• Title/Summary/Keyword: thiophene derivatives

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Synthesis of New Blue OLEDs with Biphenyl Structure and Relationship between EL Efficiency and Drift Mobility (Biphenyl 구조를 가진 새로운 청색 유기 발광 재료의 합성 및 EL효율과 이동도의 관계에 대한 연구)

  • Lee, Tae-Hoon;Ryu, Jung-Yi;Kim, Tae-Hoon;Nam, Jang-Hyun;Park, Seong-Soo;Son, Se-Mo
    • Journal of the Korean Graphic Arts Communication Society
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    • v.22 no.2
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    • pp.179-198
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    • 2004
  • Organic electroluminescent devices are light-emitting diodes in which the active materials consist entirely of organic materials. Recently, many fluorescent organic materials have been reported and the study on synthesis and application of new organic light-emitting materials has been demanded. This paper reports the optical and electrical characteristics of OLEDs using novel polymers containing biphenyl structure. First, Optical properties of novel light-emitting biphenyl derivatives doped with poly(9-vinyl carbazole)(PVK) and emitted blue, bluish green color, which is attributed to the overlap area between PL spectrum of host(PVK) and absorption spectra of guests(polymer). This is correspondent with F$\"{o}$rster energy transfer process in the blends. And, OLED devices were fabricated using poly (3,4-ethylenedioxy thiophene) (PEDOT) as a hole injection material and tris-(8-hydroxyquinoline) aluminum ($Alq_3$) as an electron transporting material. EL devices fabricated as ITO/PEDOT/PVK doped with biphenyl derivatives/$Alq_3$/Li:Al and I-V-L chatacteristics and emitting efficiency of EL devices were examined. Finally, the drift mobility of PVK doped with biphenyl derivatives and $Alq_3$ were measured by TOF technique varying applied electric field. EL efficiency was increased as the ratio of hole mobility of PVK doped with biphenyl derivatives and electron mobility of $Alq_3$ was close to one.

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Synthesis of Some New Cytidine and Inosine Derivatives

  • Youssif, Shaker;Mohamed, Enaiat K.;Sayed Ahmed, Ahmed F.;Ghoneim, Amira A.
    • Bulletin of the Korean Chemical Society
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    • v.26 no.12
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    • pp.2021-2026
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    • 2005
  • The oxidation of cytidine 1 and inosine 5 by sodium metaperiodate followed by the reaction of the product with $CH_3I$ in NaOH afforded 2',4'-dihydroxyhexopyranosyl derivatives 2 and 14 respectively. The reaction of thiophene-2-carboxylic acid or furfural with cytidine were taken place via cycloaddition afforded adducts 3 and 4 respectivily. The bromination of inosine 5 or its 2',3'-O-isopropylidine inosine 6 led to the formation of 8-bromoanalogue 7 and 8, respectively. The reaction of 8-bromo-2',3'-O-isopropylidine inosine (8) with ethylglycinate hydrochloride afforded 8-ethoxycarbonylmethylaminoinosine 9. The alkylation of the compound 6 with urea led to the formation of 3-carbonylaminoinosine 10. The oxidation of 6 with DCC afforded 4'-formyl derivative 11, which on reaction with ethyl glycinate hydrochloride followed by reaction with sodium cyanoborohydride afforded 12, while the treatment of dialdehyde inosine 13 with ethyl cyanoacetate in the presence of 0.5 N NaOH afforded compound 15.

Synthesis and Characterization of Oligothiophene Derivative

  • Kim, Hyung-Sun;Park, Jong-Won;Ahn, Jun-Hwan;Kim, Yun-Hi;Kwon, Soon-Ki;Do, Lee-Mi
    • 한국정보디스플레이학회:학술대회논문집
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    • 2004.08a
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    • pp.665-668
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    • 2004
  • Oligothiophene derivatives have been well-known as an p-type channel material.$^1$ Here, we report novel oligothiophene derivative containing methylene linkage as an p-type channel material. Oligothiophene derivative containing methylene linkage BHTM was synthesized and characterized. BHTM was prepared by a palladium-catalyzed cross-coupling reaction via zinc-substituted thiophene. BHTM exhibited high thermal stability and at least one transition temperature.

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Electrical and Optical Properties of Substituted Heterocyclic Conducting Polymers (치환 복소환 도전성 고분자의 전기.광학적 성질)

  • ;;;Katsumi Yoshino
    • The Transactions of the Korean Institute of Electrical Engineers
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    • v.40 no.1
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    • pp.91-98
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    • 1991
  • Electrical conductivity of poly (3-alkylthiophene) derivatives with substituted long alkyl chain such as poly (3-butylthiophene), poly (3-hexylthiophene), poly (3-octylthiophene), poly (3-decylthiophene), poly (3-dodecylthiophene), and poly (3-docosylthiophene) increases with increasing temperature. However, after attaining a maxiumum value, it decreases with further temperature increase. Hysteresis is also observed in the temperature dependence of conductivity and absorption spectra. The absorption spectra also changes rapidly at the phase transition. These phenomena are discussed in terms of the increase of the energy band gap in the liquid states due to the decrease of co-planarity of thiophene rings accompanied by remarkable conformation changes.

Hologram Quantitative Structure Activity Relationship Analysis of JNK Antagonists

  • Kulkarni, Seema A.;Madhavan, Thirumurthy
    • Journal of Integrative Natural Science
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    • v.8 no.2
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    • pp.81-88
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    • 2015
  • c-Jun N-terminal kinase-3 (JNK3) is a member of the mitogen-activated protein kinase family (MAPK), and plays an important role in neurological disorders. Therefore, identification of selective JNK3 inhibitor may contribute towards neuroprotection therapies. In this work, we performed hologram quantitative structure-activity relationship (HQSAR) on a series of thiophene trisubstituted derivatives. The best predictions were obtained for HQSAR model with $q^2=0.628$ and $r^2=0.986$. Statistical parameters from the generated QSAR models indicated the data is well fitted and have high predictive ability. HQSAR result showed that atom, bond and chirality descriptors play an important role in JNK3 activity and also shows that electronegative groups is highly favourble to enhance the biological activity. Our results could be useful to design novel and selective JNK3 inhibitors.

Design and Synthesis of New Amides and Thioamides Derived from 3,4-Ethylenedioxythiophene as Potential Anticonvulsants

  • Kulandasamy, Ravi;Adhikari, Airody Vasudeva;Stables, James P.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.11
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    • pp.3318-3326
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    • 2010
  • Five new series of 3,4-ethylenedioxythiophene derivatives carrying important pharamacophores, viz., amide, ester, ether and active secondary aryl moieties have been designed and synthesized through multistep reactions starting from thiodiglycolic ester and diethyl oxalate. They have been characterized by elemental and spectral data. All the target compounds have been screened for their anticonvulsant activity at three different models viz. maximal electroshock (MES), subcutaneous metrazole (scMET), and 6 Hz screen and evaluated for their neurotoxicity in rotorod model. Compound 6a emerged as lead with no neurotoxicity. All the five series of compounds are safe in the toxicity studies at the maximum dose of 300 mg/kg of body weight. Amongst the tested compounds, the ester pharmacophore with thioamide fragment has showed better activity than the other analogs.

Mass Spectroscopical Properties of Benzoyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices

  • Jeon, Kyu-Ok;Jun, Jung-Ho;Yu, Ji-Sook;Lee, Chang-Kiu
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1840-1844
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    • 2004
  • The mass spectra of benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans which have substituents at the m- and p-positions of the benzoyl ring were analyzed to find correlations against the Hammett substituent parameter ${\sigma}\;and\;{\sigma}^+$. The slopes of the plots of the intensities of the fragments from the heterocycles against those of the benzene gave sets of meaningful values for the indices of aromaticity of the heterocycles: benzene 1.00; thiophene 0.94, pyrrole 0.82, and furan 0.74.

POTENT INHIBITION OF HUMAN CYTOCHROME P450 1 ENZYMES BY DIMETHOXYPHENYL VINYL THIOPHENE

  • Lee, Sang-Kwang;Kim, Sang-Hee;Kim, Mie-Young;Chun, Young-Jin
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.312.3-313
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    • 2002
  • Recently we have reported that various hydroxystilbenes show strong inhibition of human P450 1 activity. A series of synthetic trans-stilbene derivatives were prepared and their inhibitory potentials were evaluated with the bacterial membrane of recombinant human P450 1A1, 1A2 or 1B1 coexpressed with human NADPH-P450 reductase to find new candidates for cancer chemoprevention, Of the compounds tested. SY-021 (3.5-dimethoxyphenyl vinyl thiophene) exhibited a potent inhibition of human P450 181 with an IC$_{50}$ value of 2 nM. SY-021 also showed the inhibitrion of P450 1A1 with IC$_{50}$ value of 61 nM and P450 1A2 with IC$_{50}$ value of 11 nM. SY-021 showed 31-fold selectivity for P450 1B1 over P450 1A1 and 6-fold selectivity for P450 1B1 over 1A2. We have further investigated the inhibition kinetics of P450 1A1. 1A2 and 1B1 by SY-021. The modes of inhibition by SY-021were non-compeitive for all three P450 1 enzymes. Effect of preincubation with NADPH on inhibition of P450 1B1 by SY-021 was determined. These results suggest that SY-021 is one of the mostj potent inhibitor of human P450 1 enzymes and may be considered as a good candidate for a cancer chemopreventive agent in human

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A First Synthesis and Physical Properties of Asymmetric Anthracenes-Thiophenes Bridged with Ethylene

  • Hwang, Min Ji;Park, Ji Hee;Jeong, Eun Bin;Kang, Il;Lee, Dong Hoon;Park, Chan Eon;Singh, O.M.;Choi, HoJune;Kim, Yoon-Hi;Yoon, Yong Jin;Kwon, Soon-Ki;Lee, Sang-Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3810-3816
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    • 2012
  • Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of $2.6{\times}10^{-2}cm^2/Vs$ and $4.4{\times}10^{-3}cm^2/Vs$, respectively, in solution processed OTFTs.

2-Hexylthieno[3,2-b]thiophene-substituted Anthracene Derivatives for Organic Field Effect Transistors and Photovoltaic Cells

  • Jo, So-Young;Hur, Jung-A;Kim, Kyung-Hwan;Lee, Tae-Wan;Shin, Ji-Cheol;Hwang, Kyung-Seok;Chin, Byung-Doo;Choi, Dong-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.3061-3070
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    • 2012
  • Novel 2-hexylthieno[3,2-b]thiophene-containing conjugated molecules have been synthesized via a reduction reaction using tin chloride in an acidic medium. They exhibited good solubility in common organic solvents and good self-film and crystal-forming properties. The single-crystalline objects were fabricated by a solvent slow diffusion process and then were employed for fabricating field-effect transistors (FETs) along with thinfilm transistors (TFTs). TFTs made of 5 and 6 exhibited carrier mobility as high as 0.10-0.15 $cm^2V^{-1}s^{-1}$. The single-crystal-based FET made of 6 showed 0.70 $cm^2V^{-1}s^{-1}$ which was relatively higher than that of the 5-based FET (${\mu}=0.23cm^2V^{-1}s^{-1}$). In addition, we fabricated organic photovoltaic (OPV) cells with new 2-hexylthieno [3,2-b]thiophene-containing conjugated molecules and methanofullerene [6,6]-phenyl C61-butyric acid methyl ester ($PC_{61}BM$) without thermal annealing. The ternary system for a bulk heterojunction (BHJ) OPV cell was elaborated using $PC_{61}BM$ and two p-type conjugated molecules such as 5 and 7 for modulating the molecular energy levels. As a result, the OPV cell containing 5, 7, and $PC_{61}BM$ had improved results with an open-circuit voltage of 0.90 V, a short-circuit current density of 2.83 $mA/cm^2$, and a fill factor of 0.31, offering an overall power conversion efficiency (PCE) of 0.78%, which was larger than those of the devices made of only molecule 5 (${\eta}$~0.67%) or 7 (${\eta}$~0.46%) with $PC_{61}BM$ under identical weight compositions.