• Title/Summary/Keyword: ether linkage

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Synthesis and Characterization of Alternating Block Copolycarbonates Containing Constituent Groups of Polysulfone

  • Lee, Jung-Ah;Yoo, Seung-Hoo;Jho, Jae-Young;Lee, Jong-Chan
    • Macromolecular Research
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    • v.11 no.6
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    • pp.437-443
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    • 2003
  • A series of alternating and alternating block copolycarbonates containing the constituent groups of polysulfone was synthesized through a multi-step solution condensation method. For the regulation of block length, monodisperse oligomers were prepared by using a large excess of the bisphenols and were subsequently incorporated into the copolymer chains. Separating the unreacted bisphenols from the oligomers by dissolution/precipitation steps took advantage of solubility differences. The structures of the monomers, oligomers, and copolymers were characterized and confirmed by GPC, NMR spectroscopy, mass spectrometry, and elemental analysis. Monodispersity of the oligomers, which is critical for control over the block length in the copolymers, was confirmed by GPC and mass spectrometry. Of the two constituent groups of the polysulfone, the sulfone linkage stiffens the polycarbonate copolymer chain, while the ether linkage softens it.

Development and Charateriztion of Molybdophosphoric Acid Bonded Polyether Ether Ketone Polymer Composite Membrane for Water Electrolysis (수전해용 MoPA 결합된 폴리에테르 에테르 케톤 고분자 복합막의 개발 및 특성)

  • KIM, MIN JIN;KIM, BO YOUNG;MOON, SANG-BONG;CHUNG, JANG HOON
    • Transactions of the Korean hydrogen and new energy society
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    • v.28 no.4
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    • pp.338-344
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    • 2017
  • Polyoxometal molybdophosphoric acid (MoPA) bonded polyether ether ketone (PEEK) composite membrane for water electrolysis has been investigated. The composited membrane, covalently cross linked (CL) sulfonated polyether ether ketone (SPEEK) with a bonded MoPA, was prepared in sulfonation of PEEK, cross linkage reaction with 1,4-diiodobutane, and addition with MoPA. PEEK was covalently cross-linked with 1,4-diiodobutane to improve mechanical strength and was added with MoPA to increase proton conductivity. MoPA should be fixed to back bone of SPEEK to prevent bleeding out. Therefore, the carbonyl group of SPEEK was reduced with NaBH4 and 3-isocyanatepropyltriethoxysilane (ICPTES) was added. The MoPA bonded composite was produced in the reaction of MoPA with 3-mercaptopropyltrimethoxvsilane (MPTMS). In conclusion, MoPA bonded CL-SPEEK composite membrane featured 0.129 S/cm of proton conductivity at $80^{\circ}C$, and 2,156 hours of chemical stability in Fenton test. These properties are better than those of membranes of other SPEEK system.

Effect of Linkage Groups on the Properties of Semi-flexible Liquid Crystalline Polymers (연결기가 반 유연성 액정중합체의 물성에 미치는 영향)

  • Park, Jong-Ryul;Yoon, Doo-Soo;Bang, Moon-Soo
    • Applied Chemistry for Engineering
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    • v.26 no.4
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    • pp.445-451
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    • 2015
  • Semi-flexible liquid crystalline polymers containing a mesogenic group and an octamethylene flexible spacer in the main chain were synthesized by solution polycondensation. The mesogenic group in the polymer consists of four aromatic rings connected by ester and ketone, ether, sulfide, methylene, sulfone, or isopropylidene linkage groups. This paper discusses effects of the central linker of the mesogenic group on polymer properties. The structures and properties of synthesized polymers were investigated by $^1H$-NMR, FT-IR, differential scanning calorimeter (DSC), thermogravimetric analyzer (TGA), X-ray diffractometer (XRD), and polarizing optical microscope (POM). Polymers having bent linkage groups exhibited low thermal transition temperatures, narrow mesophase temperature ranges, low liquid crystallinity, and good solubilities in organic solvents, while those having bulky linkage groups were amorphous and exhibited high glass transition temperatures.

Diastereoselective Synthesis of (+)-Frontalin

  • Jung, Jung-Hwa;Kim, Hee-Doo
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.345.3-346
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    • 2002
  • In connection with the asymmetric synthesis of chiral l.2-diol. we report here the total synthesis of (+)-frontalin using diastereoselective alkylation featuring tridentate chelation-controlled asymmetric alkylation of a-hydroxyketone, in which the chiral auxiliary is attached to the hydroxyl group as ether linkage. The starting D-glyceraldehyde acetonide was converted (S)- [(4R)-2.2-dimethyH,3-dioxolan-4-yl] (4-methoxyphenyl) methanol. (omitted)

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Synthesis of New Bicyclic Aziridines Containing Chalcone Analogs and Investigation of Their Photochromic Properties

  • Besharati-Seidani, Tayebeh;Mahmoodi, Nosrat O.
    • Bulletin of the Korean Chemical Society
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    • v.34 no.3
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    • pp.875-883
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    • 2013
  • Ten new derivatives of 1,3-diazabicyclo[3.1.0]hex-3-enes linked via ether linkage to chalcones were synthesized and characterized by UV, FT-IR, $^1H$ NMR and $^{13}C$ NMR spectral techniques. The spectra of all synthesized compounds, confirmed structure-photochromic behavior relationships (SPBR) both in solution or in solid state by irradiation under UV light at 254 nm. In other efforts for first time photochromic behavior of ketoaziridines has been investigated.

Reagentselective reduction of 25(R)-1,4,6-spirostatrien-3-one

  • Ma, Eun-Sook;Kim, Hak-Soon;Kim, Eun-Jung;Jung, Won-Young;Choi, Tae-Young
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.234.1-234.1
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    • 2003
  • Spicatoside A and spicatoside B were isolated from Liriopis tuber. Spicatoside A has anticancer activity and it is composed of 1 ${\beta}$-hydroxy diosgenin and trisaccharides. Spicatoside B has the preventive effect of diabetes mellitus and also has 1 ${\beta}$-hydroxy derivatives, which is clevaged the ether linkage of F ring of diosgenin. Therefore, selective synthesis of 1 ${\beta}$-hydroxydiosgenin is required. (omitted)

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Studies on the Decomposition of Environmental Pollutants by Utilizing Microorganisms (미생물을 이용한 환경오염원의 분해에 관한 연구 II)

  • 이재구;김기철;김창한
    • Korean Journal of Microbiology
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    • v.20 no.2
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    • pp.53-66
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    • 1982
  • 1. When Chong Ju and Chung Ju soils possessing different physicochemical properties were treated with 500 ppm of TOK and incubated in flooded anaerobic condition for 2, 4, and 6 months, respectively, they produced 4-Chloro-4'-amino diphenyl ether, 2,4-Dichloro-4'-amino diphenyl ether(amin-TOK), N-[4'-(4-Chlorophenoxy)] phenyl acetamide, and N-[4'-(4-Chlorophenoxy)] phenyl formamide as the metabolities. This result indicates that TOK undergose the reduction of its $NO_2\;to\;NH_2$ group, dechlorination, acetylation, and formylation under this condition. The cleavage of ether linkage does not occur. In addition, TOK degrades more readily in Chung Ju soil which is characterized by pH 6.43 and higher contents of $Ca^{++}$ and C.E.C. than in Chong Ju soil which is lower in pH, $Ca^{++}$, and C.E.C. 2. In the aerobic incubation of TOK of 25ppm in Chung Ju soil suspension for 21 days, the ratio of the resulting metabolites, TOK : amino-TOK : 4-Chloro-4'-amino diphenyl ether was 100 : 130 : 76. Meanwhile, in the 42 day incubation, the ratio was 100 : 19 : 5, which indicates that TOK in aerobic condition dose not necessrily degrade as a function of the incubation period. 3. The citrate buffer extract of Chung Ju soil has the capability of degrading TOK, which was verified to be due to the action of the microorganisms involved. 4. Twelye strains of soil bacteria were isolated from the TOK-treated soils. In the incubation of TOK in pure cultures of the respective isolates, the strain T-1-1 isolated from Chong Ju soil had almost no degradability whereas the strain T-2-3 was the most potent. The degradation of TOK by the isolates constituted mostly the reduction of the nitro group to amino group. 5. In a test for the degradability of TOK by some selected microorganisms, Pseudomonas species were more potent than fungi. Yet, Isolate B which had been isolated from Chung Ju soil suspension was the most potent.

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Synthesis of Ochnaflavone and Its Inhibitory Activity on PGE2 Production

  • Kim, Sung Soo;Vo, Van Anh;Park, Haeil
    • Bulletin of the Korean Chemical Society
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    • v.35 no.11
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    • pp.3219-3223
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    • 2014
  • Ochnaflavone, a naturally occurring biflavonoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a C-O-C linkage, was first synthesized and evaluated its inhibitory activity on $PGE_2$ production. Total synthesis was accomplished through modified Ullmann diaryl ether formation as a key step. Coupling reactions of 4'-halogenoflavones and 3'-hydroxy-5,7,4'-trimethoxyflavone were explored in diverse reaction conditions. The reaction of 4'-fluoro-5,7-dimethoxyflavone (2c) and 3'-hydroxy-5,7,4'-trimethoxyflavone (2d) in N,N-dimethylacetamide gave the coupled compound 3 in 58% yield. Synthetic ochnaflavone strongly inhibited PGE2 production ($IC_{50}=1.08{\mu}M$) from LPS-activated RAW 264.7 cells, which was due to reduced expression of COX-2. On the contrary, the inhibition mechanism of wogonin was somewhat different from that of ochnaflavone although wogonin, a natural occurring anti-inflammatory flavonoid, showed strong inhibitory activity of $PGE_2$ production ($IC_{50}=0.52{\mu}M$), and seems to be COX-2 enzyme inhibition. Our concise total synthesis of ochnaflavone enable us to provide sufficient quantities of material for advanced biological studies as well as to efficiently prepare derivatives for structure-activity relationship study.

The Photoreactivity of 2-Halobenzyl Phenyl Ether (2-할로벤질 페닐 에델의 광반응성)

  • Park, Yong Tae;Kim, Young Hee;Shin, Hyun Il
    • Journal of the Korean Chemical Society
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    • v.42 no.2
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    • pp.203-208
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    • 1998
  • The photochemical reactivities of 2-halobenzyl phenyl ether, in which 2-halobenzyl moiety are tethered to phenyl moiety by the etheral alkyl linkage, has been studied. In the presence of nitrogen, the photochemical reaction of 2-chlorobenzyl phenyl ether (1) produces mainly phenol and photo-Fries type reaction products, while the corresponding bromo analog 2 produces photocyclization and photoreduced products, along with phenol and photo-Fries type products. The former result implies that since chlorine is bound to the benzyl ring firmly, the rather weaker $CH_{2}-O$ bond of 1 is cleavaged to produce the photo-Fries type product. The latter implies that the photoinduced fission of phenyl-bromine bond of 2 can compete with the fission of $CH_{2}-O$ bond, since the bond energy of phenyl-bromine is lower than that of phenyl-chlorine. Since by the presence of oxygen the formation of phenol is not affected much, the formation of photo-Fries type products is changed a little, and the formations of photocyclization and photoreduced products are affected effectively, a singlet state is involved in the formation of phenol, and both singlet and triplet state may be involved in the formation of photo-Fries type reaction, while a triplet state is involved in the formation of photocyclization and photoreduction products.

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Glass Transition Behavior of Dendritic Polymers Containing Mobile Aliphatic Polyether Cores and Glassy Peripheral Polystyrenes

  • Song, Jie;Cho, Byoung-Ki
    • Bulletin of the Korean Chemical Society
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    • v.29 no.6
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    • pp.1167-1172
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    • 2008
  • We investigated the glass transition temperatures ($T_g$) of dendrons consisting of conformationally mobile aliphatic polyether dendritic cores plus glassy peripheral polystyrenes (PSs), and linear PSs in the molecular weight range of 1000-8500 g/mol. We compared their $T_g$ behavior depending on their polymeric architecture. The linear PSs show a typical growth of $T_g$ up to 92.5 ${^{\circ}C}$ as the molecular weight increases to 8300 g/mol, while the dendrons display nearly constant $T_g$ values of 58-61 ${^{\circ}C}$, despite the increase of molecular weight with each generation. The striking contrast of Tg behavior would be mainly attributed to the fact that the dendrons keep the ratio of $N_e$/M ($N_e$: number of peripheral chain ends, M: molecular weight) over all the generations. Additionally, for the influence of dendritic spacers on glass transition temperature we prepared dimeric PSs with different linkage groups such as aliphatic ether, ester and amide bonds. We found that the dimer with the ether spacer exhibited the lowest glass transition at 55.4 ${^{\circ}C}$, while the amide linked dimer showed the highest glass transition temperature at 74.2 ${^{\circ}C}$. This indicates that the peripheral PS chains are effectively decoupled by the conformationally flexible ether spacer. The results from this study demonstrated that polymeric architecture and dendritic core structures play a crucial role in the determination of glass transition behavior, providing a strategy for the systematic engineering of polymer chain mobility.