- ORGANIC COMPOUNDS, ORGANIC LIGHT EMITTING DIODE AND ORGNIC LIGHT EMITTING DISPLAY DEVICE INCLUDING THE COMPOUNDS
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The present invention provides an organic compound represented by following chemical formula. The organic compound has retardation fluorescence characteristics and is used in an organic light emitting layer of an organic light emitting diode, thereby improving light emitting efficiency of the organic light emitting diode and an organic light emitting display device.COPYRIGHT KIPO 2019
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Paragraph 0139-0143
(2019/08/23)
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- Design, synthesis and cytotoxic activity of water-soluble quinones with dibromo-p-benzoquinone cores and amino oligo(ethylene glycol) side chains against MCF-7 breast cancer cells
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A series of novel quinones was synthesized by reacting tetrabromo-p-benzoquinone with amino oligo(ethylene glycol) dendrons of generation numbers g = 0-2. According to the performed shake-flask experiments, their aqueous solubility (S = 18 mg l?1-1.6 g ml?1) and partition coefficients (log?Poct/wat = 2.53-0.21) can be tuned in a wide range as a function of g. In vitro cytotoxicity assays of tetrabromo-p-benzoquinone and its derivatives against MCF-7 human breast cancer cells showed a concentration- and generation-specific biological activity with IC50-values as low as 0.8 μM. Further investigations revealed a considerable selectivity against cancer cells, as indicated by a weak cytotoxicity against human skin fibroblast cells (>80% survival) within the studied range of concentrations. The results demonstrate that these novel amino oligo(ethylene glycol) dendrons depict versatile tools to ameliorate physical and pharmacological characteristics of extremely hydrophobic molecules and make them susceptible to biological applications.
- Scherz, Leon F.,Abdel-Rahman, Engy A.,Ali, Sameh S.,Schlüter, A. Dieter,Abdel-Rahman, Mona A.
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p. 662 - 672
(2017/03/30)
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- Spectroscopic and thermal investigations on the charge transfer interaction between risperidone as a schizophrenia drug with some traditional π-acceptors: Part 2
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The focus of present investigation was to assess the utility of non-expensive techniques in the evaluation of risperidone (Ris) in solid and solution states with different traditional π-acceptors and subsequent incorporation of the analytical determination into pharmaceutical formulation for a faster release of risperidone. Charge-transfer complexes (CTC) of risperidone with picric acid (PA), 2,3-dichloro-5,6-dicyano-p-benzoquinon (DDQ), tetracyanoquinodimethane (TCNQ), tetracyano ethylene (TCNE), tetrabromo-p-quinon (BL) and tetrachloro-p-quinon (CL) have been studied spectrophotometrically in absolute methanol at room temperature. The stoichiometries of the complexes were found to be 1:1 ratio by the photometric molar ratio between risperidone and the π-acceptors. The equilibrium constants, molar extinction coefficient (εCT) and spectroscopic-physical parameters (standard free energy (ΔGo), oscillator strength (f), transition dipole moment (μ), resonance energy (RN) and ionization potential (ID)) of the complexes were determined upon the modified Benesi-Hildebrand equation. Risperidone in pure form was applied in this study. The results indicate that the formation constants for the complexes depend on the nature of electron acceptors and donor, and also the spectral studies of the complexes were determined by (infrared, Raman, and 1H NMR) spectra and X-ray powder diffraction (XRD). The most stable mono-protonated form of Ris is characterized by the formation of +NH (pyrimidine ring) intramolecular hydrogen bonded. In the high-wavenumber spectral region ~3400 cm-1, the bands of the +NH stretching vibrations and of the pyrimidine nitrogen atom could be potentially useful to discriminate the investigated forms of Ris. The infrared spectra of both Ris complexes are confirming the participation of +NH pyrimidine ring in the donor-acceptor interaction.
- El-Habeeb, Abeer A.,Al-Saif, Foziah A.,Refat, Moamen S.
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p. 464 - 477
(2013/04/23)
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- The mediatory activity of Ce(IV)/Ce(III) redox system immobilized in nafion film on glassy carbon
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Properties of the glassy carbon modified with Ce(III) ions immobilized in Nafion film and the catalytic activity of these ions or the catalytic activity of the modified conducting phase in electrochemical oxidation of some hydroquinone, phenylenediamine and 4-hydroxybenzoic acid derivatives were investigated. The redox activity was characterized in aqueous solutions of perchloric acid by cyclic voltammetry. The redox process was diffusion-limited which can suggest that the cerium(III) ions immobilized in the Nafion multilayer was rate-controlling. The increase of anodic peaks of investigated compounds during oxidation on the modified electrode (GC/Nafion/Ce(III)), and drastic decrease of cathodic peak related to Ce(IV) ions reduction, points to the mediatory activity of these ions. The increase of oxidation currents observed during preparative electrolyses indicates the catalytic properties of the modified conducting phase. The preparative electro-oxidation of investigated compounds showed that the 100% conversion of the substrate occurs in the shortest time on glassy carbon modified with Ce(III) ions immobilized in Nafion film. AFM tapping mode phase imaging was used to identify the hydrophobic and hydrophilic regions of Nafion perfluorosulfonate cation exchange membranes. The clusters agglomerates have a range of sizes from 5 to 30 nm.
- Domagala,Dziegiec,Cichomski,Grobelny
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p. 1049 - 1061
(2008/09/19)
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- An efficient synthesis of 2,5-diamino-1,4-benzoquinone
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A novel and efficient synthesis of 2,5-diamino-1,4-benzoquinone is described. The reaction involves a palladium/charcoal hydrogenolysis as the key step and provides the desired product in only four steps and very good overall yield. Georg Thieme Verlag Stuttgart.
- Mereyala, Hari Babu,Chary, Mahankhali Venu,Kantevari, Srinivas
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p. 187 - 189
(2007/10/03)
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- Acivated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XII. Bromination of 4-acylaminophenols
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Exhaustive bromination of 4-acylaminophenols gives the corresponding 2-acylamino-3,5,6-tri-bromo-1,4-benzoquinones.
- Avdeenko,Marchenko,Yusina,Konovalova,Ludchenko
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p. 1787 - 1792
(2007/10/03)
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- Photoinduced electron transfer between acenaphthylene and 1,4-benzoquinones. Formation of dimers of acenaphthylene and 1 : 1-adducts and effect of excitation mode on reactivity of the charge-transfer complexes
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Photochemical reactions of acenaphthylene (ACN) with 1,4-benzoquinones (BQs) of varying reduction potentials in solution have been investigated in order to determine final products and quantum yields of the reactions and to get an insight into the factors
- Haga, Naoki,Takayanagi, Hiroaki,Tokumaru, Katsumi
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p. 734 - 745
(2007/10/03)
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- Charge transfer interaction of chloranil and bromanil with tertiary amines
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The formation of charge transfer complexes between triethylamine, tributylamine, trioctylamine and the π-acceptors, chloranil and bromanil in 1,2-dichloroethane has been investigated spectrophotometrically. The formation constants of the resulting 1:1 molecular complexes are determined and the rate of formation constants of monosubstituted products estimated. The stabilities of the complexes of both π- acceptors vary in the order triethylamine > tributylamine > trioctylamine.
- Saikia, Binapani,Suryanarayana,Ghosh, Anil C.
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p. 604 - 606
(2007/10/03)
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- BROMINATION OF 4-ARENESULFONAMIDOPHENOLS (OR 1-NAPHTHOLS) AND N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINON-4-IMINES
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2,3,6-Tribromo-N-phenylsulfonyl-1,4-benzoquinon-4-imines are formed on bromination of 4-arenesulfonamidophenols and N-aryl-sulfonyl-1,4-benzoquinon-4-imines but 2-bromo-N-arylsulfonyl-1,4-naphthoquinon-4-imines are formed from 4-arenesulfonamido-1-naphthols and N-arylsulfonyl-1,4-naphthoquinon-4-imines.
- Avdeenko, A. P.,Velichko, N. V.
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p. 1687 - 1692
(2007/10/02)
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- Reactive dyestuffs
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Triphendioxazine reactive dyestuffs of the general formula STR1 with the substituent definition given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups or amide groups. They give red dyeings with high wet- and light-fastnesses.
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- Oxidation Using Quaternary Ammonium Polyhalides. VIII. Oxidation of 1,4-Benzenediols with Benzyltrimethylammonium Tribromide
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The reaction of 1,4-benzenediols with 1.1 equiv of benzyltrimethylammonium tribromide in dichloromethane in the presence of aqueous sodium acetate at room temperature gave 2,5-cyclohexadiene-1,4-diones in good yields.On the other hand, the reaction of 1,4-benzenediols with a large excess of the reagent in aqueous acetic acid at 40-60 deg C gave polybromo-substituted 2,5-cyclohexadiene-1,4-diones in good yields.
- Kajigaeshi, Shoji,Morikawa, Yukihiro,Fujisaki, Shizuo,Kakinami, Takaaki,Nishihira, Keigo
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p. 336 - 338
(2007/10/02)
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- HIGHLY STEREOSPECIFIC THERMOLYSIS OF SPIROOXETANES CONTAINING TETRAHALOGENATED 1,4-BENZOQUINONE MOIETIES
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Thermolysis of cis- and trans-spirooxetanes (1) proceeded with 94-100percent retention of stereochemistry to give stilbene (2) and quinones (3).Important role of a concerted pathway was assumed.
- Oshima, Takumi,Nagai, Toshikazu
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p. 3443 - 3444
(2007/10/02)
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- CATALYTIC AND STOICHIOMETRIC BROMINATION OF AROMATIC COMPOUNDS IN AQUEOUS TRIFLUOROACETIC ACID IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS
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The mono- and polybromination of benzene, halogenobenzenes, toluene, p-xylene, anisole, biphenyl, benzotrifluoride, benzoic acid, p-nitro- and p-carboxytoluene, p-methoxybenzonitrile, tetralin, and naphtalene were studied in trifluoroacetic acid and its aqueous solutions in systems containing stoichiometric amounts of bromine or alkali-metal bromide and stoichiometric or catalytic (in the presence of oxygen or air) amounts of nitrogen-containing oxidizing agent (nitrogen(IV) oxide, alkali-metal nitrate or nitrite).It is suggested that the brominating agent under the investigated conditions is nitryl bromide NO2Br.Under the conditions of catalytic bromination anthracene is oxidized to anthraquinone with a preparative yield.
- Cheprakov, A. V.,Makhon'kov, D. I.,Rodkin, M. A.,Beletskaya, I. P.
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p. 217 - 223
(2007/10/02)
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- Energetic Comparison between Photoinduced Electron-Transfer Reactions from NADH Model Compounds to Organic and Inorganic Oxidants and Hydride-Transfer Reactions from NADH Model Compounds to p-Benzoquinone Derivatives
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Kinetics studies on photoinduced electron-transfer reactions from dihydropyridine compounds (PyH2) as being NADH model compounds to organic and inorganic oxidants and hydride-transfer reactions from PyH2 to p-benzoquinone derivatives (Q) in the absence and presence of Mg2+ ion are reported by determining over 150 rate constants.These results, combined with the values of Gibbs energy change of the photoinduced electron-transfer reactions as well as those of each step of the hydride-transfer reactions as being the e--H+-e- sequence, which are determined independently, revealed that the rate constants of the photoinduced electron-transfer reactions obey the Rehm-Weller-Gibbs energy relationship and that the activation barrier of the hydride-transfer reactions from PyH2 to Q is dependent solely on the Gibbs energy changes of the initial electron transfer from PyH2 to Q and the following proton transfer from PyH2.+ to Q.- and thus independent of the Gibbs energy change of the final electron transfer from PyH. to QH..The retarding effect of Mg2+ ion observed on the photoinduced electron transfer and hydride-transfer reactions of PyH2 is ascribed to the positive shifts of the redox potentials of the ground and excited states of PyH2 due to the complex formation with Mg2+ ion.
- Fukuzumi, Shunichi,Koumitsu, Shintaro,Hironaka, Katsuhiko,Tanaka, Toshio
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p. 305 - 316
(2007/10/02)
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- REACTION OF HYDROGEN BROMIDE WITH N-(p-TOLYL)- AND N-(p-TOLYLSULFONYL)-1,4-BENZOQUINONE MONOIMINES
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In the reaction of hydrogen bromide with N-(p-tolyl)-1,4-benzoquinone monoimines bromination of the p-tolyl fragment takes place as well as nucleophilic addition.Bromination is fully suppressed by the addition of resorcinol to the reaction mass.In the case of N-(p-tolylsulfonyl)-1,4-benzoquinone monoimine the products from the entry of two bromine atoms at the ortho position to the oxygen atom are formed sucessively.
- Toropin, N. V.,Burmistrov, K. S.,Burmistrov, S. I.,Zaichenko, N. L.
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p. 894 - 899
(2007/10/02)
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- Triphendioxazine dyestuffs
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Triphendioxazine dyestuffs of the formula STR1 having the substituent meanings specified in the descriptive part, are highly suitable for dyeing and printing hydroxyl- or amido-containing materials, in particular fibre materials, and produce wash-fast dyeings and prints.
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- DETECTION OF AN INTERMEDIATE TERNARY COMPLEX IN THE REDUCTION OF p-BENZOQUINONE DERIVATIVES BY AN NADH MODEL COMPOUND IN THE PRESENCE OF Mg2+ ION
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A transient charge-transfer (CT) band of a ternary complex due to the CT transition from an NADH model compound - Mg2+ ion complex to a p-benzoquinone derivative was observed in the reduction of a p-benzoquinone derivative by an NADH model compound in the presence of Mg2+ ion in acetonitrile.The role of the ternary complex in the reduction by an NADH model compound is reported.
- Fukuzumi, Shunichi,Nishizawa, Nobuaki,Tanaka, Toshio
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p. 1755 - 1758
(2007/10/02)
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- Molecular Interaction Between p-Benzoquinone and Piperidines
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The molecular interactions between piperidine and some methyl substituted piperidines as donors and p-benzoquinone as acceptor have been investigated spectrophotometrically in chloroform medium.The absorption in the visible region is dependent on the polarity of the solvent.The charge transfer excitation energy, intensity of the absorption bands and equilibrium constant values have been computed and the stability of the complexes discussed.The ionisation potentials of the donors have also been calculated.Based on these molecular interactions, detection and determination of benzoquinone and detection of donors, at microgram level, have been proposed.
- Muralikrishna, U,Krishnamurthy, Mannam
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p. 1018 - 1020
(2007/10/02)
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- Synthesis of 2,5-Disubstituted 3,6-Diamino-1,4-benzoquinones
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A general synthetic approach to a wide variety of 2,5-disubstituted 3,6-diamino-1,4-benzoquinones was developed.Bromanil was diaminated with ammonia, and adjacent NH2 and OH groups were protected as benzoxazoles by treatment with a carboxylic acid chloride followed by a polyphosphate ester cyclization-dehydration.The resulting 2,5-dibromobenzobis(oxazoles) were monolithiated by halogen-metal exchange with n-butyllithium and then reacted with a variety of electrophiles.The remaining bromide was replaced in a similar fashion.Alternatively the second bromide was replaced by reaction with ? allylnickel halide complexes.The benzoxazole protecting group could be hydrolyzed with zinc(II) chloride/HCl-aqueous ethanol under an inert atmostphere.Air oxidation of the resulting hydroquinone under neutral conditions gave the desired 2,5-disubstituted 3,6-diamino-1,4-benzoquinone in good to excellent overall yield.This method was used to synthesize precursors to the basic ring system of the mitomycin antineoplastic antibiotics.Acid hydrolysis of the benzoxazole protecting group under oxidizing conditions resulted in the production of 2,5-disubstituted 3,6-dihydroxy-1,4-benzoquinone.Methylation followed by reaction with ammonia gave the desired diaminoquinone.
- Hegedus, Louis S.,Odle, Roy R.,Winton, Peter M.,Weider, Paul R.
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p. 2607 - 2613
(2007/10/02)
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