• Title/Summary/Keyword: Benzo[1,2,5]thiadiazole

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Synthesis and Photovoltaic Properties of New π-conjugated Polymers Based on Benzo[1,2,5]thiadiazole (Benzo[1,2,5]thiadiazole을 기본 골격으로 한 공액고분자의 합성 및 광전변환특성 연구)

  • Bea, Jun Huei;Lim, Gyeong Eun;Kim, Joo Hyun
    • Applied Chemistry for Engineering
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    • v.24 no.4
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    • pp.396-401
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    • 2013
  • Alternating copolymers, poly[9-(2-octyl-dodecyl)-9H-carbazole-alt-4,7-di-thiophen-2-yl-benzo[1,2,5]thiadiazole] (PCD20TBT) and poly[9,10-bis-(2-octyl-dodecyloxy)-phenanthrene-alt-4,7-di-thiophen-2-yl-benzo[1,2,5]thiadiazole] (PN40TBT), were synthesized by the Suzuki coupling reaction. The copolymers were soluble in common organic solvents such as chloroform, chlorobenzene, 1,2-dichlorobenzene, tetrahydrofuran and toluene. The maximum absorption wavelength and the band gap of PCD20TBT were 535 nm and 1.75 eV, respectively. The maximum absorption wavelength and the band gap of PN40TBT were 560 nm and 1.97 eV, respectively. The HOMO and the LUMO energy level of PCD20TBT were -5.11 eV and -3.36 eV, respectively. As for PN40TBT, the HOMO and the LUMO energy level of PCD20TBT were -5.31 eV and -3.34 eV, respectively. The polymer solar cells (PSCs) based on the blend of copolymer and PCBM (1 : 2 by weight ratio) were fabricated. The power conversion efficiencies of PSCs based on PCD20TBT and PN40TBT were 0.52% and 0.60%, respectively. The short circuit current density ($J_{SC}$), fill factor (FF) and open circuit voltage ($V_{OC}$) of the device with PCD20TBT were $-1.97mA/cm^2$, 38.2% and 0.69 V. For PN40TBT, the $J_{SC}$, FF, and $V_{OC}$ were $-1.77mA/cm^2$, 42.9%, and 0.79 V, respectively.

Synthesis and Photovoltaic Properties of Low Band Gap π-Cojugated Polymer Based on 4,7-Di-thiophen-2-yl-benzo[1,2,5]thiadiazole (4,7-Di-thiophen-2-yl-benzo[1,2,5]thiadiazole을 기본으로 한 고분자의 합성 및 광전변환 특성)

  • Shin, Woong;You, Hyeri;Park, Jeong Bae;Park, Sang Jun;Jeong, Mi Seon;Moon, Myung-Jun;Kim, Joo Hyun
    • Applied Chemistry for Engineering
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    • v.21 no.2
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    • pp.137-141
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    • 2010
  • Poly [4,7-Di-thiophen-2-yl-benzo(1,2,5)thiadiazole]-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene (PPVTBT) was synthesized by the Heck coupling reaction between 4,7-Di-thiophen-2-yl-benzo(1,2,5)thiadiazole and 1,4-bis(dodecyloxy)-2,5-divinylbenzene. The maximum absorption and band gap of PPVTBT were 550 nm and 1.74 eV, respectively. The HOMO and LUMO energy level of PPVTBT were -5.24 eV and -3.50 eV, respectively. The photovoltaic device based on the blend of PPVTBT and (6)-1-(3-(methoxycarbonyl)propyl)-{5}-1-phenyl[5,6]-$C_{61}$ (PCBM) (1 : 6 by weight ratio) was fabricated. The efficiency of device was 0.16%. The short circuit current density (Jsc), fill factor (FF) and open-circuit voltage (Voc) of the device was $0.74mA/cm^{2}$, 31% and 0.71 V, respectively, under AM 1.5 G and 1 sun condition ($100mA/cm^{2}$).

A Novel Donor-Acceptor-Acceptor-Acceptor Polymer Containing Benzodithiophene and Benzimidazole-Benzothiadiazole-Benzimidazole for PSCs

  • Tamilavan, Vellaiappillai;Song, Myungkwan;Agneeswari, Rajalingam;Kim, Sangjun;Hyun, Myung Ho
    • Bulletin of the Korean Chemical Society
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    • v.35 no.4
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    • pp.1098-1104
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    • 2014
  • New electron deficient acceptor-acceptor-acceptor type of monomer unit composed of weak electron accepting benzimidazole and relatively strong electron accepting benzothiadiazole derivatives namely 4,7-bis(6-bromo-1-(2-ethylhexyl)-1H-benzo[d]imidazol-2-yl)benzo[c][1,2,5]thiadiazole (BBB) was synthesized. The Stille polycondensation of the newly synthesized BBB monomer with electron donating 2,6-bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene (BDT) afforded donor-acceptor-acceptor-acceptor type of polymer namely 2,6-(4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene)-alt-4,7-bis(1-(2-ethylhexyl)-1H-benzo[d]imidazol-2-yl)benzo[c][1,2,5]thiadiazole (PBDTBBB). The opto-electrical studies revealed that the absorption band of PBDTBBB appeared in the range of 300 nm-525 nm and its highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels were positioned at -5.18 eV and -2.84 eV, respectively. The power conversion efficiency (PCE) of the polymer solar cell (PSC) prepared from PBDTBBB:PC71BM (1:2 wt %) blend was 1.90%.

Synthesis and Characterization of Novel Red-Light-Emitting Materials with Push-Pull Structure Based on Benzo[1,2,5]thiadiazole Containing Arylamine as an Electron Donor and Cyanide as an Electron Acceptor

  • Ju, Jin-Uk;Jung, Sung-Ouk;Zhao, Qinghua;Kim, Yun-Hi;Je, Jong-Tae;Kwon, Soon-Ki
    • Bulletin of the Korean Chemical Society
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    • v.29 no.2
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    • pp.335-338
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    • 2008
  • New efficient red emitter having short p?-conjugation length and asymmetric bulky structure, 2-(7-diphenylamino-benzo[1,2,5]thiadiazole-4-ylmethylene)-malononitrile, was synthesized and characterized. Using this material as a dopant, we fabricated electroluminescence device with a structure of ITO/DNTPD/NPD/BTZA (5 wt% in Alq3)/Alq3/LiF/Al. The device exhibited a high brightness of 761 cd/m2 at a driving voltage of 4.8 V, and current efficiency is 0.75 cd/A. The Commission International de IEclairage (CIE) coordinates of the EL device were found to be (0.62, 0.37) at 10 mA/cm2.

Synthesis and Characterization of New Dihydroindolo[3,2-b]indole and 5,6-Bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole-Based Polymer for Bulk Heterojunction Polymer Solar Cells

  • Kranthiraja, Kakaraparthi;Gunasekar, Kumarasamy;Song, Myungkwan;Gal, Yeong-Soon;Lee, Jae Wook;Jin, Sung-Ho
    • Bulletin of the Korean Chemical Society
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    • v.35 no.5
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    • pp.1485-1490
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    • 2014
  • We have designed and developed a new ladder type tetrafused ${\pi}$-conjugated building block such as dihydroindolo[3,2-b]indole (DINI) and investigated its role as an electron rich unit. The photovoltaic properties of a new semiconducting ${\pi}$-conjugated polymer, poly[[5,10-bisoctyl-5,10-dihydroindolo[3,2-b]indole-[5,6- bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole]], represented by PDINI-OBTC8 are described. The new polymer PDINI-OBTC8 was synthesized in donor-acceptor (D-A) fashion, where fused ${\pi}$-conjugated tetracyclic DINI, and 5,6-bis(octyloxy)-4,7-di(thiophen-2-yl) benzo[c][1,2,5]thiadiazole (OBTC8) were employed as electron rich (donor) and electron deficient (acceptor) moieties, respectively. The conventional bulk heterojunction (BHJ) device structure ITO/PEDOT:PSS/PDINI-OBTC8:PCB71M/LiF/Al was utilized to fabricate polymer solar cells (PSCs), which comprises the blend of PDINI-OBTC8 and [6,6]-phenyl-$C_{71}$-butyric acid methyl ester ($PC_{71}BM$) in BHJ network. A BHJ PSC that contain PDINI-OBTC8 delivered power conversion efficiency (PCE) value of 1.68% with 1 vol% of 1,8-diidooctane (DIO) under the illumination of A.M 1.5G 100 $mW/cm^2$.

Study on the Efficient White Organic Light-Emitting Diodes using the Material of Binaphthyl Group (Binaphthyl group 기반의 물질을 이용한 효율적인 White OLED 소자에 대한 연구)

  • Yeo, Hyun-Ki
    • Journal of the Korean Applied Science and Technology
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    • v.29 no.3
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    • pp.459-465
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    • 2012
  • We had synthesized a green dopant material based on the binaphthyl group, 7,7'-(2,2'dimethoxy-1,1'-binaphthyl-3,3'-diyl) bis(4-(thiophen -2-yl) benzo[e][1,2,5] thiadiazole (TBT). We also fabricated the white organic light emitting diode (OLED) with a phosphorescent blue emitter : iridium(III)bis[(4,6-di-fluoropheny)-pyridinato -N,C2]picolinate (FIrpic) doped in N,N'-dicarbazolyl-3,5-benzene (mCP) of hole transport type host material and both TBT and bis(2-phenylquinolinato)- acetylacetonate iridium(III) (Ir(pq)2acac) doped in 1,3,5-tris(N-phenylbenzimidazole -2-yl)benzene (TPBi) of electron transport type host material. As a result, the property of white OLED using TBT, which demonstrated a maximum luminous efficiency and external quantum efficiency of 5.94 cd/A and 3.23 %, respectively. It also showed the pure white emission with Commission Internationale de I'Eclairage (CIE) coordinates of (0.34, 0.36) at 1000 nit.

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%.

Induction of Disease Resistance by Acibenzolar-S-methyl, the Plant Activator against Gray Mold (Botrytis cinerea) in Tomato Seedlings (저항성 유도물질(acibenzolar-S-methyl)처리에 의한 토마토 잿빛곰팡이병 발병억제)

  • Lee Jung-Sup;Kang Nam-Jun;Seo Sang-Tae;Han Kyoung-Suk;Park Jong-Han;Jang Han-Ik
    • Research in Plant Disease
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    • v.12 no.1
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    • pp.40-45
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    • 2006
  • The plant defence activator, Acibenzolar-S-methyl [benzo (1,2,3) thiadiazole-7-carbothioic acid-S-methyl ester, ASM] was assayed on tomato seedlings for its ability to induce resistance against Botrytis cinerea, the causal agent of gray mold in tomato. Pre-treatment of plants with ASM reduced the severity of the disease as well as the growth of the mycelium in plants. In ASM treated plants, reduction in disease severity (up to 55%) was correlated with suppression of mycelia growth (up to 46.5%) during the time course of infection. In plants treated with ASM, activities of peroxidase were determined as markers of resistance. Applications of ASM induced Progressive and significant increase of the enzyme in locally treated tissues. Such responses were expressed earlier and with a much higher magnitude when ASM-treated seedlings were challenged with the pathogen, thus providing support to the concept that a signal produced by the pathogen is essential for triggering enhanced synthesis and accumulation of the enzymes. No such activities were observed in water-treated control plants. Therefore, the slower symptom development and reduction in mycelium growth in ASM treated plants might be due to the increase in activity of oxidative and antioxidative protection systems in plants.