• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.33 no.3
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• pp.194-200
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• 2020

Perylene bisimide derivatives are developed for red organic phosphor because of their advantages, such as excellent luminous efficiency and high thermal stability. Despite these advantages, they have poor solubility characteristics in organic solvents and short emission wavelength as red organic phosphor for hybrid light-emitting diodes (LEDs). In this study, we prepared terrylene bisimide using a coupling reaction and swallow-tail imide group, which has excellent solubility. The structures and properties of swallow-tail terrylene bisimide (9C) were analyzed using ¹H-nuclear magnetic resonance (¹H-NMR), Fourier-transform infrared (FT-IR), UV/Vis spectroscopy, and thermal gravimetric analysis (TGA). The maximum absorption wavelength of (9C) in the UV/Vis spectrum was 647 nm, and the maximum emission wavelength was 676 nm. In the TGA, (9C) demonstrated good thermal stability with less than 5 wt% weight loss up to 415℃. In the solubility test, (9C) has a good solubility of more than 5 wt% in chloroform and dichloromethane. When the compounds (9C) were mixed with PMMA (polymethly methacrylate), the films showed peaks at 680 nm in the PL spectra. The results verify the suitability of (9C) as a red organic phosphor for hybrid LEDs.

• Journal of the Korean Chemical Society
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• v.36 no.2
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• pp.318-323
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• 1992

Following seven new nucleophilic adducts of sulfilimine compounds were prepared by the addition of 1-methyl-5-mercapto-1,2,3,4-tetrazole to vinylsulfilimine derivatives; S-Phenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-tolyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-m-tolyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-chlorophenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-bromophenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-methoxyphenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine and S-p-nitrophenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine. The structures of these adducts were confirmed by elemental analyses, MP, UV, IR-and NMR-Spectra.

• YAKHAK HOEJI
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• v.31 no.5
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• pp.330-337
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• 1987

The weak UV absorbing ephedrine alkaloids such as ephedrine, pseudoephedrine, methylephedrine and norephedrine could be analyzed by charge-transfer spectrophotometric method. The results obtained are summarized as follows: (1) It was possible to determine a weak UV absorbing ephedrine alkaloids using the intense charge-transfer UV bands in chloroform. (2) This method was suitable for the spectrophotometric determination of ephedrine alkaloids in mixed pharmaceutical preparation. (3) Linear relationship was found between absorbance and concentration in the range of 1.0$\times$$10^{-5}M$~5$\times$$10^{-5}M$ of ephedrine ($\varepsilon$= 2.72$\times$$10^{4}LM^{-1}cm^{-1}$ and pseudoephedrine ($\varepsilon$=2.84$\times$$10^{4]LM^{-1}cm^{-1}$), 1.0$\times$$10^{-5}M$~5$\times$$10^{-5}$M of methylephdrine ($\varepsilon$=1.68$\times$$10^{4}LM^{-1}cm^{-1}$) and 1/3$\times$$10^{-4}M$~4/3$\times$$10^{-4}M$ of norephedrine ($\varepsilon$=0.74$\times$$10^{4}LM^{-1}cm^{-1}$. (4) CT- complex of ephedrine, pseudoephedrine and methylephedrine has absorption maxima at 293nm and norephedrine have absorption maximum at 253nm. (5) CT-complexes were formed in a 1:1 ratio between ephedrine alkaloids and iodine in chloroform. (6) By UV, IR, and $^1H$-NMR spectra, it could be inferred that CT-complexes were formed by interaction between the basic nitrogen of ephedrine alkaloids as electron (n) donor and iodine as electron ($\sigma$) acceptor.

• Journal of Life Science
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• v.14 no.1
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• pp.91-97
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• 2004

As a part of our study on the improvement of anticonvulsant, here we report the synthesis of N-acyl-$\alpha$-aminosuc-cinimides 1 and N-acyl-$\alpha$-aminoglutarimides 2. (R)-Benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylester 6a, (R)-4-nifro-benzoic acid 4-benzyloxycarbonylamino-2- oxo-pyrrolidin-1-yl ester 6b, (R) -4-nitro-benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6c, and (R)-propionic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6d were synthesized from (R)-2-benzyloxy carbonylamino-succinic acid 3 as a starting meterial. (R)-(3- Benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid methyl ester 10a, (R)-(3-benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid ethy1 ester 10b, an d (R)-2-(3-benzyloxycarbonylamino-2,6- diox o-piperidin-1-yl oxy)-propionic acid methyl ester l0c were synthesized from (R)- 3-carbobenzyloxy-amino-glutarmic acid 7 as a starting meterial. The yield, mp, IR, $^1H-NMR,\; and^{13}C$- NMR spectra of the products 6a, 6b, 6c, 6d, 10a, l0b, l0c are summarized in footnote. The biological studies of these compounds are in progress and will be reported in future.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.30 no.1
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• pp.48-53
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• 2017

We report the studies on the red organic phosphor by using perylene bisimide derivatives. Even though perylene bisimide derivatives have excellent thermal stability and luminous efficiency, they have low solubility in organic solvents. In this research, modified perylene bisimide derivative, N,N'-Bis(4-bromo-2, 6-diisopropylphenyl)-1, 6, 7, 12-tetraphenoxyperylene-3, 4, 9, 10-tetracarboxyl bisimide (1C), has been prepared by the reaction of phenol with N,N'-Bis(4-bromo-2, 6-diisopropylphenyl)-1, 6, 7, 12-tetrachloroperylene-3, 4, 9, 10-tetracarboxyl bisimide (1B) in presence of DMF, at $70^{\circ}C$. The synthesized (1C) was characterized by using $^1H-NMR$, FT-IR, UV/V is spectroscopy, and TGA. The absorbtion and emission of (1C) was shown at 576 nm and 610 nm in UV/V is spectrum. In TGA thermogram, (1C) showed good thermal stability without significant weight loss to $220^{\circ}C$. And in the solubility analysis, (1C) with phenoxy group showed the good solubility in general organic solvents. The blended films of (1C) with PMMA (polymethyl methacrylate) at different weight % concentration such as 10, 5, 1 weight % have been prepared. The blended film was shown at 616 nm when monitored at 450 nm in PL emission spectra.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.32 no.1
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• pp.86-92
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• 2019

Although perylene bisimide derivatives have advantages such as excellent thermal stability and high luminance efficiency, they have poor solubility characteristics in organic solvents. In this research, in order to improve the solubility characteristics, we prepared perylene bisimide derivatives (1C) and (2C) with swallow-tail substituted imide, which is known to lead to excellent solubility. The structures and properties of swallow-tail perylene bisimide (1C) and (2C) were analyzed by $^1H-NMR$, FT-IR, UV/Vis spectroscopy, and thermogravimetric analysis (TGA). The maximum absorption wavelengths of (1C) and (2C) in the UV/Vis spectrum were 558 nm and 556 nm, respectively, and the maximum emission wavelengths were 602 nm and 600 nm, respectively. In the TGA, (1C) demonstrated good thermal stability with less than 5 wt% weight loss up to $242^{\circ}C$. In the solubility test, (1C) and (2C) exhibited solubilities of more than 5 wt% in chloroform, ethyl acetate, and dimethylformamide, but not in methanol. When the compounds (1C) and (2C) were mixed with PMMA (polymethyl methacrylate), thin films showed peaks at 679 nm and 677 nm, respectively, in the photoluminescence spectra. (1C) was found to be a possible candidate as red organic phosphor for hybrid LEDs.

• Journal of Life Science
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• v.24 no.8
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• pp.873-879
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• 2014

The constituents from the needles of the pine tree, Pinus densiflora, were purified and investigated for antithrombotic activity. The needles were initially extracted three times with 70% ethanol, and the extract was sequentially fractionated with chloroform and n-butanol. The aqueous layer formed after n-butanol fractionation was subjected to purification by medium pressure and high pressure liquid chromatography. The two neolignans, 2, 3-dihydro-7-hydroxyl-3-hydroxymethyl-2-(4'-hydroxyl -3-methoxyphenyl)-5-benzofuranpropanol-3-O-${\alpha}$-rhamnopyranoside (a neolignan glycoside) and 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4'-hydroxyphenyl-3'-methoxy)-5-benxofuran propanol 4'-O-${\alpha}$-rhamnopyranoside (icariside $E_4$) were identified by $^1H$ and $^{13}C$ NMR spectra. The effect of the purified compounds, the neolignan glycoside and icariside $E_4$ on thrombin inhibition were investigated by measuring thrombin clotting time in plasma. As a result, the clotting of the neolignan glycoside was delayed four times compared to that of icariside $E_4$. In addition, an analysis of the inhibition effect by changing the concentration showed that the clotting time was delayed in accordance with an increase in the concentration of the neolignan glycoside. Furthermore, we examined the interaction of thrombin and fibrinogen to clarify the action mechanism. As a result, the delay of clotting time in the response of thrombin and pure fibrinogen may indicate that neolignan glycosides inhibit the thrombin action in a direct manner, leading to the suppression of fibrin generation.

• The Korean Journal of Pesticide Science
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• v.10 no.4
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• pp.249-261
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• 2006

Fifty compounds such as ester, sulfonyl ester, carbamate, ether and phosphoyl ester derivatives of 4-isopropyl-3-methylphenol(I) and 5-isopropyl-3-methylphenol(II) were synthesized. These derivatives were identified by IR, GC/MS and $^1H$-NMR spectra. Their in vitro antifungal activities were tested against 10 plant pathogenic fungi. Among them, several compounds showed potent in vitro antifungal activity. The selected compounds showing potent in vitro antifungal activity were tested for their in vivo antifungal activities against 5 plant diseases such as rice blast, rice sheath blast, cucumber anthracnose, cucumber gray mold and tomato late blight. As a result, 4-isopropyl-3-methylphenyl(2-amino-thiazole-4-yl)methoxyiminoacetate(I-7a) showed a potent in vivo antifungal activity against rice blast. Both methyl (4-isopropyl-3-methylphenoxy)acetate(I-4d) and methyl (5-isopropyl-3-methylphenoxy)acetate(II-4d) effectively inhibited the development of cucumber gray mold.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.30 no.9
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• pp.577-582
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• 2017

The white light of a hybrid LED is obtained by using red and green organic fluorescent layers made of polymethylmethacrylate (PMMA) films, which function as color down-conversion layers of blue light-emitting diodes. In this research, we studied the fluorescence properties of a red organic fluorophore, employing perylene bisimide derivatives applicable to hybrid LEDs. The solubility, thermal stability, and luminous efficiency are important characteristics of organic fluorophores for use in hybrid LEDs. The perylene fluorescent compounds (1A and 1B) were prepared by the reaction of 4-bromophenol and 4-iodophenol with N,N'-bis(4-bromo-2,6-diisopropylphenyl)-1, 6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxyl diimide (1) in the presence of dimethyl formaldehyde (DMF) at $70^{\circ}C$. The synthesized derivatives were characterized by using $^1H-NMR$, FT-IR, UV/Vis absorption and PL spectra, and TGA analysis. Compounds 1A and 1B showed absorption and emission at 570 nm and 604 nm in the UV/Vis spectrum. We also documented favorable solubility and thermal stability characteristics of the perylene fluorophores in our work. Perylene fluorophore 1, with the 4-bromophenol substituent 1A, exhibited particularly good thermal stability and solubility in organic solvents.

• Korean Journal Plant Pathology
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• v.14 no.3
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• pp.191-202
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• 1998

About 300 actinomycetes were isolated from two forest and one sea-shore soil and tested for inhibitory effects on mycelial growth of six plant pathogenic fungi Magnaporthe grisea, Alternaria mali, Colletotrichum gloeosporioides, Phytophthora capsici, Fusarium oxysporum f. sp. cucumerinum, and Rhizoctonia solani. Among 300 actinomycetes tested, only 16 actinomycetes showed the antifungal activity against the test fungi. Isolate NH 50 was selected for production and purification of antifungal antibiotic substances. Actinomycete isolate NH 50 displayed the broad antifungal spectra against 11 plant pathogenic fungi. To identify actinomycete isolate NH 50, cultural characteristics on various agar media, diaminopimelic acid type, and morphological characteristics by scanning electron microscopy were examined. As a result, actinomycete isolate NH 50 was classified as a rare actinomycete that had LL-DAP type and did not produce spores. After incubation of isolate NH 50 in yeast extract-malt extract-dextrose broth, antifungal compound NH-B1 that inhibited mycelial growth of some plant pathogenic fungi was purified from the methanol eluates of XAD-16 resins by a series of purification procedures, i.e., silica gel flash chromatography, C18 flash chromatography, Sephadex LH-20 column chromatography, silica gel medium pressure liquid chromatography (MPLC), C18 MPLC, and high pressure liquid chromatography (HPLC). UV spectrum and 1HNMR spectrum of antifungal compound NH-B1 dissolved in methanol were examined. The antibiotic NH-B1 showed the major peaks at 230 and 271.2nm. Based on the data of 1H-NMR spectrum, NH-B1 was confirmed to be an extremely complex polymer of sugars called polysaccharides. The antibiotic NH-B1 showed strong antifungal activity against Alternaria solani and Cercospora kikuchi, but weak activity against M. grisea.