- Benzochalcogendiazole-based conjugated molecules: Investigating the effects of substituents and heteroatom juggling
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A convenient and effective synthetic approach for benzochalcogendiazole-based small molecules has been achieved using polyaniline (PANI)-anchored palladium as a heterogeneous catalyst. The photophysical properties of the synthesized benzochalcogendiazole-based small molecules, having different terminal substituents, have been compared. Moreover, the structural aspects, including the packing patterns and non-bonding interactions of the conjugated molecules, have been investigated using the single crystal X-ray diffraction (SCXRD) technique.
- Patel, Heta A.,Bhanvadia, Viraj J.,Mande, Hemant M.,Zade, Sanjio S.,Patel, Arun L.
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- Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells
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A series of conjugated polymer bearing 4H-cyclopenta[def]phenanthrene (CPP) unit have been synthesized and was evaluated in bulk heterojunction solar cell. The alternating copolymers with CPP unit were incorporated with 4,7-dithienyl-2,1,3-benzothiadiazol
- Kim, Jinwoo,Park, Sung Heum,Cho, Shinuk,Jin, Youngeup,Kim, Jaehong,Kim, Il,Lee, Jin Sook,Kim, Joo Hyun,Woo, Han Young,Lee, Kwanghee,Suh, Hongsuk
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- A solution-processable deep red molecular emitter for non-doped organic red-light-emitting diodes
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A new solution-processable deep red emitter, TCTzC, containing dithienylbenzothiadiazole unit and four alkyl-linked peripheral carbazole groups, is designed and synthesized in high yield by Suzuki coupling reaction. The four peripheral carbazole substituents enhance the hole-transport ability, glass transition temperature, decompose temperature and film forming ability of TCTzC. The single-layered device based on TCTzC shows saturated deep red electroluminescence with a CIE coordinate of (0.70, 0.30). The current efficiency and quantum efficiency of TCTzC is two times higher than the compound without the four peripheral carbazole groups. The higher device performance is obtained when TPBi is applied and the external quantum efficiency could reach to 0.93%.
- Wang, Zhiming,Lu, Ping,Xue, Shanfeng,Gu, Cheng,Lv, Ying,Zhu, Qing,Wang, Huan,Ma, Yuguang
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- Synthesis of thiophene-based building blocks via facile α-monoiodination
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A new procedure to selectively α-monoiodinate symmetrical thiophene-capped segments is described. The monoiodinated derivatives are further modified, giving access to a variety of thiophene-based building blocks, which are useful for e.g. oligomer synthesis via segmental coupling.
- Boas, Ulrik,Dhanabalan, Anantharaman,Greve, Daniel R.,Meijer
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- Structure modification and annealing effect of polymer bulk heterojunction solar cells based on polyfluorene derivatives
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Three low bandgap polyfluorene copolymers containing a donor-acceptor-donor moiety have been synthesized via Suzuki and Stille polymerization reactions. Their bandgaps and molecular energy levels (highest occupied molecular orbital and lowest unoccupied molecular orbital) varied with different polymerization methods. The molecular weight of the copolymer increased significantly through copolymerizing with a monomer having a long alkyl side chain. In order to investigate their photovoltaic properties, polymer solar cell devices based on the copolymers were fabricated with a structure of indium tin oxide/poly(styrene sulfonic acid)-doped poly(ethylene dioxythiophene)/copolymers:[6,6]-phenyl-C61- butyric acid methyl ester (PCBM)/LiF/Al under the illumination of AM 1.5G, 100 mW/cm2. We found that the annealing temperature had a profound effect on the power conversion efficiency (PCE) of the devices with a blend of poly[9,9-didodecylfluorene-alt-(bis-thienylene) benzothiadiazole] (PF12-TBT) and PCBM. The PCE of the solar cell based on PF12-TBT/PCBM (1:4) annealing at 70 °C for 20 min was 4.13% with an open-circuit voltage (Voc) of 1.02 V, fill factor of 55.9%, and a short-circuit current (Jsc) of 7.24 mA/cm2. Copyright
- Lee, Jung-Feng,Hsu, Steve Lien-Chung,Lee, Po-I,Chuang, Hung-Yi,Chen, Jen-Sue,Chou, Wei-Yang
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- Synthesis of enantiomers of mononuclear Ru(II) complexes with 10,13-diaryl substituted dppz ligands
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An array of enantiomerically pure mononuclcear [Ru(bpy)2(dppz)] 2 + derivatives with 10,13-diaryl substituted dppz ligand has been synthesized and characterized (bpy = bipyridine, dppz = pyrido-[3,2-a:2′, 3′-c]phenazine). These new complexes exhibit substantially similar absorption spectra, resembling the parent complex [Ru(bpy)2(dppz)] 2 +, and the enantiomerically pure analogues show the similar CD spectra in buffer solution despite the structural difference.
- Li, Minna,Zhao, Ming,Peng, Shiqi
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- Combination of donor characters in a donor-acceptor-donor (DAD) type polymer containing benzothiadiazole as the acceptor unit
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A benzothiadiazole bearing donor-acceptor-donor (D-A-D) type monomer (M3) was synthesized using the combination of 3, 4- ethylenedioxythiophene (EDOT) and thiophene donor units to understand the effect of donor strength on the optoelectronic and electrochemical properties. The resulting monomer was polymerized electrochemically (P3) and compared with its symmetrical thiophene (P1) and EDOT (P2) bearing homologues whether there exists a combination of the electrochemical and optical characteristics. Also, copolymer studies were performed with symmetrical thiophene (M1) and EDOT (M2) containing monomers in order to compare the results with P3. Cyclic voltammetry (CV) and spectroelectrochemistry results revealed that P3 is a low band gap polymer (1.18 eV) having both p-and n-type property which is superior to the copolymers synthesized using M1 and M2.
- Sendur, Merve,Balan, Abidin,Baran, Derya,Karabay, Baris,Toppare, Levent
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- New conjugated alternating benzodithiophene-containing copolymers with different acceptor units: Synthesis and photovoltaic application
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Two new alternating low band gap D-A copolymers with different acceptor structures of 4,8-bis-(5-bromothiophene-2-yl)-benzo[1,2,5]thiadiazole (P1) and 4,8-dithiophene-2-yl-benzo[1,2-c;4,5-c′]-bis-[1,2,5]thiadiazole (P2) and a common BDT donor segment have been synthesized under Stille reaction conditions and characterized. The polymers showed good solubility, broad absorption bands and optical band gaps of 1.62 eV and 1.16 eV for P1 and P2, respectively. Bulk heterojunction (BHJ) polymer solar cells based on P1 and P2 as electron donors and fullerene derivatives (PC60BM and PC70BM) as acceptor were fabricated and their photovoltaic response was investigated. The overall power conversion efficieny (PCE) achieved for BHJ solar cells based on P1:PC60BM, P2:PC60BM, P1:PC70BM and P2:PC 70BM blends cast from THF solvent is about 2.17%, 0.80%, 3.45% and 1.19%, respectively. The higher PCE for the device based on P1 has been attributed to the high value of hole mobility for P1 as compared to P2 and a larger driving force i.e. LUMO-LUMO offset, for photo-induced charge transfer for P1:PCBM BHJ active layer. The PCE has been further increased up to 5.30% and 1.58% for P1:PC70BM and P2:PC70BM blends cast from DIO/THF solvent, which is attributed to the improved crystallinity and a more balanced charge transport in the device. The Royal Society of Chemistry.
- Keshtov,Marochkin,Kochurov,Khokhlov,Koukaras,Sharma
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- Easily attainable phenothiazine-based polymers for polymer solar cells: Advantage of insertion of S,S-dioxides into its polymer for inverted structure solar cells
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Two donor-(D-) acceptor (A) type polymers based on a soluble chromophore of phenothiazine (PT) unit that is a tricyclic nitrogen-sulfur heterocycle, have been synthesized by introducing an electron-deficient benzothiadiazole (BT) building block copolymerized with either PT or phenothiazine-S,S-dioxide (PT-SS) unit as an oxidized form of PT. The resulting polymers, PPTDTBT and PPTDTBT-SS are fully characterized by UV-vis absorption, electrochemical cyclic voltammetry, X-ray diffraction (XRD), and DFT theoretical calculations. We find that the maximum absorption of PPTDTBT is not only markedly red-shifted with respect to that of PPTDTBT-SS but also its band gap as well as molecular energy levels are readily tuned by the insertion of S,S-dioxides into the polymer. The main interest is focused on the electronic applications of the two polymers in organic field-effect transistors (OFETs) as well as conventional and inverted polymeric solar cells (PSCs). PPTDTBT is a typical p-type polymer semiconductor for OFETs and conventional PSCs based on this polymer and PC71BM show a power conversion efficiency (PCE) of 1.69%. In case of PPTDTBT-SS, the devices characteristics result in: (i) 1 order of magnitude higher hole mobility (μ = 6.9 × 10-4 cm2 V-1 s -1) than that obtained with PPTDTBT and (ii) improved performance of the inverted PSCs (1.22%), compared to its conventional devices. Such positive features can be accounted for in terms of closer packing molecular characteristics owing either to the effects of dipolar intermolecular interactions orientated from the sulfonyl groups or the relatively high coplanarity of PPTDTBT-SS backbone.
- Kim, Gyoungsik,Yeom, Hye Rim,Cho, Shinuk,Seo, Jung Hwa,Kim, Jin Young,Yang, Changduk
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- Strongly red-fluorescent novel donor-π-bridge-acceptor-π-bridge-donor (D-π-A-π-D) type 2,1,3-benzothiadiazoles with enhanced two-photon absorption cross-sections
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Novel donor-π-bridge-acceptor-π-bridge-donor (D-π-A-π-D) type 2,1,3-benzothiadiazole fluorescent dyes connected to the N,N-diarylamino terminus via various type π-conjugate spacers exhibits large two-photon absorption cross-sections and high fluorescent quantum yields in orange-red color.
- Kato, Shin-Ichiro,Matsumoto, Taisuke,Ishi-I, Tsutomu,Thiemann, Thies,Shigeiwa, Motoyuki,Gorohmaru, Hideki,Maeda, Shuichi,Yamashita, Yoshiro,Mataka, Shuntaro
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- A low band gap donor-acceptor copolymer containing fluorene and benzothiadiazole units: Synthesis and photovoltaic properties
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A new low band gap copolymer containing dialkylfluorene and 4,7-dithienyl-2,1,3-benzothiadiazole (TBT), poly(fluorenevinylene-alt-4,7- dithienyl-2,1,3-benzothiadiazole) (PF-TBT) was synthesized by Heck cross-coupling polymerization. The copolymer is soluble in common organic solvents such as chloroform, tetrahydrofuran and chlorobenzene. The TGA result indicated that the copolymer possesses good thermal stability. The absorption, electrochemical and photovoltaic properties of PF-TBT were investigated and compared with those of poly(fluorenevinylene-alt-4,7-diphenyl-2,1,3- benzothiadiazole) (PF-DBT) whose structure is similar to PF-TBT. The copolymer exhibited a broad absorption band with an absorption edge close to 700 nm and an optical band gap of 1.82 eV. Cyclic voltammetry studies indicated that the relatively low HOMO energy level assured a higher open circuit voltage (V oc) when PF-TBT is used as the donor material in a photovoltaic cell. The bulk heterojunction (BHJ) solar cell using PF-TBT as the donor and [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as the acceptor with the structure of ITO/PEDOT:PSS/copolymer:PCBM/LiF/Al, exhibited a Voc of 0.86 V, short-circuit current density (Jsc) of 3.97 mA cm -2, fill factor (FF) of 0.35, and a power conversion efficiency (PCE) of 1.18% under one sun of AM 1.5 solar simulator illumination (100 mW cm -2).
- Pei, Jianing,Wen, Shanpeng,Zhou, Yinhua,Dong, Qingfeng,Liu, Zhaoyang,Zhang, Jibo,Tian, Wenjing
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- Effect of end group functionalisation of small molecules featuring the fluorene-thiophene-benzothiadiazole motif as emitters in solution-processed red and orange organic light-emitting diodes
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A series of red fluorescent materials (compounds 1-4), which each contain the symmetric fluorene-thiophene-BT-thiophene-fluorene core, is presented along with their performance in solution-processed OLED devices. Extending the molecular conjugation throug
- Fell, Valentin H. K.,Findlay, Neil J.,Breig, Benjamin,Forbes, Clarissa,Inigo, Anto R.,Cameron, Joseph,Kanibolotsky, Alexander L.,Skabara, Peter J.
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- A polymer gel electrolyte to achieve ≥6% power conversion efficiency with a novel organic dye incorporating a low-band-gap chromophore
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A quasi-solid-state dye-sensitized solar cell with novel organic sensitizers incorporating a benzothiadiazole chromophore showed excellent long-term stability, which exhibited 10% decrease during the 1000 h light soaking; the optimized cell gave a short circuit photocurrent density of 12.03 mA cm-2, an open circuit voltage of 0.720 V and a fill factor of 0.76, corresponding to an overall conversion efficiency of 6.61% under standard global AM 1.5 solar conditions. The Royal Society of Chemistry 2008.
- Kim, Jeum-Jong,Choi, Hyunbong,Lee, Ji-Won,Kang, Moon-Sung,Song, Kihyung,Kang, Sang Ook,Ko, Jaejung
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- C-H arylation of unsubstituted furan and thiophene with acceptor bromides: Access to donor-acceptor-donor-type building blocks for organic electronics
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Pd-catalyzed direct arylation (DA) reaction conditions have been established for unsubstituted furan (Fu) and thiophene (Th) with three popular acceptor building blocks to be used in materials for organic electronics, namely 4,7-dibromo-2,1,3-benzothiadia
- Matsidik, Rukiya,Martin, Johannes,Schmidt, Simon,Obermayer, Johannes,Lombeck, Florian,Nübling, Fritz,Komber, Hartmut,Fazzi, Daniele,Sommer, Michael
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- Synthesis of thieno[3,4-b]pyrazine-based and 2,1,3-benzothiadiazole-based donor-acceptor copolymers and their application in photovoltaic devices
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Two kinds of thieno[3,4-6]pyrazine-based monomers, 2,3-dimethyl-5,7-di(2- bromothien-5-yl)-thieno[3,4-b]pyrazine and 2,3-diphenyl-5,7-di(2-bromothien-5- yl)-thieno[3,4-p]pyrazine, were synthesized via an improved synthetic route. These two monomers and 4,7-di(2-bromothien-5-yl)-2,l,3-benzothiadiazole were copolymerized with three donor segments (fluorene, carbazole, and indolocarbazole) separately by a Suzuki cross-coupling reaction to give six types of 5,7-dithien-2-yl-thieno[3,4-p]pyrazine (DTTP)-based donor- acceptor (D-A) copolymers (TP1-6) and three types of 5,7-dithien-2-yl-2,l,3- benzothiadiazole (DTBT)-based D-A copolymers (PF-DTBT, PC-DTBT, and PIC-DTBT). The optical properties, electrochemical behavior, and energy levels of these nine copolymers were investigated. The photovoltaic performance of the copolymers was compared and discussed considering their energy levels.
- Zhou, Erjun,Cong, Junzi,Yamakawa, Shimpei,Wei, Qingshuo,Nakamura, Motoshi,Tajima, Keisuke,Yang, Chunhe,Hashimoto, Kazuhito
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- Effect of thiophene/furan substitution on organic field effect transistor properties of arylthiadiazole based organic semiconductors
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Four donor-acceptor (D-A) type organic semiconductors, consisting of 5-hexylthiophene with thiophene/furan flanked benzothiadiazole/naphthothiadiazole, were investigated for organic field effect transistor (OFET) application. Despite being an analogue of thiophene, furan has received less attention in organic electronics due to its dissimilar properties to thiophene and instability in photochemical oxidation. Nevertheless, this study determines that furan could display comparable charge transport properties to its analogue. The extension of the electron-accepting thiadiazole core with the benzo group and different heteroatom flanking groups were investigated to show that the performance of OFETs is dependent on the molecular orbital, geometry, and packing. Bottom-gate bottom-contact device configuration was used to study the OFET transport properties of all the molecules. We successfully proved that a furan unit is a promising building block with a mobility (μmax) of 0.0122 cm2 V-1 s-1 for devices employing furan-substituted benzothiadiazole as the channel layer.
- Pachariyangkun, Anna,Suda, Masayuki,Hadsadee, Sarinya,Jungsuttiwong, Siriporn,Nalaoh, Phattananawee,Pattanasattayavong, Pichaya,Sudyoadsuk, Taweesak,Yamamoto, Hiroshi M.,Promarak, Vinich
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- A versatile approach to organic photovoltaics evaluation using white light pulse and microwave conductivity
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State-of-the-art low band gap conjugated polymers have been investigated for application in organic photovoltaic cells (OPVs) to achieve efficient conversion of the wide spectrum of sunlight into electricity. A remarkable improvement in power conversion efficiency (PCE) has been achieved through the use of innovative materials and device structures. However, a reliable technique for the rapid screening of the materials and processes is a prerequisite toward faster development in this area. Here we report the realization of such a versatile evaluation technique for bulk heterojunction OPVs by the combination of time-resolved microwave conductivity (TRMC) and submicrosecond white light pulse from a Xe-flash lamp. Xe-flash TRMC allows examination of the OPV active layer without requiring fabrication of the actual device. The transient photoconductivity maxima, involving information on generation efficiency, mobility, and lifetime of charge carriers in four well-known low band gap polymers blended with phenyl-C61-butyric acid methyl ester (PCBM), were confirmed to universally correlate with the PCE divided by the open circuit voltage (PCE/Voc), offering a facile way to predict photovoltaic performance without device fabrication.
- Saeki, Akinori,Yoshikawa, Saya,Tsuji, Masashi,Koizumi, Yoshiko,Ide, Marina,Vijayakumar, Chakkooth,Seki, Shu
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- Novel red-emitting fluorene-based copolymers
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A series of novel soluble conjugated copolymers derived from 9,9-dioctylfluorene (DOF) and 4,7-di-2-thienyl-2,1,3-benzothiadiazole (DBT) were synthesized by a palladium-catalyzed Suzuki coupling reaction with different feed ratios of DOF to DBT. Owing to exciton confinement on the DBT site, exciton emission is centred on the DBT chromophore and gives rise to saturated red emission. Polyfluorene fluorescence is quenched completely at DBT concentrations as low as 1% in the solid film. Devices based on these copolymers emit a saturated red light. Chromaticity coordinates are around x = 0.70, y = 0.30 for the copolymers. The emission peaks are shifted from 628 nm to 674 nm when DBT content increases from 1 to 35%. The highest quantum efficiency achieved with device configuration of ITO/PEDT/PFO-DBT/Ba/A1 was 1.4% for the copolymer with 15% DBT content.
- Hou, Qiong,Xu, Yishe,Yang, Wei,Yuan, Min,Peng, Junbiao,Cao, Yong
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- Synthesis and photovoltaic studies on novel fluorene based cross-conjugated donor-acceptor type polymers
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Direct arylation polymerization (DAP) is emerging as a promising green, cheap, simple, and efficient environment friendly method for synthesizing conjugated polymers without involving any organometallic reagent. We report fluorene based novel cross-conjugated alternate and random copolymers for polymer solar cells (PSCs), which were synthesized by DAP and/or Yamamoto polymerization under appropriate reaction conditions to obtain high molecular weight. These cross-conjugated polymers possess absorption maxima in the range of 490–520 nm and have narrow band gap (1.7–2.05 eV) which is suitable for bulk heterojuntion (BHJ) type organic solar cells. Among the synthesized polymers, the highest number average molecular weight (Mn) i.e. 43.1 kg mol?1 was obtained for polymer P2b (poly((9H-fluoren-9-ylidene)methylene)bis((2-ethylhexyl)sulfane)-alt-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole)), and so good polymeric films were formed for P2b. Thus, BHJ films were prepared for P2b for device performance studies and the morphology of these films was studied by atomic force microscopy (AFM). Polymer P2b was blended with the fullerene derivative [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) in different ratios and under the illumination of solar simulator with Air Mass global (AM 1.5G) irradiated at 100 mW cm?2. Power conversion efficiency (PCE) of 1.4% has been achieved for BHJs in ratio of 1:2 of P2b: PC71BM in simply processed devices. This result indicates that cross-conjugated polymers can be tapped as potential donors for BHJs as the PCE obtained is the highest among this type of cross-conjugated polymers.
- Sharma, Bhavna,Alam, Firoz,Dutta, Viresh,Jacob, Josemon
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- Synthesis, photophysics, and electroluminescence of high-efficiency saturated red light-emitting polyfluorene-based polyelectrolytes and their neutral precursors
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High-efficiency saturated red light-emitting polyelectrolytes and their neutral precursors: aminoalkyl-substituted polyfluorenes (PFN) with different 4,7-di-2-thieny1-2,1,3-benzothiadiazole (DBT) contents were synthesized by Suzuki coupling reaction. Their quaternized ammonium polyelectrolyte derivatives were obtained through a post-polycondensation treatment on the terminal amino groups. The resulting copolymers are soluble in polar solvents. Narrow band-gap (NBG) DBT units incorporated into the polymer backbone act as exciton traps. As a result, all the polymers emit red light specific to the DBT segments under UV excitation in the solid state. It was found out that the PFN-DBT copolymers show good device performance when high work-function metals, such as Al, are used as the electron-injection cathode replacing conventional low work-function cathodes such as Ca and Ba. It has been shown that these polymers also can be used as electron injection layers (ETL) in double layer structures in polymer light-emitting diodes (PLEDs). Double layer devices, with PFN-DBT as an electron injection layer on top of conventional RGB light-emitting polymers, with high work-function metal cathodes emit light exclusively from the RGB polymers and show high external quantum efficiency. The Royal Society of Chemistry 2005.
- Huang, Fei,Hou, Lintao,Shen, Huilin,Jiang, Jiaxing,Wang, Feng,Zhen, Hongyu,Cao, Yong
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- Cell imaging using red fluorescent light-up probes based on an environment-sensitive fluorogen with intramolecular charge transfer characteristics
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We report a general strategy to design and synthesize red fluorescent light-up probes for cellular imaging based on a fluorogen with intramolecular charge transfer characteristics. This journal is the Partner Organisations 2014.
- Feng, Guangxue,Liu, Jie,Zhang, Ruoyu,Liu, Bin
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- Synthesis and characterization of star-shaped donor-acceptor-donor structures
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A Sonogashira coupling reaction led to star-shaped 1,3,5-tris({5-[7- (thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl]thiophen-2-yl}ethynyl)benzene derivatives. The star-shaped molecules were optically analyzed, and - depending on their substitution pattern - they displayed bathochromically shifted absorptions, which were compared to their nonlinked arm precursors. The materials displayed a highly interesting morphology in bulk when blended with [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). One derivative formed columnar structures and revealed prospective use in photodiodes. Copyright
- Pelz, Simon,Zhang, Jinming,Kanelidis, Ioannis,Klink, Dennis,Hyzak, Lukas,Wulf, Volker,Schmitz, Oliver J.,Gasse, Jan-Christoph,Frahm, Ronald,Puetz, Andreas,Colsmann, Alexander,Lemmer, Uli,Holder, Elisabeth
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- Synthesis and properties of new benzothiadiazole-based push-pull dyes for p-type dye sensitized solar cells
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We report the synthesis of three new push-pull dyes specially designed for the sensitization of mesoporous p type semi-conductor NiO for the construction of p type dye sensitized solar cells (pDSC). Their structure stems from the conjugation of the well-k
- Farré, Yoann,Raissi, Mahfoudh,Fihey, Arnaud,Pellegrin, Yann,Blart, Errol,Jacquemin, Denis,Odobel, Fabrice
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- Highly π-extended polymers based on phenanthro-pyrazine: Synthesis, characterization, theoretical calculation and photovoltaic properties
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Two novel narrow bandgap conjugated polymers containing phenanthro-pyrazine unit have been successfully synthesized by the Stille coupling reaction. Comparing to the common polymers containing dithiophen-quinoxaline or dithiophen-thieno[3,4-b]pyrazine moi
- Wang, Zhiming,Gao, Zhao,Feng, Ying,Liu, Yulong,Yang, Bing,Liu, Dandan,Lv, Ying,Lu, Ping,Ma, Yuguang
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- Significantly improved photovoltaic performances of the dithiophene-benzothiadiazole-alt-fluorene copolymers by incorporating carbazole units in fluorene moiety
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To exploit an effective way to improve polymeric photovoltaic performance, a series of dithiophene-benzothiadiazole-alt-fluorene copolymers containing carbazole groups at C-9 positions of the alternating fluorene units (PFO-FCz-DBT) were synthesized and characterized. The effect of the carbazole groups on the optophysical, electrochemical, and photovoltaic properties of these copolymers was investigated. By comparison, this type of copolymers with carbazole units exhibited significantly improved photovoltaic properties than poly(2,7-(9,9-dioctyl-fluorene)-alt-5,5-(4′,7′-di-2-thienyl- 2′,1′,3′-benzothiadiazole) (PFO-DBT) in the bulk heterojunction solar cells. A maximum power-conversion efficiency (PCE) of 2.41% and a highest short-circuit current density (Jsc) of 9.68 mA cm -2 were obtained for the PFO-FCz-DBT30, which are about two times higher than the corresponding levels for the PFO-DBT30. This work demonstrated that introducing a hole-transporting carbazole unit into copolymer is a simple and effective method to improve the Jsc and PCE. Copyright
- Liu, Ming,Wang, Yafei,Zhang, Zhiyong,Li, Jianming,Liu, Yu,Tan, Hua,Ni, Meijun,Lei, Gangtie,Zhu, Meixiang,Zhu, Weiguo
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- Highly Efficient Luminescent Solar Concentrators Based on Benzoheterodiazole Dyes with Large Stokes Shifts
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Five extended π-conjugated systems with electron donor (D) and acceptor (A) moieties have been synthesized. Their basic D-A-D structural motif is a benzothiadiazole unit symmetrically equipped with two thiophene rings (S2T). Its variants include 1) the same molecular framework in which sulfur is replaced by selenium (Se2T), also with four thiophene units (Se4T) and 2) a D’-D-A-D system having a N-carbazole donor moiety at one end (CS2T) and a D’-D-A-D-A’ array with a further acceptor carbonyl unit at the other extremity (CS2TCHO). The goal is taking advantage of the intense luminescence and large Stokes shifts of the five molecules for use in luminescent solar concentrators (LSCs). All of them exhibit intense absorption spectra in the UV/Vis region down to 630 nm, which are fully rationalized by DFT. Emission properties have been studied in CH2Cl2 (298 and 77 K) as well as in PMMA and PDMS matrices, measuring photoluminescence quantum yields (up to 98 percent) and other key optical parameters. The dye–PMMA systems show performances comparable to the present state-of-the-art, in terms of optical and external quantum efficiencies (OQE=47.6 percent and EQE=31.3 percent, respectively) and flux gain (F=10.3), with geometric gain close to 90. LSC devices have been fabricated and tested in which the five emitters are embedded in PDMS and their wave-guided VIS luminescence feeds crystalline silicon solar cells.
- Gao, Sheng,Balan, Bamisha,Yoosaf, Karuvath,Monti, Filippo,Bandini, Elisa,Barbieri, Andrea,Armaroli, Nicola
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- An ultra-highly sensitive and selective self-enhanced AIECL sensor for public security early warning in a nuclear emergencyviaa co-reactive group poisoning mechanism
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The worldwide application of nuclear power has created the potential risk of a nuclear accident, which has been a challenge to public security. In nuclear leakages, I2radioisotopes would cause rapid, global pollution. Therefore, highly sensitive and selective I2sensors exhibit their significance in nuclear accident early warnings and treatments. Herein, a conjugated polymer was developed for I2vapor monitoring with an ultra-low limit of detection (LOD). This polymer, modified with a tertiary amine as a co-reactive group, exhibits aggregation-induced electrochemiluminescence (AIECL) and self-enhanced ECL behaviors. It is noteworthy that the tertiary amine also acts as I2vapor capturing and sensing groups to give a LOD of 0.13 ppt. Excellent selectivity was obtained in various interfering atmospheres. A new mechanism was discovered for designing vapor sensors, which is summarized as co-reactive group poisoning (CGP). To meet the high efficiency requirement of nuclear emergency monitoring, an I2sensor modified screen printed carbon electrode was used due to its low cost, lack of need for pretreatment and suitability for mass production. A matching upwardly photosensitive ECL dark box was further designed. This study reports ECL vapor monitoring for the first time and provides a novel strategy for early warning of a nuclear emergency, suggesting its significance in environmental and public security fields.
- Hua, Daoben,Liu, Peng,Pan, Jian-Bin,Wang, Ziyu,Wu, Xinqi,Xu, Jing-Juan,Xu, Meiyun,Zhang, Nan
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- Organic dyes end-capped with perfluorophenyl anchors: Synthesis, electrochemical properties and assessment of sensitization capacity of titania photoanodes
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In the present work, organic sensitizers are synthesized and attached on TiO2 photoanodes via Ti-O-C bonds. All sensitizers, designed for this purpose are symmetrical and have two perfluorophenyl end groups, which can lead to stable non-hydroly
- Giannopoulos, Panagiotis,Raptis, Dimitrios,Theodosiou, Krystallia,Andreopoulou, Aikaterini K.,Anastasopoulos, Charalampos,Dokouzis, Alexandros,Leftheriotis, George,Lianos, Panagiotis,Kallitsis, Joannis K.
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Read Online
- Electropolymerization of D-A-D type monomers consisting of thiophene and quionaxline moieties for electrochromic devices and supercapacitors
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Three donor-acceptor-donor (D-A-D) type monomers (ThQ-Ph, ThQ-PhOMe and ThQ-Th) based on thiophene substituted quinoxaline derivates were synthesized and further electropolymerized for electrochromic and supercapacitor applications. The present redox-acti
- Zhu, Jianjun,Wang, Wenyuan,Chen, Hongjin,Han, Yiying,Liu, Jian
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- Triazole derivative containing boron-nitrogen group, polymer and preparation methods and applications of triazole derivative and polymer
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The invention belongs to the technical field of organic photoelectricity, and discloses a triazole derivative containing a boron-nitrogen group, a polymer and preparation methods and applications of the triazole derivative and the polymer. The chemical st
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Paragraph 0052; 0055-0056
(2020/07/07)
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- Phenolic Bis-styrylbenzo[ c]-1,2,5-thiadiazoles as Probes for Fluorescence Microscopy Mapping of Aβ Plaque Heterogeneity
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A fluorescent bis-styryl-benzothiadiazole (BTD) with carboxylic acid functional groups (X-34/Congo red analogue) showed lower binding affinity toward Aβ1-42 and Aβ1-40 fibrils than its neutral analogue. Hence, variable patterns of neutral OH-substituted bis-styryl-BTDs were generated. All bis-styryl-BTDs showed higher binding affinity to Aβ1-42 fibrils than to Aβ1-40 fibrils. The para-OH on the phenyl rings was beneficial for binding affinity while a meta-OH decreased the affinity. Differential staining of transgenic mouse Aβ amyloid plaque cores compared to peripheral coronas using neutral compared to anionic bis-styryl ligands indicate differential recognition of amyloid polymorphs. Hyperspectral imaging of transgenic mouse Aβ plaque stained with uncharged para-hydroxyl substituted bis-styryl-BTD implicated differences in binding site polarity of polymorphic amyloid plaque. Most properties of the corresponding bis-styryl-BTD were retained with a rigid alkyne linker rendering a probe insensitive to cis-trans isomerization. These new BTD-based ligands are promising probes for spectral imaging of different Aβ fibril polymorphs.
- Zhang, Jun,Konsmo, Audun,Sandberg, Alexander,Wu, Xiongyu,Nystr?m, Sofie,Obermüller, Ulrike,Wegenast-Braun, Bettina M.,Konradsson, Peter,Lindgren, Mikael,Hammarstr?m, Per
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p. 2038 - 2048
(2019/02/26)
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- Organic semiconductor compound and electronic device using the same
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The present invention relates to an organic semiconductor compound having excellent hole transport properties, and an electronic device using the same. The organic semiconductor compound of the present invention comprises a first repeating unit represente
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Paragraph 0166; 0170-0172
(2019/12/13)
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- Efficient aggregated luminescent material and preparation method thereof
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The invention relates to an efficient aggregated luminescent material and a preparation method thereof. The preparation method comprises the following steps: (1) Stille coupling of thienyl; (2) N-bromosuccinimide (NBS) bromination; (3) [2.2] paracycloalkane cross-coupling. The synthetic process of the luminescent material provided by the invention is simple in conditions and relatively low in preparation cost; at the same time, the luminescent material has relatively good aggregated luminescence property and optical stability, and can realize thorough application researches in stimulated emission depletion (STED) ultra-high resolution imaging.
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Paragraph 0022; 0024-0027; 0036-0038; 0041-0043
(2019/10/23)
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- Electron donor-free photoredox catalysis: Via an electron transfer cascade by cooperative organic photocatalysts
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Electron-donating sacrificial reagents are highly important for certain photo-redox reactions. However, the use of excessive amounts of sacrificial reagents, mostly amines, often leads to undesired side products and is especially troublesome for product purification. Herein, we take the light-induced electron transfer cascade process of natural photosystems as a role model and assemble organic photocatalysts into cooperative photocatalyst couples. The cooperative photocatalyst couples could undergo intermolecular electron transfer to facilitate the charge separation process and overcome the need for an extra electron donor. Time-resolved photoluminescence spectroscopy was conducted to precisely characterize the photo-excited dynamics within the cooperative photocatalyst couples. As a model photoredox reaction, the carbon-carbon formation reaction between heteroarenes and malonates, which usually requires electron-donating sacrificial reagents such as amines, was conducted to demonstrate the feasibility of the cooperative photocatalyst couples under visible light irradiation. A significant reaction conversion improvement from trace conversion for a single photocatalyst system to over 90% by cooperative photocatalyst couples was achieved.
- Wang, Lei,R?rich, Irina,Ramanan, Charusheela,Blom, Paul W. M.,Huang, Wei,Li, Run,Zhang, Kai A. I.
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p. 3539 - 3547
(2018/07/29)
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- Molecular Design of Donor-Acceptor-Type Organic Photocatalysts for Metal-free Aromatic C?C Bond Formations under Visible Light
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Metal-free and photocatalytic radical-mediated aromatic C?C bond formations offer a promising alternative pathway to the conventional transition metal-catalyzed cross-coupling reactions. However, the formation of aryl radicals from common precursors such as aryl halides is highly challenging due to their extremely high reductive potential. Here, we report a structural design strategy of donor-acceptor-type organic photocatalysts for visible light-driven C?C bond formations through the reductive dehalogenation of aryl halides. The reduction potential of the photocatalysts could be systematically aligned to be ?2.04 V vs. SCE via a simple heteroatom engineering of the donor-acceptor moieties. The high reductive potential of the molecular photocatalyst could reduce various aryl halides into aryl radicals to form the C?C bond with heteroarenes. The designability of the molecular photocatalyst further allowed the synthesis of a high LUMO (lowest unoccupied molecular orbital) polymer photocatalyst by a self-initiated free radical polymerization without compromising its LUMO level. (Figure presented.).
- Wang, Lei,Byun, Jeehye,Li, Run,Huang, Wei,Zhang, Kai A. I.
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p. 4312 - 4318
(2018/10/02)
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- Access to small molecule semiconductors: Via C-H activation for photovoltaic applications
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The first methodology of ruthenium carboxylate-catalysed single step oxidative cross coupling that challenges the conventional Stille and Suzuki coupling reactions, affording BT and MFBT derivatives in the absence of protecting groups, was developed. Both mono and bi-arylated derivatives are formed in moderate to high yields (30-75%). Innately high selectivity, low catalyst loading and lack of formation of regio-isomers ensure the large-scale synthesis of various photonic and electronic materials employing this method.
- Shome, Sanchari,Singh, Surya Prakhash
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supporting information
p. 7322 - 7325
(2018/07/06)
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- Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications
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A series of low band gap, planar conjugated polymers, P1 (PFDTBT), P2 (PFDTDFBT) and P3 (PFDTTBT), based on fluorene and benzothiadiazole, was synthesized. The effect of fluorine substitution and fused aromatic spacers on the optoelectronic and photovoltaic performance was studied. The polymer, derived from dithienylated benzothiodiazole and fluorene, P1, exhibited a highest occupied molecular orbital (HOMO) energy level at -5.48 eV. Density functional theory (DFT) studies as well as experimental measurements suggested that upon substitution of the acceptor with fluorine, both the HOMO and lowest unoccupied molecular orbital (LUMO) energy levels of the resulting polymer, P2, were lowered, leading to a higher open circuit voltage and short circuit current with an overall improvement of more than 110% for the photovoltaic devices. Moreover, a decrease in the torsion angle between the units was also observed for the fluorinated polymer P2 due to the enhanced electrostatic interaction between the fluorine substituents and sulfur atoms, leading to a high hole mobility. The use of a fused π-bridge in polymer P3 for the enhancement of the planarity as compared to the P1 backbone was also studied. This enhanced planarity led to the highest observed mobility among the reported three polymers as well as to an improvement in the device efficiency by more than 40% for P3.
- Viswanathan, Vinila N.,Rao, Arun D.,Pandey, Upendra K.,Kesavan, Arul Varman,Ramamurthy, Praveen C.
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supporting information
p. 863 - 873
(2017/06/21)
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- TRI-(ADAMANTYL)PHOSPHINES AND APPLICATIONS THEREOF
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In one aspect, phosphine compounds comprising three adamantyl moieties (PAd3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.
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Page/Page column 31
(2017/05/17)
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- Suzuki-Miyaura Micellar Cross-Coupling in Water, at Room Temperature, and under Aerobic Atmosphere
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Recently, oxygen-equilibrated water solutions of Kolliphor EL, a well-known surfactant, have been seen to form nanomicelles with oxygen-free cores. This has prompted the successful testing of the core environment as a green medium for palladium-catalyzed Suzuki-Miyaura cross couplings. The versatility of these conditions is endorsed by several examples, including the synthesis of relevant molecular semiconductors. The reaction medium can also be recycled, opening the way for an extremely easy and green chemistry compliant methodology.
- Mattiello, Sara,Rooney, Myles,Sanzone, Alessandro,Brazzo, Paolo,Sassi, Mauro,Beverina, Luca
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supporting information
p. 654 - 657
(2017/02/10)
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- Nitric oxide probe based on fluorescent double-response mechanism and synthesis and application thereof
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The invention discloses a molecular design and preparation method of a nitric oxide fluorescent probe based on a double-response mechanism. The structure of the nitric oxide fluorescent probe can be represented by a general formula (I) (please see the formula in the description), wherein Spacer represents a single bond or acetylene bond or thiophene or substituted aryl unit, Ar represents one of an aryl group, a substituted aryl group, a heterocyclic aryl group and substituted aryl amine, and the substituted group can be one of a hydrophilic ether chain, a sulfonic acid group, quaternary ammonium salt and the like. The key steps of synthesis of the probe molecule can be achieved through a Suzuki coupling reaction or a C-H activation coupling reaction and the like. The probe molecule has the advantages of being high in sensitivity, good in selectivity, short in response time, good in membrane permeability, low in background noise, capable of achieving direct observation and fluorescence-ultraviolet-visible spectrum dual-band response and the like, is a brand-new sensing detection platform and has a good application prospect.
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Paragraph 0051; 0052; 0053; 0055
(2017/04/03)
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- Linking design and properties of purine-based donor-acceptor chromophores as optoelectronic materials
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Creating new building blocks for donor-acceptor conjugated systems is an important task for continued development of materials for organic electronics. Purines were introduced into small-molecule π-conjugated systems via Stille cross-coupling using stannylated derivatives of benzodithiophene, thiophene, or dithienylbenzothiadiazole to generate a series of "purine-π-purine" chromophores having high thermal stability, long excited-state lifetimes, and high quantum yields. Photophysical and electrochemical property characterization indicate that depending on the choice of a conjugated bridging unit, purines behave as either an electron-donating or an electron-accepting unit in these small-molecule donor-acceptor chromophores. Specifically, while purine chromophores do not exhibit charge transfer character when linked to a thiophene unit, purinyl units act as a weak acceptor when coupled with benzodithiophene and as a weak donor when coupled with dithienylbenzothiadiazole. In addition to fundamental insights into the molecular design of purine-based chromophores and their charge-transfer character, the results and synthetic tailorability of purines suggest that they may be compelling building blocks in conjugated materials for optical and electronic devices and sensors.
- Collier, Graham S.,Brown, Lauren A.,Boone, Evan S.,Kaushal, Meesha,Ericson, M. Nance,Walter, Michael G.,Long, Brian K.,Kilbey, S. Michael
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p. 6891 - 6898
(2017/07/22)
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- Effects of including electron-withdrawing atoms on the physical and photovoltaic properties of indacenodithieno[3,2-b]thiophene-based donor-acceptor polymers: towards an acceptor design for efficient polymer solar cells
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Three new D-A polymers PIDTT-DTBO, PIDTT-DTBT and PIDTT-DTFBT, using indacenodithieno[3,2-b]thiophene (IDTT) as the electron-rich unit and benzoxadiazole (BO), benzodiathiazole (BT) or difluorobenzothiadiazole (FBT) as the electron-deficient unit, were synthesized via a Pd-catalyzed Stille polymerization. The included electron-withdrawing atoms of the acceptor portion were varied between O, S, and F for tailoring the optical and electrochemical properties and the geometry of structures. Their effects on the film topography, photovoltaic and hole-transporting properties of the polymers were thoroughly investigated via a range of techniques. As expected, the stronger electron-withdrawing BO unit affords red-shifted absorption, low-lying HOMO and LUMO levels for the polymer PIDTT-DTBO. However, it depicts lower hole mobility and a less efficient charge collection in the active layer compared to the polymer PIDTT-DTBT. In addition, degradation of the solubility is observed in the fluorinated polymer PIDTT-DTFBT. As a result, a BHJ PSC (ITO/PEDOT:PSS/polymer:PC71BM/interlayer/Al) fabricated with PIDTT-DTBT attains the best power conversion efficiency (PCE) of 4.91%. These results thus demonstrate the potential effects of electronegative atoms on IDTT-based polymers and the structure-function correlations of such electron-donor materials for efficient PSCs.
- Cai, Ping,Xu, Xiaofeng,Sun, Jiangman,Chen, Junwu,Cao, Yong
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p. 20440 - 20450
(2017/04/21)
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- Tri(1-adamantyl)phosphine: Expanding the Boundary of Electron-Releasing Character Available to Organophosphorus Compounds
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We report here the remarkable properties of PAd3, a crystalline air-stable solid accessible through a scalable SN1 reaction. Spectroscopic data reveal that PAd3, benefiting from the polarizability inherent to large hydrocarbyl groups, exhibits unexpected electron releasing character that exceeds other alkylphosphines and falls within a range dominated by N-heterocyclic carbenes. Dramatic effects in catalysis are also enabled by PAd3 during Suzuki-Miyaura cross-coupling of chloro(hetero)arenes (40 examples) at low Pd loading, including the late-stage functionalization of commercial drugs. Exceptional space-time yields are demonstrated for the syntheses of industrial precursors to valsartan and boscalid from chloroarenes with ~2 × 104 turnovers in 10 min.
- Chen, Liye,Ren, Peng,Carrow, Brad P.
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supporting information
p. 6392 - 6395
(2016/06/09)
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- For solution treated organic solar cell of low band gap containing ruthenium complex
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This invention relates to a class of ruthenium(II) bis(aryleneethynylene) complexes for use in bulk heterojunction (BHJ) solar cell devices, and the method of synthesizing thereof. This invention also relates to a BHJ solar cell device comprising the ruth
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Page/Page column 13
(2017/06/02)
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- Structural Design Principle of Small-Molecule Organic Semiconductors for Metal-Free, Visible-Light-Promoted Photocatalysis
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Herein, we report on the structural design principle of small-molecule organic semiconductors as metal-free, pure organic and visible light-active photocatalysts. Two series of electron-donor and acceptor-type organic semiconductor molecules were synthesized to meet crucial requirements, such as 1) absorption range in the visible region, 2) sufficient photoredox potential, and 3) long lifetime of photogenerated excitons. The photocatalytic activity was demonstrated in the intermolecular C?H functionalization of electron-rich heteroaromates with malonate derivatives. A mechanistic study of the light-induced electron transport between the organic photocatalyst, substrate, and the sacrificial agent are described. With their tunable absorption range and defined energy-band structure, the small-molecule organic semiconductors could offer a new class of metal-free and visible light-active photocatalysts for chemical reactions.
- Wang, Lei,Huang, Wei,Li, Run,Gehrig, Dominik,Blom, Paul W. M.,Landfester, Katharina,Zhang, Kai A. I.
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supporting information
p. 9783 - 9787
(2016/08/10)
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- Synthesis, photophysical, electrochemical and single-crystal x-ray diffraction study of (Z)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile
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The optical characteristics, redox properties, thermogravimetric stability and single-crystal X-ray diffraction study of (Z)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile are examined using ultraviolet–visible spectrophotometry, cyclic voltammetry, thermal gravimetric analysis–diffraction scanning calorimetry analysis, single-crystal X-ray diffraction and density functional theory calculations. Evidently, the crystal structure of compound 6 is sustained by a number of weak nonconventional intermolecular forces of attraction such as C-H?…?N, C-H?…?π donor–acceptor interactions.
- Bhanvadia, Viraj J.,Patel, Heta A.,Sharma, Neha N.,Patel, Arun L.
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p. 1052 - 1061
(2016/07/16)
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- A comparative study of the effect of fluorine substitution on the photovoltaic performance of benzothiadiazole-based copolymers
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Two conjugated alternating copolymers to be used as the donor materials of the active layers in polymer solar cells have been designed and synthesized via a Stille coupling reaction. The alternating structure consisted of 4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b′]dithiophene (BDT) as the donor unit and benzo[c][1,2,5]thiadiazole (BT) or fluorinated benzo[c][1,2,5]thiadiazole (FBT) as the acceptor unit, along with a thiophene group as the π-bridge between the donor and acceptor units. Since the donor units have attached alkoxy pendant chains, both polymers were soluble in common organic solvents. UV-vis spectra of both copolymers exhibited broad absorption bands in the range of 325-900 and 380-900 nm, respectively, and corresponding low band gaps of 1.82 and 1.80 eV. After fluorination of the BT unit, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the polymer were lowered and estimated to be -5.51 and -3.71 eV, respectively. It was found that substitution of an F atom into the BT units facilitated the intramolecular charge transfer. In comparison with the nonfluorinated polymer, the photovoltaic performance of the fluorinated polymer was significantly improved due to the enhanced Jsc and Voc. Based on the ITO/PEDOT:PSS/polymer:PC61BM/LiF/Al device structure, the optimal device efficiency was obtained from a device with a blend of PBDTFBT and PC61BM at a weight ratio of 1:1. For this blend ratio, the values of Jsc and power conversion efficiency (PCE) obtained at room temperature are 7.98 mA cm-2 and 3.62%, respectively, under the illumination of AM 1.5 (100 mW cm-2).
- Wang, Tzong-Liu,Yang, Chien-Hsin,Chuang, Yao-Yuan
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p. 47676 - 47686
(2016/06/06)
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- FLUOROALKYLFLUORENE DERIVATIVES
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There are provided compounds of the formula D-S1-A-S2-B1 wherein A comprises a 2,7- disubstituted 9,9-fluoroalkyl fluorene diradical of the formula wherein S1, S2, D and B1 have meanings given in the description that are useful as charge transport and emissive materials for the fabrication of electronic devices such as diodes, transistors, and photovoltaic devices.
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Page/Page column 46
(2015/11/09)
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- Vacuum-depositable thiophene- and benzothiadiazole-based donor materials for organic solar cells
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Three (D-A-D)-type electron donor materials, containing 2,1,3-benzothiadiazole as the electron-withdrawing core, and benzothiophene, naphthalene, and thiophene as electron-donating terminal groups, were synthesized for vacuum-depositable small-molecule organic solar cells. The donor material containing thiophene as the terminal group, DT, shows a maximum power conversion efficiency of 4.13%, a short-circuit current density of 9.89 mA cm-2, an open-circuit voltage of 0.86 V, and a fill factor of 0.48, in a bulk heterojunction solar cell with a blend ratio of DT:C70 = 1 : 4 under simulated AM 1.5 solar irradiation at 100 mW cm-2.
- Jeon, Yongjun,Kim, Tae-Min,Kim, Jang-Joo,Hong, Jong-In
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p. 9591 - 9595
(2015/12/01)
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- PROCESS FOR THE PREPARATION OF BENZOHETERO [1,3] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS
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Process for the preparation of a benzohetero[1,3]diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero[1,3]diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.
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Paragraph 0083; 0084; 0085; 0086; 0087
(2014/08/19)
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- Small band gap D-π-A-π-D benzothiadiazole derivatives with low-lying HOMO levels as potential donors for applications in organic photovoltaics: A combined experimental and theoretical investigation
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In an attempt to develop small organic molecules with potential applications as donors in organic photovoltaic (OPV) devices, we have synthesized and characterized four novel benzothiadiazole (A) core structured D-π-A-π-D dyes featuring carbazole and benzocarbazole as donors (D) and fluorene and thiophene as spacers (π). The effects of the π-spacer units and variations in donor strength on the photophysical, electrochemical and thermal properties of the molecules have been investigated in detail. The replacement of fluorene by thiophene as a π-spacer promotes planarity, resulting in a larger bathochromic absorption shift, enhanced emission profiles and an enhanced intramolecular charge transfer (ICT) transition. The introduction of the benzocarbazole unit creates a low-lying HOMO level, as inferred from cyclic voltammetry studies. All the dyes exhibit remarkable thermal robustness. Theoretical calculations have been carried out to understand the structure-property relationships of the synthesized materials. The results obtained from the characterization methods reveal that the dyes with thiophene π-spacers show better optoelectronic properties compared to their fluorene counterparts. Solution-processable bulk-heterojunction devices with a structure of ITO/PEDOT:PSS (38 nm)/active layer/Ca (20 nm)/Al (100 nm) were fabricated using the materials investigated in this study as donors and (6,6)-phenyl C 61-butyric acid methyl ester (PC61BM) as an acceptor. A power conversion efficiency of 1.62% for the molecule with thiophene as a spacer and carbazole as donor/PC61BM was achieved for the preliminary photovoltaic devices under simulated AM 1.5 illumination (100 mW cm -2).
- Paramasivam, Mahalingavelar,Gupta, Akhil,Raynor, Aaron M.,Bhosale, Sheshanth V.,Bhanuprakash,Jayathirtha Rao
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p. 35318 - 35331
(2014/11/12)
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- PROCESS FOR THE PREPARATION OF BENZOHETERO [ 1, 3 ] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS
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Process for the preparation of a benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero [ 1, 3 ] diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.
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Page/Page column 26-27
(2013/03/26)
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- Optical activity of heteroaromatic conjugated polymer films prepared by asymmetric electrochemical polymerization in cholesteric liquid crystals: Structural function for chiral induction
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We electrochemically polymerized various achiral heteroaromatic monomers in left-handed helical cholesteric liquid crystal (CLC) media. Circular dichroism (CD) spectroscopy revealed that most of the resulting conjugated polymer films exhibited both the first negative and second positive Cotton effects near their absorption maxima. This indicates left-handed helical aggregation of the conjugated main chains, which is consistent with left-handed helical order of the CLC. This result suggests that the left-handed helical CLC environment induced left-handed helical aggregation of the polymers during the electrodeposition. However, CD intensity of the polymers depends on the structure of the parent monomers. Systematic investigation of the relationship between monomer structures and optical activity of the polymers indicates that linearity of the conjugated main chains and excluded volume interaction between the monomers and the CLC are important factors for producing optical activity of the polymers.
- Kawabata, Kohsuke,Takeguchi, Masaki,Goto, Hiromasa
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p. 2078 - 2091
(2013/06/04)
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- Polyarylene synthesis by cross-coupling with HOMSi reagents
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Cross-coupling reaction of dibromoarenes with HOMSi reagents (organo[2-(hydroxymethyl)phenyl]dimethylsilanes), or alternatively bromoarenes with arylene-bisHOMSi reagents, proceeded smoothly in the presence of a Pd catalyst and a weak base, and ter- or quaterarenes are produced in excellent yields. The present reaction was successfully applied to polyarylene synthesis using 4,7-dibromobenzothiadiazole or a 2,7-dibromofluorene derivative along with a 2,7-fluorenylenebisHOMSi reagent.
- Shimizu, Kenta,Minami, Yasunori,Nakao, Yoshiaki,Ohya, Ken-Ichiro,Ikehira, Hideyuki,Hiyama, Tamejiro
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supporting information
p. 45 - 47
(2013/02/25)
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- Metal-free organic dyes with benzothiadiazole as an internal acceptor for dye-sensitized solar cells
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We synthesized three metal-free organic dyes (H11-H13) consisting of a 3,6-disubstituted carbazole, benzothiadiazole, and cyanoacrylic acid. All the dyes exhibited high molar extinction coefficients and suitable energy levels for electron transfer from the electrolyte to the TiO2 nanoparticles. Under standard AM 1.5G solar irradiation, the device using dye H13 with co-adsorbed chenodeoxycholic acid (CDCA) displayed the best performance: an open-circuit voltage (Voc) of 0.71 V, a short-circuit current density (Jsc) of 12.69 mA cm-2, a fill factor (FF) of 0.71, and a power conversion efficiency (PCE) of 6.32%. The PCE was ~79% of that for commercially available N719 cells (8.02%) under the same conditions.
- Lee, Woochul,Seng, Ji Yeon,Hong, Jong-In
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p. 9175 - 9182
(2013/10/01)
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- Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials
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The synthesized benzothiadiazole-based series fluorophores as potential wavelength-shifting materials exhibit large Stokes shifts (>160 nm) with multiple broad absorbance bands from UV region to 600 nm and a strong fluorescence peak around 700 nm (in CHCl3). Intramolecular charge transfer (ICT) characters of the synthesized compounds are examined using UV-vis and photoluminescence solvatochromic shift measurements. Among the synthesized compounds, the fluorophores with asymmetrical structures exhibit larger Stokes shifts than those with symmetrical structures due to large dipole moment changes upon excitation. The fluorophores with electron-donating methoxyl groups attached to the triphenylamine donors are found to have strong ICT properties. Photophysical experimental results are supported by theoretical calculations using Density Function Theory (DFT) and Time Dependent Density Function Theory (TD-DFT) methods. Calculated frontier molecular orbitals (MOs) of ground states on these fluorophores showed an increase in ICT character up to 50% from HOMO to LUMO. Geometric optimization calculations of the excited state reveal that these fluorophores show a more planar structure for the excited state than the ground state, which allows more π-π* overlap and leads to larger Stokes shifts and higher quantum yields.
- Li, Yilin,Scudiero, Louis,Ren, Tianhui,Dong, Wen-Ji
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experimental part
p. 51 - 59
(2012/06/18)
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- PROCESS FOR THE SYNTHESIS OF BENZOTHIADIAZOLE COMPOUNDS
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The invention relates to a significantly improved process for the preparation of benzothiadxazole compounds which can be used in the production of Luminescent Solar Concentrators, (LSC). In particular, the synthesis process of the present invention is oriented towards the preparation of 4, -di-2-thienyl- 2,1,3-benzo-thiadiazole.
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Page/Page column 11; 17-18
(2012/02/02)
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- Simple access to sol-gel precursors bearing fluorescent aromatic core units
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Di-, tri-, and tetrathienyl-substituted polycyclic aromatic fluorophores were prepared from different aryldi-, aryltri-, or aryltetrahalides by a simple and fast Suzuki coupling. The reaction was optimized for the synthesis of the desired materials on mul
- Hemgesberg, Maximilian,Ohlmann, Dominik M.,Schmitt, Yvonne,Wolfe, Monique R.,Mueller, Melanie K.,Erb, Benjamin,Sun, Yu,Goossen, Lukas J.,Gerhards, Markus,Thiel, Werner R.
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supporting information; experimental part
p. 2142 - 2151
(2012/06/04)
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- Photovoltaic devices using semiconducting polymers containing head-to-tail-structured bithiophene, pyrene, and benzothiadiazole derivatives
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An alternating copolymer composed of heal-to-tail-structured 3,4'-dihexyl-2,2'-bithiophene (DHBT) and pyrene units [poly(DHBT-alt-PYR)] was synthesized using a Stille coupling reaction for use in photovoltaic devices as a p-type donor. For the reduction of the bandgap energy of poly(DHBT-alt-PYR), 4,7-bis(3'-hexyl-2,2'-bithiophen-5-yl)benzo[c][1,2,5]thiadiazole (BHBTBT) units were introduced into the polymer. Poly(DHBT-co-PYR-co-BHBTBT)s were synthesized using the same polymerization reaction. The synthesized polymers were soluble in common organic solvents and formed smooth thin films after spin casting. The optical bandgap energies of the polymers were obtained from the onset absorption wavelengths. The measured optical bandgap energy of poly(DHBT-alt-PYR) was 2.47 eV. As the BHBTBT content in the ter-polymers increased, the optical bandgap energies of the resulting polymers decreased. The bandgap energies of poly(50DHBT-co-40PYR-co-10BHBTBT) and poly(50DHBT-co-20PYR-co-30BHBTBT) were 1.84 and 1.73 eV, respectively. Photovoltaic devices were fabricated with a typical sandwich structure of ITO/PEDOT:PSS/active layer/LiF/Al using the polymers as electron donors and [6,6]-phenyl C71-butyric acid methyl ester as the electron acceptor. The device using poly(50DHBT-co-20PYR-co- 30BHBTBT) showed the best performance among the fabricated devices, with an open-circuit voltage, short-circuit current, fill factor, and maximum power conversion efficiency of 0.68 V, 5.54 mA/cm2, 0.35, and 1.31%, respectively.
- Kim, Ji-Hoon,Lee, Sunyoung,Kang, In-Nam,Park, Moo-Jin,Hwang, Do-Hoon
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scheme or table
p. 3415 - 3424
(2012/08/29)
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- D-A-D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties
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Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]- 1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl} -2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICT) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells.
- Zeng, Shaohang,Yin, Lunxiang,Jiang, Xueying,Li, Yanqin,Li, Kechang
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scheme or table
p. 229 - 235
(2012/09/07)
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- High charge carrier mobility, low band gap donor-acceptor benzothiadiazole-oligothiophene based polymeric semiconductors
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A series of benzothiadiazole oligothiophene and oligo(thienylene vinylene) donor-acceptor (D-A) copolymers were synthesized and characterized. These low optical band gap materials (~1.5 eV) are capable of absorbing photons in the range of 400-800 nm and exhibit good thermal stability. Their hole mobilities, determined using an organic field-effect transistor (OFET) architecture, vary over a range of 3 orders of magnitude and strongly correlate with the molecular ordering and morphology of the respective thin films. Spin-coated films of the poly(benzothiadiazole-sexithiophene) PBT6, which exhibits a highly crystalline lamellar π-π stacked edge-on orientation on the OFET substrate, possesses a hole mobility of ca. 0.2 cm2/V·s. Vinylene-containing analogs PBT6V2 and PBT6V2′ are amorphous and exhibit very low mobilities. The molecular weight of PBT6 has a strong influence on the electronic properties: a sample with a lower molecular weight exhibits a mobility approximately 1 order of magnitude lower than the high molecular weight homologue, and the absorption maximum is appreciably blue-shifted. The hole mobility of PBT6 is further enhanced by a factor of ca. 3 through fabrication of the OFET by drop casting. OFETs fabricated by this process exhibit mobilities of up to 0.75 cm2/V·s and ION/OFF ratios in the range of 106-107. These results demonstrate the potential of incorporating benzothiadiazole units into polythiophene derivatives to develop high-mobility semiconducting polymers.
- Fu, Boyi,Baltazar, Jose,Hu, Zhaokang,Chien, An-Ting,Kumar, Satish,Henderson, Clifford L.,Collard, David M.,Reichmanis, Elsa
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p. 4123 - 4133
(2013/01/15)
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- Introduction of perylene units for enhanced interchain interaction in conjugated polymers for organic photovoltaic devices
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A series of semiconducting copolymers, poly[2,7-(9,9′- dioctylfluorene)-alt-5,5′-(4′,7′-di-2-thienyl-2′, 1′,3′-benzothiadiazole)] (PFDTBT), poly[2,2′-(9,9-dioctyl-9H- fluorene-2,7-diyl)dithiophene-alt-5,5′-(4′,7′-di-2-thienyl- 2′,1′,3′-benzothiadiazole)] (PFD2TBT), and their ter-polymers containing perylene units were synthesized using Suzuki coupling polymerization. The perylene units were introduced to improve the charge-transport ability by enhancing the π-π interaction between polymer chains. The resulting polymers were characterized by 1H NMR, elemental analysis, DSC, and TGA. The synthesized polymers were soluble in common organic solvents, and formed smooth and uniform spin-coated thin films. All of the polymers studied were found to exhibit good thermal stability, losing less than 5% of their weight upon heating to approximately 350 °C. Perylene- containing polymers showed higher field-effect mobilities than the corresponding PFDTBT or PFD2TBT polymers because of the enhanced π-π interaction between polymer chains upon the introduction of perylene units. Bulk heterojunction solar cells were fabricated with configuration of ITO/PEDOT:PSS/polymer:PC71BM/ TiOx/Al. The devices using the perylene-containing polymers showed higher short-circuit currents, and fill factors than the corresponding PFDTBT or PFD2TBT devices. One of the fabricated devices using a perylene-containing copolymer showed a maximum power conversion efficiency of 3.16%, with a short circuit current density of 9.61 mA/cm2, open circuit voltage of 0.81 V, and fill factor of 41%.
- Kim, Ji-Hoon,Kim, Hee Un,Mi, Dongbo,Jin, Sung-Ho,Shin, Won Suk,Yoon, Sung Cheol,Kang, In-Nam,Hwang, Do-Hoon
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experimental part
p. 2367 - 2376
(2012/06/29)
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