• 제목/요약/키워드: Stille reaction

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A Benzodithiophene-based Semiconducting Polymer for Organic Thin Film Transistor

  • Hong, Jung-A;Kim, Ran;Yun, Hui-Jun;Park, Joung-Man;Shin, Sung Chul;Kim, Yun-Hi
    • Bulletin of the Korean Chemical Society
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    • 제34권4호
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    • pp.1170-1174
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    • 2013
  • Benzodithiophene based organic semiconducting polymer was designed and synthesized by stille coupling reaction. The structure of polymer was confirmed by NMR and IR. The weight average molecular weight ($M_w$) of polymer was 8,400 using GPC with polydispersity index of 1.4. The thermal, optical and electrochemical properties of polymer were characterized by TGA and DSC, UV-vis absorption and cyclic voltammetry. OTFT device using PBDT-10 exhibited the mobility of $7.2{\times}10^{-5}\;cm^2\;V^{-1}\;s^{-1}$ and $I_{on}/I_{off}$ of $2.41{\times}10^3$. The film morphology and crystallinity of PBDT-10, was studied using AFM and XRD.

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

  • 성기호;윤대희;우제완
    • 공업화학
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    • 제24권5호
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    • pp.537-543
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    • 2013
  • 본 연구에서는 유기박막태양전지로 적용 가능한 push-pull 구조의 고분자를 합성하여 그 특성을 확인하였다. 전자주개 물질로는 benzodithiophene 유도체를 도입하였고, 전자받개물질은 benzothiadiazole 유도체를 사용하여 Stille coupling 반응으로 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)를 합성하였다. 각 합성 단계별 단량체의 확인은 $^1H-NMR$과 GC-MS를 통해 이루어졌으며, 합성된 conjugated polymer는 GPC, TGA, UV-Vis, cyclic voltammetry를 이용하여 물리적, 광학적 및 전기화학적 특성을 확인하였다. PDBDT-TBTD의 수평균 분자량은 6200이였으며, 초기 분해온도(5% weight loss temperature, $T_d$)값은 $323^{\circ}C$로 측정 되었다. 박막형태에서의 최대 흡수파장은 599 nm이며, 광학적 밴드갭(${E_g}^{opt}$)은 1.70 eV으로 확인되었다. 유기박막태양전지 소자는 ITO/PEDOT : PSS/PDBDT-TBTD : $PC_{71}BM/BaF_2/Ba/Al$ 구조로 제작하였으며, PDBDT-TBTD와 $PC_{71}BM$를 1 : 2 (w/w)의 비율로 블렌딩하여 광활성층으로 사용하였다. 제작된 소자는 solar simulator으로 광전변환효율을 확인하였고, 최대 광전변환효율은 2.1%이었다.

Potential Antitumor ${\alpha}$-methylene-${\gamma}$-butyrolactone-bearing nucleic acid bases. 2. synthesis of $5^I-Methyl-5^I$-[2-(5-substituted uracil-1-yl)ethyl]-$2^I-oxo-3^I$-methylenetetrahydrofurans

  • Kim, Jack-C.;Kim, Ji-A;Park, Jin-Il;Kim, Si-Hwan;Kim, Seon-Hee;Choi, Soon-Kyu;Park, Won-Woo
    • Archives of Pharmacal Research
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    • 제20권3호
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    • pp.253-258
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    • 1997
  • Ten, heretofore unreported, $ 5^I-methyl-5^I-[2-(5-substituted uracil-1-yl)ethyl)]-2^I-oxo-3^I$-methylenetetrahydrofurans (H, F, Cl, Br, I, $ CH_3$,$CF_3$,$CH_2CH_3$,$ CH=CH2$, SePh) (7a-j) were synthesized and evaluated against four cell lines (K-562, FM-3A, P-388 and U-937). For the preparation of ${\alpha}$-methylene-${\gamma}$-butyrolactone-linked to 5-substituted uracils (7a-j), the convenient Reformasky type reaction was employed which involves the treatment of ethyl ${\alpha}$-(bromomethyl)acrylate and zinc with the respective 1-(5-substituted uracil-1-yl)-3-butanone (6a-j). The 5-substituted uracil ketones (6a-j) were directly obtained by the respective Michael type reaction of vinyl methyl ketone with the $K_2CO_3$(or NaH)-treated 5-substituted uracils (5a-j) in the presence of acetic acid in the DMF solvent. The .alpha.-methylene-.gamma.-butyrolactone compounds showing the most significant antitumor activity are 7e, 7f, 7h and 7j (inhibitory concentration $(IC_50)$ ranging from 0.69 to $2.9 {\mu}g/ml$), while 7b, 7g and 7i have shown moderate to significant activity. The compounds 7a, 7c and 7d were found to be inactive. The synthetic intermediate compounds 6a-j were also screened and found marginal to moderate activity where compounds 6b and 6g showed significant activity $(IC_50:0.4~2.8 {\mu}g/ml)$.

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Synthesis and Photovoltaic Properties of Copolymer Containing Fused Donor and Difluoroquinoxaline Moieties

  • Song, Suhee;Choi, Hyo Il;Shin, In Soo;Hyun, Myung Ho;Suh, Hongsuk;Park, Seong Soo;Park, Sung Heum;Jin, Youngeup
    • Bulletin of the Korean Chemical Society
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    • 제35권10호
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    • pp.2963-2968
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    • 2014
  • We report synthesis and photovoltaic properties of two new conjugated copolymers, PCPDTQxF and PDTSQxF, with 6,7-difluoro-2,3-dihexylquinoxaline unit prepared by Stille coupling reaction. The advantage of 6,7-difluoro-2,3-dihexylquinoxaline based copolymer are high PCEs due to lower HOMO energy level, long wavelength absorption and high hole mobility. The solid films of PCPDTQxF and PDTSQxF showed absorption bands with maximum peaks at about 623 and 493 nm and the absorption onsets at 711 and 635 nm, corresponding to band gaps of 1.74 and 1.95 eV, respectively. The oxidation onsets of the PCPDTQxF and PDTSQxF polymers were estimated to be 0.68 and 0.95 V, which correspond to HOMO energy levels of -5.48 and -5.75 eV, respectively. The PDTSQxF has lower HOMO energy level as compared to PCPDTQxF to lead higher $V_{OC}$ value. The device comprising PCPDTQxF:PCBM (1:2) dissolved to a concentration of 1 wt % in ODCB showed $V_{OC}$ value of 0.62 V, $J_{SC}$ value of $1.14mA/cm^2$, and FF of 0.35, which yielded PCE of 0.25%.