- Synthesis and anti-Pneumocystis carinii pneumonia activity of novel dicationic dibenzothiophenes and orally active prodrugs
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Dicationic carbazoles have been found to be highly active against a rat model of Pneumocystis carinii pneumonia (PCP). Unfortunately, amidoxime derivatives, designed as prodrugs, were inactive against PCP even though the corresponding amidines were highly active. In the present work, a series of 2,8- and 3,7-bis cationic dibenzothiophenes was synthesized and assayed for anti-PCP activity. Three of the compounds proved to be more potent and less toxic than a standard anti-PCP drug (pentamidine) when given intravenously. Unlike the carbazoles, a dibenzothiophene amidoxime prodrug given orally reduced the parasite load by more than 99%. While no quantitative correlation was seen between anti-PCP activity and DNA binding, a strong level of DNA binding was found to be necessary for antimicrobial activity.
- Patrick, Donald A.,Hall, James Edwin,Bender, Brendan C.,McCurdy, Donald R.,Wilson, W. David,Tanious, Farial A.,Saha, Shankar,Tidwell, Richard R.
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Read Online
- ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE
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An organic optoelectronic device and a display device including the organic optoelectronic device, the organic optoelectronic device including an anode and a cathode facing each other, a light emitting layer between the anode and the cathode, a hole transport layer between the anode and the light emitting layer, and a hole transport auxiliary layer between the light emitting layer and the hole transport layer, wherein the light emitting layer includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 3,
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Paragraph 0328; 0333; 0334
(2020/05/29)
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- Double-(S, S - dioxo - dibenzo thiophene) and high output compound and its preparation method and application
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The invention discloses a bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and a preparation method and application thereof. The existence of bi-sulfuryl in the bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is more beneficial for improving the electron affinity of molecules. Alkyl chains are introduced on a five-membered ring, so that the solubility of monomers in an organic solvent can be obviously improved. The plane conjugacy of the compound is better, and is beneficial for the transmission of a current carrier. Higher D-A mutual effect existing in the molecules of the compound endows higher fluorescence of the material. The bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is synthesized and obtained through common organic chemistry reactions such as substitution reactions, Suzuki coupling and ring-closure reactions and oxidation reactions. The compound has good solubility in the organic solvent, and is suitable for solution processing. The compound has wide application prospects in the fields of organic luminescence display, organic photovoltaic cells and organic field-effect tubes.
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Paragraph 0107-0109; 0112
(2019/06/26)
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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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- Cyclization of 2-Biphenylthiols to Dibenzothiophenes under PdCl2/DMSO Catalysis
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A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2/DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system.
- Zhang, Tao,Deng, Guigang,Li, Hanjie,Liu, Bingxin,Tan, Qitao,Xu, Bin
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p. 5439 - 5443
(2018/09/13)
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- Evaporable organic semiconductive material and use thereof in an optoelectronic component
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The invention relates to compounds of general formula IIIa and their use in optoelectronic components.
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Page/Page column 38; 39
(2015/10/05)
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- CARBAZOLE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICE
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Provided are a carbazole derivative and an organic electroluminescent device with expanded light emitting lifespan, comprising the carbazole derivative. The carbazole derivative is represented by general formula (1).COPYRIGHT KIPO 2016
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Paragraph 0121; 0125; 0126
(2016/10/10)
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- CARBAZOLE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICE
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The present invention provides a carbazole derivative and an organic electroluminescent device with improved light emitting lifespan. The present invention provides a carbazole derivative represented by general formula (1) and an organic electroluminescen
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Paragraph 117; 0122-0124
(2016/10/27)
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- Facile preparation of dibenzoheterocycle-functional nanoporous polymeric networks with high gas uptake capacities7
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A consolidated ionothermal strategy was developed for the polymerization of thermally unstable nitriles to construct high performance materials with permanent porosity, and carbazole, dibenzofuran, and dibenzothiophene were separately introduced into covalent triazine-based networks to investigate the effects of heterocycles on the gas adsorption performance. Three nitriles, namely 3,6-dicyanocarbazole, 3,6-dicyanodibenzofuran, and 3,6- dicyanodibenzothiophene, were designed and synthesized, which were readily converted to heat-resistant intermediates at a moderate temperature and then polymerized to create highly porous poly(triazine) networks instead of the traditional one-step procedure. This documents an improved strategy for the successful construction of heterocyclic-functional triazine-based materials. The chemical structures of monomers and polymers were confirmed by 1H NMR, FTIR, and elemental analysis. Such polymers with high physical-chemical stability and comparable BET surface areas can uptake 1.44 wt % H2 at 77 K/1 bar and 14.0 wt % CO2 at 273 K/1 bar and present a high selectivity for gas adsorption of CO2 (CO2/N2 ideal selectivity up to 45 at 273K/1.0 bar). The nitrogen- and oxygen-rich characteristics of carbazole and dibenzofuran feature the networks strong affinity for CO2 and thereby high CO2 adsorption capacity. This also helps to thoroughly understand the influence of pore structure and chemical composition on the adsorption properties of small gas molecules.
- Wu, Shaofei,Liu, Yao,Yu, Guipeng,Guan, Jianguo,Pan, Chunyue,Du, Yong,Xiong, Xiang,Wang, Zhonggang
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p. 2875 - 2882
(2014/06/09)
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- Optical activity of heteroaromatic conjugated polymer films prepared by asymmetric electrochemical polymerization in cholesteric liquid crystals: Structural function for chiral induction
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We electrochemically polymerized various achiral heteroaromatic monomers in left-handed helical cholesteric liquid crystal (CLC) media. Circular dichroism (CD) spectroscopy revealed that most of the resulting conjugated polymer films exhibited both the first negative and second positive Cotton effects near their absorption maxima. This indicates left-handed helical aggregation of the conjugated main chains, which is consistent with left-handed helical order of the CLC. This result suggests that the left-handed helical CLC environment induced left-handed helical aggregation of the polymers during the electrodeposition. However, CD intensity of the polymers depends on the structure of the parent monomers. Systematic investigation of the relationship between monomer structures and optical activity of the polymers indicates that linearity of the conjugated main chains and excluded volume interaction between the monomers and the CLC are important factors for producing optical activity of the polymers.
- Kawabata, Kohsuke,Takeguchi, Masaki,Goto, Hiromasa
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p. 2078 - 2091
(2013/06/04)
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- 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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p. 28 - 33,6
(2020/08/24)
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- Dibenzo[b,d]thiophene based oligomers with carbon-carbon unsaturated bonds for high performance field-effect transistors
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Dibenzo[b,d]thiophene (DBT) based oligomers with carbon-carbon double and triple bonds were synthesized. Their thermal stability and energy levels were studied by thermal analyses, UV-vis absorption spectra and electrochemistry. Single crystals of 3,7-bis
- Wang, Chengliang,Wei, Zhongming,Meng, Qing,Zhao, Huaping,Xu, Wei,Li, Hongxiang,Hu, Wenping
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scheme or table
p. 544 - 551
(2010/11/16)
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- Dibenzothiophene derivatives: From herringbone to lamellar packing motif
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It is generally believed that π-π stacking would be much more efficient than herringbone stacking for the transporting of charge carriers. The electron-withdrawing group sulphone unit was introduced into dibenzothiophene (DBT) derivatives, and lamellar st
- Wang, Chengliang,Dong, Huanli,Li, Hongxiang,Zhao, Huaping,Meng, Qing,Hu, Wenping
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scheme or table
p. 4155 - 4160
(2011/11/12)
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- Dibenzothiophene derivatives as new prototype semiconductors for organic field-effect transistors
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New prototype semiconductor materials based on dibenzothiophene (DBT) derivatives were successfully synthesized by a convergent approach using palladium catalyzed Stille coupling reactions. Thermogravimetric analysis, UV-vis spectra and electrochemistry results indicated these materials had good thermal and photooxidation stability. X-Ray diffraction measurements of the vacuum-evaporated films showed enhanced crystalline order with increasing substrate deposition temperature. The ordered vacuum-evaporated films with charge carrier mobility as high as 7.7 × 10-2 cm2 V-1 s-1 and an on/off ratio of nearly 1 × 10 7 had been achieved with 3,7-bis(5′-hexyl-thiophen-2′-yl) -dibenzothiophene (3,7-DHTDBTT). These results suggest that the 3,7-substituted DBT system is a good prototype for new type organic semiconductors and will play a more important role in organic semiconductors. The Royal Society of Chemistry.
- Gao, Jianhua,Li, Liqiang,Meng, Qing,Li, Rongjin,Jiang, Hui,Li, Hongxiang,Hu, Wenping
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p. 1421 - 1426
(2008/02/07)
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- Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof
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Methods of treating Pneumocystis carinii pneumonia comprise administering a therapeutically effective amount of a dicationic dibenzofuran compound described by Formula (I). Methods of treating Pneumocystis carinii pneumonia also comprise administering a therapeutically effective amount of a dicationic dibenzothiophene compound described by Formula (II). Novel compounds are also disclosed, and are represented by the Formulae (I) and (II).
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- Dibenzothienobisbenzothiophene - A novel fused-ring oligomer with high field-effect mobility
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Conjugated oligomers with rigid, fused-ring structure are of interest for organic field-effect transistors where strong π-π interaction between adjacent molecules is required to obtain high charge carrier mobilities. Dibenzo[b,b']thieno[2,3-f:5,4-f']bis[1]benzothiophene (DBTBT) has been synthesized by a novel route, the key step of which is the acid-induced intramolecular cyclization reaction of aromatic methyl sulfoxides. Field- effect transistors (FETs) with thin, polycrystalline DBTBT films deposited by vacuum sublimation exhibit high field-effect mobilities of 0.15 cm2 (Vs)-1 and ON-OFF current ratios > 106. The coupling reaction is not regioselective and different regioisomers have been identified. Degraded FET performance is observed when the sublimed films contain a mixture of different isomers.
- Sirringhaus, Henning,Friend, Richard H.,Wang, Changsheng,Leuninger, Joerg,Muellen, Klaus
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p. 2095 - 2101
(2007/10/03)
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- Redox and EPR spectral behaviour of radical cations of dibenzothiophene and some of its derivatives
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The radical cations of dibenzothiophene 1 and its 2,8-[2H2]-isotopomer (2), a series of methylated dibenzothiophenes, viz. 2,8- (3), 3,7- (4) and 4,6-dimethyldibenzothiophene (5), and 2,4,6,8-tetramethyldibenzothiophene (6), as well as 2,2′- (7) and 4,4′-bidibenzothiophene (8) have been generated in 1,1,1,3,3,3-hexafluoropropan-2-ol, mostly by TlIII trifluoroacetate or 4-tolyl-TlIII trifluoroacetate oxidation. From the hyperfine coupling constants obtained, it is concluded that the 2- and 4-positions of 1.+ are the carbon atoms possessing the highest spin density. This assignment agrees with results of high-level quantum-chemical calculations, placing the 2B1 state as the lowest energy level of 1.+. Acta Chemica Scandinavica 1997.
- Eberson, Lennart,Hartshorn, Michael P.,Persson, Ola,Radner, Finn
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p. 492 - 500
(2007/10/03)
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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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