- Copper(I) Catalysed Formation of 3-Methoxy-2,5-dimethylthiophene and 3,4-Dimethoxy-2,5-dimethylthiophene
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3-Methoxy-2,5-dimethylthiophene and 3,4-dimethoxy-2,5-dimethylthiophene have been prepared from 3,4-dibromo-2,5-dimethylthiophene and sodium methoxide using Cu(I)Br as a catalyst.The influence of some cosolvents and reaction temperature is investigated.Best results are obtained by refluxing in DMF at 125 deg C for 4 hours.The mixture is easily separated by flash chromatography.
- Peeters, Luc D.,Jacobs, Sven G.,Eevers, Walter,Geise, Herman J.
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- Synthesis, computational and electrochemical characterization of a family of functionalized dimercaptothiophenes for potential use as high-energy cathode materials for lithium/lithium-ion batteries
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We present a family of a novel class of organosulfur compounds based on dimercaptothiophene and its derivatives, with a variety of functional groups (electron-donating or electron-withdrawing groups) and regiochemistries, designed as potential high-energy cathode materials with sufficient charge/discharge cyclability for lithium/lithium-ion rechargeable batteries. This study uses as a point of departure the electrochemical and computational understanding of the electrocatalytic effect of poly(3,4-ethylenedioxythiophene) (PEDOT) towards the redox reactions of 2,5-dimercapto-1,3,4-thiadiazole (DMcT). The effective redox potentials of these materials exhibited good correlation with the highest-occupied molecular orbital (HOMO) levels predicted via computational modeling. Furthermore, the redox reactions of all the compounds studied were electrocatalytically accelerated at PEDOT film-coated glassy carbon electrodes (GCEs), although some materials exhibited higher energy output than others. By using this approach we have identified several compounds that exhibit clear promise as potential cathode materials and have characterized the molecular interactions between the organosulfur compounds and PEDOT film surfaces involved in the electrocatalytic reactions. The Royal Society of Chemistry 2007.
- Kiya, Yasuyuki,Henderson, Jay C.,Hutchison, Geoffrey R.,Abruna, Hector D.
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- Phthalocyanine-related macrocycles: Cross cyclotetramerisation products from 3,4-dicyanothiophenes, 2,3-dicyanothiophene and 3,6- dialkylphthalonitriles
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Examples of the novel tribenzo[b,g,1]thiopheno[3,4-q]porphyrazine and tribenzo[b,g,1]thiopheno[2,3-q]porphyrazine ring systems have been obtained by cross cyclotetramerisation reactions of 3,6-dialkylphthalonitriles with 3,4-dicyanothiophenes and 2,3-dicyanothiophene respectively. Dibenzodithiopheno[2,3]porphyrazines and benzotrithiopheno[2,3]porphyrazines have also been recovered. Octaoctyl tribenzo[b,g,1]thiopheno[3,4- q]porphyrazine, in particular, shows a strongly split Q-band absorption in the far red region of the spectrum, one component of which is highly bathochromically shifted relative to the corresponding band in octaoctyl phthalocyanine. The compounds, most of which exhibit columnar liquid crystal behaviour, form even, transparent spin-coated films which exhibit a broad band absorption envelope, in some instances extending from 600 nm to beyond 800 nm. Reaction of 2,3-dicyanothiophene with a 2,5-dialkyl-3,4- dicyanothiophene, the latter in excess, gives a product mixture rich in macrocycles derived predominantly from involvement of the former. (C) 2000 Elsevier Science Ltd.
- Cook, Michael J.,Jafari-Fini, Ali
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- NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY ON PROSTAGLANDIN E2 RECEPTOR AND USES THEREOF
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The present application relates to a novel compound having inhibitory activity on prostaglandin E2 receptor and uses thereof, and provides a compound represented by formula I, a solvate, stereoisomer or pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the same, and a method of using the same.
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Paragraph 266-269
(2022/03/07)
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- Regulating exciton bonding energy and bulk heterojunction morphology in organic solar cells: Via methyl-functionalized non-fullerene acceptors
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Electron-deficient end groups (EGs) are very important for non-fullerene small molecule acceptors (NF-SMAs) to tune their absorption, energy levels, and crystallization properties. Herein, we designed and synthesized three SMAs, namely, BTTIC-0M, BTTIC-2M, and BTTIC-4M by adding the methyl unit into 2-(6-oxo-5,6-dihydro-4H-cyclopenta[c]thiophen-4-ylidene)malononitrile (CPTCN). Methyl group, with its slight electron-donating ability, significantly elevates the LUMO energy levels but does not seriously affect the bandgaps of the CPTCN-based SMAs, which helps to reduce the energy loss (Eloss). In-depth dynamic theoretical simulations of the donor-acceptor (D-A) complex reveal that the exciton bonding energy (BE) can be fine-tuned by continuously increasing the methyl groups on the end groups of the SMAs. Methyl-substituted EG reduces the driving force and also enhances the BE of the charge transport (CT) state exciton, leading to a decrease in the exciton dissociation efficiencies. However, we found that one methyl-functionalized CPTCN enables PBDB-T:BTTIC-2M-based organic solar cells (OSCs) to achieve a power conversion efficiency (PCE) as high as 13.15%. Though PBDB-T:BTTIC-2M-based OSCs exhibit a slightly lower exciton dissociation efficiency than those of PBDB-T:BTTIC-0M, a more favorable superficial and internal morphology is attained in the PBDB-T:BTTIC-2M bulk-heterojunction layer, which balances the electron and hole mobilities and diminishes the bimolecular recombination. Comparatively, BTTIC-4M failed to realize a high performance owing to its adverse interactions with the polymer chain and the multiscale phase separation in the blend films. Actually, adjusting the number of methyl groups on the end group is done to compensate the current-voltage losses within the OSC devices with complicated contributions from absorption spectra, LUMO energy levels, exciton bonding energies, and morphologies.
- Gao, Wei,Liu, Tao,Luo, Zhenghui,Zhang, Lin,Ming, Ruijie,Zhong, Cheng,Ma, Wei,Yan, He,Yang, Chuluo
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p. 6809 - 6817
(2019/03/26)
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- Synthesis of phenylcarbazole-thiophene-based structural isomers as unipolar host materials for blue PHOLEDs and their device performance
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New high triplet-energy host materials, which are symmetrically or asymmetrically designed by using phenylcarbazole and thiophene moieties, were synthesized by Suzuki-Miyaura cross-coupling reactions and their device performances of blue phosphorescent organic light-emitting diodes were also investigated. The synthesized compounds showed a high triplet energy (>2.84 eV) and good thermal stability. Highly efficient blue PHOLEDs were obtained when employing the symmetric compounds having C2 symmetry as the host material and bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic) as the guest material. Their maximum external quantum efficiency of the device reached as high as 18.9% with blue color coordinate of (0.15, 0.35).
- Choi, Seung-Won,Lee, Jun Yeob,Hwang, Seok-Ho
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p. 1413 - 1421
(2014/05/20)
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- Tetraanionic N2O2-coordinating ligands as potential building blocks for supramolecular magnetic networks
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A bisoxamate ligand containing three different types of coordination sites was designed and synthesized. The developed synthetic strategy was adopted to prepare a related 1,2-bis(2-hydroxybenzamido)benzene-derived ligand. Nickel(ii) complexes of both the
- Milek, Magdalena,Witt, Alexander,Streb, Carsten,Heinemann, Frank W.,Khusniyarov, Marat M.
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p. 5237 - 5241
(2013/05/21)
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- INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES
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The present invention relates to compounds of formula (1) as claimed in claim 1, their use in the treatment or the prevention of viral disorders, including HIV. (Formula I)
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Page/Page column 126
(2012/10/18)
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- Regioselective palladium(0)-catalyzed cross-coupling reactions and metal-halide exchange reactions of tetrabromothiophene: Optimization, scope and limitations
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The Suzuki reaction of tetrabromothiophene with arylboronic acids provides a regioselective approach to various 5-aryl-2,3,4-tribromothiophenes, symmetrical 2,5-diaryl-3,4-dibromothiophenes, and tetraarylthiophenes. Unsymmetrical 2,5-diaryl-3,4-dibromo thiophenes are prepared by Suzuki reaction of 5-aryl-2,3,4-tribromothiophenes. Tetraarylthiophenes containing two different types of aryl groups are obtained by Suzuki reactions of 2,5-diaryl-3,4- dibromothiophenes. During the optimization of the conditions of each individual reaction, the solvent, the catalyst and the temperature play an important role. In several cases, classical conditions.
- Tung, Dang Thanh,Tuan, Dang Thanh,Rasool, Nasir,Villinger, Alexander,Reinke, Helmut,Fischer, Christine,Langer, Peter
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experimental part
p. 1595 - 1609
(2011/02/25)
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- THIOPHENECARBOXAMIDE DERIVATIVES AS EP4 RECEPTOR LIGANDS
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The invention is directed to thiophenecarboxamide derivatives of formulae I and II as EP4 receptor ligands, antagonists or agonists, useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoi
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Page/Page column 51-52
(2008/06/13)
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- Triplet MLCT photosensitization of the ring-closing reaction of diarylethenes by design and synthesis of a photochromic rhenium(I) complex of a diarylethene-containing 1,10-phenanthroline ligand
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Synthesis of the diaryle-thene-containing ligand LI based on Suzuki cross-coupling reaction between thienyl boronic acid and the dibromophenanthroline ligand is reported. On coordination to the rhenium(I) tricarbonyl complex system, the photochromism of L1 could be photosensitized and consequently extended from intraligand excitation at λ≤340nm in the free ligand to metal-to-ligand charge-transfer (MLCT) excitation atλ≤480nm in the complex. The photo-chromic reactions were studied by 1HNMR, UV/Vis, and steady-state emission spectroscopy. Photosensitization was further probed by ultrafast transient absorption and time-resolved emission spectroscopy. The results provided direct evidence that the formation of the closed form by the MLCT-sensitized photochromic process was derived from the 3MLCT excited state. This supports the photosensitization mechanism, which involves an intramolecular energy-transfer process from the 3MLCT to the 3IL(L1) state that initiated the ring-closure reaction. The photophysical and electrochemical properties of the complex were also investigated.
- Ko, Chi-Chiu,Kwok, Wai-Ming,Yam, Vivian Wing-Wan,Phillips, David Lee
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p. 5840 - 5848
(2008/03/28)
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- PHOTOCHROMIC DIARYLETHENE-CONTAINING COORDINATION COMPOUNDS AND THE PRODUCTION THEREOF
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Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower en
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- Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
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Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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- N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
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Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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Page column 87
(2010/01/30)
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- Synthesis of novel chiral thiophene-, benzothiophene- and benzofuran-oxazoline ligands and their use in the enantioselective Pd-catalyzed allylation
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Novel thiophene, benzothiophene and benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0°C.
- Tietze, Lutz F.,Lohmann, J. Klaas
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p. 2083 - 2085
(2007/10/03)
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- Photochemical and electrochemical behavior of thiophene-S-oxides
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The photochemical and electrochemical behavior of thiophene-S-oxides as a class was studied for the first time. It was shown that in both cases deoxygenation of the S-O functionality takes place. The outcome of the photoirradiation is very dependent on th
- Thiemann, Thies,Ohira, Daisuke,Arima, Kazuya,Sawada, Tsuyoshi,Mataka, Shuntaro,Marken, Frank,Compton, Richard G.,Bull, Steven D.,Davies, Stephen G.
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p. 648 - 653
(2007/10/03)
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- Synthesis, polymerization and characterization of substituted dithieno [3,4-b: 3',4'-d] thiophenes
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Chemical or electrochemical oxidation of substituted dithieno [3,4- b:3',4'-d]thiophenes provides polymers with defined regiochemical structures. These materials have lower bandgaps (0.7-0.9 eV) than the unsubstituted fused heteroarene. Potential cycling of the 1,3-dimethyl substituted polymer film shows repetitive p- and n-dopability. The chemically-prepared dioctyl analog is soluble in common solvents such as chloroform, dichloromethane and THF. However, overoxidation of the polymers at an electrode surface presents a limitation to the polymerization of substituted analogs of the parent fused heteroarene.
- Inaoka, Seiji,Collard, David M.
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p. 1719 - 1725
(2007/10/03)
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- Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane
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The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.
- Li, YuanQiang,Thiemann, Thies,Mimura, Keisuke,Sawada, Tsuyoshi,Mataka, Shuntaro,Tashiro, Masashi
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p. 1841 - 1850
(2007/10/03)
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- THIENYL-, FURYL- AND PYRROLYL SULFONAMIDES AND DERIVATIVES THEREOF THAT MODULATE THE ACTIVITY OF ENDOTHELIN
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Thienyl-, furyl-and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl) furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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- Halogenation Using Quaternary Ammonium Polyhalides. XXXI. Halogenation of Thiophene Derivatives with Benzyltrimethylammonium Polyhalides
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The reactions of thiophene derivatives with benzyltrimethylammonium tetrachloroiodate, benzyltrimethylammonium tribromide, and benzyltrimethylammonium dichloroiodate in acetic acid or in acetic acid-zinc chloride under mild conditions gave chloro-, bromo-, and iodo-substituted thiophene derivatives, respectively, in satifactory yields.
- Okamoto, Tsuyoshi,Kakinami, Takaaki,Fujimoto, Hiroshi,Kajigaeshi, Shoji
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p. 2566 - 2568
(2007/10/02)
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