• Title/Summary/Keyword: coupling reaction

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The Synthesis of the Stable IVDU Derivative for Imaging HSV-1 TK Expression (체내 안정형 HSV1-tk (Herpes Simplex Virus Type-1 Thymidine Kinase) 영상용 IVDU 유도체의 합성)

  • Kim, Eun-Jung;Choi, Tae-Hyun;Ahn, Soon-Hyuk;Kim, Byoung-Soo;Park, Hyun;Cheon, Gi-Jeong;Rhee, Hak-June;An, Gwang-Il
    • Nuclear Medicine and Molecular Imaging
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    • v.43 no.5
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    • pp.478-486
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    • 2009
  • Purpose: 5-iododeoxyuridine analogues have been exclusively developed for the potential antiviral and antitumor therapeutic agents. In this study, we synthesized carbocyclic radioiododeoxyuridineanalogue (ddIVDU) and carbocyclic intermediate as efficient carbocyclic radiopharmaceuticals. Materials and Methods: The synthesis is LAH reduction, hetero Diels-Alder reaction as key reactions including Pd(0)-catalyzed coupling reaction together with organotin. MCA-RH7777 (MCA) and MCA-tk (HSV1-tk positive) cells were treated with various concentration of carbocyclic ddIVDU, and GCV. Cytotoxicity was measured by the MTS methods. For in vitro uptake study, MCA and MCA-tk cells were incubated with 1uCi of [$^{125}I$]carbocyclic ddIVDU. Accumulated radioactivity was measured after various incubation times. Results: The synthesis of ddIVDU and precursor for radioiodination were achieved from cyclopentadiene in good overall yield, respectively. The radioiododemetallation for radiolabeling gave more than 80% yield with > 95% radiochemical purity. GCV was more toxic than carbocyclic ddIVDU in MCA-tk cells. Accumulation of [$^{125}I$]carbocyclic ddIVDU was higher in MCA-tk cells than MCA cells. Conclusion: Biological data reveal that ddIVDU is stable in vitro, less toxic than ganciclovir (GCV), and selective in HSV1-tk expressed cells. Thus, this new carbocyclic nucleoside, referred to in this paper as carbocyclic 2',3'-didehydro-2',3'-dideoxy-5- iodovinyluridine (carbocyclic ddIVDU), is a potential imaging probe for HSV1-tk.

Synthesis of Long-Chain Unsaturated Acetates (장직쇄상(長直鎖狀) 불포화(不飽和) 초산화합물(醋酸化合物)의 합성(合成)에 관(關)한 연구(硏究))

  • Oh, Sung-Ki
    • Applied Biological Chemistry
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    • v.19 no.1
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    • pp.1-23
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    • 1976
  • The female moths of Lepidoptera comprising over 1,000,000 described species possess long-chain unsaturated alcohols or esters as the typical structure of potential sex attractants. In this experiment, various stereoisomers of $C_{16}-unsaturated$ acetates were synthesized for potential sex attractants; e.g., $CH_3(CH_2)_mCH=CH(CH_2)_nOR$ (m=0-12, n=1-13, R=H and $-COCH_3$). Seventeen acetates were spectrometrically examined so that the data would provide a ready catalog of gas chromatography and mass spectrometric data for comparison with natural insect sex attractants. Exclusively cis and trans isomers were obtained by the catalytic and chemical reduction methods, respectively. Commercially available $CH_3(CH_2)_mBr,\;CH_3(CH_2)_mC{\equiv}CH,\;HC{\equiv}C(CH_2)_nOH\;and\;HO(CH_2)_n\;OH$ were used for the synthetic starting material. 1-Alkynes, $CH_3(CH_2)_m\;C{\equiv}CH$ exceeding nine methylene groups did not condense with alkyl dihalides. The yield of coupling products was gradually decreased with increasing the molecular weight of diols. In the coupling reaction of $BrCH_2CH_2$ OTHP with acetylene gas, the tetrahydropyranyl ether of bromohydrin produced undesirable elimination product. In this experiment, it seems that p-toluenesulfonic acid is greatly favoured hydrolyzing agent over dilute sulfuric acid in the hydrolysis of the tetrahydropyranyl ether of long-chain alkynols.

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Synthesis and Characterization of Power Conversion Efficiency of D/A Structure Conjugated Polymer Based on Benzothiadiazole-Benzodithiophene (Benzothiadiazole-benzodithiophene을 기반으로 한 D/A구조의 공액 고분자 합성 및 광전변환 효율 특성 개선 연구)

  • Seong, Ki-Ho;Yun, Dae-Hee;Woo, Je-Wan
    • Applied Chemistry for Engineering
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    • v.24 no.5
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    • pp.537-543
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    • 2013
  • In this study, the push-pull structure polymer for organic photo voHaics (OPVs) was synthesized and characterized. The poly{4,8-didodecyloxybenzo[1,2-b;3,4-b]dithiophene-alt-5,6-bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]-thiadiazole} (PDBDT-TBTD) was synthesized by Stille coupling reaction using the benzothiadiazole (BTD) derivative as an electron acceptor and benzodithiophene (BDT) derivative as an electron donor. The structure of monomers and polymers was identified by $^1H-NMR$ and GC-MS. The optical, physical and electrochemical properties of the conjugated polymer were identified by GPC, TGA, UV-Vis and cyclic voltammetry. The number average molecular weight ($M_n$) and initial decomposition temperature (5% weight loss temperature, $T_d$) of PDBDT-TBTD were 6200 and $323^{\circ}C$, respectively. The absorption maxima on the film was about 599 nm and the optical band gap was about 1.70 eV. The structure of device was ITO/PEDOT : PSS/PDBDT-TBTD : $PC_{71}BM/BaF_2/Ba/Al$. PDBDT-TBTD and $PC_{71}BM$ were blended with the weight ratio of 1:2 which were then used as an optical active layer. The power conversion efficiency (PCE) of fabricated device was measured by solar simulator and the best PCE was 2.1%.

A Study on Designing an Effective Support Point for After-Stern Tube Bearings Concerning Shaft Alignment (추진축계 정렬시 선미관 베어링 유효지지점 설정에 관한 연구)

  • Lee, Jae-ung;Kim, Yeonwon;Kim, Jung-Ryul
    • Journal of the Korean Society of Marine Environment & Safety
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    • v.24 no.6
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    • pp.803-809
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    • 2018
  • Generally, the gap-and-sag method is used in the shipbuilding stage before coupling the shafts to check whether they are installed at the same position as designed and derived from shaft alignment calculation. The primary installed propeller shaft becomes a reference point, the position of the remaining shafts are sequentially determined through the gap-and-sag value derived from the deflection and deflection angle at each shaft flange by own weight. If the reference point varies against the design value, it would have a series of effects on the installation of the remaining shafts. Moreover, after coupling the shafts, even if the bearing reaction forces derived from measurement are satisfied by the allowable limit range, consequently it might have an adverse effect on the stability of the shafting system by not being able to estimate the relative slope angle between the propeller shaft and the after-stern tube bearing. In this paper, to deal with above-mentioned phenomenon, the theoretical calculations related to designing an effective support point of the aft stern tube bearing and analysis by measurement is conducted through a case of open-up inspections. Based on this, a shaft installation guideline is proposed to minimize the misalignment related to preventing wiping damage of the after-stern tube bearing.

Synthesis and Characterization of Polyethylenimine-conjugated Polydiacetylene Liposome as a Gene Delivery Carrier (폴리디아세틸렌 리포좀 표면에 저분자량의 폴리에틸렌이민을 연결한 새로운 유전자 전달체 합성 및 특징 연구)

  • Lee, Young Hwa;Yim, Kang Hyuck;Heo, Jungseok;Choi, Joon Sig
    • Polymer(Korea)
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    • v.38 no.1
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    • pp.43-48
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    • 2014
  • In this paper, we made a new polycationic polymeric liposome composed of low molecular weight polyethylenimine (PEI) and 10,12-pentacosadiynoic acid (PCDA). PCDA liposome was prepared by ultraviolet irradiation. PEI was further conjugated on the surface of the polymerized PCDA liposome using coupling reagents to make PCDA-PEI. The blue-to-red transition of PCDA liposome was observed during the coupling reaction. The size distribution of liposome and complexes with plasmid DNA was measured by dynamic light scattering (DLS). The complex formation was also identified by agarose gel electrophoresis and PicoGreen reagent assay. We confirmed the complex formation of the polymeric liposome with DNA and then performed transfection and cytotoxicity assay in HEK 293 and HeLa cells. As a result, PCDA-PEI showed significant gene transfection efficiency and low cytotoxicity. This study shows that PEI-conjugated PCDA liposome could be an efficient gene or drug delivery carrier.

Synthesis of Polyimide Crosslinked Silica-based Aerogel with Enhanced Mechanical Properties and Its Physico-chemical Properties (폴리이미드 가교로 기계적 강도가 향상된 실리카 기반 에어로겔의 합성 및 물리화학적 특성 분석)

  • Kim, Jiseung;Choi, Haryeong;Kim, Taehee;Lee, Wonjun;Lee, Hong-Sub
    • Journal of the Microelectronics and Packaging Society
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    • v.29 no.4
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    • pp.9-14
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    • 2022
  • Silica aerogel is a porous material with a very low density and high specific surface area. Still, its application is limited due to its weak mechanical properties due to structural features. To solve this problem, a method of complexing it with various polymers has been proposed. We synthesized polyimide cross-linked silica aerogel by the sol-gel process to obtain high mechanical properties. Tetraethyl orthosilicate (TEOS) was used as a precursor to make silica aerogel, and 3- aminopropyltriethoxysilane (APTES) was used as a coupling agent for cross-linking polyimide. Polyimide was synthesized using pyromellitic dianhydride and 3,5-diaminobenzoic acid, and mechanical properties were improved by crosslinking polyimide with 10 repeating units in the polyimide chain using the reaction formula ${\frac{n_1}{n_2}}={\frac{n}{n+1}}$ To realize silica aerogel, polyimide having various weight ratios was added before gelation, resulting in a 19-fold or greater increase in maximum compressive strength compared to pure silica aerogel. From this study, an enhancement of silica aerogel could be enhanced through polymer cross-linking bonds.

A Comparative Study on the Removals of 1-Naphthol by Natural Manganese Oxides and Birnessite (천연망간산화물과 버네사이트에 의한 1-Naphthol의 제거 특성 비교)

  • Lee, Doo-Hee;Harn, Yoon-I;Kang, Ki-Hoon;Shin, Hyun-Sang
    • Journal of Korean Society of Environmental Engineers
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    • v.31 no.4
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    • pp.278-286
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    • 2009
  • In this study, four natural Mn oxides ($NMO_1-NMO_4$) was characterized using x-ray diffraction, scanning electron microscopy, and their removal efficiency for 1-naphthol (1-NP) in aqueous phase, using batch reactor, was investigated. The results were compared with one another and a synthetic manganese oxide, birnessite. The NMOs have a various Mn minerals including pyrolusite (${\beta}-MnO_2$), cryptomeltane (${\alpha}-MnO_2$) as well as birnessite (${\delta}-MnO_2$) depending on their sources, which results in different removal efficiencies (removals, kinetics) and reaction types (sorption or oxidative-transformation). The comparative study showed that $NMO_1$ (electrolytic Mn oxide) have a higher removal efficiency for 1-NP via oxidative-transformation compared to birnessite. The 1-NP removals by NMOs were followed by pseudo-first order reaction, and the surface area-normalized specific rate constants ($K_{surf},\;L/m^2$ min) determined were in order of $NMO_1(3.31{\times}10^{-3})$>${\delta}-MnO_2(1.48{\times}10^{-3}){\fallingdotseq}NMO_3(1.46{\times}10^{-3})$>$NMO_2(0.83{\times}10^{-3})$>$NMO_4(0.67{\times}10^{-3})$. From the solvent extraction experiments with the Mn oxide precipitates after reaction, it was observed that the oxidative-transformation rates of 1-NP were in order of $NMO_1{\fallingdotseq}{\delta}-MnO_2$>$NMO_3$>$NMO_4{\gg}NMO_2$ and the analysis of HPLC chromatogram and UV-Vis. absorption ratios ($A_{2/4}$, $A_{2/6}$) on the supernatant confirmed that the reaction products were oligomers formed by oxidative-coupling reaction. Results from this study proved that natural Mn oxide (except $NMO_2$) used in this experiment can be effectively applied for the removal of naphthols in aqueous phase, and the removal efficiencies are depending on the surface characters of the Mn oxides.

Dielectric and Piezoelectric Properties of Lead-free (Bi0.5Na0.5)TiO3-(Bi0.5K0.5)TiO3 Ceramics (비납계 (Bi0.5Na0.5)TiO3-(Bi0.5K0.5)TiO3 세라믹의 유전 및 압전 특성)

  • Cho J. A.;Kuk M.-H.;Sung Y. S.;Lee S. H.;Song T. K.;Jeong S. J.;Song J. S.;Kim M.-H.
    • Korean Journal of Materials Research
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    • v.15 no.10
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    • pp.639-643
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    • 2005
  • Lead-free $[Bi_{0.5}(Na_{1-x}K_x)_{0.5}TiO_3](x=0\~1.0)$ ceramics were prepared using a solid state reaction method and their structural and electrical characteristics were investigated. X-ray investigations indicated that the rhombohedral-tetragonal morphotropic phase boundary(MPB) of the $[Bi_{0.5}(Na_{1-x}K_x)TiO_3$ ceramics exists in the range of $x=0.16\~0.20$. The optimum values of piezoelectric constant$(d_{33})$, dielectric constant, and electromechanical coupling factor $(k_p)$ were obtained at $x=0.16\~0.20$ of the MPB region.

Synthesis and Properties of Diarylamino-Substituted Linear and Dendritic Oligoquinolines for Organic Light-Emitting Diodes

  • Lee, Ho-Joon;Xin, Hao;Park, Seong-Min;Park, Seog-Il;Ahn, Taek;Park, Dong-Kyu;Jenekhe, Samson A.;Kwon, Tae-Woo
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1627-1637
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    • 2012
  • The coupling reaction between 5-bromo-3-phenylbenzo[c]isoxazole and diphenylamine followed by further condensation with a mono-, di- or ter-acetyl aromatic compound in the presence of diphenyl phosphate at $145^{\circ}C$ gave a novel asymmetric diarylquinolines, oligoquinolines with diphenylamine endgroups, and a first generation quinoline dendrimer in 41-82% isolated yield. The electrochemical and photophysical properties of the oligoquinolines were characterized by cyclic voltammograms (CVs) and spectroscopy. All the quinolines emit bright sky blue light due to charge transfer from quinoline group to diphenly amine with very high quantum efficiency (> 90%). Organic light-emitting diodes (OLEDs) were fabricated using these quinolines as emitting materials. Among different device architectures explored, OLEDs with a structure of ITO/PEDOT (40 nm)/TAPC (15 nm)/D-A quinoline (40 nm)/TPBI (30 nm)/LiF (1 nm)/Al using TAPC as an electron blocking layer and TPBI as a hole blocking layer gave the best performance. A high external quantum efficiency in the range of 1.2-2.3% were achieved in all the quinolines with the best performance in BBQA(5). Our results indicate diarylamino-substituted oligoquinoline and dendrimer are promising materials for OLEDs applications.

Synthesis of Crosslinked Poly(POEM-co-AMPSLi-co-GMA) Electrolytes and Physicochemical Properties (가교결합형 poly(POEM-co-AMPSLi-co-GMA) 전해질의 합성과 물리화학적 특성)

  • Choi, Da-In;Ryu, Sang-Woog
    • Journal of the Korean Electrochemical Society
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    • v.17 no.1
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    • pp.65-70
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    • 2014
  • In this study, crosslinked poly(POEM-co-AMPSLi-co-GMA)s were prepared by epoxy coupling of GMA after radical copolymerization of AMPS, POEM and GMA followed by acid-base titration reaction between sulfonic acid of AMPS and $Li_2CO_3$. It was observed that the crystalline melting temperature of POEM was effected by mol% of components and shifted to lower value by lithiation of AMPS group. The ionic conductivity of crosslinked polymer electrolyte was decreased by addition of GMA but maintained over $1.0{\times}10^{-6}S\;cm^{-1}$ until 16 mol%. Particularly, the self-doped polymer electrolyte with 2 mol% of GMA showed its ionic conductivity as high as $4.08{\times}10^{-6}S\;cm^{-1}$ at room temperature and electrochemical stability up to 6 V. In addition, 0.11 MPa of modulus and 270% of elongation were obtained from the free standing film of crosslinked polymer electrolyte.