- Towards novel thieno-fused subporphyrazines via functionalized thiophene precursors
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Thieno-fused subporphyrazines (TPs) containing a central and axially substituted boron atom are a class of compounds with interesting optical and redox properties. Here we present our efforts towards expanding this class of compounds using various thiophene substrates that were prepared by cyanation or nitration of 3,4-dibromothiophene. Moreover, we show that one TP derivative forms a 2:1 complex in the solid state with C70.
- Rasmussen, Mads Georg,Gotfredsen, Henrik,Kadziola, Anders,Nielsen, Mogens Br?ndsted
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- New regiosymmetrical dioxopyrrolo- and dihydropyrrolo-functionalized polythiophenes
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(Chemical Equation Presented) We present the synthesis of two N-alkylated poly(dioxopyrrolothiophene)s and two N-alkylated poly(dihydropyrrolothiophene)s with potential application in the field of conducting polymers. The polymers are synthesized from the corresponding 2,5-dibromothiophenes by an Ullmann-type polymerization and a Stille-type polymerization, respectively. The two N-alkylated poly(dihydropyrrolothiophene)s are the first examples of amino-functionalized polythiophenes built from regiosymmetrical thiophene monomers.
- Nielsen, Christian B.,Bjornholm, Thomas
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- From Red to Green Luminescence via Surface Functionalization. Effect of 2-(5-Mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4- c]pyrrole-4,6-dione Ligands on the Photoluminescence of Alloyed Ag-In-Zn-S Nanocrystals
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A semiconducting molecule containing a thiol anchor group, namely 2-(5-mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione (abbreviated as D-A-D-SH), was designed, synthesized, and used as a ligand in nonstoichiometric quaternary nanocrystals of composition Ag1.0In3.1Zn1.0S4.0(S6.1) to give an inorganic/organic hybrid. Detailed NMR studies indicate that D-A-D-SH ligands are present in two coordination spheres in the organic part of the hybrid: (i) inner in which the ligand molecules form direct bonds with the nanocrystal surface and (ii) outer in which the ligand molecules do not form direct bonds with the inorganic core. Exchange of the initial ligands (stearic acid and 1-aminooctadecane) for D-A-D-SH induces a distinct change of the photoluminescence. Efficient red luminescence of nanocrystals capped with initial ligands (λmax = 720 nm, quantum yield = 67%) is totally quenched and green luminescence characteristic of the ligand appears (λmax = 508 nm, quantum yield = 10%). This change of the photoluminescence mechanism can be clarified by a combination of electrochemical and spectroscopic investigations. It can be demonstrated by cyclic voltammetry that new states appear in the hybrid as a consequence of D-A-D-SH binding to the nanocrystals surface. These states are located below the nanocrystal LUMO and above its HOMO, respectively. They are concurrent to deeper donor and acceptor states governing the red luminescence. As a result, energy transfer from the nanocrystal HOMO and LUMO levels to the ligand states takes place, leading to effective quenching of the red luminescence and appearance of the green one.
- Kowalik, Patrycja,Bujak, Piotr,Wróbel, Zbigniew,Penkala, Mateusz,Kotwica, Kamil,Maroń, Anna,Pron, Adam
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- CRYSTAL FORMS OF THIOPHENE DERIVATIVES
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Disclosed is crystal form I of compound (S)—N-[5-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4,6-dioxo-5,6-dihydro-4H-thieno[3,4-c]pyrrole-1-yl]acetamide.
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Paragraph 0272
(2021/05/14)
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- Synthesis and characterization of an A2BC type phthalocyanine and its visible-light-responsive photocatalytic H2 production performance on graphitic carbon nitride
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A highly asymmetric A2BC type zinc phthalocyanine (Zn-di-PcNcTh) has been designed and synthesized. The Zn-di-PcNcTh used a π electron rich thiophene ring in place of the benzenoid rings of phthalocyanine which acted as an electron donor, diphenylphenoxy substituents to retard aggregation and a carboxyl-naphthalene unit as an electron acceptor. The asymmetric phthalocyanine shows a strongly split Q-band and wide spectral absorption in the visible/near-IR light region, which can extend the spectral response region of graphitic carbon nitride (g-C3N4) from ~450 nm to more than 800 nm. By using it as a sensitizer of 1.0 wt% Pt-loaded graphitic carbon nitride (g-C3N4), the experimental results indicate that Zn-di-PcNcTh-Pt/g-C3N4 shows a H2 production efficiency of 249 μmol h-1 with an impressive turnover number (TON) of 9960.8 h-1 under visible light (λ ≥ 420 nm) irradiation, much higher than that of pristine Pt/g-C3N4. Owing to the introduction of a highly bathochromic shift of 3,4-dicyanothiophene and the valuable "push-pull" effect from the thiophene (electron donor) to the carboxyl-naphthalene (electron acceptor) unit, Zn-di-PcNcTh/g-C3N4 gives an extremely high apparent quantum yield (AQY) of 2.44%, 3.05%, and 1.53% under 700, 730, and 800 nm monochromatic light irradiation, respectively, under optimized photocatalytic conditions.
- Guo, Yingying,Song, Shuaishuai,Zheng, Ya,Li, Renjie,Peng, Tianyou
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supporting information
p. 14071 - 14079
(2016/11/05)
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- A versatile approach to organic photovoltaics evaluation using white light pulse and microwave conductivity
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State-of-the-art low band gap conjugated polymers have been investigated for application in organic photovoltaic cells (OPVs) to achieve efficient conversion of the wide spectrum of sunlight into electricity. A remarkable improvement in power conversion efficiency (PCE) has been achieved through the use of innovative materials and device structures. However, a reliable technique for the rapid screening of the materials and processes is a prerequisite toward faster development in this area. Here we report the realization of such a versatile evaluation technique for bulk heterojunction OPVs by the combination of time-resolved microwave conductivity (TRMC) and submicrosecond white light pulse from a Xe-flash lamp. Xe-flash TRMC allows examination of the OPV active layer without requiring fabrication of the actual device. The transient photoconductivity maxima, involving information on generation efficiency, mobility, and lifetime of charge carriers in four well-known low band gap polymers blended with phenyl-C61-butyric acid methyl ester (PCBM), were confirmed to universally correlate with the PCE divided by the open circuit voltage (PCE/Voc), offering a facile way to predict photovoltaic performance without device fabrication.
- Saeki, Akinori,Yoshikawa, Saya,Tsuji, Masashi,Koizumi, Yoshiko,Ide, Marina,Vijayakumar, Chakkooth,Seki, Shu
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supporting information
p. 19035 - 19042
(2013/01/15)
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- THIOPHENE DERIVATIVES
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Disclosed is a compound of formula (1), wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the present application.
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Page/Page column 25
(2012/04/17)
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- OLIGOTHIOPHENES DERIVATIVES
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The present invention is directed to new oligothiophene derivatives and their use as a semiconductor material in electronic devices. More specifically, the present invention relates to new 3,4-dicyanooligothiophenes derivatives, processes for manufacturing thereof, and to their use as organic n-type (electron-transporting) semiconductors, in particular, in field-effect transistors (FET).
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Page/Page column 57
(2011/04/13)
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- Preparation and characterization of nonclassical tetraazaporphyrin, bis(4-methylpyridine)[1,3,5,7,9,11,13,15-octaphenyltetra(3,4-thieno) tetraazaporphyrinato]ruthenium(II)
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The tetramerization reaction of 2,5-diphenyl-3,4-dicyanothiophene (2) proceeded on treatment with ruthenium(III) trichloride, DBU, and 4-methylpyridine in 2-ethoxyethanol at 135 °C to give bis(4-methylpyridine) [1,3,5,7,9,11,13,15-octaphenyltetra(3,4-thie
- Kimura, Takeshi,Iwama, Takashi,Namauo, Toshiharu,Suzuki, Eiichi,Fukuda, Takamitsu,Kobayashi, Nagao,Sasamori, Takahiro,Tokitoh, Norihiro
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experimental part
p. 888 - 894
(2011/05/04)
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- Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties
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The synthesis and the characterization of twelve new soluble oligothiophenes, possessing two to four 3,4-dicyanothiophene units in their backbone, are described. These semiconductors are prepared through Stille coupling and/or homo-coupling reactions. Cyclic voltammetry studies have been performed to evaluate their stability as n-type semiconducting materials under ambient conditions. The measured electrochemical and optical properties are fully supported by quantum-chemical calculations.
- Balandier, Jean-Yves,Quist, Florence,Amato, Claire,Bouzakraoui, Sa?d,Cornil, Jér?me,Sergeyev, Sergey,Geerts, Yves
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scheme or table
p. 9560 - 9572
(2011/01/12)
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- DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
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- PYRROLINE-2-ONE DERIVATIVES AGAINST CELL RELEASING TUMOR NECROSIS FACTOR, PREPARATION METHODS AND USES THEREOF
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Compounds represented by Formula (I) or Formula (II), their pharmaceutically acceptable salts or hydrates wherein A, B and E independently represent CH2 or CO; D represents S, NH, or NC1-6 alkylhydrocarbyl; R represents H or R3, R1 represents H, or 1-2 same or different occurrences of radical(s) selected from the group consisting of F, Cl, Br, C1-4 alkylhydrocarbyl, OH, OC1-4 alkylhydrocarbyl, NO2, NHC(O)C1-4 alkylhydrocarbyl, NH2, NH(C1-4 alkylhydrocarbyl), N(C1-4 alkylhydrocarbyl)2; and R2 represents F, CF3, H or C1-4 alkylhydrocarbyl; are active inhibitors of TNFα. Provided are also preparation methods and uses thereof.
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Page/Page column 11
(2009/09/07)
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- PYRROLINE DERIVATIVES AGAINST CELL RELEASING TUMOR NECROSIS FACTOR, PREPARATION METHODS AND USES THEREOF
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Compounds represented by Formula (I) or Formula (II) against cell releasing TNFα, their pharmaceutically acceptable salts or hydrates and preparation methods and uses thereof, in which A and B represent CH2, CO, SO, or SO2; D represents S, NH, or NC1-6 alkyl; R1 represents H, or one or two same or different radical(s) selected from the group consisting of F, Cl, Br, C1-4 alkyl,OH,OC1-4 alkyl,NO2,NHC(O)C1-4 alkyl,NH2,NH(C1-4 alkyl), or N(C1-4 alkyl)2.
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Page/Page column 10
(2009/08/14)
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- 5H-THIENO [3,4-c]PYRROLE-4, 6-DIONE DERIVATIVES AGAINST CELL RELEASING TUMOR NECROSIS FACTOR
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Taught are derivatives of 5H-thieno (3,4-c) pyrrole-4,6-dione, their organic, and inorganic salts, methods of synthesis of these derivatives, and their application as active pharmaceutical-ingredients useful as inhibitors of TNFα, the derivative being represented by the general formula (I): in which R1 represents H, C1-6alkyl, OR4, OC(O)R5, NO2, NHC(O)R6, or NR7R8; R2 represents H, a halogen, or C1-6alkyl; R3 represents H, methyl, isopropyl, allyl, benzyl, CH2CO2 (C1-6alkyl), or CH2(CH2)nR9; R4, R5, R6, R7, and R8 each independently and at each occurrence represents H, or C1-6alkyl; R9 represents H, C1-6alkyl, OH, OC1-6alkyl, NH2, NHC1-6alkyl, N(C1-6alkyl)2, or CO2(C1-6alkyl); and n represents 1, 2, 3, or 4.
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Page/Page column 26
(2008/12/08)
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- DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
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Page/Page column 18
(2008/12/08)
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- 5H-THIOENO(3,4-c)PYRROLE-4,6-DIONE DERIVATIVES AND THEIR USE AS TUMOR NECROSIS FACTOR INHIBITORS
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Taught are derivatives of 5H-thioeno(3,4-c)pyrrole-4,6-dione, their organic, and inorganic salts, methods of synthesis of these derivatives, and their application as active pharmaceutical-ingredients useful as inhibitors of TNFα, the derivative being represented by the general formula (I): in which R1 represents H, C1-6alkyl, OR4, OC(O)R5, NO2, NHC(O)R6, or NR7R8; R2 represents H, a halogen, or C1-6alkyl; R3 represents H, methyl, isopropyl, allyl, benzyl, CH2CO2(C1-6alkyl), or CH2(CH2)nR9; R4, R5, R6, R7, and R8 each independently and at each occurrence represents H, or C1-6alkyl; R9 represents H, C1-6alkyl, OH, OC1-6alkyl, NH2, NHC1-6alkyl, N(C1-6alkyl)2, or CO2(C1-6alkyl); and n represents 1, 2, 3, or 4.
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Page/Page column 12
(2008/12/07)
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- Palladium-Catalyzed Cyanation Reactions of Thiophene Halides
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The described method provides an efficient cyanation reaction of thiophene halides using tris(dibenzylidene-acetone)dipalladium(0), 1,1′-bis- (diphenylphosphino)ferrocene) and zinc powder as the catalyst system and Zn(CN)2 as the cyanide source
- Erker, Thomas,Nemec, Stephanie
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- Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease
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The invention provides compounds of Formula I: 1where in W is 2These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful to treat diseases or conditions in which α7 is known to be involved.
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- Substituted 7-aza[2.2.1]bicycloheptanes for the treatment of disease
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The invention provides compounds of Formula I: which may be in the form of pharmaceutical acceptable salts or compositions, are useful in treating diseases or conditions in which α7 nicotinic acetylcholine receptors (nAChRs) are known to be involved.
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- The interplay of bent-shape, lateral dipole and chirality in thiophene based di-, tri-, and tetracatenar liquid crystals
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A range of mesogenic molecules varying in both bend angle and strength of lateral dipole were synthesized, and their phase behavior was characterized by polarizing microscopy, thermal analysis, X-ray diffraction, and electrooptical measurements. We find t
- Eichhorn, S. Holger,Paraskos, Alexander J.,Kishikawa, Keiki,Swager, Timothy M.
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p. 12742 - 12751
(2007/10/03)
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- Alternating donor/acceptor repeat units in polythiophenes. Intramolecular charge transfer for reducing band gaps in fully substituted conjugated polymers
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This paper describes a method to limit the band gap widening that occurs in fully substituted conjugated polymers. This is done by constructing step growth [AB] polymers where the A-units are electron rich and the B-units are electron deficient. The thiophene-based polymers were prepared by modified Stille polymerizations using Pd(0)/CuI catalyst systems in which aryldibromides were coupled with aryldistannanes. The donor units were N,N′-(bis-tert-butoxycarbonyl)-3,4-diaminothiophene, N,N′-(bis-tert-butoxycarbonyl)-N,N′-(dimethyl)-3,4-diaminothiophene, 3,4-diaminothiophene, or 3,4-dialkoxythiophenes while the acceptor units were 3,4-dinitrothiophene, 3,4-(N-n-butylimido)thiophene, or 3,4-diketone-containing thiophenes. The optical spectra showed λmax values ranging from 400 to 676 nm (solution) and 400-768 (film) for these fully substituted polythiophenes, consistent with significant decreases in the band gaps. Intramolecular charge transfer character between the consecutive units explained the lowering of the band gaps. Two polymer systems based solely on electron deficient thiophenes were prepared via an Ullmann coupling which had optical absorption maxima that were in the range of 300-340 nm; considerably smaller than the λmax values for the donor/acceptor systems. Several model trimers were prepared which had significantly shorter wavelength optical absorptions than their corresponding polymers, thus confirming the need for the extended polymeric backbones.
- Zhang, Qing T.,Tour, James M.
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p. 5355 - 5360
(2007/10/03)
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- Preparation and Characterisation of Thienonaphthoquinones and their Radical Ions
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Three naphthothiophene-4,9-diones (thienonaphthoquinones) have been prepared and their redox properties studied by chemical, electrochemical and EPR spectroscopic methods.All three quinones were readily reduced electrochemically to the corresponding radical anions and subsequently to dianions.The cyclic voltammograms showed evidence of ion pairing of the dianions.All three quinones were also electrochemically oxidised to radical cations.The structures and thermodynamic properties of the quinones, the radical cations, radical anions and dianions were studied by the semi-empirical AM1 method.The experimental redox potentials were found to correlate with the computed energies of the appropriate frontier MOs.The electrochemically generated radical anions were observed by EPR spectroscopy and shown to decay with second-order kinetics.The rate constants increased as the electron-releasing character of the substituents in the benzene ring increased.The only EPR spectroscopically detectable radical cation was that from the 6,7-dimethoxynaphthothiophene-4,9-dione.Attempts by electrochemical and chemical methods to polymerise the thienonaphthoquinones were unsuccessful.
- Crayston, Joe A.,Iraqi, Ahmed,Mallon, Philip,Walton, John C.
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p. 1589 - 1596
(2007/10/02)
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- A Contribution to the Direct Observation of a Didehydroheteroaromatic with a Five-Membered Ring: 2,3-Didehydrothiophene
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The flash vacuum pyrolysis and the photolysis of 2,3-thiophenedicarboxylic acid anhydride (6) were investigated by using the technique of matrix isolation combined with FT-IR spectroscopy.No conclusive proof for the existence of 2,3-didehydrothiophene (1) could be found, but two hitherto unknown isomers were isolated and characterized: vinylidenethioketene (10) and thioformylvinylidenecarbene (15). Key Words: Matrix isolation / Photolysis / Vibrational spectra, theoretical / 2,3-Didehydrothiophene / Calculations, ab initio, semi-empirical
- Teles, Joaquim Henrique,Hess, Andes B.,Schaad, Lawrence J.
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p. 423 - 432
(2007/10/02)
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- The Synthesis of 5,8-Difluoronaphthothiophene-4,9-dione and its Facile Conversion to 2--5--8-fluoronaphthopyrrole-4,9-dione
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The synthesis of 5,8-difluoronaphthothiophene-4,9-dione (2a) has been accomplished.Treatment of 2a with 2,2-dimethylaminoethylamine leads to 2--5--8-fluoronaphthopyrrole-4,9-dione (6).
- Krapcho, A. Paul,Petry, Mary E.
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p. 1509 - 1510
(2007/10/02)
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- RADICAL IONS 49. Redox Reactions of some Thiphene Derivatives
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Trimethylsilyl- and cyano-substituted thiophenes can be reduced in THF using potassium and the resulting radical anions can be characterized by their electron spin resonance spectra.Attempts to oxidize thiophene derivatives with low first ionization potentials to their radical cations using the ALCl3/H2CCl2 oxidizing system failed except for dithienyldisulfide, the radical cation of which rearranges under the reaction conditions to the one of dithieno-p-dithiin.The photoelectron and electron spin resonance spectroscopic assignments are supported by MNDO as well as parametrized HMO calculations.
- Bock, H.,Roth, B.
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p. 211 - 224
(2007/10/02)
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