- Synthesis and optical and electrochemical properties of a bispyrimidinium-dibenzothiophene-S,S-dioxide-based cationic conjugated polymer
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A novel n-type cationic conjugated polymer (PFSOmiCl), consisting of bispyrimidinium-dibenzothiophene-S,S-dioxide and fluorene scaffolds, was developed from its polymeric precursor (PFSOmi) through an intramolecular cyclization reaction. In comparison with PFSOmi, PFSOmiCl exhibits significant bathochromical absorption and photoluminescence spectra in both solution and film form, as well as a more hydrophilic film surface. Cyclic voltammetry tests demonstrate that PFSOmiCl possesses a deep lowest unoccupied molecular orbital (LUMO) energy level of??4.18?eV, which is comparable to the LUMO energy levels of common fullerene derivatives. These unique properties endow PFSOmiCl with great utilization potential in organic optoelectronic devices. Moreover, this research offers a novel guideline for designing new conjugated polyelectrolytes.
- Chen, Guiting,Yang, Wei,Zhang, Bin
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Read Online
- Fluorescent and electrochromic polymers from 2,8-di(carbazol-9-yl)dibenzothiophene and its S,S-dioxide derivative
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We report the synthesis and characterization of two carbazole-endcapped monomers, namely 2,8-di(carbazol-9-yl)dibenzothiophene (SCz) and 2,8-di(carbazol-9-yl)dibenzothiophene S,S-dioxide (SO2Cz), and their derived polymers PSCz and PSO2Cz prepared by both FeCl3 oxidative coupling and electropolymerization processes. The dilute solutions of PSCz and PSO2Cz prepared by chemical oxidative coupling exhibited fluorescent and solvatochromic behavior. Thin polymeric films could be robustly electrodeposited onto the surface of the ITO-glass substrate by repetitive cyclic voltammetry scanning of monomers SCz and SO2Cz in an electrolyte solution between 0 and 1.8?V. The electrochemically generated polymer films exhibited two reversible oxidation redox couples due to successive oxidations of the biscarbazole unit. These polymer films also revealed good electrochemical and electrochromic stability, with coloration change from a colorless neutral state to yellow, green and blue oxidized states. Switching ability of the polymers was evaluated by kinetic studies upon measuring the percent transmittance (%T) at their maximum contrast point, indicating that the polymers exhibit moderate electrochromic performance.
- Hsiao, Sheng-Huei,Wu, Li-Chu
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- High-performance bipolar host materials for blue TADF devices with excellent external quantum efficiencies
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New bipolar host molecules composed of carbazole, pyridoindole, and dibenzothiophene (DBT) were synthesized for blue thermally activated delayed fluorescence (TADF)-based organic light-emitting diodes (OLEDs). 2,8-Di(9H-carbazol-9-yl)dibenzo[b,d]thiophene, 9-(8-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-2-yl)-9H-pyrido[2,3-b]indole, and 2,8-bis(9H-pyrido[2,3-b]indol-9-yl)dibenzo[b,d]thiophene were prepared based on the selective reactivity at the 2,8-positions of DBT. The new symmetric and asymmetric host materials exhibited high triplet energies (2.89-2.95 eV). 4,5-Di(9H-carbazol-9-yl)phthalonitrile (2CzPN) was selected as an emitting dopant for achieving sky-blue emissions in TADF-OLEDs. 2CzPN-doped TADF-OLEDs, whose configuration is ITO (50 nm)/HATCN (7 nm)/TAPC (75 nm)/host:6% 2CzPN (20 nm)/TmPyPB (50 nm)/LiF (15 nm)/Al (100 nm), showed low driving voltages and high external quantum efficiencies (EQEs). These results are attributed to the well-controlled bipolar character of the host giving a better charge balance in the emitting layer. In particular, the device containing ZDN:6% 2CzPN showed an unprecedentedly high EQE of 25.7% (at 0.074 mA cm-2).
- Kang, Ju Sik,Hong, Tae Ryang,Kim, Hyung Jong,Son, Young Hoon,Lampande, Raju,Kang, Byoung Yeop,Lee, Chiho,Bin, Jong-Kwan,Lee, Bang Sook,Yang, Joong Hwan,Kim, Jinwuk,Park, Sungnam,Cho, Min Ju,Kwon, Jang Hyuk,Choi, Dong Hoon
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- Novel thienyl-dibenzothiophene oligomers end-capped by hexylphenyl groups as potential organic semiconductor materials
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Novel thienyl-dibenzothiophene oligomers end-capped by hexylphenyl groups, 2,8-bis[5-(4-n-hexylphenyl)-2-thienyl]dibenzothiophene (28HPTDBT) and 3,7-bis[5-(4-n-hexylphenyl)-2-thienyl]dibenzothiophene (37HPTDBT), have been synthesized using Stille cross-coupling reactions. Newly synthesized oligomers were investigated by Ultraviolet-visible (UV-vis) and photoluminescence (PL) spectroscopy, cyclic voltammogram, and thermal analysis. Strong intermolecular-interactions, appropriate energy band gaps and low HOMO energy levels imply that the two oligomers are promising candidate materials for durable organic electronic devices.
- Duan, Zongfan,Hoshino, Daiki,Ohuch, Hirokuni,Yanagi, Yuichiro,Nishioka, Yasushiro,Yang, Zhigang,Hirao, Toshio,Taguchi, Mitsumasa
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- Novel dibenzothiophene chromophores with peripheral barbituric acceptors
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A series of novel chromophores based on central 2,8-disubstituted dibenzothiophene (DBT) or dibenzothiophene-S,S-dioxide (DBTO) has been designed and prepared. The interconnection of DBT(O) central scaffold with two peripheral barbituric acceptors via various π-spacer allowed significant property tuning of target chromophores. Four new final chromophores and six DBT(O)-intermediates have been successfully synthesized and fully characterized. Experimental and calculated data showed that the fundamental properties are affected by the chromophore A-π-D-π-A or A-π-A-π-A arrangement (DBT vs. DBTO) and the π-linker (ethenylene vs. ethynylene). Thorough structure-property relationships have been elucidated and discussed in detail.
- Sperátová, Michaela,Jedyrka, Jaroslaw,Pytela, Old?ich,Kityk, Iwan V.,Reshak,Bure?,Klikar
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- Novel phenylene-thiophene oligomer derivatives with dibenzothiophene 5,5-dioxide core: Synthesis, characterization, and applications in organic solar cells
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Donor-acceptor-donor oligomers with dibenzothiophene 5,5-dioxide core and end-cap phenylene-thiophene substitutes were newly synthesized. New oligomers were characterized by UV-vis absorption and photoluminescence spectroscopy, cyclic voltammetry, and app
- Duan, Zongfan,Huang, Xianqiang,Fujii, Shunjiro,Kataura, Hiromichi,Nishioka, Yasushiro
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- A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems
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We designed a straightforward synthetic route towards a full-fledged family of π-extended helicenes: superhelicenes. They have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via a central five-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses. Mixed stacks of M- and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.
- Amsharov, Konstantin Y.,B?nisch, Simon,G?rling, Andreas,Guldi, Dirk M.,Haines, Philipp,Hampel, Frank,Jelfs, Kim E.,Jux, Norbert,Nelson, Jenny,Reger, David,Schmidt, Julia A.,Ullrich, Tobias
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supporting information
p. 18073 - 18081
(2021/07/16)
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- Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
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A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.
- Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
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supporting information
p. 1621 - 1629
(2020/02/04)
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- Small molecule light-emitting material based on naphthothiodibenzofuran unit, preparation method and applications thereof
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The invention discloses a small molecule light-emitting material based on a naphthothiodibenzofuran unit, a preparation method and applications thereof, wherein the naphthothiodibenzofuran unit is beneficial to improving the electron affinity and promoting the injection and transmission of electrons, and has high fluorescence efficiency and high chemical stability. According to the invention, thesmall molecule light-emitting material based on the naphthothiodibenzofuran unit is obtained through a Suzuki or C-N coupling reaction, and has high thermal stability, good film-forming property and good dissolvability; and after the small molecule light-emitting material based on the naphthothiodibenzofuran unit is dissolved by adopting a common organic solvent, and the light emitting layer of alight-emitting diode is prepared through spin coating, vacuum evaporation, ink-jet printing or printing film formation.
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Paragraph 0059-0062
(2020/03/06)
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- Photophysical properties and optical power limiting ability of Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at different positions
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Two series of Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at different positions have been synthesized. In the absorption spectra, the Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 3,6-position have blue-shift with respect to the corresponding analogs bearing fluorene-type ligands with ethynyl units at 2,7-position, showing better transparency in the visible light region. Moreover, the Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 3,6-position show stronger triplet emission than corresponding analogs bearing fluorene-type ligands with ethynyl units at 2,7-position in the photoluminescent (PL) spectra. Furthermore, these Pt(II) polyynes were applied to optical power limiting (OPL) field. The Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 2,7-position show better OPL performance than the corresponding analogs with fluorene-type ligands of ethynyl units at 3,6-position. Therefore, changing the position of the ethynyl units in fluorene-type ligands can not only effectively control the photophysical properties of the Pt(II) polyynes, but also has an important effect on their OPL ability.
- Tian, Zhuanzhuan,Yang, Xiaolong,Liu, Boao,Zhong, Daokun,Zhou, Guijiang
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supporting information
p. 28 - 36
(2019/06/05)
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- Structural controlled pure metallo-triangular assembly through bisterpyridinyl Dibenzo[b,d]thiophene, Dibenzo[b,d]furan and Dibenzo[b,d]carbazole
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A novel family of metallocycles was constructed by a one-pot self-assembly of three analogous bis(terpyridine) ligand monomers L1-L3, having different bent angles, with metal ions (Zn2+ or Cd2+). The dibenzo[b,d]thiophene-containing ligand L3 assembled with the metal ions to form a single trimer, whereas the dibenzo[b,d]furan-containing ligand L2 and dibenzo[b,d]carbazole-containing ligand L1 formed a mixture of trimers and tetramers. Heteroatoms (N, O, S) significantly contributed to the molecular size of the assemblies, owing to the bent angle of the bis-terpyridines ligands.
- Liu, Qianqian,Yang, Xiaoyu,Wang, Meng,Liu, Die,Chen, Mingzhao,Wu, Tun,Jiang, Zhiyuan,Wang, Pingshan
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supporting information
p. 2400 - 2405
(2019/03/14)
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- Novel yellow phosphorescent iridium complexes with dibenzothiophene-S,S-dioxide-based cyclometalated ligand for white polymer light-emitting diodes
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We have designed and synthesized two novel yellow phosphorescent iridium complexes using dibenzothiophene-S,S-dioxide-based cyclometalated ligand for the first time, which are capable of producing highly efficient yellow and white polymer light-emitting devices (PLEDs). The resulted iridium complexes display good thermal stability and high photoluminescence quantum yields. Both yellow and white PLEDs are fabricated with an identical single-emission-layer configuration of ITO/PEDOT:PSS/emission layer (EML)/CsF/Al. For the yellow phosphorescent PLEDs based on (p-CzFSOPy)2IrPic, the best device performances with a peak luminous efficiency (LE) of 13.3 cd/A and a peak external quantum efficiency (EQE) of 5.3% are achieved. More importantly, the two-element WPLEDs containing iridium (III)bis (2-(4,6-difluorophenyl)-pyridinato-N,C2′) picolinate (FIrpic) as blue and (p-CzFSOPy)2IrPic as yellow phosphors doped into a PVK:OXD-7 matrix at an appropriate ratio exhibited a maximum LE of 19.2 cd/A, a maximum EQE of 9.6%, an extremely high luminance of 18717 cd/m2 and Commission Internationale de L'Eclairage (CIE) coordinate of (0.317, 0.448). Moreover, at a luminance for practical application of 1000 cd/m2, the LE still remains as high as 19.0 cd/A, with a very slight decrease.
- Liang, Aihui,Luo, Ming,Liu, Yusheng,Wang, Han,Wang, Zhiping,Zheng, Xiaoyan,Cao, Tian,Liu, Dewang,Zhang, Yong,Huang, Fei
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p. 637 - 645
(2018/07/29)
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- Ruthenium complex luminescent material containing dibenzothiophene sulfone group and use thereof
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The invention discloses a ruthenium complex luminescent material containing a dibenzothiophene sulfone group and a use thereof. The ruthenium complex takes a dibenzothiophene sulfone pyridine derivative as a ring metal ligand and takes picolinic acid as an auxiliary ligand; and a hole transport unit is introduced on the ring metal ligand, to balance the electron and hole transport capability of the ruthenium complex. The ruthenium complex is doped in PVK and PBD to form a light-emitting layer, and a high-efficiency polymer yellow light device is obtained; the ruthenium complex and FIrPic are mixed as a dopant, are doped into polymer PVK and OXD-7 to form a light-emitting layer. The complementary color principle is utilized to obtain an efficient polymer white light device, and the application of an OLED in flat panel display and white light lighting is promoted.
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Paragraph 0046; 0049; 0050; 0051
(2019/01/05)
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- Efficient deep-blue electroluminescence based on phenanthroimidazole-dibenzothiophene derivatives with different oxidation states of the sulfur atom
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Developing efficient deep-blue materials is a longterm research focus in the field of organic light-emitting diodes (OLEDs). In this paper, we report two deep-blue molecules, PITO and PISF, which share similar chemical structures but exhibit different pho
- Tang, Xiangyang,Shan, Tong,Bai, Qing,Ma, Hongwei,He, Xin,Lu, Ping
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p. 552 - 560
(2017/03/15)
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- HETEROCYCLIC COMPOUNDS AND THEIR USE IN ELECTRO-OPTICAL OR OPTO-ELECTRONIC DEVICES
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Compounds exhibiting high hole mobility and/or high glass transition temperatures together with favourable HOMO, LUMO and triplet levels are provided which are 2-(4'-Diphenylamino)phenyl-8-(1'-thianthrenyl)- dibenzothiophene and 4-(1-Thianthrenyl)-bis(tri
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Page/Page column 11
(2017/02/09)
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- Bipolar small molecular light-emitting material based on naphthothiodibenzofuran unit as well as preparation method and application of bipolar small molecular light-emitting material
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The invention discloses a bipolar small molecular light-emitting material based on a naphthothiodibenzofuran unit as well as a preparation method and application of the bipolar small molecular light-emitting material. The preparation method provided by th
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Paragraph 0037; 0038; 0039; 0040
(2017/07/19)
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- Diphenanthro-2,8-sulfur dibenzofuran unit-based bipolar micromolecular luminescent material, as well as preparation method and application thereof
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The invention discloses a diphenanthro-2,8-sulfur dibenzofuran unit-based bipolar micromolecular luminescent material, as well as a preparation method and application thereof. The diphenanthro-2,8-sulfur dibenzofuran unit-based bipolar micromolecular lumi
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Paragraph 0037; 0038; 0039; 0040
(2017/09/18)
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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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Page/Page column 20
(2017/08/08)
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- Synthesis and optical and electrochemical properties of water-soluble cationic fluorophores based on bispyridinium and dibenzothiophene-S,S-dioxide
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Two novel water-soluble π-conjugated small molecules based on dibenzothiophene-S,S-dioxide and bispyridinium salts, named FSOPyCl and FSOmiCl, were successfully synthesized. Both molecules showed deep blue light emission, with photoluminescence peaks at about 408 and 405 nm in aqueous solution, respectively. Their photoluminescence quantum yields (PLQYs) in aqueous solution were as high as 68.9% and 50.3%, respectively. Electrochemical measurements suggested that they have excellent electron affinity, with lowest unoccupied molecular orbital (LUMO) energy levels at ?3.78 and ?3.94 eV, respectively. Due to their unique properties including large planarity, good thermal stability, excellent electron affinity and high fluorescence efficiency, FSOPyCl and FSOmiCl may be promising construction units for preparing water/alcohol-soluble conjugated materials with good optoelectronic performance.
- Chen, Guiting,He, Ruifeng,Yang, Wei,Zhang, Bin
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p. 1696 - 1703
(2017/02/23)
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- Blue oligomer based on dibenzothiophene-S,S-dioxide unit and preparation method and application of blue oligomer
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The invention discloses a blue oligomer based on a dibenzothiophene-S,S-dioxide unit and a preparation method and application of the blue oligomer. The blue oligomer is mainly characterized by comprising a fluorene structure unit and the dibenzothiophene-S,S-dioxide structure unit. The preparation method mainly comprises the step of preparation of the blue oligomer based on the dibenzothiophene-S,S-dioxide unit. Due to the fact that the electroluminescence efficiency and the spectral stability are improved by introducing the dibenzothiophene-S,S-dioxide structure unit into the oligomer, the novel oligomer blue-light emitting material is obtained. According to the obtained blue oligomer based on the dibenzothiophene-S,S-dioxide unit, an electroluminescence device prepared through film formation of a solution processing method is high in efficiency, good in spectral stability and suitable for being adopted as a light-emitting layer of a light-emitting diode and a flat-panel displayer.
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Paragraph 0074; 0075; 0076; 0077; 0090; 0091; 0092; 0093
(2017/03/08)
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- Bipolar luminescent material based on aromatic heterocyclic-2,8-S,S-dioxodibenzothiophene unit as well as preparation method and application of bipolar luminescent material
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The invention discloses a bipolar luminescent material based on an aromatic heterocyclic-2,8-S,S-dioxodibenzothiophene unit as well as a preparation method and an application of the bipolar luminescent material. The bipolar luminescent material is prepare
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Paragraph 0041; 0042; 0043; 0044
(2017/07/19)
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- Bipolar molecular luminescent material based on dithiofluorene unit, as well as preparation method and application of bipolar molecular luminescent material
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The invention discloses a bipolar molecular luminescent material based on a dithiofluorene unit, as well as a preparation method and application of the bipolar molecular luminescent material. The bipolar molecular luminescent material based on the dithiof
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Paragraph 0037; 0038; 0039; 0040
(2018/03/13)
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- Blue to light gray electrochromic polymers from dodecyl-derivatized thiophene Bis-substituted dibenzothiophene/dibenzofuran
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3-Dodecylthiophene end-capped two monomers: 2,8-bis-(4-dodecyl-thiophen-2-yl)-dibenzothiophene (DBT-3DTh) and 2,8-bis-(4-dodecyl-thiophen-2-yl)-dibenzofuran (DBF-3DTh) were synthesized via Stille coupling reaction. Both monomers exhibited emission peaks at about 400 nm with fluorescence quantum yields ranging from 0.16 to 0.21. The corresponding electroactive polymers poly(2,8-bis-(4-dodecyl-thiophen-2-yl)-dibenzothiophene) (PDBT-3DTh) and poly(2,8-bis-(4-dodecyl-thiophen-2-yl)-dibenzofuran) (PDBF-3DTh) were obtained by electropolymerization method and displayed good electrochemical stability. Both polymers switched between light gray in the neutral state and blue in the oxidized state. Kinetic investigations showed that PDBT-3DTh exhibited a maximum optical contrast (ΔT %) of 25.23% at 575 nm with the coloration efficiency (CE) of 196 cm2 C-1. However, the electrochromic properties of PDBF-3DTh were inferior to PDBT-3DTh. Further detailed discussions with EDOT and 3-alkylthiophenes end-capped DBT/DBF hybrid electrochromic polymers were comparatively studied.
- Lin, Kaiwen,Zhao, Yao,Ming, Shouli,Liu, Hongtao,Zhen, Shijie,Xu, Jingkun,Lu, Baoyang
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p. 1468 - 1478
(2016/04/26)
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- Bipolar micromolecular luminescent material based on 4-(9H-carbazole-9-yl) aniline and preparation method and application thereof
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The invention discloses a bipolar micromolecular luminescent material based on 4-(9H-carbazole-9-yl) aniline and a preparation method and application thereof. The material is mainly characterized in that the 4-(9H-carbazole-9-yl) aniline is used as a hole transport center unit, and bipolar micromolecules with the 4-(9H-carbazole-9-yl) aniline as the center are obtained by selecting groups with an electron transmission function. The bipolar micromolecules prepared through the method can be used for making a luminescent layer of an organic light emitting diode.
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Paragraph 0066; 0068
(2016/10/09)
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- COMPOUNDS AND THEIR USE AS BACE1 INHIBITORS
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The present invention relates to compounds of Formula (I) or a stereoisomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein X, Y, Z, Q, W, m, u, ring (A), R2, R3, R4, R5 and R6, are as defined in the specification and claims. The present invention provides a pharmaceutical composition containing the compounds of Formula (I) and a therapeutic method of treating and/or preventing Downs syndrome, β-amyloid angiopathy, disorders associated with cognitive impairment, Alzheimer's disease, memory loss, attention deficit symptoms associated with Alzheimer's disease, neurodegenerative diseases, pre-senile dementia, senile dementia and dementia associated with Parkinson's disease, Alzheimer's disease and/or Down syndrome, age-related macular degeneration (AMD), glaucoma, olfactory function impairment, traumatic brain injury, progressive muscle diseases, Type II diabetes mellitus and cardiovascular diseases (stroke).
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Page/Page column 80
(2016/11/17)
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- Pigment additives, method of manufacturing the same and pigment dispersion compositions containing the same
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The present invention refers to novel pigment additive, manufacturing method thereof and relates to a pigment dispersion composition including, using additives pigment of the present invention optical properties surface, dispersibility and excelling in dispersion stability and have a color property, a pigment dispersion composition provides. (by machine translation)
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Paragraph 0125-0128
(2017/01/26)
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- Metal-Ion-Induced Switch of Liquid-Crystalline Orientation of Metallomacrocycles
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A new series of shape-persistent imine-bridged macrocycles were synthesized based on dynamic covalent chemistry. The macrocycles had an alternating sequence of dibenzothiophene and N,N′-bis(salicylidene)-ethylenediamine (salen) tethering branched alkyl ch
- Kawano, Shin-ichiro,Hamazaki, Takashi,Suzuki, Atsushi,Kurahashi, Kenshin,Tanaka, Kentaro
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supporting information
p. 15674 - 15683
(2016/10/24)
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- High triplet energy electron transport type exciton blocking materials for stable blue phosphorescent organic light-emitting diodes
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High triplet energy electron transport materials with dibenzothiophene and dibenzofuran cores modified with a diphenyltriazine unit were investigated as electron transport type exciton blocking materials for stable blue phosphorescent organic light-emitting diodes. The two exciton blocking materials showed high triplet energy above 2.80 eV and enhanced quantum efficiency of the blue phosphorescent devices by more than 40% while maintaining stability of the pristine blue devices without the high triplet energy exciton blocking layer.
- Kang, Yu Jin,Lee, Jun Yeob
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p. 109 - 114
(2016/03/04)
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- The interplay of thermally activated delayed fluorescence (TADF) and room temperature organic phosphorescence in sterically-constrained donor-acceptor charge-transfer molecules
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A series of phenothiazine-dibenzothiophene-S,S-dioxide charge-transfer molecules have been synthesized. Increasing steric restriction around the donor-acceptor bond significantly alters contributions from TADF and phosphorescence. Bulky substituents on th
- Ward, Jonathan S.,Nobuyasu, Roberto S.,Batsanov, Andrei S.,Data, Przemyslaw,Monkman, Andrew P.,Dias, Fernando B.,Bryce, Martin R.
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supporting information
p. 2612 - 2615
(2016/02/18)
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- S,S-dioxo-dibenzothiophene onium salt based polymer precursor monomer and polymer, and preparation method therefor and application thereof
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The present invention discloses an S,S-dioxo-dibenzothiophene onium salt based polymer precursor monomer and polymer, and a preparation method therefor and an application thereof. When the polymer disclosed by the present invention is used as a cathode interface modification layer of a photovoltaic device, an interfacial dipole interaction can be formed between an active layer and the cathode so as to reduce an effective work function of the cathode and increase an open circuit voltage; the polymer has a relatively deep lowest unoccupied molecular orbital (LUMO) energy level, and can be in good ohmic contact with an electron acceptor of the active layer so as to promote extraction of an electron and increase a short-circuit current; and a freely movable ion of the polymer can perform n-type doping on the electron acceptor PCBM to form [PCBM]-, so that transmission efficiency of the electron is improved. The polymer can be dissolved in polar solvents such as dimethyl sulfoxide (DMSO), methanol and N,N-dimethylformamide (DMF), so that an interface mixing phenomenon can not occur between a polymer layer and the active layer when a multi-layer device is constructed.
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Paragraph 0040; 0041
(2016/11/28)
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- Synthesis and electro-optical properties of new conjugated hybrid polymers from EDOT end-capped dibenzothiophene and dibenzofuran
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Two novel EDOT end-capped monomers, namely, 2,8-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-dibenzothiophene (DBT-EDOT), and 2,8-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-dibenzofuran (DBF-EDOT), were synthesised via Stille coupling and electropolymerised to form conjugated polymers P(DBT-EDOT) and P(DBF-EDOT). The monomers exhibited blue-light-emitting characteristics, and DFT calculations revealed band gap values of 4.20 eV for DBT-EDOT and 4.34 eV for DBF-EDOT, while those of the corresponding polymers were brought down to 2.46 eV for P(DBT-EDOT) and 2.58 eV for P(DBF-EDOT), respectively. Moreover, both of the polymers displayed good electrochromic properties with colour switching between yellow in the reduced state and purple in the oxidised state. Structure characterisation and properties of monomers and as-formed polymers using FTIR spectroscopy, UV-vis spectroscopy, surface morphology, fluorescence spectroscopy, electrochemistry, and spectroelectrochemistry, together with structure-property relationships, were systematically investigated and comprehensively discussed.
- Lin, Kaiwen,Zhen, Shijie,Ming, Shouli,Xu, Jingkun,Lu, Baoyang
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p. 2096 - 2105
(2015/03/18)
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- ORGANIC LIGHT COMPOUND AND ORGANIC LIGHT DEVICE USING THE SAME
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PURPOSE: An organic luminescent compound and an organic light device for the solar power generation using the same are provided to offer high luminous efficiency, luminescent brightness, chromatic purity, and luminescence lifetime. CONSTITUTION: An organi
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Paragraph 0125; 0126; 0127; 0128
(2016/10/08)
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- High Tg fluoranthene-based electron transport materials for organic light-emitting diodes
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In this study, fluoranthene-based derivatives with a high thermal stability were synthesized for applications in organic electroluminescent devices. The two derivatives synthesized in this study, bis(4-(7,9,10-triphenylfluoranthen-8-yl)phenyl)sulfane (TPFDPS) and 2,8-bis(7,9,10-triphenylfluoranthen-8-yl)dibenzo[b,d]thiophene (TPFDBT), were characterized by cyclic voltammetry, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). TPFDPS exhibits a high Tg of 210 °C while TPFDBT is crystalline in nature. Both the derivatives are thermally stable up to 500 °C. The charge transport studies reveal predominant electron transport properties. Subsequently, we fabricated blue OLEDs with 2-tert-butyl-9,10-bis-(β-naphthyl)-anthracene (TBADN) as the emitting layer to demonstrate the applications of these molecules as an electron transporting layer.
- Kumar, Shiv,Patil, Satish
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p. 6351 - 6357
(2015/08/11)
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- Dibenzothiophene-Based Phosphine Oxide Host and Electron-Transporting Materials for Efficient Blue Thermally Activated Delayed Fluorescence Diodes through Compatibility Optimization
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Thermally activated delayed fluorescence (TADF) organic light-emitting diodes arise from the development of high-performance host materials and carrier transporting materials fitting for TADF dyes with optimized respective properties and interplays, making simultaneous performance improvement and device structure simplification feasible. In this work, a highly efficient blue TADF diode with simplified four-layer structure was successfully achieved by utilizing bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (DMAC-DPS) as blue emitter, 4,6-bis(diphenylphosphoryl)dibenzothiophene (DBTDPO) as host, and 4,6-bis(diphenylphosphoryl)dibenzothiophene sulfone (46DBSODPO) as electron-transporting layer. The compatibilities between DBTDPO and DMAC-DPS and DBTDPO and 46DBSODPO were optimized with respect to configuration, polarity, energy level, and interfacial interaction, resulting in the unchanged roughness of ~0.25 nm before and after doping, high photoluminescence quantum yield over 85%, and reduced interfacial exciplex emissions. With the similar triplet excited energy (T1) of ~3.0 eV but inferior electrical properties compared to its analogues 28DBSODPO and 37DBSODPO, besides the homogeneity with DBTDPO, 46DBSODPO suppressed the formation of interfacial exciplex and dipole for efficient exciton confinement and electron injection and transportation, in virtue of the steric effects of its ortho-substituted phosphine oxide groups. Consequently, DBTDPO and 46DBSODPO endowed their DMAC-DPS based four-layer devices with the state-of-the-art performance, for example, the maximum external quantum efficiency over 16%, which was more than two-fold of those of conventional electron-transporting material 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene (TmPyPB). This design strategy about material compatibility could pave a way for developing high-performance blue TADF diodes with simplified configurations.
- Fan, Chaochao,Duan, Chunbo,Wei, Ying,Ding, Dongxue,Xu, Hui,Huang, Wei
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p. 5131 - 5140
(2015/08/04)
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- IODINATION PROCESS, MONOMER AND POLYMER
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The present invention relates to processes for the preparation of iodinated compounds of formula (I): (Formula (I)) wherein R1 is the same or different in each occurrence and is a substituent; m independently in each occurrence is 0, 1, 2 or 3; and X independently in each occurrence is NR2, PR2, -CR22-, -SiR22, O or S wherein R2 is the same or different in each occurrence and is a substituent.
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Page/Page column 26; 27
(2015/11/17)
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- Active-alkali metal promoted reductive desulfurization of dibenzothiophene and its hindered analogues
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Dibenzothiophene and some related organosulfur compounds are efficiently reductively desulfurized under mild reaction conditions, with Na and/or Li metal in the presence of a catalytic amount of tetraphenylethylene in THF at room temperature. This simple methodology was applied to the synthesis of several substituted biphenyls, thus realizing a connection between the directing properties of the sulfur atom of dibenzothiophene and the efficiency of 1,2-dianions of tetraphenylethane as homogenous electron transfer reagents.
- Pittalis, Mario,Azzena, Ugo,Pisano, Luisa
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p. 207 - 211
(2013/01/15)
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- Synthesis, experimental and theoretical characterization, and field-effect transistor properties of a new class of dibenzothiophene derivatives: From linear to cyclic architectures
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We report the synthesis and characterization of a bis-dibenzothiophene cyclic dimer containing bis-ethylene linkages (DBT-CM) and of the corresponding mono-ethylene-linked 'linear' cis- and trans-isomers (cis- and trans-DBT-LM, respectively). The varied molecular architectures lead to notable differences both in terms of the solid-state packing and the molecular electronic and optical properties. X-ray crystallography reveals that the cyclic architecture of DBT-CM leads to a more densely packed stacking configuration that imparts stronger intermolecular electronic coupling for both hole and electron transport amongst adjacent molecules, while characterization of the thin-film morphology and crystallinity uncovers important temperature-dependent properties of the films as a function of the molecular architecture. Moreover, the redox, electronic structure, and optical properties of DBT-CM vary distinctly from those of its linear counterparts. The intramolecular reorganization energies for hole and electron transport for DBT-CM are markedly smaller than the linear counterparts, while the dispersion for the highest valence band (and the intermolecular electronic coupling for hole transport) is the largest for the series. The more favorable molecular packing/morphology characteristics and charge-transport properties (within the Marcus framework) of DBT-CM manifest themselves in thin-film field-effect transistor studies, where a field-effect hole-carrier mobility 0.026 cm2 V-1 s-1 is measured, a value one-order-of-magnitude larger than either linear analog. The Royal Society of Chemistry 2012.
- Qiao, Yali,Wei, Zhongming,Risko, Chad,Li, Hong,Bredas, Jean-Luc,Xu, Wei,Zhu, Daoben
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scheme or table
p. 1313 - 1325
(2012/04/10)
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- Photodeoxygenation of dibenzothiophene S-oxide derivatives in aqueous media
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The use of atomic oxygen (O(3P)) as potent oxidant In water has suffered from the lack of a facile, efficient source. The photodeoxygenatlon of aromatic sulfoxides to the corresponding sulfides in organic solvents has been suggested to produce O(3P) in low quantum yields. The photolysis of 4,6-dihydroxymethyldibenzothiophene S-oxide and 2,8- dihydroxymethyldibenzothiophene S-oxide in water results in deoxygenation at significantly higher quantum yields than In organic solvents. Depending upon conditions, a variable amount of oxidation of the hydroxymethyl substituent into an aldehyde was observed to accompany deoxygenation. Analysis of the photoproducts Indicated the deoxygenation occurred by at least two different pH-sensitive mechanisms. Under basic conditions, photoinduced electron transfer yielding a hydroxysulfuranyl radical that decomposed by heterolytlc S-O cleavage was thermodynamically feasible. The thermodynamics of photoinduced electron transfer were expected to become increasingly unfavorable as the pH of the solution decreased. Thus, at neutral and acidic pH, an S-O bond scission mechanism was suspected. The observed increase In the photodeoxygenation quantum yields was consistent with charge separation accompanying S-O bond scission. Oxidative cleavage of alkenes In aerobic conditions suggested O(3P) was produced during photolysis In these conditions; however, the formation of discrete O-/HO may occur, particularly at low pH.
- Korang, James,Grither, Whitney R.,McCulla, Ryan D.
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supporting information; experimental part
p. 4466 - 4476
(2010/06/13)
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- Tuning the optoelectronic properties of 4,4′-N, N′-dicarbazole- biphenyl through heteroatom linkage: New host materials for phosphorescent organic light-emitting diodes
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(Equation Presented). Five carbazole end-capped heterofluorenes (CzHFs) designed by structurally mimicking 4,4′-N,N′-dicarbazole-biphenyl (CBP) via connecting the biphenyl core of CBP with the linking atom of C, P, N, O, and S, respectively, were synthesized successfully, and their optoelectronic properties were investigated. The theoretical calculations and experimental results demonstrate that CzHFs are potential green, red, and even blue hosts for phosphorescent light-emitting diodes (PHOLEDs) with more desirable localization and energy levels of HOMO and LUMO and also higher triplet energy than CBP.
- Zhang, Shenglan,Chen, Runfeng,Yin, Jun,Liu, Feng,Jiang, Hongji,Shi, Naien,An, Zhongfu,Ma, Cong,Liu, Bin,Huang, Wei
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supporting information; experimental part
p. 3438 - 3441
(2010/09/18)
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- Synthesis, photophysical and electrochemical properties of 2,8-diaryl-dibenzothiophene derivatives for organic electronics
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A series of 2,8-p-diaryldibenzothiophene derivatives were synthesized and characterized. These molecules have electron withdrawing or electron donating groups at the para phenyl position, which alters the electronic properties of these derivatives. The qu
- Nayak, Pabitra K.,Agarwal, Neeraj,Periasamy
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experimental part
p. 119 - 124
(2010/11/02)
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- Photochemistry and photophysics of halogen-substituted dibenzothiophene oxides
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Dibenzothiophene-5-oxide (DBTO) cleanly produces dibenzothiophene (DBT) on direct photolysis, but with very low quantum yield. A proposed mechanism involves scission of the S-O bond which is coupled to an intersystem crossing step, thus producing the sulfide and O(3P) via a unimolecular pathway. To test this hypothesis, heavy atom substituted DBTOs were prepared and photolyzed. Iodo-, bromo-, and chloro-substituted DBTOs show higher quantum yields for deoxygenation than does the parent molecule, in the order consistent with an intersystem crossing-related heavy atom effect. 2-Iododibenzothiophene also undergoes photochemical deiodination. Phosphorescence data are consistent with heavy-atom assisted intersystem crossing.
- Nag, Mrinmoy,Jenks, William S.
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p. 8177 - 8182
(2007/10/03)
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- Improvement of color purity in blue-emitting polyfluorene by copolymerization with dibenzothiophene
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High molecular weight, readily soluble copolymers of 9,9-dioctylfluorene and dibenzothiophene (DBTh) comonomer (less than or equal to 50 mol%) are synthesized by Suzuki polycondensation. PL efficiencies and EL external quantum efficiencies of random copolymers decrease with increasing DBTh content. For the alternating copolymer, a PL efficiency of 62% and an EL external quantum efficiency of 0.42% are obtained. Excimer emission is effectively depressed when the DBTh content is greater than 20 mol%. It is indicated that the meta-linkages of 2,8-substitution of DBTh are effective in enhancing blue emission of polyfluorene.
- Yang, Wei,Hou, Qiong,Liu, Chuanzhen,Niu, Yuhua,Huang, Jian,Yang, Renqiang,Cao, Yong
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p. 1351 - 1355
(2007/10/03)
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- The synthesis of new dibenzothiophen amino acid and cyclophane derivatives
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Some novel dibenzothiophen amino acid and cyclophane derivatives have been produced as a result of synthetic studies on the development of dibenzothiophen-based antibacterial compounds. Allylation through a Stille reaction has produced 2-allyl-8-bromodibenzothiophen (3a) and 2,8-diallyldibenzothiophen (3b). Under different conditions, the Stille reaction also produced 2-bromo-8-(prop-1-enyl)dibenzothiophen (4a) and 2,8-di(prop-1-enyl)dibenzothiophen (4b) via double bond isomerization. Olefin metathesis with (3b) and methyl N-acetylallylglycinate (5) produced two homodimers, the novel [4](5,11)[4](18,24)dibenzothiophenophane-2,15-diene (6), as a mixture of geometrical isomers, and dimethyl (E)- and (Z)-(R,S)-2,7-diacetamidooct-4-enedioate (8), and the two cross-metathesis products methyl (E)- and (Z)-(R,S)-2-acetamido-6-(8-allyldibenzothien-2-yl)hex-4-enoate (7a) and dimethyl (E)- and (Z)-(R,S)-6,6′-(dibenzothiophen-2,8-diyl)bis(2-acetamidohex-4-enoate) (7b). Palladium-catalysed hydrogenation of the homodimer (6) and the cross-metathesis products (7a,b) yielded the corresponding reduced compounds (9) and (10a,b), respectively. CSIRO 2000.
- Bremner, John B.,Keller, Paul A.,Pyne, Stephen G.,Robertson, Alan D.,Skelton, Brian W.,White, Allan H.,Witchard, Helen M.
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p. 535 - 540
(2007/10/03)
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- Substituted dibenzothiophenes having antiangiogenic activity
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The invention provides novel substituted dibenzothiophenes of Formulae (I), (II), (III) and (IV) which have antiangiogenic activity and further provides a method using substituted dibenzothiophenes of Formula (V) as antiangiogenic agents.
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- Hydrodesulfurization of Alkyldibenzothiophenes over a NiMo/Al2O3 Catalyst: Kinetics and Mechanism
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The transformation mechanism of dibenzothiophene, 4-methyldibenzothiophene, 4,6-dimethyldibenzothiophene, and 2,8-dimethyldibenzothiophene has been studied in a batch reactor over an industrial NiMo/Al2O3 hydrotreating catalyst at 573 K under 5 MPa of hydrogen pressure. A detailed mechanistic study including competitive catalytic experiments proved that the adsorption of the most refractory molecules at the catalyst surface was not the rate-determining step for their transformation. Our results imply that the hydrodesulfurization of these compounds occurs on one single type of sites by a flat adsorption, leading to a preliminary partial hydrogenation of one aromatic ring. Variations in reactivities of the dibenzothiophene derivatives were thus explained by different reaction rates for the C-S bond scission due to steric hindrance generated by the methyl substitution near the sulfur atom.
- Meille, Valerie,Schulz, Emmanuelle,Lemaire, Marc,Vrinat, Michel
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- Hydrodesulfurization of Organosulfur Heterocycles by Metal Hydride-Nickel(0) Complexes: Accelerated Single-Electron Transfer in Carbon-Sulfur Bond Cleavage
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The novel nickel complex, LiAlH2(THF)n.C10H8N2.Ni (2), which result from the interaction in a THF solution of (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel (1) with LiAlH4 in a 1:1 molar ration is powerful desulfurizing agent in homogeneous solution for such aromatic sulfur heterocycles as dibenzothiophene (3), phenoxathiin (11), phenothiazine (12), and thianthrene(13).When employed in a 2:1 molar ratio with the heterocyclic substrate, 2 produces the corresponding ring-opened desulfurization products (biphenyl, diphenyl ether, diphenylamine, and benzene, respectively) in high yields.In contrast, 1 effects predominantly ring contraction during desulfurization and yields dibenzofuran, carbazole, and dibenzothiophene from 11, 12, and 13, respectively.From consideration of relative desulfurization rates for substituted dibenzothiophenes, deuterium labeling experiments, and the chemical reactivity differences for 1 and 2, it is concluded that these reagents desulfurize via single-electron-transfer mechanism and that radical anoins are crucial reactive intermediates.The greater reactivity of 2 is ascribed to its anionic nickel character.
- Eisch, John J.,Hallenbeck, Lawrence E.,Han, Kyoung Im
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p. 7763 - 7767
(2007/10/02)
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