KR101615817B1 - Novel compound, method of manufacturing the compound, and chemical sensor including the compound - Google Patents
Novel compound, method of manufacturing the compound, and chemical sensor including the compound Download PDFInfo
- Publication number
- KR101615817B1 KR101615817B1 KR1020140103233A KR20140103233A KR101615817B1 KR 101615817 B1 KR101615817 B1 KR 101615817B1 KR 1020140103233 A KR1020140103233 A KR 1020140103233A KR 20140103233 A KR20140103233 A KR 20140103233A KR 101615817 B1 KR101615817 B1 KR 101615817B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- ethylamine
- formula
- compound represented
- chemical sensor
- Prior art date
Links
Images
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plasma & Fusion (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
Abstract
In a novel compound, a method for producing the same, and a chemical sensor comprising the same, the novel compound is represented by the following formula (1).
[Chemical Formula 1]
In formula (1), A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 3 carbon atoms .
Description
The present invention relates to a novel compound, a method for producing the same, and a chemical sensor including the same, and a novel compound used for the detection of an ethylamine compound, a method for producing the compound, and a chemical sensor including the same.
A wide variety of amine-based compounds are widely used in the production of fertilizers, pharmaceuticals, surfactants, physiological buffer substances, colorants and the like. In particular, ethylamine is a colorless, flammable liquid used for raw materials for vulcanization accelerators, selective solvents, pharmaceutical raw materials and the like, and produces odors similar to ammonia. Exposure to ethylamine has a detrimental effect on the human body, such as irritation of the eyes and edema of the cornea. Therefore, even a trace amount of ethylamine needs to be detected and quantified.
Isotachophoresis, ion chromatography, thin layer chromatography, gas chromatography, high performance liquid chromatography and capillary electrophoresis are known as methods for separating and detecting amine compounds. Recently, Various optical-sensing methods have also been proposed. However, these methods have a low selectivity and sensitivity to ethylamine compounds and a slow sensing speed.
SUMMARY OF THE INVENTION Accordingly, the present invention has been made in view of the above problems, and it is an object of the present invention to provide a novel compound having a high sensitivity and selectivity to ethylamine compounds.
Another object of the present invention is to provide a process for producing the above compound.
It is a further object of the present invention to provide a chemical sensor comprising such a compound.
The novel compound according to one embodiment for realizing the object of the present invention described above is represented by the following general formula (1).
[Chemical Formula 1]
In formula (1), A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 3 carbon atoms .
In one embodiment, the compound represented by Formula 1 may be a hemicyanine dye.
In one embodiment, the compound represented by Formula 1 may be represented by Formula 2 or Formula 3 below.
(2)
(3)
In one embodiment, the compound represented by Formula 1 may exhibit an absorption peak at 350 nm to 470 nm.
In one embodiment, the compound represented by Formula 1 may react with an ethylamine compound to change its absorbance and color.
In one embodiment, the compound represented by Formula 1 may react with an ethylamine compound to reduce the absorbance of the absorbance peak at 350 nm to 470 nm.
In one embodiment, the compound represented by Formula 1 may react with an ethylamine compound to exhibit an absorption peak at 550 nm to 600 nm.
According to another aspect of the present invention, there is provided a method for producing a novel compound. In the above production method, 2,5-dihydroxybenzaldehyde is reacted with a compound represented by the following general formula (4).
[Chemical Formula 4]
In formula (4), A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, and R 1 represents an alkyl group having 1 to 3 carbon atoms.
In one embodiment, the compound represented by Formula 4 is 2,3-methylbenzothiazolium iodide or 1,2,3,3-tetramethylindenylium iodide (1,2,3 , 3-tetramethylindolenium iodide).
According to another aspect of the present invention, there is provided a chemical sensor comprising a compound represented by the following general formula (1).
[Chemical Formula 1]
In formula (1), A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 3 carbon atoms .
In one embodiment, the compound represented by Formula 1 may react with an ethylamine compound to change its absorbance and color. At this time, the ethylamine compound may include ethylamine, diethylamine or triethylamine.
In one embodiment, the compound represented by Formula 1 may react with the ethylamine compound to decrease the absorbance of the absorption peak at 350 nm to 470 nm.
In one embodiment, the compound represented by Formula 1 may react with the ethylamine compound to exhibit an absorption peak at 550 to 600 nm.
In one embodiment, the compound represented by Formula 1 is mixed with a polymer, wherein the chemical sensor may be in the form of a nanofiber.
In one embodiment, the polymer may comprise poly (acrylonitrile) (PAN).
In one embodiment, a compound represented by the following formula (5) or a compound represented by the following formula (6) may be further included.
[Chemical Formula 5]
[Chemical Formula 6]
In formulas (5) and (6), R 1 independently represents an alkyl group having 1 to 3 carbon atoms, and R 4 and R 5 each independently represent hydrogen or an ethyl group.
According to such a novel compound, a method for producing the same, and a chemical sensor including the same, the compound having a novel structure reacts with an ethylamine-based compound to change its absorbance and color. The compound having such properties can be used as a chemical sensor for detecting an ethylamine-based compound as a hemicyanine dye. The compound can detect and recover the ethylamine compound within a range of a few seconds, and can provide a chemical sensor with a high sensing speed.
1A is a diagram for explaining the absorbance and color change of the compound according to Example 1 of the present invention before and after the addition of the ethylamine compound.
FIG. 1B is a view for explaining the HOMO-LUMO energy of the compound according to Example 1 of the present invention before and after the addition of the ethylamine compound. FIG.
1C is a view for explaining the 1 H-NMR change of the compound according to Example 1 of the present invention before and after the addition of the ethylamine compound.
2A is a diagram for explaining the absorbance and the color change of the compound according to Example 2 of the present invention before and after the addition of the ethylamine compound.
FIG. 2B is a view for explaining the HOMO-LUMO energy of the compound according to Example 2 of the present invention. FIG.
2C is a diagram for explaining the 1 H-NMR change of the compound according to Example 2 of the present invention before and after the addition of the ethylamine compound.
3 is a diagram for explaining the detection ability of a chemical sensor including the compound according to Example 2. Fig.
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. It is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and similarities. It is to be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but on the contrary, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.
The terms first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.
The terminology used in this application is used only to describe a specific embodiment and is not intended to limit the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the term "comprises" or "having" is intended to designate the presence of stated features, elements, etc., and not one or more other features, It does not mean that there is none.
Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.
Novel compounds and methods for their preparation
The novel compounds according to the present invention are represented by the following formula (1).
[Chemical Formula 1]
Wherein A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, each of R 1 , R 2 and R 3 independently represents a group having 1 to 3 carbon atoms Alkyl group.
The compound represented by the formula (1) may be a hemicyanine dye.
The compound represented by formula (1) may exhibit absorption peaks in a wavelength range of about 350 nm to about 470 nm, and react with an ethylamine-based compound to change absorbance and color. Examples of the ethylamine compound include ethylamine, diethylamine, and triethylamine.
When the compound represented by the general formula (1) reacts with the ethylamine-based compound, the intensity of the absorption peak, that is, the absorbance decreases in the wavelength range of about 350 nm to about 470 nm and the decrease in the absorbance increases as the content of the ethylamine- .
For example, the compound represented by
(2)
The compound represented by formula (2) may exhibit absorption peaks in the wavelength range of about 350 nm to about 470 nm. For example, the compound represented by the formula (2) may exhibit absorption peaks in the wavelength range of 357 nm to 361 nm and the wavelength range of 440 nm to 444 nm, respectively. At this time, the compound represented by the general formula (2) can be reddish.
The compound represented by the general formula (2) reacts with an ethylamine-based compound to change its absorbance and color. When the compound represented by the general formula (2) reacts with the ethylamine-based compound, the absorbance of the absorption peak exhibiting in the wavelength range of about 350 nm to about 470 nm is decreased. As the content of the ethylamine compound reacting with the compound represented by the general formula (2) is increased, the absorbance gradually decreases. At the same time, a new absorption peak appears in the wavelength range of 550 nm to 600 nm, which is not revealed by the compound itself represented by the general formula (2). For example, when the compound represented by the formula (2) reacts with an ethylamine-based compound, a new absorption peak may appear in the range between 587 nm and 591 nm. The absorbance of the new absorption peak gradually increases as the content of the ethylamine compound reacting with the compound represented by the general formula (2) increases, and it can be seen that as the absorbance of the new absorption peak increases, the color changes to red to dark green.
Specifically, when the compound represented by the formula (2) reacts with the ethylamine compound, a compound represented by the following formula (2-1) can be produced.
[Formula 2-1]
The new absorption peak in the range between 587 nm and 591 nm may be due to the compound represented by the formula (2-1). As the amount of the ethylamine compound to be reacted with the compound represented by the general formula (2) increases, the amount of the compound represented by the general formula (2-1) is increased and thus the absorbance of the new absorption peak can be increased. The compound represented by the general formula (2-1) can be restored to the compound represented by the general formula (2) within about 5 seconds.
When the ethylamine compound is added to the compound represented by the general formula (2), the hydroxyl group (-OH) of the compound and the nitrogen atom (N) of the ethylamine compound are combined and charge transfer occurs therebetween, The electron density is changed. Accordingly, delocalization of the pi-electrons of the entire molecule in the state where the compound represented by the formula (2) and the ethylamine compound are bonded can be performed to form the compound represented by the formula (2-1). The compound represented by the general formula (2) exhibits an absorption peak at about 350 nm to about 470 nm, but after being reacted with the ethylamine compound by the bathochromic effect caused by delignification of the pi-electrons, The absorption peak at about 470 nm decreases and the color changes from red to dark green by showing a new absorption peak in the wavelength range of 550 nm to 600 nm.
Absorbance appearing in the wavelength range of 550 nm to 600 nm when 2.7 equivalents of the ethylamine compound is added to 1 equivalence (equiv.) Of a solution of about 5 x 10 < -5 > The absorbance of the peak can be maximized. That is, when the ethylamine-based compound is ethylamine, the detection limit of ethylamine in the compound represented by the formula (2) may be about 1 × 10 -4 M.
In one embodiment, the compound represented by formula (1) may include a compound represented by formula (3).
(3)
The compounds represented by formula (3) may exhibit absorption peaks in the wavelength range of about 350 nm to about 470 nm. For example, the compound represented by formula (3) may exhibit absorption peaks in the wavelength range of 371 nm to 375 nm and the wavelength range of 460 nm to 464 nm, respectively. At this time, the compound represented by the general formula (3) may be yellow. The compound represented by the general formula (3) does not exhibit an absorption peak within the wavelength range of 550 nm to 700 nm.
The compound represented by the formula (3) reacts with an ethylamine-based compound to decrease the absorbance of the absorption peak in the wavelength range of about 350 nm to about 470 nm. Specifically, when the compound represented by the general formula (3) reacts with the ethylamine-based compound, the absorbance of the absorption peak decreases in a wavelength range of about 350 nm to about 470 nm and the color changes from yellow to colorless and can be visualized . As the content of the ethylamine compound reacting with the compound represented by the general formula (3) is increased, the absorbance of the absorption peak gradually decreases, and no new absorption peak appears. When 1.4 equivalents of the ethylamine compound is added to one equivalent of a solution of about 5 x 10 -5 M containing the compound represented by the general formula (3), the absorption peak does not occur in the wavelength range of about 350 nm to about 470 nm It can be recognized as colorless. That is, when the ethylamine-based compound is ethylamine, the detection limit of the ethylamine in the compound represented by the formula (3) may be about 1 10 -4 M.
When the compound represented by the general formula (3) reacts with the ethylamine-based compound, a compound represented by the following general formula (3-1) can be produced.
[Formula 3-1]
In Formula (3-1), R 4 and R 5 each independently represent hydrogen or an ethyl group. R 4 and R 5 may vary depending on the kind of the ethylamine compound.
In the compound represented by the general formula (3), the carbon linked to the indolenine is carbon in the alpha position and the carbon linked to the dihydroxybenzaldehyde is in the beta position. At this time, in LUMO, the electron density of alpha carbon is lowest among the electron density at other positions in the molecule including carbon at the beta position. Thus, the nucleophilic ethylamine compound can be nucleophilic added at the alpha position to form the compound represented by Formula 3-1.
As the content of the ethylamine-based compound increases, the amount of the compound represented by the general formula (3) decreases and conversely, the compound represented by the general formula (3-1) is generated. As a result, the absorbance of the absorption peak gradually decreases in the wavelength range of about 350 nm to about 470 nm , And when it reaches the threshold value, it is recognized as colorless.
The compound represented by the formula (1) is prepared by reacting 2,5-dihydroxybenzaldehyde with a compound represented by the following formula (4).
[Chemical Formula 4]
In formula (4), A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, and R 1 represents an alkyl group having 1 to 3 carbon atoms.
The compound represented by the general formula (4) includes 2,3-methylbenzothiazolium iodide or 1,2,3,3-tetramethylindolenium iodide. can do.
Dihydroxybenzaldehyde, the compound represented by the formula (4) and ethanol are mixed and refluxed for a predetermined time in a nitrogen gas atmosphere, followed by cooling and filtration and recrystallization to obtain the compound represented by the formula (1) Can be manufactured.
Chemical sensor
The chemical sensor according to the present invention comprises a compound represented by the general formula (1). The chemical sensor is a sensor for detecting an ethylamine compound, and can be used for detecting an ethylamine compound by utilizing the fact that the compound according to the present invention reacts with an ethylamine compound to change its absorbance and color.
The compound represented by the formula (1) can be used by mixing with a polymer. The chemical sensor according to the present invention together with the polymer may be in nanofiber form. The polymer may include, but is not limited to, poly (acrylonitrile) (PAN).
The chemical sensor in the form of nanofibers can be formed by electro-spinning a monomeric compound constituting the polymer and a compound represented by the formula (1). For example, a polymer solution containing the monomer compound and the compound is prepared, injected into the electrospinning device, and the nozzle of the electrospinning device discharges the polymer solution. Nanofibers are formed on the surface of the collector as the collectors are integrated in the discharged polymer solution. Since the nanofiber includes the compound represented by the general formula (1), when the nanofiber mat, which is a nanofiber aggregate, is exposed to an ethylamine compound, the color of at least a part of the aggregate of the nanofibers changes and after the removal of the ethylamine compound And is restored to the color of the original nanofiber aggregate after a predetermined time has elapsed. At this time, the predetermined time may be within 5 seconds.
The characteristics of the chemical sensor may vary depending on the kind of the compound contained therein, and the reaction characteristics of the compound with respect to the ethylamine compound are substantially the same as those described above, so that a detailed description thereof will be omitted.
As described above, the compound represented by formula (I) reacts with an ethylamine compound to change the absorbance and color. A compound having such properties can be used as a chemical sensor for detecting an ethylamine compound. The compound can detect and recover the ethylamine compound within a range of a few seconds, and can provide a chemical sensor with a high sensing speed.
Hereinafter, specific production methods and characteristics of the compounds represented by the formulas (2) and (3) and the ability to detect ethylamine will be described. The embodiments are merely examples, and the present invention is not limited thereto.
Preparation of compound-1
2.17 mmol (0.3 g) of 2,5-dihydroxybenzaldehyde purchased from Sigma-Aldrich Co. (company name, USA), 2,3-methylbenzothiazolium iodide ) 2.12 mmol (0.6 g) and 20 mL of etha were prepared.
The crude product was filtered and recrystallized in ethanol to give the compound represented by
1 H NMR (400 MHz, DMSO -d 6): δ 4.30 (s, 3H, N + -CH 3), 6.86 (d, J = 8.8Hz, 1H), 6.93 (d, J = 8.8Hz, 1H) , 7.37 (d, J = 2.84,1H), 7.91-7.76 (m, 3H), 8.25-8.19 (m, 2H), 8.38 (d, J = 7.44 Hz, ), 10.24 (s, 1 H, -OH).
EA: anal.calcd. C 16 H 14 INO 2 S: C 46.73, H 3.43, N 3.41, S 7.80, Found C 46.39, H 3.42, N 3.70, S 7.77%. [M] + - I = 284.3.
mp: 281-282 ° C.
A 5 × 10 -5 mol / L solution containing the compound represented by the formula (2) was dissolved in a solvent in which dimethyl sulfoxide (DMSO) and water (H 2 O) were mixed in a weight ratio of 1: Solution. The absorption spectrum according to the wavelength of the first initial solution was measured. Then, the absorption spectrum according to the wavelength was measured while increasing the ethylamine to 2.7 equivalents. Further, the color when the ethylamine was 0 equivalent and the color when 2.7 equivalents were taken. The results are shown in Fig.
1A is a diagram for explaining the absorbance and color change of the compound according to Example 1 of the present invention before and after the addition of the ethylamine compound.
Referring to FIG. 1A, the absorption spectrum of the first initial solution shows a first absorption peak at about 359 nm, and a second absorption peak at about 442 nm. As the content of ethylamine increases, the absorbance of the first absorption peak and the second absorption peak gradually decreases, and a new absorption peak appears at about 589 nm.
It can be seen that as the content of ethylamine increases, the absorbance of each of the first and second absorption peaks gradually decreases, and the absorbance of the absorption peak at about 589 nm gradually increases. In the absorption spectrum of a solution containing 2.7 equivalents of ethylamine, the absorption peak at about 589 nm exhibits the maximum absorbance. It can be seen that an isosbestic point appears at about 497 nm.
Further, in the photographed photographs, it can be seen that when the ethylamine is 0 equivalent, that is, the compound represented by the formula (2) itself is visibly red and 2.7 equivalents of ethylamine is visibly recognized as dark green.
MO energy level and NMR data -1
HOMO and LUMO of molecular orbital energy were calculated for each of the compound prepared and the compound after reaction with ethylamine, and the result is shown in FIG. 1B. Further, data were obtained using a nuclear magnetic resonance (NMR) spectrometer, and the results are shown in FIG. 1C. The MO energy was calculated with the DMol 3 program in a Materials Studio 4.3 package (trade name, Accelrys, USA) using a generalized gradient approximation (GGA) level Perleew Burke Ernzerhof function. (B. Delley, J. Chem. Phys., 92 (1990) 508-517 (2000) 7786-7764.)
FIG. 1B is a view for explaining the HOMO-LUMO energy of the compound according to Example 1 of the present invention before and after the addition of the ethylamine compound. FIG. 1C is a graph showing the HOMO-LUMO energy of the compound according to Example 1 of the present invention before and after the addition of the ethylamine compound ≪ 1 > H-NMR of the compound according to the present invention. In Fig. 1C, (a) is the NMR data before the reaction with ethylamine, and (b) is the NMR data after the reaction.
1B and 1C, the HOMO-LUMO difference (ΔE) of the compound represented by the formula (2) is about 1.526 eV and the HOMO-LUMO difference (ΔE) of the compound produced by the reaction of the compound with ethylamine is 1.349 eV . It can be seen that bathobhromic absorption occurs due to decrease in ΔE after the reaction with ethylamine, and electron transfer in the molecule occurs when the compound represented by
In the NMR data, as shown in FIG. 1 (c), the hydroxyl group of the compound represented by
Preparation of compound-2
2.17 mmol (0.3 g) of 2,5-dihydroxybenzaldehyde (purchased from Sigma-Aldrich Corporation, USA), 1,2,3,3-tetramethylindenylium iodide , 2,3,3-tetramethylindolenium iodide) 2.12 mmol and 20 mL of a mixture of ethers was prepared.
The crude product was filtered and recrystallized in ethanol to give the compound of formula 3 according to example 2 of the present invention (yield: < RTI ID = 0.0 > 16%)
1 H NMR (400 MHz, DMSO -d 6): δ 1.74 (s, 6H, - (CH 3) 2), 4.08 (S, 3H, -N + -CH 3), 6.87 (d, J = 8.84Hz 2H), 8.48 (d, J = 6.36 Hz, 1H), 6.99 (d, J = 8.84 Hz, 1H), 7.47 (s, 1H), 7.57-7.65 1H), 9.23 (S, IH, -OH), 10.42 (S, IH, -OH).
EA: anal. calcd. C19H20INO2: C 54.17, H 4.79, N 3.32, Found C 53.94, H 4.83, N 3.29%.
[M] < + & gt ; -I = 294.3.
mp: 266-268 ° C.
A 5 × 10 -5 mol / L solution containing the compound represented by the formula (3) was dissolved in a solvent in which dimethyl sulfoxide (DMSO) and water (H 2 O) were mixed in a weight ratio of 1: Initial solution was prepared. The absorption spectrum according to the wavelength of the second initial solution was measured. Then, the absorption spectrum according to wavelength was measured while increasing the ethylamine to 1.4 equivalents. Further, the color when the ethylamine was 0 equivalent and the color when 1.4 equivalents were taken. The results are shown in Fig.
2A is a diagram for explaining the absorbance and the color change of the compound according to Example 2 of the present invention before and after the addition of the ethylamine compound.
Referring to FIG. 2A, the absorption spectrum of the second initial solution shows a first absorption peak at about 373 nm, and a second absorption peak at about 462 nm. As the content of ethylamine gradually increases, the absorbance of the first absorption peak and the second absorption peak gradually decreases. It can be seen that as the content of ethylamine increases, the absorbance of each of the first and second absorption peaks gradually decreases. In the absorption spectrum of the solution containing 1.4 equivalents of ethylamine, the wavelength range of 373 nm to 700 nm No absorption peak appears.
In addition, it can be seen from the photographed pictures that when the ethylamine is 0 equivalent, that is, the compound represented by the formula (3) itself is visibly yellow and 1.4 equivalents of ethylamine is recognized as colorless.
MO energy level and NMR data -2
HOMO and LUMO of molecular orbital energy were calculated for each of the prepared compound and the compound after reaction with ethylamine, and the result is shown in FIG. 2B. Further, data were obtained using a nuclear magnetic resonance (NMR) spectrometer, and the results are shown in FIG. 2C. MO energy was calculated using the DMol 3 program (product name) and a Perdeew Burke Ernzerhof (PBE) function at the GGA (generalized gradient approximation) level.
FIG. 2B is a graph for explaining the HOMO-LUMO energy of the compound of Example 2 of the present invention, and FIG. 2C is a graph showing the 1 H-NMR spectrum of the compound of Example 2 of the present invention before and after the addition of the ethylamine compound Fig. In FIG. 2C, (a) is the NMR data before the reaction with ethylamine, and (b) is the NMR data after the reaction.
Referring to FIGS. 2B and 2C, it can be seen that the LUMO energy level of the heterocyclic dye represented by Formula 3 is low. When the pi-electron density of LUMO was calculated by the PPP (Pariser-Parr-Pople) MO method, the electron density at the alpha position was the lowest. Thus, it can be seen that when ethylamine is added, the nucleophilic addition takes place at the alpha position.
In the NMR data, a peak due to hydrogen in the aromatic ring of the compound represented by the formula (3) is shown at 6.99 ppm as shown in Fig. 2c (a), but after the reaction with ethylamine as shown in Fig. 2c (b) At 5.71 ppm, the peak shifts to the upfield. This can be said to be the addition of ethylamine to the compound represented by the general formula (3) to give a nucleophilic addition reaction.
Manufacture of chemical sensors
After poly (acrylonitrile) (PAN) and compound (3) were dissolved in dimethylformamide (DMF) solution, the solution was injected into a syringe pump and a high voltage of about 20 kV And the nanofibers were collected through electrospinning to prepare a chemical sensor according to Example 3 of the present invention in the form of a nanofiber mat.
Evaluation of ethylamine detection ability of chemical sensor
A steel image was obtained at intervals of 2.5 seconds while the nanofiber mat was exposed to ethylamine for about 5 seconds. Steel amylase was obtained at intervals of 2.5 seconds for about 5 seconds after removal of ethylamine, and the result is shown in FIG. 3 . Still images were taken with video clips (video camera-VIXIA HFM 31 Canon, Japan).
3 is a diagram for explaining the detection ability of a chemical sensor including the compound according to Example 2. Fig.
Referring to FIG. 3, the nanofiber mat shows brown color as a whole before being exposed to ethylamine. However, after exposure to ethylamine, deep red stains appear immediately on the part, and after 5 seconds, It can be seen that the color is broader and the color becomes more intense. Subsequently, after removing the ethylamine, after 5 seconds passed, it is found that the nanofiber mat is in the same state as the initial state. That is, the presence of ethylamine is detected in a clearly short period of time, and the speed at which it is washed is also very fast.
The description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features presented herein.
Claims (17)
And a polymer compound mixed with the compound represented by the formula (1)
Wherein the nanofibers are removed from the nanofibers when they are no longer exposed to the ethylamine compound after the nanofibers are exposed to the ethylamine compound,
Nanofiber type chemical sensors for the detection of ethylamine compounds;
[Chemical Formula 1]
In formula (1), A 1 represents -S- or -C (R 2 R 3 ) -, X represents Cl or I, R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 3 carbon atoms .
The compound represented by the above formula (1)
Ethylamine-based compound to change its absorbance and color.
Nanofiber type chemical sensor for the detection of ethylamine compounds.
The ethylamine-based compound
And at least one selected from the group consisting of ethylamine, diethylamine, and triethylamine.
Nanofiber type chemical sensor for the detection of ethylamine compounds.
The compound represented by the above formula (1)
And the absorbance of the absorption peak at 350 nm to 470 nm is decreased by reacting with the ethylamine-based compound.
Nanofiber type chemical sensor for the detection of ethylamine compounds.
The compound represented by the above formula (1)
Characterized in that an absorption peak occurs at 550 nm to 600 nm upon reaction with the ethylamine-based compound.
Nanofiber type chemical sensor for the detection of ethylamine compounds.
The polymer compound
Characterized in that it is poly (acrylonitrile) (PAN).
Nanofiber type chemical sensor for the detection of ethylamine compounds.
A compound represented by the following formula (5) or a compound represented by the following formula (6), mixed with the polymer compound,
Nanofiber type chemical sensors for the detection of ethylamine compounds;
[Chemical Formula 5]
[Chemical Formula 6]
In formulas (5) and (6), R 1 independently represents an alkyl group having 1 to 3 carbon atoms, and R 4 and R 5 each independently represent hydrogen or an ethyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140103233A KR101615817B1 (en) | 2014-08-11 | 2014-08-11 | Novel compound, method of manufacturing the compound, and chemical sensor including the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140103233A KR101615817B1 (en) | 2014-08-11 | 2014-08-11 | Novel compound, method of manufacturing the compound, and chemical sensor including the compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160019175A KR20160019175A (en) | 2016-02-19 |
| KR101615817B1 true KR101615817B1 (en) | 2016-04-26 |
Family
ID=55448651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140103233A KR101615817B1 (en) | 2014-08-11 | 2014-08-11 | Novel compound, method of manufacturing the compound, and chemical sensor including the compound |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR101615817B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101883054B1 (en) * | 2016-08-01 | 2018-07-27 | 경북대학교 산학협력단 | Thiobarbituric acid-based compound and amine-based compound detecting sensor including the thiobarbituric acid-based compound |
-
2014
- 2014-08-11 KR KR1020140103233A patent/KR101615817B1/en active IP Right Grant
Non-Patent Citations (1)
| Title |
|---|
| Spectrochim Acta A Mol Biomol Spectrosc. 2012 10., Vol 96 (pp 77-81) |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20160019175A (en) | 2016-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE102008061452A1 (en) | Imidazoloperylenbisimide | |
| Moormann et al. | Synthesis of functionalized diazocines for application as building blocks in photo-and mechanoresponsive materials | |
| KR20160123327A (en) | Polymerizable compound, polymerizable composition, polymer, and optically anisotropic body | |
| EP3578550A1 (en) | Novel benzotriazole uv absorber with red shift and use thereof | |
| Lee et al. | Synthesis and optical properties of push–pull type tetrapyrazinoporphyrazines | |
| KR101615817B1 (en) | Novel compound, method of manufacturing the compound, and chemical sensor including the compound | |
| JP6264936B2 (en) | Method for producing carboxylic acid ester compound having one or more carboxy groups | |
| JP2006290869A (en) | New pyrrole derivative and photosensitive film utilizing the same | |
| Král et al. | New chiral porphyrin–brucine gelator characterized by methods of circular dichroism | |
| Qian et al. | Structural and spectral characterizations of CI Disperse Blue 148 having a new crystalline form | |
| CN109320507A (en) | Chiral fluorescent chemicals and the preparation method and application thereof based on quinoline amides folded formation | |
| CN105566199A (en) | Conjugated aralkynyl carbazole compound | |
| CN103613948B (en) | Flexible thioether chain-containing near infrared squaric acid dye, and preparation method and application thereof | |
| TWI624452B (en) | Anthraquinone compounds and use thereof | |
| Sorokin et al. | 2-Pyridone-based stilbazoles containing cyano and trifluoromethyl acceptors: Synthesis and fluorescence properties in solutions and in solid state | |
| CN106398714A (en) | Preparation method of phenylacetylene liquid crystal material | |
| KR101549347B1 (en) | Novel compound, method of manufacturing the compound, and chemical sensor including the compound | |
| CN108410202A (en) | A kind of preparation method of seven methine cyanine dyes of quinoline | |
| CN106146347B (en) | A kind of Low-molecular weight organogel factor and preparation method and organogel | |
| JPH03103477A (en) | 3-hydroxypyridineazomethin pigment and production thereof | |
| JP5035960B2 (en) | Polysulfonamide derivatives and their use | |
| KR101883054B1 (en) | Thiobarbituric acid-based compound and amine-based compound detecting sensor including the thiobarbituric acid-based compound | |
| JP2016088899A (en) | 4,4',10,10'-bidihydro acridines and manufacturing method therefor | |
| KR101653094B1 (en) | Chemical Sensor Compound Toward Hazardous Cyanide Ions And Its Preparation Method | |
| KR101754476B1 (en) | Pigment compound, chemical sensor used in detecting ethylamine-based compound and method of removing ethylamine-based compound using the chemical sensor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20190401 Year of fee payment: 4 |