- Alumina-promoted oxodefluorination
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A simple protocol for the clean preparation of heterocyclic compounds containing dibenzofuran's core via oxodefluorination of fluoroarenes on activated γ-Al2O3 is reported. Alumina can be considered as a reliable oxygen source enabling one-pot substitution of fluorine atoms and yielding benzoannulated furan derivatives. The corresponding C-F bond activation is selective towards less stable C-Br/C-I and occurs under metal- A nd solvent-free conditions.
- Amsharov, Konstantin,Mikhail, Feofanov,Vladimir, Akhmetov
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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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- Catalyst-Free Synthesis of O-Heteroacenes by Ladderization of Fluorinated Oligophenylenes
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A novel catalyst-free approach to benzoannulated oxygen-containing heterocycles from fluorinated oligophenylenes is reported. Unlike existing methods, the presented reaction does not require an oxygen-containing precursor and relies on an external oxygen source, potassium tert-butoxide, which serves as an O2? synthon. The radical nature of the reaction facilitates nucleophilic substitution even in the presence of strong electron-donating groups and enables de-tert-butylation required for the complete annulation. Also demonstrated is the applicability of the method to introduce five-, six-, and seven-membered rings containing oxygen, whereas multiple annulations also open up a short synthetic path to ladder-type O-heteroacenes and oligodibenzofurans.
- Feofanov, Mikhail,Akhmetov, Vladimir,Takayama, Ryo,Amsharov, Konstantin
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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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- Simple and efficient synthesis of various dibenzofuran carbaldehydes
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We herein report simple and efficient methods for the synthesis of various formyl derivatives of dibenzofuran. The aldehydes reported are prepared in at most three steps and in yields greater than 60% from commercially available dibenzofuran, with one exception where isomers must be separated. The protocols described involve either formylation of previously functionalized dibenzofuran derivatives or the initial introduction of the formyl group and subsequent further functionalization under standard reaction conditions as described. We have also reported an efficient and simple method for the synthesis of key methoxydibenzofurans in high yield (65% overall for two steps).
- Yempala, Thirumal,Cassels, Bruce K.
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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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- Dibenzofuran derivatives with meta- and para-triphenylamine substituents as hole-transporting materials in organic light-emitting devices
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Three novel hole-transporting materials, 3,3'-(dibenzo[b,d]furan-2,8-diyl)bis(N,N-diphenylaniline) (BF-m-TPA), 4,4'-(dibenzo[b,d]furan-2,8-diyl)bis(N,N-diphenylaniline) (BF-p-TPA) and 4,4'-(dibenzo[b,d]furan-2,6-diyl)bis(N,N-diphenylaniline) (BF-2,6-TPA), were designed and synthesized. Owing to the rigid dibenzofuran core, these BF-TPA derivatives exhibited high thermal decomposition temperatures of over 395 °C and very high LUMO energy levels. Electroluminescent (EL) devices were fabricated using these three hole-transporting materials. The best device performance was obtained for BF-m-TPA, with the maximum luminance (L) of 15,230 cd/m2, luminance efficiency (LE) of 56.5 cd/A, power efficiency (PE) of 13.3 lm/W, and external quantum efficiency (EQE) of 16.3%.
- Yun, Seong-Jae,Seo, Min Hye,Lee, Sungkoo
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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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- 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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- 3, 5 - dipyridyl phenyl derivatives, and electron transport material comprising an organic electroluminescent device using same
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PROBLEM TO BE SOLVED: To provide an electron transport material having a novel 3,5-dipyridyl phenyl derivative exhibiting electronic transport property, maintaining high triplet energy, excellent in electron injection property, hole block property and heat characteristic, and useful for a high-efficient phosphorescence organic EL element, and to provide an organic EL element using the same.SOLUTION: There is provided an element having a layer containing 3,5-dipyridyl phenyl derivative represented by the following formula (1) in an organic EL element made by laminating at least one organic layer between a pair of elements. In the formula, X, Rto Rand Rto Rare groups selected from a specific group independently.
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Paragraph 0036-0037
(2017/03/18)
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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 101; 102
(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 0117-0120
(2017/01/26)
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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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- GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 0001082
(2015/04/15)
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- NOVEL COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICE, AND ORGANIC ELECTROLUMINESCENCE DEVICE
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A specific material for organic electroluminescence device having m-phenylene skeleton in its molecule realizes a highly heat-resistant and long lifetime organic electroluminescence device capable of driving at low voltage with high efficiency.
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Paragraph 0252; 0253; 0254
(2014/04/04)
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- FUSED HETEROCYCLIC AROMATIC DERIVATIVE, ORGANIC ELECTROLUMINESCENCE ELEMENT MATERIAL, AND ORGANIC ELECTROLUMINESCENCE ELEMENT USING SAME
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A compound represented by the following formula (1). In the formula, A1 is O, S, Si(Ar1)(Ar2), P(=O)(Ar3)(Ar4), a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group including 5 to 30 ring atoms.
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Paragraph 0243-0245
(2014/08/06)
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- Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
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Provided are a heterocyclic compound which emits blue light and is represented by General Formula (G1) below, and a light-emitting element, a light-emitting device, an electronic device and a lighting device which are formed using the heterocyclic compound represented by General Formula (G1) below. The use of the heterocyclic compound represented by General Formula (G1) makes it possible to provide a light-emitting element which has high emission efficiency, and also a light-emitting device, an electronic device and a lighting device which have reduced power consumption.
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Page/Page column 72
(2011/06/24)
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- Experimental and theoretical study of two new pyrazoline derivatives based on dibenzofuran
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Two novel pyrazoline derivatives, named 2,8-bis(1,3-diphenyl-pyrazoline-5- yl)dibenzofuran (A) and 2,8-bis(1-(4-bromophenyl)-3-phenyl-pyrazoline-5-yl) dibenzofuran (B), were synthesized and characterized by elemental analysis, NMR, MS and thermogravimetric analysis. The absorption and emission spectra of them were determined by experimental methods in different polar solvents and were computed using the density functional theory (DFT) and the time-dependent density functional theory (TDDFT) at the same time. The calculated absorption and emission wavelengths are in good agreement with the experimental data. The fluorescence quantum yields and fluorescence lifetimes of them in different polar solvents were studied by means of steady state and time resolved fluorescence. The calculated reorganization energy for hole and electron indicates that the two compounds are in favor of hole transport than electron transport. The results show the two compounds present high fluorescence quantum yields and excellent thermal stability. It makes them of great interest as novel fluorescent probes and optoelectronic materials.
- Shi, He-Ping,Dai, Jian-Xin,Zhang, Xiu-Feng,Xu, Lei,Wang, Long,Shi, Li-Wen,Fang, Li
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experimental part
p. 242 - 249
(2011/12/13)
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- Heterocyclic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
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Provided are a heterocyclic compound which emits blue light and is represented by General Formula (G1) below, and a light-emitting element, a light-emitting device, an electronic device and a lighting device which are formed using the heterocyclic compound represented by General Formula (G1) below. The use of the heterocyclic compound represented by General Formula (G1) makes it possible to provide a light-emitting element which has high emission efficiency, and also a light-emitting device, an electronic device and a lighting device which have reduced power consumption.
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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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- Hybrid Host Materials For Electrophosphorescent Devices
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Compounds (including polymers) for use in hybrid host materials which can be used in electroluminescent devices. The compounds comprise at least one electron-transporting moiety and at least one hole-transporting moiety which are joined by a flexible linker. Hybrid host materials comprising the compounds exhibit stability against phase separation, elevated glass transition temperature, morphological stability against crystallization, and isolation of the electron transporting moiety and hole transporting moiety π-systems.
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- Electroluminescent Device
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Disclosed are electroluminescent devices that comprise organic layers that contain dibenzofuran compounds. The compounds are suitable components of, for example, blue-emitting, durable, organo-electroluminescent layers. The electroluminescent devices may be employed for full color display panels in, for example, mobile phones, televisions and personal computer screens.
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Page/Page column 8
(2009/05/28)
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- MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICE AND ORGANIC ELECTROLUMINESCENCE DEVICE UTILIZING THE SAME
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A material for organic electroluminescence devices of the invention which is for use in combination with at least one phosphorescent metal complex has a specific heterocyclic structure. The material for organic electroluminescence devices is used as a host material or a hole transporting material. An organic electroluminescence device having an anode, a cathode and an organic thin film layer having one or more layers which is interposed between the anode and cathode, in which at least one layer of the organic thin film layer contains the material for organic electroluminescence devices, has a high emitting efficiency, causes little pixel defects, is excellent in heat resistance, and shows a long lifetime.
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- A dibenzofuran-based host material for blue electrophosphorescence
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(Chemical Equation Presented) Dibenzofuran (DBF) is converted to a vacuum-sublimable, electron-transporting host material via 2,8-substitution with diphenylphosphine oxide moieties. Close π-π stacking and the inductive influence of P=O moieties impart favorable electron-transport properties without lowering the triplet energy. A maximum external quantum efficiency of 10.1% and luminance power efficiency of 25.9 lm/W are realized using this material as the host for the blue-green electrophosphorescent molecule, iridium(III) bis(4,6-(di-fluorophenyl)pyridinato-N,C2′)picolinate (Flrpic).
- Vecchi, Paul A.,Padmaperuma, Asanga B.,Qiao, Hong,Sapochak, Linda S.,Burrows, Paul E.
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p. 4211 - 4214
(2007/10/03)
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- Novel Bis as Antitrypanosomal Agents
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A series of novel 1,1'-(4,1-phenylene)bis was prepared and evaluated for activity against Trypanosoma rhodesiense in mice.The importance of the bis structure and the nature of the spacer between the two phenyl rings for optimal activity have been revealed.The potent parenteral activity of several analogues within this series as well as preliminary indication of oral activity lends encouragement to further development of this structural class.
- Turner, William R.,Werbel, Leslie M.
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p. 1728 - 1740
(2007/10/02)
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- DETERMINATION OF STRUCTURES OF TRI- AND TETRABROMODIBENZOFURANS FORMED IN BROMINATION OF DIBENZOFURAN
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Dibenzofuran reacted with bromine in the presence of Fe powder to afford tri- and tetrabromodibenzofurans and their structures were determined.
- Tashiro, Masashi,Yoshiya, Haruo
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p. 2349 - 2354
(2007/10/02)
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