 + , Mn 2 +, Fe 2 +, Fe 3 +, Ni 2 +, can be combined with Cu 2 +, Zn 2 +, and a variety of metal ions such as Ag +. However, fluorescence intensity changes only when binding with zinc ion (Zn 2 + ) or cadmium ion (Cd 2+ ), and color change from colorless to yellow is observed only when binding with cobalt ion (Co 2 + ) . Therefore, it can be said that the compound of Formula 1 has a specific selectivity for zinc ion (Zn 2 + ), cadmium ion (Cd 2 + ) and cobalt ion (Co 2+ ).

Using the above characteristics, the present invention provides zinc ion (Zn 2 + ), cadmium ion (Cd 2 + ) or cobalt ion (Co 2 + ) detecting agent containing the compound of formula (1). The zinc ion (Zn 2 + ), cadmium ion (Cd 2 + ) and cobalt ion (Co 2 + ) detecting agent of the present invention includes the compound of the above formula (1) and may further include a solvent. The solvent is preferably selected from among acetonitrile and an aqueous solution of acetonitrile having a volume ratio of acetonitrile to water of 1 or more, but is not limited thereto.

The present invention also provides a method for detecting zinc ion (Zn 2 + ), cadmium ion (Cd 2 + ) or cobalt ion (Co 2+ ) using the compound of formula (1). That is, the present invention provides a detection method wherein fluorescence intensity changes or color changes due to binding of a compound of formula (I) with zinc ion (Zn 2 + ), cadmium ion (Cd 2 + ) and cobalt ion (Co 2+ ).

The present invention is a fluorescence detection apparatus of the zinc ions (Zn + 2) and / or cadmium ions (Cd + 2) zinc ion containing the detection agent (Zn + 2) and / or cadmium ions (Cd 2+) may provide a chemical sensor (fluorescent chemosensor), cobalt ions (Co + 2) to provide a colorimetric chemical sensors (colorimetric chemosensor) detected by the detection device of the cobalt ion (Co 2+) containing, and the detection The apparatus is preferably a probe.

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

Example  1. Preparation of compound of formula (1)

0.43 g (2.1 mmol) of 2-chloro-N- (quinolin-8-yl) acetamide and 0.43 g (2 mmol) of 2 - [(pyridin- 0.39 mL (2.2 mmol) of diisopropylethylamine and 0.37 g (2.2 mmol) of potassium iodide were dissolved in 30 mL of acetonitrile. The reaction mixture solution was refluxed and stirred at 60 DEG C for one day while introducing nitrogen gas Respectively. Cooling the mixture at room temperature under reduced pressure to remove the solvent to obtain an oily product of a yellow, and chloroform and methanol (volume ratio of CHCl 3: CH 3 OH = 90 : 1) to column chromatography using a pure product as 1.61g , And the yield was 89.6%.

The resulting compound was analyzed for its structure by 1 H-NMR, 13 C-NMR, HRMS (ESI) and EA analysis, and it was confirmed that the compound had the structure of Formula 1.

1 H-NMR (DMSO-d 6, 400 MHz, 25 ℃): δ 11.4 (s, 1H), 9.92 (s, 1H), 8.98 (d, 1H), 8.60 (d, 1H), 8.53 (d, 2H), 7.58 (d, IH), 7.54 (t, IH), 7.27 (t, IH) ), 7.05 (t, IH), 6.78 (m, 2H) ppm.

13 C-NMR (DMSO-d 6, 400 MHz, 25 ℃): δ 169.7, 158.1, 157.3, 148.7, 148.5, 139.1, 137.6, 136.3, 134.5, 131.5, 129.9, 128.2, 127.5, 123.6, 122.9, 122.2, 121.9, 119.3, 117.5, 177.1, 59.1, 58.5, 56.5 ppm.

HRMS (ESI): [M + H] < + >; calcd, 399.17, found, 399.07%.

EA: Anal. Calcd for C 24 H 22 N 4 O 2 (398.46): C 72.34, H 5.57, N 14.06%;

Found: C 72.15, H 4.95, N 13.75%.

Experimental Example  1. Fluorescence of compounds of formula < RTI ID = 0.0 > 1 < / RTI & Color change  analysis

(1) Fluorescence analysis

The compound of Formula 1 prepared in Example 1 was dissolved in an acetonitrile solvent to prepare a solution at a concentration of 10 μM. Various metal ions (Ag +, Al + 3, Ca + 2, Cd + 2, Co + 2, Cr 3+, Cu + 2, Fe + 2, Fe + 3, Ga + 3, Hg + 2, In + 3 , K +, Mg 2 +, Mn 2 +, Na +, Ni 2 +, Pb 2 +, Zn 2 +) of a compound solution (10 of the formula (1) a metal ion solution (0.02 M) was dissolved in acetonitrile solvent μM) were added to 1.5 mL of each sample to observe changes in fluorescence intensity. All of the metal ion solutions were prepared using the nitrate salt of each metal ion.

When zinc ion (Zn 2+ ) was added, the fluorescence intensity was the greatest at 510 nm. When the cadmium ion (Cd 2+ ) was added, the fluorescence intensities of zinc ions And an increase in fluorescence intensity corresponding to about one-third was shown (Fig. 1). When other metal ions were added, the fluorescence intensity was hardly changed.

Accordingly, it was confirmed that the compound of formula (I) of the present invention can selectively detect zinc ion (Zn 2+ ) and cadmium ion (Cd 2+ ) through fluorescence intensity change.

For practical application, the fluorescence assay was carried out under the same conditions as above except that the solvent was 50% acetonitrile aqueous solution (water: acetonitrile = 1: 1, v / v). As a result, in the case of zinc ion (Zn 2 + ), the fluorescence intensity was greatly increased at a wavelength similar to the above experiment. The cadmium ion (Cd 2+ ) also exhibited the highest fluorescence intensity at a wavelength near 510 nm and an increase of fluorescence intensity about three times greater than the zinc ion (FIG. 3). In the case of other metal ions, an increase in fluorescence intensity was hardly observed.

That is, the compound of formula (I) can be used as a fluorescence sensor for zinc ion (Zn 2 + ) and cadmium ion (Cd 2+ ) in a solution of acetonitrile and acetonitrile.

(2) Color change  analysis

The compound of formula (1) was dissolved in acetonitrile solvent to prepare a solution of the compound of formula (1) at a concentration of 40 μM. In 3 mL solution, acetonitrile is dissolved in reel solvent a variety of metal ions, prepared in 0.02 M concentration (Mn 2 +, Fe 3 + , Fe 2 +, Co 2 +, Ni 2 +, Cu 2 +, Zn 2 +, Cd 2+, Hg 2 +, Na +, K +, Mg 2 +, Ca 2 +, Al 3 +, Ag +, Pb 2 +, Cr 3 +, Ga 3 +, In 3 +) of each solution was 6.0 μL And the color change was observed. As a result of the color change analysis, it was confirmed that when the solution of the compound of Chemical Formula 1 was loaded with another metal ion solution, there was almost no color change and that the color changed from colorless to yellow only in the case of cobalt ion (Co 2 + ) (FIG.

Therefore, it was confirmed that the compound of formula (I) of the present invention selectively detects cobalt ions (Co 2 + ) through color change.

Experimental Example  2. Zinc ion (Zn 2+ )on  Application of Compound of Chemical Formula 1

(1) fluorescence and Absorbance ( UV - vis ) analysis

The compound of Formula 1 prepared in Example 1 above was dissolved in acetonitrile to prepare a 10 μM solution of the compound of Formula 1. Increasing by 1 μM, the concentration of zinc ions (Zn 2 +) in 3 mL the solution at 0 to 21 μM using the fluorescence intensity of a fluorescent device, UV-vis instrument (Perkin-Elmer model Lambda 2S UV / vis spectrometer) The absorbance was measured and the results are shown in FIGS. 4 and 5, respectively.

Fluorescence intensity analysis showed the highest fluorescence intensity near 510 nm. The fluorescence intensity increased with increasing concentration of zinc ion (Zn 2 + ), and when the concentration of zinc ion (Zn 2+ ) became more than 10 μM The fluorescence intensity was increased but the increase width was small (Fig. 4).

In the case of the absorption analysis by UV-Vis, the absorbance decreased at 243 nm and 319 nm with increasing zinc ion concentration, and the absorbance increased at 260 nm and 370 nm. In addition, the complexes are formed (-Zn 2+ compound of formula (1)) of 250nm, 285nm, and the like, respectively, the extinction point (isosbestic point) was found in the 340nm, compound with zinc ion (Zn 2+) of the formula (1) at this point (Fig. 5).

(2) a compound of formula Zinc ion (Zn 2+ )of  Combination analysis: Misplat ( Job's plot ) Experiment

Job's plot was measured using a UV-Vis (Perkin-Elmer model Lambda 2S UV / vis spectrometer) to examine the binding ratio of the compound of formula (1) prepared in Example 1 and zinc ion (Zn 2+ ) ≪ / RTI >

The zinc ion (Zn 2+ ) and the compound of formula (1) were dissolved in an acetonitrile solvent to prepare a solution concentration of 20 μM, respectively. 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5 for the solution of the compound of formula 1, 5, 4.5, 4, 3.5, 3, 2.5, , And 5 mL were added, mixed well, and Job's plot was obtained through UV-vis.

When the compound represented by the formula [Zn 2 + ] / ([compound of formula 1] + [Zn 2 + ])] has the highest absorbance at 0.5, the compound of formula 1 and the zinc ion form a complex , The coupling ratio was 1: 1 (FIG. 6).

(3) Binding inhibition experiment

The effect of other metal ions on the change in fluorescence intensity of the solution containing the compound of formula (I) and the zinc ion (Zn 2+ ) is shown in FIG. The compound (1 equivalent) of the other metal ions of formula (I) was dissolved in acetonitrile solvent (Cd 2 +, Cr 3 + , Cu 2 +, Co 2 +, Ca 2 +, Fe 3 +, Fe 2 +, Mn 2 +, Mg 2 +, Ni 2 +, K +, Hg 2+, Ag +, Na +, Al 3 +, Pb 2 + , Ga 3 + , and In 3 + ) were added to each well, and the fluorescence intensity was measured by adding 1 equivalent of zinc ion (Zn 2 + ).

Cd 2 + , Cr 3 + , Ca 2 +, Fe 3 +, Mn 2 +, Mg 2 +, K +, Hg 2 +, Ag +, Na +, Al 3 +, Pb 2 +, Ga 3 +, In 3 + and so on of the metal ions formula 1 < / RTI > compound and zinc ion (Zn < 2 + & gt ; ) did not interfere with fluorescence intensities. However, rather the interaction of Cu 2 +, Co 2 +, Fe 2 +, Ni 2 +, such as the metal ion is the fluorescence intensity increases as seen, the compounds and zinc ions (Zn 2 +) of formula I to interfere with the interference .

Experimental Example  3. Cadmium ions (Cd 2+ )on  Application of Compound (1)

(1) Fluorescence analysis

The compound of Formula 1 prepared in Example 1 was dissolved in an aqueous acetonitrile solution (acetonitrile: HEPES (4- (2-hydroxyethyl) -1-piperazineethanesulfonic acid) in a volume ratio of 1: 1) 1 was prepared.

The concentration of cadmium ion (Cd 2+ ) in the solution was gradually increased from 0 to 20 μM by 1 μM, and the fluorescence intensity was measured with a fluorescence instrument. The result is shown in FIG. It showed the greatest fluorescent intensity at 520nm, increasing the concentration of cadmium ions (Cd 2 +) was the fluorescence intensity gradually increases, an increase in the fluorescence intensity of starting the addition of cadmium ions (Cd 2 +) with 13 μM concentration Lt; / RTI >

(2) a compound of formula Cadmium ions (Cd 2+ )of  Binding assay: Job's  plot

Job's plots were obtained using UV-Vis to determine the binding ratio between the compound of Formula 1 prepared in Example 1 and cadmium ion (Cd 2+ ).

Cadmium ion (Cd 2+ ) and compound of formula (1) were dissolved in acetonitrile aqueous solution (acetonitrile: HEPES volume ratio = 1: 1) to prepare solution concentrations of 20 μM, respectively. 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 5, 5, 5, 4.5, and 5 mL, respectively. After mixing well, Job's plots were obtained through UV-vis.

([Cd 2 +] / ( [ compound of formula 1] + [Cd 2 +] )) when expressed in terms of, most showed a high absorbance, and thus the compounds and cadmium (Cd 2 +) in the formula (I) ions at 0.5 When the complex was formed, it was found that the coupling ratio was 1: 1 (FIG. 9).

(3) Binding inhibition experiment

The effect of other metal ions on the fluorescence intensity change of the compound of formula (I) and the solution containing cadmium ion (Cd 2+ ) is shown in FIG. Acetonitrile other metal ions in the compound of formula (I) is dissolved in 1 equivalent aqueous reel (Cd 2 +, Zn 2 + , Cr 3 +, Cu 2 +, Co 2 +, Ca 2 +, Fe 3 +, Fe 2 +, Mn 2 +, Mg 2 +, Ni 2+, K +, Hg 2 +, Ag +, Na +, Al 3 +, Pb 2 + , Ga 3 + , In 3 + ) were added to the reaction solution, respectively, followed by the addition of 1 equivalent of cadmium ion (Cd 2 + ).

Ca 2 +, Fe 3 +, Fe 2 +, Mn 2 +, Mg 2 +, K +, Ag +, Na +, Al 3 +, Pb 2 +, Ga 3 +, In 3 + and so on of the metal ions formula compound with cadmium ions of one does not interfere with the interaction of (Cd + 2) did not significantly interfere with the fluorescence intensity increases, Zn 2 +, Cr 2 + , Cu 2 +, Co 2 +, Ni 2 +, Hg 2 + strongly interfered with the interaction between the compound of formula (1) and cadmium ion (Cd 2 + ), and the metal ions other than the zinc ion (Zn 2+ ) .

Experimental Example  4. Compounds of formula 1 and Cadmium ion ( CD 2 + ) Complex  Formation and crystal structure analysis

Compound (1) (0.0125 mmol) and cadmium nitrate (Cd (NO 3 ) 2 ) (0.0125 mmol) were dissolved in 1 mL of acetonitrile and mixed with each other. The mixed solution was allowed to stand at room temperature for one day, 6 mL of diethyl ether was slowly added to the mixed solution, and the mixture was allowed to stand at room temperature for several days to obtain colorless crystals. The crystal structure of the complex was analyzed by X-ray analysis, and the results are shown in FIG. It was confirmed that the compound of formula (1) and the cadmium ion (Cd 2 + ) were bound in a one-to-one bond. It was confirmed that the oxygen atom and the nitrogen atom of the amide and the nitrogen atom of the pyridine were distributed in the cadmium ion (Cd 2 + ) Could.

Experimental Example  5. Cobalt ion (Co 2+ )on  Application of Compound of Chemical Formula 1

(One) Color change  And Absorbance ( UV - vis ) analysis

The compound of Formula 1 prepared in Example 1 was dissolved in an acetonitrile solvent to prepare a 25 μM solution of the compound of Formula 1. It was while increasing the solution with 1.5 equivalent of the concentration of cobalt ion (Co 2 +) in 0 eq using UV-vis instrument (Perkin-Elmer model Lambda 2S UV / vis spectrometer) measurement of absorbance, also the result 12. As a result, the absorbance gradually increased with increasing concentration of cobalt ion (Co 2+ ) at 260 nm and 390 nm, and the increase in absorbance was slight from the addition of about 1 equivalent of cobalt ion (Co 2+ ).

And so on using the extinction point (isosbestic point) is not obvious, electrospray mass spectrometry (ESI-mass spectroscopy) to determine the reaction compound and the cobalt ion (Co 2 +) of the formula (1) precisely to that which compound is produced (Fig. 13). As a result, it was confirmed that the nitrogen atom of pyridine, the nitrogen atom of amide, the nitrogen atom of amine, the oxygen atom of phenol, and the nitrogen atom of quinoline were coordinated to cobalt.

(2) The compound of the formula (1) and the cobalt ion Co 2 + ): ≪ tb > < Job's  plot

A job's plot was obtained using UV-Vis to determine the ratio of the compound of Formula 1 prepared in Example 1 and cobalt ion (Co 2+ ).

The cobalt ion (Co 2+ ) and the compound of formula (1) were each dissolved in acetonitrile solvent to prepare a solution concentration of 20 μM, and the compound solution of formula (1), (4.5), (3.5) 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, and 5 mL of cobalt solution were added to each of the wells for 1.5, 1, (Job's plot).

When represented by the formula ([Co 2 +] / ( [ compound of formula 1] + [Co 2 +] )), showed the highest absorbance at 0.5, and as a result, the compounds and the cobalt ion of the formula 1 (Co 2 + ) Was 1: 1 (Fig. 14).

(3) Binding inhibition experiment

In order to confirm whether or not the compound of formula (1) can selectively detect cobalt ions (Co 2 + ) even in the presence of other metal ions, a disturbance experiment was conducted. Thus, the influence of other metal ions on the color change of the solution containing the compound of formula (I) and the cobalt ion (Co 2 + ) was investigated and shown in FIG.

The compound (1 equivalent) of the other metal ions of formula (I) was dissolved in acetonitrile solvent (Cd 2 +, Cr 3+, Cu 2 +, Co 2 +, Ca 2 +, Fe 3 +, Fe 2 +, Mn 2 +, Mg 2 +, Ni 2 +, K +, Hg 2 +, Ag +, Na +, Al 3 +, Pb 2 + , Zn 2 + , Ga 3 + , and In 3+ ) were added to the reaction mixture, and one equivalent of cobalt ion (Co 2+ ) was added thereto to observe the color change.

As a result, all of the metal ions was confirmed not to interfere with the compound and the cobalt ion of cobalt ions (Co + 2) does not interfere with the interaction of the (Co 2+), a color change is detected in the general formula (1) (Fig. 15 ). Therefore, it has been confirmed that the compound of the formula (1) has high selectivity for cobalt ions (Co 2+ ) even in the presence of other metal ions and thus can be used as an effective detecting agent.

Claims (9)

delete delete A cadmium ion (Cd 2+ ) or cobalt ion (Co 2+ ) detecting agent comprising a quinoline compound represented by the following formula (1).
[Chemical Formula 1]
Figure 112016011230132-pat00020
 The method of claim 3,
Wherein the detecting agent may further comprise a solvent and the solvent is one selected from the group consisting of acetonitrile and acetonitrile aqueous solution, wherein the cadmium ion (Cd 2+ ) or the cobalt ion (Co 2+ Detecting agent. delete The method of claim 4,
Wherein the acetonitrile aqueous solution has a volumetric ratio of acetonitrile to water volume of at least 1 (cd 2+ ) or cobalt ion (Co 2+ ). A method for detecting a cadmium ion (Cd 2+ ) or a cobalt ion (Co 2+ ) using a quinoline compound represented by the following formula (1).
[Chemical Formula 1]
Figure 112016011230132-pat00021
 Claim 3 of the cadmium ions (Cd 2+) or cobalt ion (Co 2+) detecting the ions of cadmium (Cd 2+) or cobalt ion (Co 2+) detection apparatus comprising a. The method of claim 8,
Characterized in that the detection device is a probe. A detection device of cadmium ion (Cd 2+ ) or cobalt ion (Co 2+ ).
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