• Bulletin of the Korean Chemical Society
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• 제33권8호
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• pp.2789-2792
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• 2012

• Archives of Pharmacal Research
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• 제20권3호
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• pp.288-290
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• 1997

An efficient synthesis of 3-(E)-hydroxy- and 3-(E)-acetoxypropenylcephem derivatives, key intermediates for the synthesis of 3-(E)-propenylcephalosporins was achieved via Stille coupling reaction of 3-trifloxycephem with 3-(E)-tributylstannylallylic alcohol.

• Bulletin of the Korean Chemical Society
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• 제34권7호
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• pp.2099-2104
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• 2013

We present here an efficient and simple method for preparation of highly active Pd heterogeneous catalyst (CNT-Pd), specifically by reaction of dichlorobis(triphenylphosphine)palladium ($Pd(PPh_3)_2Cl_2$) with thiolated carbon nanotubes (CNTs). The as-prepared CNT-Pd catalysts demonstrated an excellent catalytic activity for the carbon-carbon (C-C) cross-coupling reactions (i.e. Suzuki, Stille, and decarboxylative coupling reactions) under mild conditions. The CNT-Pd catalyst could easily be removed from the reaction mixture; additionally, in the decarboxylative coupling of iodobenzene and phenylpropiolic acid, it showed a six-times recyclability, with no loss of activity. Moreover, once its activity had decreased by repeated recycling, it could easily be reactivated by the addition of phosphine ligands. The remarkable recyclability of the decarboxylative coupling reaction is attributable to the high degree of dispersion of Pd catalysts in CNTs. Aggregation of the Pd catalysts is inhibited by their strong adhesion to the thiolated CNTs during the chemical reactions, thereby permitting their recycling.

• Bulletin of the Korean Chemical Society
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• 제17권2호
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• pp.153-158
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• 1996

The synthesis of common skeleton of podosporin A and aureol was studied through cationic olefin cyclization as a key step. The generation of thermodynamic silyl enol ether or enol acetate under known conditions gave regioselectivity of 88:12. The enolate alkylation of 2,3-dimethylcyclohexanone with 2,5-dimethoxybenzyl bromide at the more substituted site via lithium enolate gave poor yield. In this case an organozincate or an ammonium enolate also proved to be ineffective or not practical in terms of yield. Side chain elongation of the substituted cyclohexanone 13 through Grignard reaction, Wittig reaction, or Shappiro reaction did not proceed because of steric hindrance and side reactions. However, Stille coupling reaction via enol triflate produced the desired product 18 in high yield. The advanced intermediate 22, which was efficiently synthesized from 18, produced 24 instead of the desired product under a cationic olefin cyclization condition, indicating that the cyclization occurred in a stepwise mannervia the organomercury intermediate 23.

• Bulletin of the Korean Chemical Society
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• 제28권7호
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• pp.1175-1182
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• 2007

A series of new organic semiconductors hexyl end-capped thiophene-anthracene oligomers containing the anthracene moiety in the center of the oligomers are synthesized. The target oligomers have been obtained by Stille coupling reactions as key step reactions. The synthesized thiophene-anthracene oligomers were characterized by 1H-NMR, 13C-NMR and high-resolution mass spectroscopy, respectively. All of the oligomers are soluble in chlorinated solvents. Their optical, thermal and electrochemical properties were measured. The hexyl end-capped oligomers and their unsubstituted oligomers exhibit the same absorption behavior in dilute toluene solution. Hexyl end-capped bis-terthienylanthracene oligomer is observed to show liquid crystalline mesophase at 166 oC in heating process. The thermal analyses as well as the electrochemical measurement data indicate that the designed materials show better thermal and oxidation stability than the corresponding oligothiophenes without anthracene core. Fluorescence lifetimes and fluorescence quantum yields of the thiophene-anthracene oligomers are measured to be 10-14 ps and 3.4-9.9 × 10?3 which are much shorter and lower than those of oligothiophenes respectively.

• 폴리머
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• 제39권1호
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• pp.71-77
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• 2015

본 연구에서는 전자가 풍부한 구조단위(dithienosilole 및 benzodithiophene)와 전자가 부족한 구조단위(difluorobenzothiadiazole)를 주사슬에 교대로 갖는 작은 밴드갭 공중합체를 Stille 짝지움 반응을 이용하여 합성하였다. $^1H$ NMR을 통하여 각 단계별 화합물과 고분자의 구조를 확인하였다. GPC, TGA, UV-vis 분광분석기 및 cyclic voltammetry를 이용하여 합성한 고분자의 특성을 조사하였다. 합성한 공액고분자와 $PC_{70}BM$을 1:1.5, 1:2, 1:3, 1:3.5 및 1:4의 중량비로 혼합하여 ITO/PEDOT:PSS/polymer:$PC_{70}BM/Al$의 구조로 유기태양전지 소자를 제작하여 그 광전특성을 조사하였다. 고분자:$PC_{70}BM$의 혼합비율이 1:3에서 최고 1.0%의 광전변환효율이 달성되었다. TEM 실험을 통하여 1:3 혼합비율에서 유기태양전지에 가장 적합한 나노규모로 상분리가 일어났으며, 다른 혼합비율에서는 고분자와 $PC_{70}BM$의 뭉침현상에 기인하여 태양전지 특성이 낮아졌다.

• 폴리머
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• 제37권6호
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• pp.694-701
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• 2013

프탈이미드 유도체와 티오펜 단량체들을 이용하여 새로운 고분자인 poly((5,5-(2-butyl-5,6-bisdecyloxy-4,7-dithiophen-2-yl-isoindole-1,3-dione))-alt-(2,5-thiophene))(T-TI24T)를 Stille법을 이용하여 합성하였다. T-TI24T의 수평균 분자량은 86500 g/mol로 매우 높으며 클로로포름, 1,2-디클로로벤젠, 톨루엔과 같은 용매에 매우 잘 용해된다. 또한 $380^{\circ}C$까지 매우 우수한 열적 안정성을 갖고 있다. T-TI24T는 꽤 낮은 호모에너지 준위(-5.33 eV)를 갖고 있다. 서로 다른 T-TI24T와 (6)-1-(3-(methoxycarbonyl)-{5}-1-phenyl[5,6]-fullerene(PCBM)의 무게비를 갖는 블렌드를 광활성층으로 하는 태양전지를 제작하여 특성을 살펴본 결과 고분자와 PCBM의 비율이 1:3일 때 가장 최적화된 결과를 보였으며, 이 때 광전변환 효율과 개방전압은 각각 0.199%와 0.99였다. T-TI24T 기반 태양전지들은 비록 매우 작은 광전변환 효율을 갖지만 잘 알려진 P3HT:PC61BM으로 구성된 태양전지와 비교해 큰 매우 큰 개방전압을 갖는다(약 0.5 V).

• 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.

• 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.

• 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%.