• Title/Summary/Keyword: benzothiadiazole

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Time-Dependent Density Functional Theory Study on Cyclopentadithiophene-Benzothiadiazole-Based Push-Pull-Type Copolymers for New Design of Donor Materials in Bulk Heterojunction Organic Solar Cells

  • Ku, Ja-Min;Kim, Dae-Kyun;Ryu, Taek-Hee;Jung, Eun-Hwan;Lansac, Yves;Jang, Yun-Hee
    • Bulletin of the Korean Chemical Society
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    • v.33 no.3
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    • pp.1029-1036
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    • 2012
  • Push-pull-type copolymers - low-band-gap copolymers of electron-rich fused-ring units (such as cyclopentadithiophene; CPDT) and electron-deficient units (such as benzothiadiazole; BT) - are promising donor materials for organic solar cells. Following a design principles proposed in our previous study, we investigate the electronic structure of a series of new CPDTBT derivatives with various electron-withdrawing groups using the time-dependent density functional theory and predict their power conversion efficiency from a newlydeveloped protocol using the Scharber diagram. Significantly improved efficiencies are expected for derivatives with carbonyl [C=O], carbonothioyl [C=S], dicyano [$C(CN)_2$] and dicyanomethylene [C=$C(CN)_2$] groups, but these polymers with no long alkyl side chain attached to them are likely to be insoluble in most organic solvents and inapplicable to low-cost solution processes. We thus devise several approaches to attach alkyl side chains to these polymers while keeping their high efficiencies.

Enhanced Onion Resistance against Stemphylium Leaf Blight Disease, Caused by Stemphylium vesicarium, by Di-potassium Phosphate and Benzothiadiazole Treatments

  • Kamal, Abo-Elyousr A.M.;Mohamed, Hussein M.A.;Aly, Allam A.D.;Mohamed, Hassan A.H.
    • The Plant Pathology Journal
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    • v.24 no.2
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    • pp.171-177
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    • 2008
  • In this study, we investigated the induced defense response and protective effects against Stemphylium vesicarium by application of benzothiadiazole ($Bion^{(R)}$) and di-potassium phosphate salt $(K_2HPO_4)$ to onion. Onion leaves were sprayed with $Bion^{(R)}$ and $K_2HPO_4$, then inoculated 2 days later with a virulent strain of S. vesicarium under greenhouse conditions. Disease severity and activities of peroxidase (PO), polyphenoloxidase, phenylalanine ammonia-lyase (PAL) and phenol contents were evaluated in the treated leaf tissues. Reduction in the disease severity was observed in plants treated with $Bion^{(R)}$ and $K_2HPO_4$. Onion plants treated with $Bion^{(R)}$ and $K_2HPO_4$ and inoculated with the pathogen showed significantly higher PAL activity, PO activity, and phenol contents than inoculated water-treated plants 2 days after the treatment. In conclusion, the results of this study provide evidence that application of simple non-toxic chemical solutions as di-potassium phosphate and $Bion^{(R)}$ can control Stemphylium leaf blight of onion.

Interfacial Electronic Structures of Poly[N-9''-hepta-decanyl-2,7-carbazole-alt- 5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] and [6,6]-phenyl C60 Butyric Acid Methyl Ester

  • Lee, Jung-Han;Seo, Jung-Hwa;Schlaf, Rudy;Kim, Kyoung-Joong;Yi, Yeon-Jin
    • Proceedings of the Korean Vacuum Society Conference
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    • 2012.02a
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    • pp.277-277
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    • 2012
  • PCDTBT (Poly[N-9''-hepta-decanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)]) is an attractive material as a semiconducting polymer for organic thin film transistor (OTFT) and organic solar cell (OSC). High power conversion efficiency (~6%) under simulated AM 1.5G solar illumination of bulk-heterojunction solar cell with PCDTBT and [6,6]-phenyl C60 butyric acid methyl ester (PC61BM) blend was reported. In OSC, it is known that the band alignment at the interface between donor and acceptor is critical. Therefore, we studied the interfacial electronic structures of PCDTBT and PC61BM. The polymers are deposited by electro-spray on gold and In-situ x-ray and ultraviolet photoelectron spectroscopy measurements revealed the interfacial electronic structures. We obtained the energy level alignment between two materials and the different interface formation was observed with different deposition order.

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Evaluation of the Performance of an Organic Thin Film Solar Cell Prepared Using the Active Layer of Poly[[9-(1-octylnonyl)-9H-carbazole-2.7-diyl]-2.5-thiophenediyl-2.1.3-benzothiadiazole-4.7-Diyl-2.5-thiophenediyl]/[6,6]-Phenyl C71 Butyric Acid Methyl Ester Composite Thin Film

  • Ochiai, Shizuyasu;Uchiyama, Masaki;Kannappan, Santhakumar;Jayaraman, Ramajothi;Shin, Paik-Kyun
    • Transactions on Electrical and Electronic Materials
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    • v.13 no.1
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    • pp.43-46
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    • 2012
  • Organic solar cell devices were fabricated using poly[9-(1-octylnonyl)-9H-carbazole-2.7-diyl]-2.5-thiophenediyl-2.1.3-benzothiadiazole-4.7-diyl-2.5-thiophenediyl] PCDTBT/ [6,6]-phenyl $C_{71}$ butyric acid methyl ester (PC71BM) active layer deposited by spin coating. Moreover, the relationship between solar cell performance and buffer layer thickness was investigated by spin coating speed and AFM imaging of the buffer layer surface. The performance of the organic solar cell with spin-coated active layer was then evaluated, and the power conversion efficiency of the solar cell was determined to be > 5%.

Novel 4,7-Dithien-2-yl-2,1,3-benzothiadiazole-based Conjugated Copolymers with Cyano Group in Vinylene Unit for Photovoltaic Applications

  • Kim, Jin-Woo;Heo, Mi-Hee;Jin, Young-Eup;Kim, Jae-Hong;Shim, Joo-Young;Song, Su-Hee;Kim, Il;Kim, Jin-Young;Suh, Hong-Suk
    • Bulletin of the Korean Chemical Society
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    • v.33 no.2
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    • pp.629-635
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    • 2012
  • Two novel conjugated copolymers utilizing 4,7-dithien-2-yl-2,1,3-benzothiadiazole (DTBT) coupled with cyano (-CN) substituted vinylene, as the electron deficient moeity, have been synthesized and evaluated in bulk heterojunction solar cell. The electron deficient moeity was coupled with carbazole and fluorene unit by Knoevenagel condition to provide poly(bis-2,7-((Z)-1-cyano-2-(5-(7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl)-2-thienyl)ethenyl)-alt-9-(1-octylnonyl)-9H-carbazol-2-yl-2-butenenitrile) (PCVCNDTBT) and poly(bis-2,7-((Z)-1-cyano-2-(5-(7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl)-2-thienyl)ethenyl)-alt-9,9-dihexyl-9H-fluoren-2-yl) (PFVCNDTBT). The optical band gaps of PCVCNDTBT (1.74 eV) and PFVCNDTBT (1.80 eV) are lower than those of PCDTBT (1.88 eV) and PFVDTBT (2.13 eV), which is advantageous to provide better coverage of the solar spectrum in the longer wavelength region. The high $V_{oc}$ value of the PSC of PCVCNDTBT (~0.91 V) is attributed to its lower HOMO energy level ( 5.6 eV) as compared to PCDTBT ( 5.5 eV). Bulk heterojunction solar cells based on the blends of the polymers with [6,6]phenyl-$C_{61}$-butyric acid methyl ester ($PC_{61}BM$) gave power conversion efficiencies of 0.76% for PCVCNDTBT under AM 1.5, 100 mW/$cm^2$.

Synthesis and Photovoltaic Properties of Conjugated Polymers Having Push-pull Structure according to the Type of Side-chain in the N-Substituted Phenothiazine (Push-pull 구조의 공액 고분자 합성 및 Phenothiazine의 질소 원자에 치환된 Side-chain에 따른 유기박막태양전지로의 특성 연구)

  • Seong, Ki-Ho;Yun, Dae-Hee;Woo, Je-Wan
    • Applied Chemistry for Engineering
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    • v.25 no.6
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    • pp.624-631
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    • 2014
  • In this study, a new series of conjugated polymer 3-(5-(5,6-bis(octyloxy)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophen-2-yl)-10-(4-(octyloxy)phenyl)-10H-phenothiazine (P1) and 3-(5-(5,6-bis(octyloxy)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophen-2-yl)-10-(4-((2-ethylhexyl)oxy)phenyl)-10H-phenothiazine (P2) were synthesised and organic photovoltaics (OPVs) properties were characterized. The push-pull structure polymer consisted of phenothiazine derivative as an electron donor and benzothiadiazole derivative as an electron acceptor. The aliphatic chain substituted aromatic ring was substituted at the position of N in phenothiazine for the electron-rich and improved solubility. Excellent thermal stabilities of P1 and P2 were confirmed by measured Td values as 321.9 and $323.7^{\circ}C$, respectively and the degrees of polymerization were 4,911 (P1) and 5,294 (P2). The maximum absorption wavelength of P1 and P2 were 549 and 566 nm, respectively. The device was fabricated and the OPVs property was measured. As a result, the power efficiency of conversion for P1 and P2 were 0.96 and 0.90%, respectively.

Synthesis and Photovoltaic Properties of Alternating Conjugated Polymers Derived from Thiophene-Benzothiadiazole Block and Fluorene/Indenofluorene Units

  • Li, Jianfeng;Tong, Junfeng;Zhang, Peng;Yang, Chunyan;Chen, Dejia;Zhu, Yuancheng;Xia, Yangjun;Fan, Duowang
    • Bulletin of the Korean Chemical Society
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    • v.35 no.2
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    • pp.505-512
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    • 2014
  • A new donor-accepter-donor-accepter-donor (D-A-D-A-D) type 2,1,3-benzothiadiazole-thiophene-based acceptor unit 2,5-di(4-(5-bromo-4-octylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl)thiophene ($DTBTTBr_2$) was synthesized. Copolymerized with fluorene and indeno[1,2-b]fluorene electron-rich moieties, two alternating narrow band gap (NBG) copolymers PF-DTBTT and PIF-DTBTT were prepared. And two copolymers exhibit broad and strong absorption in the range of 300-700 nm with optical band gap of about 1.75 eV. The highest occupied molecular orbital (HOMO) energy levels vary between -5.43 and -5.52 eV and the lowest unoccupied molecular orbital (LUMO) energy levels range from -3.64 to -3.77 eV. Potential applications of the copolymers as electron donor material and $PC_{71}BM$ ([6,6]-phenyl-$C_{71}$ butyric acid methyl ester) as electron acceptors were investigated for photovoltaic solar cells (PSCs). Photovoltaic performances based on the blend of PF-DTBTT/$PC_{71}BM$ (w:w; 1:2) and PIF-DTBTT/$PC_{71}BM$ (w:w; 1:2) with devices configuration as ITO/PEDOT: PSS/blend/Ca/Al, show an incident photon-to-current conversion efficiency (IPCE) of 2.34% and 2.56% with the open circuit voltage ($V_{oc}$) of 0.87 V and 0.90 V, short circuit current density ($J_{sc}$) of $6.02mA/cm^2$ and $6.12mA/cm^2$ under an AM1.5 simulator ($100mA/cm^2$). The photocurrent responses exhibit the onset wavelength extending up to 720 nm. These results indicate that the resulted narrow band gap copolymers are viable electron donor materials for polymer solar cells.

Overexpression of a Rice Diacylglycerol Kinase Gene OsBIDK1 Enhances Disease Resistance in Transgenic Tobacco

  • Zhang, Weidong;Chen, Jie;Zhang, Huijuan;Song, Fengming
    • Molecules and Cells
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    • v.26 no.3
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    • pp.258-264
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    • 2008
  • A rice diacylglycerol kinase (DGK) gene, OsBIDK1, which encodes a 499-amino acid protein, was cloned and characterized. OsBIDK1 contains a conserved DGK domain, consisting of a diacylglycerol kinase catalytic subdomain and a diacylglycerol kinase accessory subdomain. Expression of OsBIDK1 in rice seedlings was induced by treatment with benzothiadiazole (BTH), a chemical activator of the plant defense response, and by infection with Magnaporthe grisea, causal agent of blast disease. In BTH-treated rice seedlings, expression of OsBIDK1 was induced earlier and at a higher level than in water-treated control seedlings after inoculation with M. grisea. Transgenic tobacco plants that constitutively express the OsBIDK1 gene were generated and disease resistance assays showed that overexpression of OsBIDK1 in transgenic tobacco plants resulted in enhanced resistance against infection by tobacco mosaic virus and Phytophthora parasitica var. nicotianae. These results suggest that OsBIDK1 may play a role in disease resistance responses.

New Low-Band Gap 2D-Conjugated Polymer with Alkylthiobithiophene-Substituted Benzodithiophene for Organic Photovoltaic Cells

  • Park, Eun Hye;Ahn, Jong Jun;Kim, Hee Su;Kim, Ji-Hoon;Hwang, Do-Hoon
    • Journal of the Korean Chemical Society
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    • v.60 no.3
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    • pp.194-202
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    • 2016
  • Two conjugated semiconducting copolymers consisting of 4,7-bis(4-(2-ethylhexyl)-2-thiophene)-2,1,3-benzothiadiazole (DTBT) and benzo[1,2-b:4,5-b']dithiophene with 5-(2-ethylhexyl)-2,2'-bithiophene (BDTBT) or 5-(2-ethylhexylthio)- 2,2'-bithiophene (BDTBT-S) were designed and synthesized as donor materials for organic photovoltaic cells (OPVs). Alkylthio-substituted PBDTBT-S-DTBT showed a higher hole mobility and lower highest occupied molecular orbital (HOMO) energy level (by 0.08 eV) than the corresponding alkyl-substituted PBDTBT-DTBT. An OPV fabricated using PBDTBT-S-DTBT showed higher VOC and JSC values of 0.83 V and 7.56 mA/cm2, respectively, than those of a device fabricated using PBDTBT-DTBT (0.74 V) leading to a power conversion efficiency of 2.05% under AM 1.5G 100 mW/cm2 illumination.