- Synthesis, structure and properties of a new two-photon photopolymerization initiator
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A new two-photon free-radical photopolymerization initiator, (E,E)-4-{2-[p′-(N,N-di-n-butylamino)stilben-p-yl]vinyl} pyridine (abbreviated to DBASVP), has been synthesized. Quantum chemistry calculations showed that the new initiator possesses a large delocalized π electron system, a large change in dipole moment on transition to the excited state anda large transition moment. The calculated two-photon absorption cross-section is as high as 881.34 × 10-50 cm4 s photon-1. The single-photon and two-photon absorption and fluorescence properties in various solvents have been investigated carefully. The new initiator exhibits outstanding solvent-sensitivity, which experimentally interprets the excellent electron delocalized properties of the molecule. A microstructure has been fabricated under irradiation at 800 nm using a 200 fs, 76 MHz Ti:sapphire femtosecond laser.
- Ren, Yan,Yu, Xiao-Qiang,Zhang, Dong-Ju,Wang, Dong,Zhang, Ming-Liang,Xu, Gui-Bao,Zhao, Xian,Tian, Yu-Peng,Shao, Zong-Shu,Jiang, Min-Hua
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Read Online
- One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols
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Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.
- Abaev, Vladimir T.,Chalikidi, Petrakis N.,Demidov, Oleg P.,Gutnov, Andrey V.,Magkoev, Taimuraz T.,Trushkov, Igor V.,Uchuskin, Maxim G.
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p. 9838 - 9846
(2021/07/28)
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- Reactions of benzyltriphenylphosphonium salts under photoredox catalysis
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The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.
- Boldt, Andrew M.,Dickinson, Sidney I.,Ramirez, Jonathan R.,Benz-Weeden, Anna M.,Wilson, David S.,Stevenson, Susan M.
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supporting information
p. 7810 - 7815
(2021/09/28)
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- Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
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A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.
- Frydrych, Ivo,Urban, Milan,?arek, Jan,Benická, Sandra,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan
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- Novel indole-based photosensitizers coupled with PEG-HEC quasi-solid-state electrolyte to improve energy conversion and stability of organic dyes based-dye sensitized solar cells
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A series of novel Indole based organic dyes were synthesized and coupled with a Poly-ethylene glycol-Hydroxy ethyl cellulose quasi-solid-state-electrolyte (PEG-HEC QSSE) polymer blended iodine electrolyte to obtain a metal-free dye-based dye-sensitized so
- Santhosh, Kamaraj,Ganesan, Shanmugam,Balamurugan, Selvaraj
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- The role of electron-transporting Benzo[f]quinoline unit as an electron acceptor of new bipolar hosts for green PHOLEDs
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We prepared three new compounds [3,6-di(9H-carbazol-9-yl)phenanthrene (3,6-DCP), 2,9-di(9H-carbazol-9-yl)benzo[f]quinoline (2,9-DCBQ), and 3,9-di(9H-carbazol-9-yl)benzo[f]-quinoline (3,9-DCBQ)] containing phenanthrene or benzo[f]quinoline as an electron-withdrawing moiety and a carbazole as electron-donating moiety, respectively, as bipolar hosts for green phosphorescent organic light emitting diodes (PHOLEDs). We intentionally substituted nitrogen atom to the C-3 position of phenanthrene moiety to prepare benzo[f]quinolinegroup. And, we found that it allowed better electron transporting behavior than the phenanthrene moiety. Meanwhile, the benzo[f]quinoline/phenanthrene core moieties significantly improved the thermal stability of those host materials, which exhibited glass transition and decomposition temperatures of 132–139 and 395–427 °C, respectively. The green PHOLEDs which were fabricated with those host materials showed the lowest operating voltage of 4.7 V at 1000 cd/m2 when we used 3,9-DCBQ. Very interestingly, it has an asymmetric structure with completely separated HOMO and LUMO in space. In contrast, 3,6-DCP having phenanthrene and carbazole moieties showed much higher operating voltage of 6.1 V which imply that replacing nitrogen at the C-3 position of phenanthrene improves carrier transport, that is, electron transporting behavior. As a result, the 3,9-DCBQ-based PHOLED showed the best overall performance, exhibiting current and power efficiencies of 48.5 cd/A and 20.6 lm/W, respectively.
- Seo, Junseok,Park, So-Ra,Kim, Mina,Suh, Min Chul,Lee, Jihoon
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p. 959 - 966
(2018/11/26)
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- NEW COMPOUNDS SUITABLE AS CATALYSTS FOR POLYMERIZATION REACTIONS
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The invention relates to a compound of formula (I) and a process for synthesizing said compound. The invention further relates to the use of said compound as a catalyst, preferably for polymerization, such as, olefin polymerization. The invention also relates to the polymers produced using said catalyst and articles comprising said polymers.
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Page/Page column 54; 65
(2019/04/10)
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- Ionic Liquids as Solvents for SN2 Processes. Demonstration of the Complex Interplay of Interactions Resulting in the Observed Solvent Effects
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Bimolecular nucleophilic substitution reactions between triphenylphosphine and benzylic electrophiles have been examined in an ionic liquid to probe interactions with species along the reaction coordinate. Trends in the rate constant were found on both varying the leaving group and the electronic nature of the aromatic ring. In all the cases considered, interactions between the components of the ionic liquid and the transition state were shown to be more significant in determining reaction outcome than previously observed for this class of reaction. This demonstrates the importance of considering interactions of the ionic liquid components with all species along the reaction coordinate when investigating the origin of ionic liquid solvent effects, along with how such effects might be exploited.
- Schaffarczyk McHale, Karin S.,Haines, Ronald S.,Harper, Jason B.
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p. 1162 - 1168
(2019/01/04)
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- Novel carbazole skeleton-based photoinitiators for led polymerization and LED projector 3D printing
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Radical chemistry is a very convenient way to produce polymer materials. Here an application of a particular photoinduced radical chemistry is illustrated. Seven new carbazole derivatives Cd1–Cd7 are incorporated and proposed as high performance near-UV photoinitiators for both the free radical polymerization (FRP) of (meth)acrylates and the cationic polymerization (CP) of epoxides utilizing Light Emitting Diodes LEDs @405 nm. Excellent polymerization-initiating abilities are found and high final reactive function conversions are obtained. Interestingly, these new derivatives display much better near-UV polymerization-initiating abilities compared to a reference UV absorbing carbazole (CARET 9H-carbazole-9-ethanol) demonstrating that the new substituents have good ability to red shift the absorption of the proposed photoinitiators. All the more strikingly, in combination with iodonium salt, Cd1–Cd7 are likewise preferred as cationic photoinitiators over the notable photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BAPO) for mild irradiation conditions featuring their remarkable reactivity. In particular their utilization in the preparation of new cationic resins for LED projector 3D printing is envisioned. A full picture of the included photochemical mechanisms is given.
- Mousawi, Assi Al,Garra, Patxi,Dumur, Frédéric,Bui, Thanh-Tuan,Goubard, Fabrice,Toufaily, Joumana,Hamieh, Tayssir,Graff, Bernadette,Gigmes, Didier,Fouassier, Jean Pierre,Lalevée, Jacques
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supporting information
(2018/01/12)
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- Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
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Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalimide analogues and evaluated their structure-activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 17l showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 17l, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXRβ. Compound 17l should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.
- Nomura, Sayaka,Endo-Umeda, Kaori,Aoyama, Atsushi,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
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supporting information
p. 902 - 907
(2015/08/24)
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- Benzoquinoline derivative and organoelectroluminescent device employing the same
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The present invention relates to a benzoquinoline derivative, a manufacturing method thereof, and an organic electroluminescent device applying the same. The organic electroluminescent device applying a benzoquinoline derivative of the present invention h
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Paragraph 0100
(2016/11/07)
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- Cyanostilbene deriv., light-emitting element, the light emitting device, lighting device and electronic device
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PROBLEM TO BE SOLVED: To provide such a novel stilbene derivative which permits the luminescence of a shorter wavelength, as is useful for a light-emitting element of a high luminous efficiency, a light-emitting device having an excellent color reproducibility and having an electric power consumption decreased, or the like. SOLUTION: This stilbene derivative is expressed by formula G11 (in the formula, with regard to R10through R12, at least one of them is a tert-butyl group, and the remainder is a hydrogen atom; with regard to R13through R15, at least one of them is a tert-butyl group, and the remainder is a hydrogen atom; and Ar4to Ar5are each a (6-25)C aryl group). COPYRIGHT: (C)2013,JPOandINPIT
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Paragraph 0395; 0396; 0397; 0398; 0399
(2019/05/01)
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- ANTI-INFECTIVE COMPOUNDS
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The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.
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Page/Page column 40
(2015/02/25)
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- Synthesis and photophysical properties of triphenylamine-based multiply conjugated star-like molecules
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Novel triphenylamine-based star-like molecules 11 were synthesized and characterized using FT-IR, 1H, 13C, and DEPT-135 NMR spectroscopy, and MALDI-TOF mass spectrometry. The absorption and emission spectra of star-like molecules were studied in different solvents. The effect of solvent polarity and aggregation studies on the absorption and emission spectra has also been studied. The new star-like molecules are found to exhibit broad absorption and emission band along with intramolecular charge transfer character. The fluorescence spectra of triphenylamine derivatives shift from blue to green wavelength on increasing the extended conjugation of the molecule. The experimental results indicate that there is cooperative enhancement originating from the inter-branch coupling and an increase in the light-harvesting ability upon increasing the conjugated molecule size.
- Balasaravanan, Rajendiran,Duraimurugan, Kumaraguru,Sivamani, Jayaraman,Thiagarajan, Viruthachalam,Siva, Ayyanar
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p. 7472 - 7480
(2015/09/02)
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- Novel Resveratrol-Based Aspirin Prodrugs: Synthesis, Metabolism, and Anticancer Activity
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(Graph Presented). Regular aspirin use has been convincingly shown to reduce the risk of colorectal cancer. However, long-term use of aspirin leads to gastrotoxicity. Herein, we designed and synthesized a novel class of resveratrol-based aspirin prodrugs to simultaneously release aspirin and resveratrol to attenuate the side effects caused by aspirin. Prodrug RAH exerted enhanced anticancer activities which are better than a physical mixture of aspirin and resveratrol as well as each individually. Metabolism of RAH in mice showed that the majority of RAH is decomposed to release resveratrol and aspirin or salicylic acid either in the intestine or after absorption. Mechanistic studies demonstrate RAH inhibits cell cycle arrest through downregulation of cyclins and induces apoptosis by activation of caspase-3 in cancer cells. These findings highlighted the improved anticancer properties of resveratrol-based aspirin prodrugs. RAH may represent novel and safe alternatives of aspirin for the purpose of daily use in the future.
- Zhu, Yingdong,Fu, Junsheng,Shurlknight, Kelly L.,Soroka, Dominique N.,Hu, Yuhui,Chen, Xiaoxin,Sang, Shengmin
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p. 6494 - 6506
(2015/09/08)
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- One-pot synthesis of gem-difluorostyrenes from benzyl bromide via olefination of phosphonium ylide with difluorocarbene
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A new approach for the synthesis of gem-difluorostyrenes from benzyl bromide is described. Quaternization of triphenylphosphine with benzyl bromide to give phosphonium salts, deprotonation of the corresponding phosphonium salts to produce phosphonium ylide, and the subsequent olefination of phosphonium ylide with difluorocarbene generated from difluoromethylene phosphobetaine (Ph3P+CF2CO2-) by decarboxylation can occur smoothly in one-pot, furnishing the final gem-difluorostyrenes in good yields.
- Deng, Xiao-Yun,Lin, Jin-Hong,Xiao, Ji-Chang
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p. 116 - 120
(2015/11/10)
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- Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes
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A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is
- Mudududdla, Ramesh,Sharma, Rohit,Abbat, Sheenu,Bharatam, Prasad V.,Vishwakarma, Ram A.,Bharate, Sandip B.
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supporting information
p. 12076 - 12079
(2015/02/19)
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- COMPOUNDS AND THEIR USE TO TREAT HISTAMINE H3 RELATED DISORDERS
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The present invention provides compounds of formula (1) and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, m, n, p, q, Q1, Q2, Q3, Q4, Q5, Q6, X1, X2, X3, X4, A1 and L1, are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.
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Page/Page column 34
(2013/03/26)
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- Syntheses of p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene by one-pot benzannulation of Diels-Alder reactions of trans-1,2-dichloroethene and dienes
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A series of substituted p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene were successfully synthesized by one-pot benzannulation of Diels-Alder reaction with 1,2-dichloroethene as an acetylene equivalent dienophile. Two chlorine atoms could be good leaving groups to easily undergo subsequent elimination reactions of Diels-Alder products at a high temperature.
- Ho, Jinn-Hsuan,Lin, Yu-Chen,Chou, Li-Ting,Chen, Ying-Zhe,Liu, Wei-Qi,Chuang, Chao-Li
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supporting information
p. 1991 - 1993
(2013/04/10)
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- Aspirin Derivatives and Uses Thereof
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The present invention provides novel aspirin derivatives useful for preventing and/or treating cancer. The novel compounds of this invention may be particularly useful for the prevention and/or treatment of cancers affecting the gastrointestinal system, s
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Paragraph 0196
(2014/02/15)
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- Ruthenium stilbenyl and diruthenium distyrylethene complexes: Aspects of electron delocalization and electrocatalyzed isomerization of the Z-isomer
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Regio- and stereoselective insertion of the terminal ethynyl functions of 4-ethynylstilbene, the E and Z isomers of 4,4′-bis(ethynylphenyl)ethene and a backbone-rigidified cyclohexenyl derivative of the Z isomer into the Ru-H bond of the complex RuClH(CO)(PiPr3)2 provides the corresponding vinyl ruthenium complexes, which have been characterized spectroscopically and by X-ray crystallography. Large red shifts of the UV/vis absorption bands evidence efficient incorporation of the vinyl metal subunit(s) into the conjugated π-system. All complexes oxidize at low potentials. The various oxidized forms of all complexes were generated and characterized by UV/vis/NIR, IR and EPR spectroscopies. These studies indicated electrocatalytic Z→E isomerization of the oxidized Z-distyrylethene complex Ru-Z2, which is prevented in its backbone-rigidified derivative Ru-Z2fix. The radical cations of the E and the configurationally stable cyclohexene-bridged Z-derivatives are spin-delocalized on the EPR time scale but charge-localized on the faster IR time scale. The degree of ground-state charge delocalization in the mixed-valent state has been quantified by the incremental shifts of the Ru-CO bands upon stepwise oxidation to the radical cations and the dications and was found to be remarkably large (19% and 9%) considering redox splittings ΔE 1/2 of just 49 or 74 mV. Quantum chemical studies with various levels of sophistication reproduce our experimental results including the electronic spectra of the neutral complexes and the intrinsically localized nature of the radical cations of the dinuclear complexes.
- Linseis, Michael,Zalis, Stanislav,Zabel, Manfred,Winter, Rainer F.
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supporting information
p. 16671 - 16692
(2013/01/15)
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- Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
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Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.
- Chalal, Malik,Vervandier-Fasseur, Dominique,Meunier, Philippe,Cattey, Hélène,Hierso, Jean-Cyrille
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experimental part
p. 3899 - 3907
(2012/07/14)
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- Novel (E)-5-styryl-2,2′-bithiophene derivatives as ligands for β-amyloid plaques
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In continuation of our investigation on the bithiophene structure as potential β-amyloid probes, a series of (E)-5-styryl-2,2′-bithiophene (SBTP) derivatives was designed and synthesized. In vitro binding showed that all of them displayed high binding affinities to Aβ1-42 aggregates (Ki = 0.10-41.05 nM). Moreover, two radio-iodinated probes, [125I]-(E)-5-(4-iodostyryl)-2,2′-bithiophene ([ 125I]8) and [125I]-(E)-5-iodo-5′-(4-methoxystyryl)- 2,2′-bithiophene ([125I]31) were prepared. Both of them displayed specific labeling of Aβ plaques in the brain sections of AD model mice with low background. In vivo biodistribution in normal mice indicated that [125I]8 exhibited high initial brain uptake (2.11% ID/g at 2 min) and rapid clearance (0.41% ID/g at 30 min). These preliminary results suggest that SBTP derivatives may be served as novel β-amyloid imaging probes.
- Cui, Mengchao,Li, Zijing,Tang, Ruikun,Jia, Hongmei,Liu, Boli
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experimental part
p. 2908 - 2916
(2011/07/08)
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- Stilbene derivatives, light-emitting element, display device, and electronic device
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A novel stilbene derivative is provided with motivation of providing a blue emissive material showing excellent color purity. The use of the stilbene derivative of the present invention allows the fabrication of a blue-emissive light-emitting element with excellent color purity. The invention also includes an electronic device equipped with a display portion in which the stilbene derivative is employed. The stilbene derivative of the present invention is represented by formula (1), in which Ar1 and Ar2 may form a 5-membered ring by being directly bonded to each other. In formula (1), A11 represents any one of substituents represented by general formulas (1-1) to (1-3). The variables shown in formula (1) and (1-1) to (1-3) are as defined in the specification.
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Page/Page column 80
(2010/06/17)
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- Stilbene derivative, light emitting element, light emitting device, and electronic appliance
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An object is to provide a novel substance which exhibits blue light emission with excellent color purity, and to provide a light emitting element and a light emitting device using the novel substance. A stilbene derivative represented by the general formula (G1) is provided. Note that in the general formula (G1), each of A1 and B1 represents any one of structures represented by the following general formulae (G1-1) to (G1-4). In addition, in each of the general formulae (G1-1) to (G1-4), each of R1 to R24 represents any one of hydrogen and an alkyl group having 1 to 4 carbon atoms. Such a stilbene derivative can exhibit blue light emission with excellent color purity.
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Page/Page column 77
(2010/08/04)
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- Stilbene Derivatives, Light-Emitting Element, Display Device, and Electronic Device
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A novel stilbene derivative is provided with motivation of providing a blue emissive material showing excellent color purity. The use of the stilbene derivative of the present invention allows the fabrication of a blue-emissive light-emitting element with
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- Stilbene Derivative, Light Emitting Element, Light Emitting Device, and Electronic Appliance
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An object is to provide a novel substance which exhibits blue light emission with excellent color purity, and to provide a light emitting element and a light emitting device using the novel substance. A stilbene derivative represented by the general formula (G1) is provided. Note that in the general formula (G1), each of A1 and B1 represents any one of structures represented by the following general formulae (G1-1) to (G1-4). In addition, in each of the general formulae (G1-1) to (G1-4), each of R1 to R24 represents any one of hydrogen and an alkyl group having 1 to 4 carbon atoms. Such a stilbene derivative can exhibit blue light emission with excellent color purity.
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- Stilbene Derivative, Light-Emitting Element, Display Apparatus, and Electronic Appliance
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An object of the present invention is to provide a novel material having heat resistance which provides blue light emission, and a light-emitting element, a display apparatus, and an electronic appliance using the material. Aspects of the invention are a stilbene derivative represented by the following general formula (1), the light-emitting element in which a layer containing a light-emitting material interposed between two electrodes is included and the stilbene derivative is contained in the layer containing a light-emitting material, the display apparatus including the light-emitting element, and the electronic appliance including the display apparatus.
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Page/Page column 34
(2010/11/30)
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- MATRIX METALLOPROTEINASE INHIBITORS
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The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over- activation of a matrix metalloproteinase using the compounds.
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(2008/06/13)
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- Stilbene Derivative, Light-Emitting Element, Light-Emitting Device, and Electronic Device
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The present invention provides a novel organic compound having excellent heat resistance. By using the novel organic compound, a light-emitting element and a light-emitting device which have excellent heat resistance can be provided. A stilbene derivative expressed by the general formula (1) is provided. Since the stilbene derivative expressed by the general formula (1) has high glass transition point, when it is used for a light-emitting element, the light-emitting element, and a light-emitting device using the light-emitting element which have excellent heat resistance can be obtained. Further, since the stilbene derivative expressed by the general formula (1) has good light emission efficiency; therefore, when it is used for a light emitting element, a light emitting element and a light emitting device which consumes less power can be obtained.
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- Stilbene derivatives, light-emitting element and light-emitting device
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The present invention provides a novel substance having an excellent color purity of blue, a light-emitting element and a light-emitting device using the novel substance. A stilbene derivative has a structure shown by the general formula (1). In the general formula (1), R1 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R2 is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms. Each of R3 to R5 is hydrogen or an alkyl group having 1 to 4 carbon atoms. Ar1 is an aryl group having 6 to 25 carbon atoms.
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Page/Page column 62; 64; 66
(2008/06/13)
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- Stilbene derivative, light emitting element material, light emitting element, light emitting device and electronic appliance
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An object of the present invention to provide a novel stilbene derivative having a large energy gap. In addition, it is another object of the present invention to provide a novel light emitting element material having a large energy gap which is suitable for a host material in a light emitting layer. Further in addition, it is another object of the present invention to provide a novel light emitting element material having a large energy gap and an electron transporting property. The present invention provides a stilbene derivative represented by a following general formula (3) and a light emitting element material including the stilbene derivative represented thereby: wherein, n is an integer of 0 or more and 2 or less and m is an integer of 1 or more and 2 or less.
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Page/Page column 15
(2008/06/13)
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- On the functionalization of [2.2](1,4)phenanthrenoparacyclophane
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Two routes for preparing functionalized [2.2](1,4) phenanthrenoparacyclophanes are described: either the parent system 2 is subjected to electrophilic substitution (bromination, Friedel-Crafts acylation, Rieche formylation: preparation of 5, 6, 7, 11 and 12) or the desired substituents are incorporated in the early stages of the synthesis by the preparation of the corresponding functionalized styryl paracyclophanes and their photocyclization to the respective phenanthrenocyclophanes. By these specific routes various bronudes (22a,b), ethers (28a-c) and phenols (29a,b) were synthesized. The latter derivatives, on oxidation, furnish para-(31) and ortho-quinonophanes (30, 32, 33), useful substrates for the preparation of cyclophanes containing phenazine subunits (36). The stilbene → phenanthrene photocyclization can also be employed for the preparation of benzothiophenophanes, e.g. 43 and 44, from the respective precursors. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Hopf, Henning,Hucker, Joachim,Ernst, Ludger
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p. 1891 - 1904
(2008/02/06)
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- Organic semiconductors
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A molecule including a chain-like core region having two ends and having at least three conjugated aromatic rings; and including at the two ends, branched groups R1 and R2 respectively, each including a C5- to C20-alkyl group. A semiconducting composition including the molecule.
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Page/Page column 18
(2008/06/13)
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- π-Extended alkylidenecycloproparenes
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Reaction of benzene-1,4-dicarboxaldehyde with anion 6 derived from 1,1-bis(trimethylsilyl)cyclopropa[b]naphthalene 1 gives 4-(methylidene-1H-cyclopropanaphthalenyl)benzaldehyde 7 as a minor product and 1,4-bis(methylidene-1H-cyclopropanaphthalenyl)benzene
- Halton, Brian,Cooney, Mark J.
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p. 118 - 122
(2008/02/02)
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- PHOSPHONIUM SALTS DERIVATIVES AND THEIR USE AS SOLUBILITY CONTROLLING AUXILIARIES
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The present invention relates to the use of compounds of formula (IA) or (IIA): insert formula (IA) and (IIA) from page 15 of the disclosure wherein A represents various substituted or unsubstituted groups such as furyl, phenyl, pyridyl, naphthyl, or thiophenyl; X- represents an anion; and L1 represents a linker, as solubility controlling auxiliaries. These compounds can also be used as solubility controlling fragments of a molecule. The invention also relates to various methods of controlling the solubility of a molecule or a substrate. Moreover, the invention also relates to various phosphonium supported reagents or various phosphonium salts derivatives.
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Page/Page column 64
(2010/02/14)
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- Structures and nonlinear optical properties of new symmetrical two-photon photopolymerization initiators
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Four new symmetrical, two-photon photopolymerization initiators, 9-(4-{(1E,11E)-4-[(E)-4-(9H-carbazol-9-yl)styryl]-2,5-dimethoxystyryl}phenyl) -9H-carbazole (1), N-(4-{(1E,8E)-4-[(E)-4-(diphenylamino)styryl]-2,5- dimethoxystyryl}phenyl)-N-phenylbenzeneami
- Yan, Yun-Xing,Tao, Xu-Tang,Sun, Yuan-Hong,Wang, Chuan-Kui,Xu, Gui-Bao,Yu, Wen-Tao,Zhao, Hua-Ping,Yang, Jia-Xiang,Yu, Xiao-Qiang,Wu, Yong-Zhong,Zhao, Xian,Jiang, Min-Hua
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p. 479 - 484
(2007/10/03)
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- Triaryl boron-based A-π-A vs triaryl nitrogen-based D-π-D quadrupolar compounds for single- and two-photon excited fluorescence
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(Equation Presented) Three new A-π-A-type compounds with trivalent boron, protected by two mesityl groups, as electron acceptor have been synthesized and investigated together with their two diphenylamino-ended D-π-D analogues. These boranes exhibit large two-photon absorption cross sections and high fluorescence quantum yields.
- Liu, Zhi-Qiang,Fang, Qi,Cao, Du-Xia,Wang, Dong,Xu, Gui-Bao
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p. 2933 - 2936
(2007/10/03)
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- Trivalent Boron as an Acceptor in Donor - π - Acceptor-Type Compounds for Single- and Two-Photon Excited Fluorescence
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The synthesis, structure, and fluorescence properties of a series of new donor - π - acceptor (D - π - A) type compounds, with a trivalent boron, protected by two mesityl groups, as acceptor, and with various typical donors and different π-conjugated bridges, are reported. All these stable organoboron compounds show intense single-photon excited fluorescence (SPEF) and two-photon excited fluorescence (TPEF) in a wide spectral range from blue to green, with the spectral peak position of the SPEF being basically the same as that of the TPEF. The remarkably strong C-B(mesityl)2 bonding, and the well-conjugated π-system, shown in X-ray crystal structures of two compounds, indicate some charge transfer features of the ground state. Meanwhile, spectral data indicate that the charge transfer from donor to acceptor is greatly enhanced in the excited states. Based on typical structural data and comprehensive spectral data, the following structure - property relationships can be drawn: 1) the moderate arylamino donor can more effectively enhance the SPEF and TPEF intensities than can the strong alkylamino donor; 2) stilbene is a better π-bridge than styrylthiophene for its capability of enhancing and blue-shifting the SPEF and TPEF of the corresponding D - π - A compounds; and 3) when compared to its boron-free precursors and other analogues, -B(mesityl)2 invariably and consistently acts as an effective SPEF and TPEF fluorophore in all this series of organoboron compounds, which may result from its strong π -electron-withdrawing and charge transfer-inducing nature in the ground-state and, more dominantly, in the excited-state. Combining all the above positive structure factors, trans-4′-N,N-diphenylamino-4-dimesitylborylstilbene (compound 3) stands out as the optimized green SPEF and TPEF emitter. This compound exhibits an SPEF quantum yield φ of 0.91 at 522 nm in THF, a TPEF cross-section σ′ that is an order of magnitude larger than that of its boron-free precursor upon excitation by 800 nm femto-second laser pulses, and a two-photon absorption section a of 3.0 × 10-48 cm 4 s. In the blue light region, trans-4′ -N-carbazolyl-4-dimesitylborylstilbene (compound 4) shows significant SPEF and TPEF properties, with φ = 0.79 at 464 nm in THF and a large σ′ value, which is five times that of fluorescein upon excitation by 740 nm femto-second laser pulses.
- Liu, Zhi-Qiang,Fang, Qi,Wang, Dong,Cao, Du-Xia,Xue, Gang,Yu, Wen-Tao,Lei, Hong
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p. 5074 - 5084
(2007/10/03)
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- π-extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge-transfer complexes
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The conjugate (E)- and (Z)-(4′-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4′-pyridylethenyl-4-phenyl-β-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4′-pyridylethenyl)-4-phenyl]-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono- and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD.
- Rodríguez, J. Gonzalo,Martín-Villamil, Rosa,Lafuente, Antonio
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p. 1021 - 1032
(2007/10/03)
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- Use of precipitons for copper removal in atom transfer radical polymerization [1]
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The use of precipitons for copper removal in atom transfer radical polymerization (ATRP) was discussed. Nitrogen ligands bearing precipitons were prepared and used to mediate ATRP. The results showed that the precipiton-bound ligands successfully mediated
- Honigfort, Mical E.,Brittain, William J.,Bosanac, Todd,Wilcox, Craig S.
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p. 4849 - 4851
(2007/10/03)
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- The spin-delocalization substituent parameter σ JJ?. Part 10. The spin-delocalizing abilities of the para-trifluorovinyl and para-acetoxy groups. Synthesis of para-trifluorovinyl-, para-vinyl-and para-acetoxy-α,β,β-trifluorostyrenes
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para-Trifluorovinyl α,β,β-trifluorostyrene (1-CF=CF2), p-acetoxy α,β,β-trifluorostyrene (1-AcO) and p-vinyl α,β,β-trifluorostyrene (1-CH=CH2) have been synthesized. The rate constants (k) for the thermal cyclodimerization of 1-CF=CF2 and 1-AcO have been measured over the temperature range 90-130 °C for 1-CF=CF2 and 110-160 °C for 1-AcO. The σmb polar substituent constants of the p-CF=CF2, p-CH=CH2 and p-AcO groups calculated from the 19F NMR chemical shifts are: for p-CF=CF2, 0.40; for p-CH=CH2, 0.03; and for p-AcO, -0.14, and the σ JJ? spin-delocalization substituent constants of the p-CF=CF2 and p-AcO groups are 0.86 and 0.35, respectively, i.e., the former is a highly effective spin-stabilizer while the latter is moderately effective. Owing to the occurrence of a small amount of side-reaction, the σ JJ? value of the p-CH=CH2 group could not be accurately measured, but it was very roughly estimated to be in the range of 0.50-0.66.
- Jiang, Xi-Kui,Ji, Guo-Zhen,Wang, Daniel Ze-Rong
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p. 173 - 178
(2007/10/03)
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- Interaction of tetrahydrostilbazoles with monoamine oxidase A and B
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1-Methyl-1,2,3,6-tetrahydrostilbazole (MTHS) and its analogs are oxidized by monoamine oxidase (MAO) A at slow rates comparable to that for the structurally similar neurotoxin, 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine, but the rates of oxidation by MAO B vary over a wide range depending on the structure of the analog. MAO A oxidation of all of the analogs yielded nonhyperbolic kinetic patterns, with little difference between the cis and trans isomers. In contrast MAO B showed hyperbolic kinetics and distinct stereoselectivity for the cis isomers. The corresponding pyridinium forms of trans-MTHS and its analogs were more potent inhibitors of MAO A (K(i) values between 0.3 and 5 μM) than of MAO B, for which the K(i) values varied greatly. The data suggest that the stringency of the MAO A active site for the geometry of the substrate molecule is less strict than that of MAO B. With MAO B, any substitution on the phenyl ring can lead to dramatic changes in the substrate properties which may be explained by the different orientation of substrate at the active site of the enzyme. Molecular geometry but not the effects of the substituents was shown to be an important factor in determining the effectiveness of substrate oxidation by MAO B.
- Sablin,Krueger,Singer,Bachurin,Khare,Efange,Tkachenko
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p. 151 - 157
(2007/10/02)
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- KINETICS AND LINEAR FREE ENERGY RELATIONSHIP OF WITTIG REACTION BETWEEN SUBSTITUTED BENZALDEHYDES AND SUBSTITUTED BENZYLIDENETRIPHENYLPHOSPHORANE
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Kinetics and linear free energy relationship (LFER) of Wittig reaction of ylides of intermediary stability have been investigated.Evidences are presented which indicate that under such cases the reaction follows a second order rate law, first order in phosphorane and aldehyde respectively, and furthermore that electron withdrawing substituents on both benzaldehyde and benzylidenetriphenylphosphorane impose rate enhancement effect upon the reaction.The mechanism of the reaction is discussed on the basis of the experimental findings
- Donxia, Li,Dexian, Wu,Yaozhong, Li,Huaming, Zhao
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p. 4161 - 4168
(2007/10/02)
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- Preparation of (E)-2-Hxdroxy-4'-Substituted Stilbenes
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Sixteen (E)-2-hydroxy-4'-substituted stilbenes have been prepared by the Wittig reaction.Direct coupling of the appropriate p-substituted benzylidenetriphenylphosphoranes with salicylaldehyde afforded the (E)-stilbenols (2) 4'-R = H(2a), Me(2b), But(2c), Ph(2d), CN(2e), NO2(2i), OMe(2k), F(2n), Cl(2o), and Br(2p).Alternatively, the Wittig reaction of o-methoxymethoxybenzylidenetriphenylphosphorane with various p-substituted benzaldehydes gave the (E)-methoxymethylstilbenols (4) which upon acidic cleavage furnished the corresponding stilbenols (2) 4'-R = CN(2e), CO2Me(2f), NMe2(2h), OH(2j), OAc(2m), and I(2q).The symmetrical (E)-2,2'-dihydroxystilbene was obtained in an analogous fashion.Reduction of nitrostilbenol (2i) yielded the corresponding aminostilbenol (2g).
- Mylona, Anastasia,Nikokavouras, John,Takakis, Ioannis M.
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p. 3514 - 3530
(2007/10/02)
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