53229-47-3Relevant articles and documents
Synthesis and characterization of three thienopyridazine-based copolymers and their application in OFET
Lim, Chia Juan,Li, Lu,Lei, Yanlian,Zhou, Feng,Wu, Bo,Liu, Xuyao,Zhu, Furong,Ong, Beng S.,Hu, Xiao,Su, Haibin,Ng, Siu-Choon
, p. 1523 - 1527 (2016)
Three low band gap thienopyridazine-based donor-acceptor conjugated polymers, PDTTPTT, PDTTPBT, and PDTTPBDT were synthesized by the Stille copolymerization of thienopyridazine with thienothiophene, benzodithiophene, and bithiophene, respectively. The optical band gaps of PDTTPTT, PDTTPBT, and PDTTPBDT polymers were determined as 1.41 eV, 1.43 eV, and 1.58 eV, respectively by UV absorption. The deep HOMO level of the three polymers was determined by cyclic voltammetry. The three polymers were fabricated to form organic field-effect transistors and their performance as p-type semiconductors were studied.
Structurally simple thienodipyrandione-containing reversible fluorescent switching piezo- and acido-chromic materials
Rao M, Rajeswara,Liao, Chia-Wei,Sun, Shih-Sheng
, p. 6386 - 6394 (2013)
We report here the structure-property correlations of a series of anthracene/pyrene derivatives grafted on a rigid, planar, and well conjugated endo-cyclic alkenyl lactone (thienodipyrandione) that exhibited aggregation induced emission. Unlike typical vinylene based solid-state fluorescence materials, rigid thienodipyrandione moieties can bestow a higher order of conformational twist as well as enhanced intermolecular interactions by C-H...O interactions due to the presence of a carbonyl group that leads to enhanced thermal stability. Compounds TDAn and TDAnPh exhibit distinct piezofluorochromic properties in which emission colors can be switched by grinding and heating. Based on a variety of spectroscopic techniques including XRD, DSC, and NMR, the observed piezochromic emission is attributed to the result of phase transition from structural crystalline (order) to amorphous (disorder) state or vice versa. Most uniquely, one of the anthracene derivatives, TDAn, displayed specific acido-fluorochromism whereas the other congener, TDAnPh, did not, even though they are structurally very similar. Crystal structure analysis revealed that a combination of various secondary interactions such as C-H...O, π-π and C-H...π interactions all play key roles in the supramolecular assemblies to display such distinctive features. The current study has disclosed a class of new stimuli-responsive materials with great potential in applications for micro-environmental sensing, optical switching and recording.
ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS
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Page/Page column 98, (2011/04/14)
Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising formula (I); Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.
Synthesis of thiophenecarboxamides, thieno[3,4-c]pyridin-4(5H)-ones and thieno[3,4-d]pyrimidin-4(3H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP)
Shinkwin, Anne E.,Whish, William J. D.,Threadgill, Michael D.
, p. 297 - 308 (2007/10/03)
Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. Treatment of 3-cyanothiophene with potassium nitrate and concentrated sulphuric acid gave 5-nitrothiophene-3-carboxamide. 4-Nitrothiophene-2-carboxamide and 5-nitrothiophene-2-carboxamide were formed similarly from 2-cyanothiophene. Reduction with tin(II) chloride gave the corresponding aminothiophenecarboxamide salts which were isolated via their N-Cbz derivatives. Lithiation of 3,4-dibromothiophene at -116°C and quenching with alkyl chloroformates gave 4-bromothiophene-3-carboxylates, which were hydrolysed to 4-bromothiophene-3-carboxylic acid. Hurtley reactions with the enolates of pentane-2,4-dione and of 1-phenylbutane-1,3-dione, followed by acyl cleavage, led to 4-(2-oxopropyl)thiophene-3-carboxylic acid and 4-phenacylthiophene-3-carboxylic acid, respectively. Condensation with ammonia in acetic acid gave 6-methyl- and 6-phenyl-thieno[3,4-c]pyridin-4-ones, which were selectively nitrated at the 1- and 7-positions or were dinitrated. Ethyl 4-acetamido- and 4-benzamido-thiophene-3-carboxylates were cyclised to 2-methyl- and 2-phenyl-thieno[3,4-d][1,3]oxazin-4-ones, respectively. Ring-opening with ammonia and recyclisation led to 2-substituted thieno[3,4-d]pyrimidin-4-ones. The aminothiophenecarboxamides are analogues of 3-aminobenzamide, a selective inhibitor of poly(ADP-ribose)polymerase (PARP); the thienopyridinones and the thienopyrimidinones are analogues of isoquinolin-1-ones and quinazolin-4-ones, respectively, which inhibit this enzyme. In preliminary assays, several thienopyridinones and thienopyrimidinones showed potent inhibitory activity against PARP. Copyright (C) 1999 Published by Elsevier Science Ltd.
Preparation and Characterisation of Thienonaphthoquinones and their Radical Ions
Crayston, Joe A.,Iraqi, Ahmed,Mallon, Philip,Walton, John C.
, p. 1589 - 1596 (2007/10/02)
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.
THE CONDUCTIVE SULFUR/CARBON MIXTURE CATHODE. AN EFFICIENT SYNTHESIS OF THIOPHENES AND RELATED COMPOUNDS FROM ACETYLENES
Guillanton, Georges Le,Do, Quang Tho,Simonet, Jacques
, p. 2261 - 2262 (2007/10/02)
The electroreduction of Michael acceptors such as acetylenic derivatives at a compact sulfur-carbon electrode in aprotic media affords thioorganic compounds, mainly thiophenes, in fairly high yields.Their formation is discussed as a function of the electronic effect of the substituents on the acetylenic triple bond.
