• Title/Summary/Keyword: benzothiadiazole

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Impact of Cyano and Fluorine Group Functionalization on the Optoelectronic and Photovoltaic Properties of Donor-Acceptor-π-Acceptor Benzothiadiazole Derived Small Molecules: A DFT and TD-DFT Study

  • Prabhat Gautam;Anurag Gautam;Neeraj Kumar
    • Korean Journal of Materials Research
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    • v.33 no.6
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    • pp.236-241
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    • 2023
  • Solar cells based on p-conjugated donor-acceptor (D-A) organic molecular systems are a promising alternative to conventional electrical energy generation. D-A molecular systems, which have a triphenylamine (TPA) moiety linked with a benzothiadiazole (BTD) moiety, open the potential development of new small molecule donors for bulk heterojunction (BHJ) solar cells. Here, a series of donor-acceptor-π-acceptor (D-A-π-A) small molecule donors (SMD) derived from triphenylamine (TPA) donor and benzothiadiazole (BTD) acceptor building blocks, were designed for BHJ organic solar cells. The small molecule donors SMD1-4 were studied using density functional theory (DFT) and time dependent-DFT (TDDFT) methods, to understand the effect of cyano and fluorine group functionalization on their properties. The effect of structure alteration by cyano and fluorine group functionalization on the optoelectronic properties, the calculated highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) and the HOMO-LUMO gaps were theoretically explored. The Voc (open-circuit photovoltage) and fill factor (FF) for SMD1-4 were obtained with a PC71BM acceptor, which showed that these organic small molecules are potential small molecule donors for organic bulk heterojunction solar cells.

Synthesis, Photovoltaic Properties and Side-chain Effect of Copolymer Containing Phenothiazine and 2,1,3-Benzothiadiazole (Phenothiazine과 2,1,3-Benzothiadiazole을 포함한 Copolymer의 합성 및 Side-chain 치환에 따른 Photovoltaic 특성 연구)

  • Yun, Dae-Hee;Yoo, Han-Sol;Seong, Ki-Ho;Lim, Jeong-Ho;Park, Yong-Sung;Wo, Je-Wan
    • Applied Chemistry for Engineering
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    • v.25 no.5
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    • pp.487-496
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    • 2014
  • In this study, three kinds of polymers based on phenothiazine-benzothiadiazole were synthesized by a Suzuki coupling reaction, and the various side-chains were substituted at the nitrogen of phenothiazine. The optical and electrochemical properties of synthesized polymers were analyzed. The results indicate that their absorption ranged from 300 to 700 nm, and also confirmed the ideal highest occupied molecular orbital (HOMO) energy level was about -5.4 eV with low band-gap energy. Photovoltaic devices were fabricated using a photoactive layer composed of a blended solution of the polymer and $PC_{71}BM$ in ortho-dichlorobenzene The device with P2HDPZ-bTP-OBT containing the branched side-chain and long chain showed the best performance; the maximum power conversion efficiency of this device was 2.4% (with $V_{OC}$ : 0.74 V, $J_{SC}$ : $6.9mA/cm^2$, FF : 48.0%).

Induction of Systemic Resistance of Benzothiadiazole and Humic Acid in Soybean Plants Against Fusarium Wilt Disease

  • Abdel-Monaim, Montaser Fawzy;Ismail, Mamdoh Ewis;Morsy, Kadry Mohamed
    • Mycobiology
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    • v.39 no.4
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    • pp.290-298
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    • 2011
  • The ability of benzothiadiazole (BTH) and/or humic acid (HA) used as seed soaking to induce systemic resistance against a pathogenic strain of Fusarium oxysporum was examined in four soybean cultivars under greenhouse conditions. Alone and in combination the inducers were able to protect soybean plants against damping-off and wilt diseases compared with check treatment. These results were confirmed under field conditions in two different locations (Minia and New Valley governorates). The tested treatments significantly reduced damping-off and wilt diseases and increased growth parameters, except the number of branches per plant and also increased seed yield. Application of BTH (0.25 g/L) + HA (4 g/L) was the most potent in this respect. Soybean seed soaking in BTH + HA produced the highest activities of the testes of oxidative enzymes followed by BTH in the four soybean cultivars. HA treatment resulted in the lowest increases of these oxidative enzymes. Similar results were obtained with total phenol but HA increased total phenol more than did BTH in all tested cultivars.

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 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%.

Systemic Induction of the Small Antibacterial Compound in the Leaf Exudate During Benzothiadiazole-elicited Systemic Acquired Resistance in Pepper

  • Lee, Boyoung;Park, Yong-Soon;Yi, Hwe-Su;Ryu, Choong-Min
    • The Plant Pathology Journal
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    • v.29 no.3
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    • pp.350-355
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    • 2013
  • Plants protect themselves from diverse potential pathogens by induction of the immune systems such as systemic acquired resistance (SAR). Most bacterial plant pathogens thrive in the intercellular space (apoplast) of plant tissues and cause symptoms. The apoplastic leaf exudate (LE) is believed to contain nutrients to provide food resource for phytopathogenic bacteria to survive and to bring harmful phytocompounds to protect plants against bacterial pathogens. In this study, we employed the pepper-Xanthomonas axonopodis system to assess whether apoplastic fluid from LE in pepper affects the fitness of X. axonopodis during the induction of SAR. The LE was extracted from pepper leaves 7 days after soil drench-application of a chemical trigger, benzothiadiazole (BTH). Elicitation of plant immunity was confirmed by significant up-regulation of four genes, CaPR1, CaPR4, CaPR9, and CaCHI2, by BTH treatment. Bacterial fitness was evaluated by measuring growth rate during cultivation with LE from BTH- or water-treated leaves. LE from BTH-treatment significantly inhibited bacterial growth when compared to that from the water-treated control. The antibacterial activity of LE from BTH-treated samples was not affected by heating at $100^{\circ}C$ for 30 min. Although the antibacterial molecules were not precisely identified, the data suggest that small (less than 5 kDa), heat-stable compound(s) that are present in BTH-induced LE directly attenuate bacterial growth during the elicitation of plant immunity.