- Soluble and easily crystallized anthracene derivatives: precursors of solution-processable semiconducting molecules
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New soluble anthracene derivatives containing thlophene and phenylenevlnylene derivatives were synthesized via well-known synthetic routes. TIPS derivatives were added at the 9,10-posltlons of anthracene for the solubility and crystailinlty. Both of the molecules were found to be promising for high charge mobility and stable organic semiconductors. The soluble anthracene core (TIPSAnt) Is a potential precursor for the synthesis of novel semiconducting materials.
- Park, Jong-Hwa,Chung, Dae Sung,Park, Jong-Won,Ahn, Taek,Kong, Hoyoul,Jung, Young Kwan,Lee, Jonghee,Yi, Mi Hye,Park, Chan Eon,Kwon, Soon-Ki,Shim, Hong-Ku
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- Molecular Oxygen Activation by Redox-Switchable Anthraquinone-Based Metal-Organic Frameworks
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A dipyridyl-substituted anthraquinone (2,6-di(pyridin-4-yl)-9,10-anthraquinone, DPAq) was incorporated as a redox-active linker molecule into crystalline coordination networks. The oxidation state of the organic linker can be selectively controlled prior to framework formation and furthermore be maintained in the solid state. Hydrogen bonding is identified to be a substantial stabilization factor. Additionally, it is shown that the anthraquinone-anthrahydroquinone redox pair can be switched reversibly even after incorporation in the solid state by a thermal treatment/soaking procedure - going along with the formation of hydrogen peroxide from molecular oxygen (air) during the oxidation process.
- De Carvalho, Jo?o Guilherme M.,Fischer, Roland A.,P?thig, Alexander
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- Effective side chain selection for enhanced open circuit voltage of polymer solar cells based on 2D-conjugated anthracene derivatives
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Two novel conjugated donor-acceptor polymers were synthesized by combining anthracene donor and benzothiadiazole acceptor with two different side chains (conjugated and non-conjugated). Their absorption spectroscopy, thermogravimetric analysis, electrochemical cyclic voltammetry, theoretical prediction, surface morphology, and photovoltaic performance were investigated. The resultant two-dimensional configuration showed good optical and electrochemical properties. By selectively introducing branched conjugated side chains and non-conjugated linear side chains on the polymer backbone, the highest occupied molecular orbital levels are low lying which results in an increased open circuit voltage for polymer solar cells. The open circuit voltage of 1.02 V in this work was among the highest value for anthracene-based polymer solar cells ever. Our results suggest a good way to regulate the molecular energy levels by selecting appropriate side chains.
- Ai,Ouyang,Liu,Wang,Peng,Islam,Ge
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- A Dipolar Anthracene Dye: Synthesis, Optical Properties and Two-photon Tissue Imaging
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Two-photon microscopy is a powerful tool for studying biological systems. In search of novel two-photon absorbing dyes for bioimaging, we synthesized a new anthracene-based dipolar dye (anthradan) and evaluated its two-photon absorbing and imaging properties. The new anthradan, 9,10-bis(o-dimethoxy-phenyl)-anthradan, absorbs and emits at longer wavelengths than acedan, a well-known two-photon absorbing dye. It is also stable under two-photon excitation conditions and biocompatible, and thus used for two-photon imaging of mouse organ tissues to show bright, near-red fluorescence along with negligible autofluorescence. Such an anthradan thus holds promise as a new class of two-photon absorbing dyes for the development of fluorescent probes and tags for biological systems.
- Moon, Hyunsoo,Jun, Yong Woong,Kim, Dokyoung,Ryu, Hye Gun,Wang, Taejun,Kim, Ki Hean,Huh, Youngbuhm,Jung, Junyang,Ahn, Kyo Han
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- CAPRYDAA, an anthracene dye analog to LAURDAN: A comparative study using cuvette and microscopy
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We synthesized an anthracene derivative with solvatochromic properties to be used as a molecular probe for membrane dynamics and supramolecular organization. A nine carbon atom acyl chain and a dimethylamino substitution were introduced at positions 2 and 6 of the anthracene ring, respectively. This derivative, 2-nonanoyl-6-(dimethylamino)anthracene (termed CAPRYDAA), is a molecular probe designed to mimic the well-known membrane probe LAURDAN's location and response in the lipid membranes. Due to the larger distance between the electron donor and acceptor groups, its absorption and emission bands are red-shifted according to the polarity of the media. The photophysical behavior of CAPRYDAA was measured in homogeneous media, synthetic bilayer and cells, both in a cuvette and in a fluorescence microscope, using one and two-photon excitation. Our results show a comparable physicochemical behavior of CAPRYDAA with LAURDAN, but with the advantage of using visible light (488 nm) as an excitation source. CAPRYDAA was also excitable by two-photon laser sources, making it easy to combine CAPRYDAA with either blue or red emission probes. In GUVs or cells, CAPRYDAA can discriminate the lipid phases and liquid-liquid phase heterogeneity. This new membrane probe shows the bathochromic properties of the PRODAN-based probes designed by Weber, overcoming the need for UV or two-photon excitation and facilitating the studies on the membrane properties using regular confocal microscopes.
- Castro-Castillo, Vicente,Gajardo, Javier,Gratton, Enrico,Gunther, German,Malacrida, Leonel,Sanchez, Susana,Sandoval-Altamirano, Catalina
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- Triisopropylsilylacetylene-functionalised anthracene-alt-benzothiadiazole copolymers for application in bulk heterojunction solar cells
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Three triisopropylsilylacetylene-functionalised anthracene (TIPSAnt) based polymers were synthesised by copolymerising TIPSAnt with either dithienyl-5,6-difluoro-benzo[c]-[1,2,5]thiadiazole, dithienyl-benzo[c]-[1,2,5]thiadiazole or dibithiophenyl-benzo[c]-[1,2,5]thiadiazole to yield PTATffBT, PTATBT-8 and PTAT2BT-8, respectively. PTAT2BT-8 demonstrated a reduced optical and electrochemical band gap, relative to PTATffBT and PTATBT-8. The HOMO level of PTAT2BT-8 (-5.32 eV) is significantly shallower compared to its counterparts. This can be attributed to increased intramolecular charge transfer along the polymer backbone; a consequence of the incorporation of additional thiophene spacer units. The photovoltaic properties of the polymers were investigated by fabricating bulk heterojunction (BHJ) polymer solar cells using PC70BM as the electron acceptor. PTATffBT displayed limited solubility in common organic solvents and could not be used for the fabrication of photovoltaic cells. Optimised photovoltaic devices fabricated from PTATBT-8 and PTAT2BT-8 demonstrated power conversion efficiencies of 2.36% and 3.15%, respectively. PTAT2BT-8 provided better efficiencies chiefly as a result of better Jsc and FF values.
- Cartwright, Luke,Taylor, Lois. J.,Yi, Hunan,Iraqi, Ahmed,Zhang, Yiwei,Scarratt, Nicholas. W.,Wang, Tao,Lidzey, David. G.
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p. 101607 - 101615
(2015)
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- Anthracene based organic dipolar compounds for sensitized solar cells
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Organic dyes that consist of an anthracene moiety between a triphenylamine donor group and a cyanoacrylic acid acceptor group displayed remarkable solar-to-energy conversion efficiency in dye-sensitized solar cells. The planar geometry of anthracene and its bulky substituents helped the dyes to form a high quality monolayer on the surface of TiO2. A typical device made with the dye AN-Bu displayed a maximal photon-to-current conversion efficiency (IPCE) 65% in the region of 350-510 nm, a short-circuit photocurrent density (Jsc) 12.78 mA cm-2, an open-circuit photovoltage (V oc) 0.73 V, and a fill factor (FF) 0.67, corresponding to an overall conversion efficiency 6.23%. In an experiment of using deoxycholic acid (DCA) as a co-absorbent, the values of Voc stayed in a similar range, yet the values of Jsc were reduced in ca. 11% due to a decrease of loading amounts. This result indicated that the quality of the dye films cannot be further improved by the adding of DCA. The photophysical properties were analyzed with the aid of a time-dependent density functional theory (TDDFT) model with the B3LYP functional.
- Lin, Yan-Zuo,Huang, Chiung Hui,Chang, Yuan Jay,Yeh, Chia-Wei,Chin, Tsung-Mei,Chi, Kai-Ming,Chou, Po-Ting,Watanabe, Motonori,Chow, Tahsin J.
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- Charge-Transfer-Induced Fluorescence Quenching of Anthracene Derivatives and Selective Detection of Picric Acid
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2,6-Divinylpyridine-appended anthracene derivatives flanked by two alkyl chains at the 9,10-position of the core have been designed, synthesized, and characterized by NMR, MALDI-TOF, FTIR, and single-crystal XRD. These anthracene derivatives are able to recognize picric acid (2,4,6-trinitrophenol, PA) selectively down to parts per billion (ppb) level in aqueous as well as nonaqueous medium. Fluorescence emission of these derivatives in solution is significantly quenched by adding trace amounts of PA, even in the presence of other competing analogues, such as 2,4-dinitrophenol (2,4-DNP), 4-nitrophenol (NP), nitrobenzene (NB), benzoic acid (BA), and phenol (PH). The high sensitivity of these derivatives toward PA is considered as a combined effect of the proton-induced intramolecular charge transfer (ICT) as well as electron transfer from the electron-rich anthracene to the electron-deficient PA. Moreover, visual detection of PA has been successfully demonstrated in the solid state by using different substrates. Explosive chemistry! Anthracene derivatives are able to recognize picric acid (PA) selectively down to the parts per billion (ppb) level in aqueous as well as nonaqueous medium. Importantly, visual detection of PA has been successfully demonstrated in the solid state using different substrates (see figure).
- Santra, Dines Chandra,Bera, Manas Kumar,Sukul, Pradip Kumar,Malik, Sudip
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- 2,6-Bis[4-(p-dihexylaminostyryl)-styryl]anthracene derivatives with large two-photon cross sections
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(Chemical Equation Presented) Anthracene derivatives with a variety of donor-acceptor substituents have been synthesized and shown to exhibit large two-photon cross sections over a wide range of wavelengths.
- Lee, Seung Kyu,Yang, Wen Jun,Choi, Jin Joo,Kim, Chang Ho,Jeon, Seung-Joon,Cho, Bong Rae
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- Synthesis of poly(anthra-9,10-quinone-2,6-diyl)
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The synthesis, via a precursor polymer, of poly(anthra-9,10-quinone-2,6-diyl) 1 is described and some of its properties are reported.
- Power, Gerald,Hodge, Philip,Clarke, Ian D.,Rabjohns, Michael A.,Goodbody, Ian
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- Synthesis and photophysical properties of multilayer emitting π-p-π fluorophores
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Fluorescence is widely used in biology, medicine, and analytical chemistry. The anthracene framework has received considerable attention for the luminescent molecular design as an attractive building unit. Herein, Luminescent “π-p-π” anthracene crystals with different multilayer stacking modes were conducted by experimental methods and theoretical calculations. It was found that “these anthracene derivatives showed strong fluorescence and stability in both solution and solid-state; A face-to-face π-π stacking arrangement dominated in N9,N10-diphenyl-2,6-bis((trimethylsilyl)ethynyl)anthracene-9,10-diamine (4), while C/N–H … π interactions were observed in the crystal lattice of 2,6-diethynyl-N9,N10-diphenylanthracene-9,10-diamine (5); The excitation processes of S0→S1 of 4 and 5 belonged to Localized Excitation; The number of photons emitted could be nearly equal to the number of photons absorbed below 120K”. This study is expected to assist in the design of photonic materials in the field of optical chemistry.
- Wang, Xiaorong,Zhao, Sanxiao,Chen, Yin,Wang, Jingang
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- Empowering organic-based negative electrode material based on conjugated lithium carboxylate through molecular design
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In this article, we describe the design and gram-scale synthesis of a new anthracene-based negative electrode material for Li-ion batteries. Based on rational design, featuring a strong electronic delocalization and a long conjugation length, this material has power performance to date unmatched for a conjugated lithium carboxylate, displaying a gravimetric capacity of 150 mAh g?1 at a cycling rate of 20 Li+/h (10 C) without any electrode engineering. Additionally, to the design, partial solubility of the fully reduced phase may also explain the electrochemical performances obtained at a low and high rate.
- Becuwe, Matthieu,Fédèle, Lionel,Ouari, Olivier,Sauvage, Frédéric,Thiam, Amadou
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- Two-Terminal Molecular Memory through Reversible Switching of Quantum Interference Features in Tunneling Junctions
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Large-area molecular tunneling junctions comprising self-assembled monolayers of redox-active molecules are described that exhibit two-terminal bias switching. The as-prepared monolayers undergo partial charge transfer to the underlying metal substrate (Au, Pt, or Ag), which converts their cores from a quinoid to a hydroquinoid form. The resulting rearomatization converts the bond topology from a cross-conjugated to a linearly conjugated π system. The cross-conjugated form correlates to the appearance of an interference feature in the transmission spectrum that vanishes for the linearly conjugated form. Owing to the presence of electron-withdrawing nitrile groups, the reduction potential and the interference feature lie close to the work function and Fermi level of the metallic substrate. We exploited the relationship between conjugation patterns and quantum interference to create nonvolatile memory in proto-devices using eutectic Ga–In as the top contact.
- Carlotti, Marco,Soni, Saurabh,Kumar, Sumit,Ai, Yong,Sauter, Eric,Zharnikov, Michael,Chiechi, Ryan C.
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p. 15681 - 15685
(2018/11/06)
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- Novel Fluorescent Fluorene-Containing Conjugated Polymers: Synthesis, Photophysical Properties, and Application for the Detection of Common Bisphenols
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Eight new fluorescent conjugated polymers were synthesized by the Suzuki polycondensation reaction of 9,9-dioctylfluorene-2,7-diboronic acid bis(1,3-propanediol) ester and a conjugated dihalogenated monomer. The photophysical properties of these polymers were investigated as well-dissolved solutions in chloroform and as nanoparticle suspensions in water. Several of the polymers had large Stokes shifts (greater than 100 nm) and others demonstrated unique changes in the fluorescence properties in aggregated verse nonaggregated forms. Preliminary applications of these polymers in the detection of common bisphenols are also reported.
- Jones, Daniel R.,Vallee, Ryan,Levine, Mindy
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supporting information
p. 2515 - 2522
(2018/11/30)
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- Two Anthracene-Based Copolymers as the Hole-Transporting Materials for High-Performance Inverted (p-i-n) Perovskite Solar Cells
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Two anthracene-based copolymers, the thiophene-bridged carbazole-anthracene copolymer (abbreviated as PCBZANT) and the thiophene-bridged triphenylamine-anthracene copolymer (abbreviated as PTPAANT), have been developed as the hole-transporting materials (HTMs) for the inverted perovskite solar cells. They were thermally stable with decomposition temperatures of 435 and 420 °C. The High Occupied Molecular Orbitals (HOMO) of -5.15 and -5.24 eV of two copolymers facilitated the hole carriers transfer from the perovskite layer (CH3NH3PbI3, HOMO: -5.4 eV) in contrast to poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS, HOMO: -4.9 eV). The solar cell with PCBZANT (abbreviated as the PCBZANT device) showed the highest power conversion efficiency (PCE) of 15.50%, while the cell with PTPAANT (abbreviated as the PTPAANT device) showed the highest PCE of 14.52%, with increases of 36.2% and 27.6%, respectively, relative to the PEDOT:PSS device. The thorough analysis disclosed that the high performance was mainly ascribed to the enhanced open-circuit voltage (VOC) and short-circuit current density (JSC), being contributed from the efficient hole-carrier extraction, the high hole mobility of two copolymers, and the high-quality perovskite film with large crystal size and less defect. With strong absorption in the range of 350-500 nm, the polymers decreased the destruction of UV-radiation on the perovskite layer as UV-filters and improved the stability of the inverted cells.
- Tong, Tong,Tan, Chao,Keller, Tina,Li, Bobo,Zheng, Chaoyue,Scherf, Ullrich,Gao, Deqing,Huang, Wei
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p. 7407 - 7416
(2018/09/27)
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- Synthesis of asymmetrically disubstituted anthracenes
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We have developed synthetic pathways toward differently substituted hydroxyanthracenes (anthrols) with the aim to investigate their photochemical reactivity in dehydration reactions. Although the syntheses of anthracenes substituted at positions 9,10 are well known, reports for the synthesis of anthracenes with different substitution patterns are scarce. Herein we review known and report novel synthetic pathways toward anthrols with substituents at 1,2-, 2,3-, and 2,6- positions. We present two synthetic approaches: (i) building of the anthracene tricyclic fused ring system from the appropriate benzene derivatives, and (ii) reduction of the corresponding anthraquinones. Reduction of 2-hydroxyanthracene-1-carbaldehyde to the corresponding alcohol yields rather unexpected 1,1′-methylenedianthracen-2-ol, whose proposed mechanism of formation is supported by experimental observations and calculations.
- ?kalamera, ?ani,Veljkovi?, Jelena,Pti?ek, Lucija,Sambol, Matija,Mlinari?-Majerski, Kata,Basari?, Nikola
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supporting information
p. 5892 - 5899
(2017/09/09)
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- Blue fluorescent compounds and organic light emitting diode devices using the same
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A blue fluorescent compound is disclosed. The blue fluorescent compound represented by the following Chemical Formula 1, where R1 and R2 are each independently selected from the group consisting of C0-C18 saturated hydrocarbon carbons, branched saturated hydrocarbons, and saturated ring hydrocarbons, and Ar1 and Ar2 are each independently selected from the group consisting of C1-C20 aromatic compounds, heteroaromatic compounds, C1-C18 saturated hydrocarbons, C1-C18 branched saturated hydrocarbons, and C1-C18 saturated ring hydrocarbons.
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(2017/08/08)
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- ARYL-SUBSTITUTED ANTHRACENE COMPOUND, PREPARATION METHOD THEREOF, AND ORGANIC THIN FILM TRANSISTOR COMPRISING THE SAME
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PURPOSE: An aryl group-substituted anthracene compound and an organic thin film transistor are provided to ensure crystallinity and thin film property. CONSTITUTION: An anthracenyl compound is denoted by chemical formula 1. An organic thin film transistor contains the anthracenyl compound of chemical formula 1. The organic thin film transistor comprises a first electrode, a second electrode, and thin film of anthracenyl compounds between the first and second electrodes. The organic thin film has a transistor top-gate/top-contact, top-gate-bottom-contact, bottom-gate/top-contact, or bottom-gate/bottom contact structure.
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Paragraph 0044-0046
(2017/08/02)
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- Fluorescent compound and production method thereof
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The invention discloses a fluorescent compound and a production method thereof. The fluorescent compound is 2,6-Dibromo-9,10-bis[2-[tris(1-methylethyl)silyl]ethynyl]anthracene. The production method comprises Sandmeyer reaction and anion reaction. 2,6-aminoanthraquinone is used; through the Sandmeyer reaction, t-Bu ONO is used as a catalyst; the 2,6-position amino groups are replaced by bromo groups; then, through the anion reaction, the butyl lithium is used as an initiator of the anion reaction; triisopropylsilylacetylene is added onto the 9, 10 sites of the 2,6-bromo anthraquinone; SnCl2.2H2O is used for cutting away hydroxyl groups formed in the 9, 10 sites; the obtained product collection is respectively performed once by silica gel chromatography column 200-300-mesh and 40-63-mesh purification methods to obtain the 2,6-Dibromo-9,10-bis[2-[tris(1-methylethyl)silyl]ethynyl]anthracene.
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Paragraph 0042; 0043
(2017/08/29)
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- NOVEL MATERIALS FOR ORGANIC ELECTROLUMINESCENCE DEVICES
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The present invention relates to a compound of the formula (1) and (2) The invention further relates to a process to produce the compound. The invention additionally relates and an electronic device containing the compound of the formula (1) or (2). The electronic device can be an organic electroluminescence devices, particularly a blue emitting device, in which compounds are used as host materials or dopants in the emitting layer and/or as hole transport materials and/or as electron transport materials.
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Paragraph 0043-0046
(2017/01/05)
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- Position effect based on anthracene core for OLED emitters
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Green-orange emitters based on anthracene core have been successfully synthesized by substitution with triphenylamine side group in the 9,10 or 2,6 positions. There are larger blue shifts in the UV-visible absorption and PL spectra of the synthesized 2,6-substituted derivative compared to the 9,10-substituted derivative. When the synthesized compounds were used as emitting layers in non-doped OLED devices, a related trend was observed in their optical properties. In particular, the OLED device containing the 2,6-substituted derivative was found to exhibit excellent characteristics, with maximum EL emission at 518 nm, pure green emission with CIE coordinates of (0.334, 0.604), and external quantum efficiency of 2.83%.
- Kang, Hyeonmi,Shin, Hwangyu,Kim, Beomjin,Park, Jongwook
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p. 3045 - 3048
(2016/03/19)
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- A cross-dipole stacking molecule of an anthracene derivative: Integrating optical and electrical properties
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Cross-dipole stacking has been addressed as a preferred motif for solid state emission, but inefficient for charge transport. Here we synthesize a new anthracene derivative, which adopts cross-stacking in the solid state with a solid state fluorescence up to 77.3% and a hole mobility of 1.47 cm2 V-1 s-1, integrating optical and electrical properties successfully. As far as we know, it is the first report of organic field-effect transistors based on cross-dipole stacking molecules.
- Liu, Jie,Meng, Lingqiang,Zhu, Weigang,Zhang, Congcong,Zhang, Hantang,Yao, Yifan,Wang, Zongrui,He, Ping,Zhang, Xiaotao,Wang, Ying,Zhen, Yonggang,Dong, Huanli,Yi, Yuanping,Hu, Wenping
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supporting information
p. 3068 - 3071
(2015/03/31)
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- Linkage position influences of anthracene and tricyanovinyl groups on the opto-electrical and photovoltaic properties of anthracene-based organic small molecules
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Anthracene-based small molecules incorporating an electron accepting tricyanovinyl (TCV) group was prepared to investigate the linkage position influences of the anthracene and TCV groups on the opto-electrical and photovoltaic properties of the molecules. The maximum absorptions of the anthracene-based molecules incorporating the TCV group at the phenyl group of the triphenylamine unit (TCV-TpaA9,10T, TCV-TpaTA9,10T, and TCV-TpaA2,6T) or at the thiophene unit (TpaA9,10T-TCV, TpaTA9,10T-TCV, and TpaA2,6T-TCV) were found to be dependent on the linkage position of the anthracene unit. The HOMO energy levels of the molecules containing TCV group at the phenyl group of the triphenylamine unit were deeper than those of the molecules containing TCV group at the thiophene unit. The solution processed small molecule organic solar cells (SMOSCs) prepared with the structure of ITO/PEDOT:PSS/TCV-TpaA9,10T or TCV-TpaA2,6T or TpaA2,6T-TCV:PC71BM (2:1 wt %)/LiF/Al exhibited a maximum energy conversion efficiency of 1.04%, 1.67%, and 1.95%, respectively, under AM 1.5 irradiation (100 mW cm-2).
- Tamilavan, Vellaiappillai,Song, Myungkwan,Agneeswari, Rajalingam,Hyun, Myung Ho
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p. 1176 - 1186
(2014/02/14)
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- Synthesis and properties of new 9,10-anthraquinone derived compounds for molecular electronics
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Fourteen new derivatives of 9,10-anthraquinone or 9,10-dimethoxyanthracene were designed, synthesised and characterised. Regarding the structure, the compounds are π-conjugated (cross and linear, respectively) and feature thiophene terminated side arms attached to five different positions of the anthraquinone or anthracene core. The synthesis of the compounds involves a cross-coupling procedure in the key reaction steps. Crystal structures of compounds 5 and 19 have been studied. The thiophene containing title compounds 1-5 can be reduced and oxidised by a two step redox process. The electrochemical parameters have been analysed by cyclic voltammetry (CV). Theoretical calculations in the framework of all-electron density functional theory (DFT) were used to investigate the electronic structure of the individual free molecules. Furthermore, calculations of the transport properties of model devices containing compounds 1-3 and respective reduced hydroquinone derivatives assembled at Au(111) electrodes were carried out to evaluate their potential for the application as redox-active switches.
- Seidel, Nadine,Hahn, Torsten,Liebing, Simon,Seichter, Wilhelm,Kortus, Jens,Weber, Edwin
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p. 601 - 610
(2013/04/10)
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- CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DIODE HAVING ORGANIC LAYER INCLUDING THE SAME
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A condensed-cyclic compound represented by Formula 1 and an organic light emitting diode including the same:
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- Condensed-cyclic compound and organic light emitting diode having organic layer including the same
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A condensed-cyclic compound represented by Formula 1 and an organic light emitting diode including the same:
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Page/Page column 23
(2011/04/18)
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- Organic Light-Emitting Device
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The present invention provides a heterocyclic compound and an organic light-emitting device including the heterocyclic compound. The organic light-emitting devices using the heterocyclic compounds have high-efficiency, low driving voltage, high luminance and long lifespan.
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(2011/04/18)
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- Synthesis of new fluorene-based copolymers containing an anthracene derivative and their applications in polymeric light-emitting diodes
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We report the synthesis of copolymers containing fluorene and highly soluble anthracene derivatives, of general formula, poly{9,9′-bis-(4- octoloxy-phenyl)-fluorene-2,7-diyl-co-9,10-bis-(decy-1-ynyl)-anthracene-2, 6-diyl}s (PFAnts). The PFAnts were synthesized via Suzuki coupling and the feed ratios of the anthracene derivative (Ant) were 1, 5, 10, 30, and 50 mol % of the total amount of monomer. PFAnts showed well-defined high molecular weights and were more soluble in conventional organic solvents. The photoluminescence spectra of PFAnts shifted to longer wavelengths with increases in Ant proportion and the PFAnts emitted various colors varying from greenish-blue to orange. The highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels trended toward enhanced hole and electron recombination balance as the Ant proportion increased, due to the better electron-accepting ability of the anthracene moiety compared to the fluorene moiety. Polymeric light-emitting diodes with the configurations ITO/PEDOT:PSS(40 nm)/polymer(60 nm)/Ca(10 nm)/Al(100 nm) (Device A) and ITO/PEDOT:PSS(40 nm)/polymer(60 nm)/Balq(40 nm)/LiF(1 nm)/Al(100 nm) (Device B) were fabricated using the polymers as emissive layers. Especially, Device B with PFAnt01 exhibited the highest measured maximum brightness of 1760 cd/m2 at 14 V, a maximum current efficiency of 1.66 cd/A, and a maximum external quantum efficiency of 0.70%. Copyright
- Lee, Kyoungmi,Park, Jong-Hwa,Park, Moo-Jin,Lee, Jonghee,Shim, Hong-Ku
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scheme or table
p. 4648 - 4657
(2012/06/16)
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- BLUE LIGHT EMITTING COMPOUND AND ORGANIC LIGHT EMITTING DIODE DEVICE COMPRISING THE SAME
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A blue light emitting compound is provided. The blue light emitting compound has a structure of the following Chemical Formula 1: wherein A1, A2, and A3 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted aromatic group, a hetero ring group, and an aliphatic group.
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- An X-shaped solution-processible oligomer having an anthracene unit as a core: A new organic light-emitting material with high thermostability and efficiency
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A new X-shaped solution-processible oligomer with a glass transition temperature of higher than 200 °C based on an anthracene derivative was prepared, and it showed good hole-transporting ability in organic light-emitting diodes (OLED). Such oligomer was also employed as the emitting layer to give the devices showing blue emission.
- Sun, Jing,Zhong, Hongliang,Xu, Erjian,Zeng, Danli,Zhang, Jianhua,Xu, Hongguang,Zhu, Wenqing,Fang, Qiang
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experimental part
p. 74 - 80
(2010/10/19)
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- THIAZOLE SYSTEM ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE USING THE SAME
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The present invention relates to novel thiazole system organic electroluminescent compounds and organic light emitting diodes comprising the same. Since the thiazole system organic electroluminescent compounds according to the invention have good luminous efficiency and life property, OLED's having very good operation lifetime can be produced.
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Page/Page column 27
(2010/08/07)
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- Synthesis and electrochemical evaluation of conjugates between 2′-deoxyadenosine and modified anthraquinone: Probes for hole-transfer studies in DNA
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(Chemical Equation Presented) Photoexcitation of anthraquinones (AQ) in association with DNA results in DNA damage mainly at guanine residues, with products from thymine oxidation also observed. Studies of adenine oxidation will be aided by systems with an increased driving force for charge transfer, achieved by adding electron-withdrawing groups to the AQ ring. Attaching AQ derivatives to adenine via a bridge with two carbon atoms should enable the intended regiocontrol within the DNA duplex structure. Herein we report the synthesis of conjugates between AQ and adenine in which the AQ moieties have been modified with a formyl, a trifluoroacetyl, and two methyl ester groups. These have been synthesized by palladium coupling of tert-butyldiphenylsilyl 5′-protected 8-ethynyl-2′-deoxyadenosine with the corresponding bromoanthraquinone intermediates. Bromo intermediates bearing formyl or trifluoroacetyl were prepared by monolithiation of 2,6-dibromoanthraquinone, a step that required protection of the anthraquinone carbonyls. A bromo intermediate bearing two methyl ester groups was obtained from 1,2,4-trimethylbenzene by Friedel-Crafts acylation with 4-bromobenzoyl chloride followed by oxidation to the tricarboxylic acid, cyclization to form the anthraquinone ring, and finally esterification. Hydrogenation of the ethynyl linker gave the ethanyl linker. Cyclic voltammetry showed that the conjugate with the two ester groups and ethynyl linker was the most easily reduced of the derivatives synthesized. These derivatives, with reduction potentials favorable for electron transfer, can be used in studies of adenine oxidation in DNA.
- Abou-Elkhair, Reham A. I.,Dixon, Dabney W.,Netzel, Thomas L.
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supporting information; experimental part
p. 4712 - 4719
(2009/10/17)
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- Organic compounds for electroluminescence and organic electroluminescent devices using the same
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Disclosed is a novel group of compounds having a general structure of anthracene body substituted with at least one thiophenyl group, which can be further substituted with various substituent groups. These new compounds are generally compatible with organic electroluminescence. Also disclosed are organic electroluminescent devices and method of making the same. The organic electroluminescent devices include at least one of the compounds in various layers thereof. Organic electroluminescent devices employing the new compounds in their light-emitting layers show outstanding stability.
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Page/Page column 74
(2009/02/11)
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- Anthraquinone derivatives affording n-type organic thin film transistors
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New anthraquinone derivatives were prepared and used as active layers of organic field-effect transistors (OFETs); these devices showed good n-type characteristics and the quinones were found to be useful for organic semiconductors in OFETs.
- Mamada, Masashi,Nishida, Jun-Ichi,Tokito, Shizuo,Yamashita, Yoshiro
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scheme or table
p. 2177 - 2179
(2009/09/06)
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- New push-pull chromophores featuring TCAQ (11,11,12,12-Tetracyano-9,10- anthraquinodimethane) and other dicyanovinyl acceptors
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Stable, highly colored push-pull chromophores with NMe2 donor and C=C(CN)2 acceptor moieties, featuring intense intramolecular charge-transfer (CT) bands in the UV/Vis spectra, are reported. In an attempt to prepare the quinoid pushpull systems 2, chromophores 10 and 11, with a central cyclohexene spacer, were obtained and characterized by X-ray analysis. A series of donor-substituted TCAQ (11,11,12,12-tetracyano-9,10-anthraquinodimethane) derivatives were synthesized, using the Knoevenagel condensation between appropriately functionalized anthraquinones and malononitrile, mediated by the Lehnert reagent (TiCl4/pyridine), as the key step. HCl addition to triple bonds was observed when this transformation was applied to alkynylated anthraquinones. Electrochemical studies by cyclic voltammetry (CV) and rotating-disk voltammetry (RDV) showed that introduction of donor substituents into the TCAQ core of 25, 26, and 31 shifts the first reduction potential to more negative values, while chromophores bearing guanidine moieties (27, 28) displayed a specific and complex redox behavior. Both electrochemical and UV/Vis data provide good evidence that D-A conjugation is more efficient through olefinic (in 10) than through acetylenic (in 37) spacers. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Bures, Filip,Bernd Schweizer,Boudon, Corinne,Gisselbrecht, Jean-Paul,Gross, Maurice,Diederich, Francois
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body text
p. 994 - 1004
(2009/04/11)
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- NOVEL ORGANIC SEMICONDUCTOR COMPOUND, AND ORGANIC THIN FILM TRANSISTOR USING THE SAME
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The present invention relates to novel mono- molecular organic semiconductor compounds and organic thin film transistors comprising the same. The organic semiconductor compounds according to the present invention are characterized by a structure of an acene derivative substituted with acetylene groups at both ends, a structure of anthracene derivative substituted with acetylene groups, or a structure of a multi-nuclear aromatic derivative functionalized by naphthalene having an electron-donor substituent at both ends.
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Page/Page column 38-40, 45
(2008/12/04)
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- Organic electroluminescence device
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Disclosed is an organic electroluminescent device comprising a structure having an anode, an emitting layer, and a cathode stacked therein, wherein a fluorescent compound represented by Formula 1 is used as a emitting material of the emitting layer or used as a dopant of the emitting layer: wherein A 1 and A 2 are independently selected from a substituted or unsubstituted C 1 -C 6 aliphatic group, a C 6 -C 20 aromatic group and a C 5 -C 19 heterocyclic group containing N, S or O, A 3 is selected from a substituted or unsubstituted C 1 -C 6 aliphatic group, a C 6 -C 20 aromatic group, a C 5 -C 19 heterocyclic group containing N, S or O, and a hydrogen atom, and substituents of A 1 , A 2 and A 3 are respectively one or more and the substituent is selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 1 alkoxy, C 1 -C 10 alkylamino, C 1 -C 10 alkylsilyl, a halogen atom, C 6 -C 10 aryl, C 6 -C 10 aryloxy, C 6 -C 10 arylamino, C 6 -C 10 arylsilyl and a hydrogen atom. Disclosed is an organic electroluminescent device comprising a structure having an anode, an emitting layer, and a cathode stacked therein, wherein a fluorescent compound represented by Formula 1 is used as a dopant of the emitting layer and a fluorescent compound by Formula 2 is used as a host of the emitting layer: where in A is independently selected from a substituted or unsubstituted C 6 -C 30 aromatic group, B is independently selected from a substituted or unsubstituted C 6 -C 30 aromatic group and a hydrogen atom, and substituents of A and B may be one or more, respectively, and the substituent is selected from the group consisting of C 1 -C 10 alkyl and a hydrogen atom.
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- NOVEL ANTHRACENE DERIVATIVES, PROCESS FOR PREPARATION THEREOF, AND ORGANIC ELECTRONIC LIGHT EMITTING DEVICE USING THE SAME
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The present invention relates to a novel anthracene derivative, a process for preparation thereof, and an organic electronic device using the same. The anthracene derivative according to the present invention can serve as a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, or a light emitting material, and particularly as a light emitting host or dopant, especially as a green host or dopant singly, in an organic electronic device including an organic light emitting device. The organic electronic device according to the present invention exhibits excellent characteristics in efficiency, drive voltage, life time, and stability.
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Page/Page column 16-17
(2010/11/28)
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- Anthracene derivative, organic electroluminescent device, and display unit
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An anthracene derivative with general formula (1) is provided: wherein X represents a substituted or unsubstituted C6-28 arylene group, or a substituted or unsubstituted C5-21 divalent heterocyclic group; A and B each independently represent a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C6-28 aryl group, or a substituted or unsubstituted C5-21 heterocyclic group, and A and B may be bonded together to form a ring; Y1 and Y2 each independently represent a hydrogen atom, a substituted or unsubstituted C1-20 alkyl group or a C1-20 alkoxy group; and Z represents a substituted or unsubstituted C6-30 aryl group atoms, a substituted or unsubstituted C5-21 heterocyclic group, a hydrogen atom, a substituted or unsubstituted C1-20 alkyl group, or a C1-20 alkoxy group.
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- SUBSTITUTED ANTHRACENES AND ELECTRONIC DEVICES CONTAINING THE SUBSTITUTED ANTHRACENES
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Substituted anthracene compounds and electronic devices containing the substituted anthracene compounds are provided.
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Page/Page column 33-35
(2010/11/30)
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- NITROGENOUS HETEROCYCLE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT EMPLOYING THE SAME
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Provided is a material for an organic EL device realizing an organic EL device capable of having a high current efficiency even at a low voltage. Provided is a derivative of heterocyclic compound having a nitrogen atom represented by the following general formula (A-1) or (A-2). In the formulae, R 1a to R 5a each represent a substituent, Ar 1a to Ar 3a each represent a single bond or a divalent connecting group, and HAr represents a group represented by a general formula (A-3) or (A-4). R 6a to R 10a each represent a substituent.
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Page/Page column 48
(2008/06/13)
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- Long-wavelength analogue of PRODAN: Synthesis and properties of Anthradan, a fluorophore with a 2,6-donor-acceptor anthracene structure
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We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polarity-sensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.
- Lu, Zhikuan,Lord, Samuel J.,Wang, Hui,Moerner,Twieg, Robert J.
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p. 9651 - 9657
(2007/10/03)
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- NEW MATERIAL FOR TRANSPORTING ELECTRONS AND ORGANIC ELECTROLUMINESCENT DISPLAY USING THE SAME
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Novel materials for electron injection/transportation and emitting layers can greatly improve the stability of an organic electroluminescent display. Electroluminescent displays incorporating these materials produce blue light at low voltage levels. These novel organic materials include compounds in which 1 to 2 imidazole functional groups are introduced in the 2 or 2,6-site of 9,10 substituted anthracene. An organic electroluminescent display with an organic compound layer of these materials has high efficiency, thermal stability, operationally stability and maintains driving voltage before and after operation.
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Paragraph 0040; 0041
(2008/06/13)
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- NEW ORGANIC COMPOUNDS FOR ELECTROLUMINESCENCE AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME
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Disclosed is a novel group of compounds having a general structure of anthracene body substituted with at least one thiophenyl group, which can be further substituted with various substituent groups. These new compounds are generally compatible with organic electroluminescence. Also disclosed are organic electroluminescent devices and method of making the same. The organic electroluminescent devices include at least one of the compounds in various layers thereof. Organic electroluminescent devices employing the new compounds in their light-emitting layers show outstanding stability.
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Page/Page column 68
(2010/02/07)
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- Synthesis and fluorescence properties of novel transmembrane probes and determination of their orientation within vesicles
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Two novel transmembrane fluorescent diester probes D and E bearing an anthracenediyl moiety in the middle of the molecule have been synthesized. Their absorption and fluorescence spectra in CHCl3 solution as well as their fluorescence characteristics in dimyristoylphosphatidylcholine (DMPC) large unilamellar vesicles were determined. Although their absorption spectra (first transition, S0 → S1) present a good overlap with the fluorescence spectrum of tryptophan, only probe E could be a good acceptor for the energy-transfer experiments, since a strong overlap exists between the absorption spectrum of tryptophan and the second transition (S0 → S2) of the absorption spectrum of probe D. The Forster critical distance R0 for energy transfer between tryptophan (donor) and probe E (acceptor) is found to be 23-24 A. Finally, linear-dichroism studies on shear-deformed DMPC vesicles show the incorporated probe E to lie essentially perpendicular to the bilayer plane. These results establish that probe E could be useful in the study of membrane-bound protein topography by the fluorescence-energy-transfer method.
- Quesada, Ernesto,Ardhammar, Malin,Norden, Bengt,Miesch, Michel,Duportail, Guy,Bonzi-Coulibaly, Yvonne,Nakatani, Yoichi,Ourisson, Guy
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p. 2464 - 2476
(2007/10/03)
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- Synthesis of poly(anthracene-2,6-diyl) and a copolymer containing alternately anthracene-2,6-diyl and p-phenylene units
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The title polymers 1 and 2 are synthesised via precursor polymers assembled by organometallic couplings using a Diels-Alder adduct of 2,6-dibromoanthracene.
- Hodge, Philip,Power, Gerald A.,Rabjohns
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- Triazinyl dyes
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Vat dyestuffs of the formula EQU1 wherein R represents alkyl with 1 to 4 carbon atoms, R1 and R2 represent hydrogen or alkyl with 1 to 4 carbon atoms and each of A1 and A2 represents a vattable radical with 3 to 7 condensed rings are characterized by improved resistance to alkali and are suitable for dyeing and printing the most diverse materials, in particular fibers made from natural or regenerated cellulose.
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