- Enhanced electrochromic performances of Polythieno[3,2-b]thiophene with multicolor conversion via embedding EDOT segment
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A heterocyclic oligomer, thieno[3,2-b]thiophene (TT) end-capped famous 3,4-ethylenedioxythiophene (EDOT) unit and their electrosynthesized polymer P(TT-EDOT-TT) have been facilely achieved. To in-depth understand the effects of structural modification on physico-chemical properties and electrochromic performances of monomers and/or polymers, the absorption spectroscopy, electrochemistry, micromorphology, and spectroelectrochemistry were systematically studied. In contrast to TT and EDOT, TT-EDOT-TT possessed extended π-conjugation and narrowed band gap in molecular level. Through carefully comparison with PTT, it has been found that the electrochromic performances of P(TT-EDOT-TT) film exhibited much higher optical contrast (69%, while 3% for PTT in the near-infrared region) and superior coloring efficiency (255.3 cm2 C?1, while 36.8 cm2 C?1 for PTT), and switching times (within 1 s, while more than 9 s for PTT). Notably, P(TT-EDOT-TT) film can achieve the mutual conversion between RGB primary colors (red–green–blue) under variable voltages, which hold quite promising for display applications.
- Xue, Yu,Xue, Zexu,Zhang, Wenwen,Zhang, Wenna,Chen, Shuai,Lin, Kaiwen,Xu, Jingkun
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- Small isomeric push-pull chromophores based on thienothiophenes with tunable optical (non)linearities
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Fourteen new D-π-A push-pull chromophores based on two isomeric thienothiophene donors and seven acceptors of various electronic natures have been designed and conveniently synthesized. In contrast to known thienothiophene push-pull molecules, the prepared small chromophores proved to be organic materials with easily tunable thermal, electrochemical and (non)linear optical properties. It has also been shown that small structural variation may result in significantly improved/varied fundamental properties. Very detailed structure-property relationships were elucidated within the systematically developed series of push-pull molecules, which may serve as a useful guide in designing new D-π-A molecules based on fused thiophene scaffolds.
- Podlesny, Jan,Pytela, Old?ich,Klikar, Milan,Jelínková, Veronika,Kityk, Iwan V.,Ozga, Katarzyna,Jedryka, Jaroslaw,Rudysh, Myron,Bure?, Filip
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supporting information
p. 3623 - 3634
(2019/04/14)
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- HETEROCYCLIC COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME
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The present invention relates to a heterocyclic compound represented by chemical formula 1 and an organic electronic device comprising the same. In chemical formula 1, X1 to X6 are S, R1 to R5 and R8 are hydrogen, R6 and R7 are the same or different from each other and each independently represents an alkyl group or an alkoxy group, and m1 and m2 are each 0 or 1.COPYRIGHT KIPO 2018
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Paragraph 0301-0304
(2018/10/26)
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- Discovery of Potent and Orally Bioavailable GPR40 Full Agonists Bearing Thiophen-2-ylpropanoic Acid Scaffold
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The free fatty acid receptor GPR40 is predominantly expressed in pancreatic β-cells and enhances insulin secretion in a glucose dependent manner. Therefore, GPR40 agonists are possible novel insulin secretagogues with reduced or no risk of hypoglycemia for the treatment of type 2 diabetes mellitus (T2DM). Chemically and structurally diverse GPR40 agonists with high safety are pursued for the clinical development of GPR40-based pharmacotherapeutics. Herein we report our design and discovery of a new chemotype of GPR40 agonists free of the typical phenylpropanoic acid scaffold. The thiophen-2-ylpropanoic acid containing GPR40 modulators functioned as full agonists with high-efficacy response (Emax) and reduced lipophilicity. Significantly, the lead compound in this series, (R)-7k, exhibited more potent in vitro glucose-stimulated insulin secretion and in vivo glucose-lowering effects (10 mg/kg, po) than the GPR40 partial agonist TAK-875, which was once in phase III clinical trials, and high selectivity over the relevant receptors GPR120 and PPARγ.
- Li, He,Huang, Qi,Chen, Cheng,Xu, Bin,Wang, He-Yao,Long, Ya-Qiu
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p. 2697 - 2717
(2017/04/21)
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- A new alkyl substituted and method for the synthesis of polythiophene
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The invention provides a method for replacing multi-thiophthene with beta-dialkyl in a synthesis formula I. The method comprises the following steps of: (f) reacting an intermediate in a formula 10 to obtain an intermediate in a formula 11; (g) reacting the intermediate in the formula 11 to obtain an intermediate in a formula 12; (h) reacting the intermediate in the formula 12 to obtain an intermediate in a formula 13; (i) reacting the intermediate in the formula 13 to obtain an intermediate in a formula 8; (j) reacting the intermediate in the formula 8 to obtain an intermediate in a formula 9; and (k) reacting the intermediate in the formula 9 to obtain a compound in a formula I. The invention further relates to the intermediate in the formula 9. The method disclosed by the invention is low in cost, simple in process, high in yield and low in pollution. The formulas 10, 11, 12, 13, 8 and 9 are shown in the description.
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- Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors
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Four π-conjugated benzo[1,2-b:4,5-b′]dithiophene (BDT) based polymers were synthesized for application in polymer solar cells. These polymers possessed desirable HOMO/LUMO levels for polymer photovoltaic applications. PBDTT-TTz and PBDTT-DTBT displayed strong absorption in the range of 300-650 nm, while PBDTT-DPP and PBDTT-TTDPP showed a further 100 nm extended absorption band. The lowest unoccupied molecular orbital energy levels of polymers were tuned effectively from -3.34 eV to -3.81 eV by fusing with different accepting units. A maximum power conversion efficiency of 2.60% was obtained from photovoltaic cells with a PBDTT-TTz:PC61BM (1:2, w/w) blend film as the active layer, with a short circuit current density of 8.37 mA cm-2, an open circuit voltage of 0.70 V, and a fill factor of 44.3%. This journal is
- Yu, Jiangsheng,Zhao, Baofeng,Nie, Xuemei,Zhou, Baojin,Li, Yang,Hai, Jiefeng,Zhu, Enwei,Bian, Linyi,Wu, Hongbin,Tang, Weihua
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p. 2248 - 2255
(2015/03/18)
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- Conjugated polymer for organic thin-film transistor comprising of Quinoxaline and Thieno[3,2-b]thiophene
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The present invention refers to [...] thieno [3, 2-b] thiophene using organic thin film transistor (organic thin-film transistor, OTFT) (conjugated polymer) relates to conjugated macromolecule type transition for electrolyte, more particularly 2, 3-bis (4- [...]) [...] -5, 8-(2, -5, 8-dibromoquinoxaline 3-Bis (4-hexylphenyl)) and 2, 5-bis (tri-n-methyl [...])-thieno [3, 2-b] thiophene (2, 5-Bis (Tri-n-methylstannyl)-thieno [3, 2-b] thiophene) Stille-coupling reactions of a produced through forging by use of conjugated macromolecule relates to (conjugated polymer). The present invention according to a heat conjugated macromolecule , each -3.3eV and -5.1eV HOMO and a LUMO value, the (band gap energy) 1.8eV band gap energy to useful as for anti-organic solar cells can be used. (by machine translation)
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- Optical activity of heteroaromatic conjugated polymer films prepared by asymmetric electrochemical polymerization in cholesteric liquid crystals: Structural function for chiral induction
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We electrochemically polymerized various achiral heteroaromatic monomers in left-handed helical cholesteric liquid crystal (CLC) media. Circular dichroism (CD) spectroscopy revealed that most of the resulting conjugated polymer films exhibited both the first negative and second positive Cotton effects near their absorption maxima. This indicates left-handed helical aggregation of the conjugated main chains, which is consistent with left-handed helical order of the CLC. This result suggests that the left-handed helical CLC environment induced left-handed helical aggregation of the polymers during the electrodeposition. However, CD intensity of the polymers depends on the structure of the parent monomers. Systematic investigation of the relationship between monomer structures and optical activity of the polymers indicates that linearity of the conjugated main chains and excluded volume interaction between the monomers and the CLC are important factors for producing optical activity of the polymers.
- Kawabata, Kohsuke,Takeguchi, Masaki,Goto, Hiromasa
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p. 2078 - 2091
(2013/06/04)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX
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Disclosed are compositions and methods for the prevention and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for preventing and/or treating diseases which are pathophysiologically related to GPR35 in a subject. The compounds having a formula (I), (II) or (III):
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- Versatile α,ω-disubstituted tetrathienoacene semiconductors for high performance organic thin-film transistors
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Facile one-pot [1 + 1 + 2] and [2 + 1 + 1] syntheses of thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (tetrathienoacene; TTA) semiconductors are described which enable the efficient realization of a new TTA-based series for organic thin-film transistors (OTFTs). For the perfluorophenyl end-functionalized derivative DFP-TTA, the molecular structure is determined by single-crystal X-ray diffraction. This material exhibits n-channel transport with a mobility as high as 0.30 cm 2V-1s-1 and a high on-off ratio of 1.8 × 107. Thus, DFP-TTA has one of the highest electron mobilities of any fused thiophene semiconductor yet discovered. For the phenyl-substituted analogue, DP-TTA, p-channel transport is observed with a mobility as high as 0.21 cm2V-1s-1. For the 2-benzothiazolyl (BS-) containing derivative, DBS-TTA, p-channel transport is still exhibited with a hole mobility close to 2 × 10-3 cm2V -1s-1. Within this family, carrier mobility magnitudes are strongly dependent on the semiconductor growth conditions and the gate dielectric surface treatment. Copyright
- Youn, Jangdae,Huang, Peng-Yi,Huang, Yu-Wen,Chen, Ming-Chou,Lin, Yu-Jou,Huang, Hui,Ortiz, Rocio Ponce,Stern, Charlotte,Chung, Ming-Che,Feng, Chieh-Yuan,Chen, Liang-Hsiang,Facchetti, Antonio,Marks, Tobin J.
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- Synthesis and characterization of new thieno[3,2-b]thiophene derivatives
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Three derivatives of thieno[3,2-b]thiophene end-capped with phenyl units have been synthesized and characterized by MALDI TOF mass spectroscopy, elemental analysis, UV-vis absorption spectroscopy and thermogravimetric analysis (TGA). All compounds were prepared using Pd-catalyzed Stille or Suzuki coupling reactions. Optical measurements and thermal analysis revealed that these compounds are promising candidates for p-type organic semiconductor applications.
- Ahmed, Moawia O.,Pisula, Wojciech,Mhaisalkar, Subodh G.
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p. 12163 - 12171
(2013/01/15)
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- Discovery of 2-(4-Methylfuran-2(5 H)-ylidene)malononitrile and thieno[3,2-b ]thiophene-2-carboxylic acid derivatives as G protein-coupled receptor 35 (GPR35) agonists
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Screening with dynamic mass redistribution (DMR) assays in a native cell line HT-29 led to identification of two novel series of chemical compounds, 2-(4-methylfuran-2(5H)-ylidene)malononitrile and thieno[3,2-b]thiophene-2- carboxylic acid derivatives, as GPR35 agonists. Of these, 2-(3-cyano-5-(3,4- dichlorophenyl)-4,5-dimethylfuran-2(5H)-ylidene)malononitrile (YE120) and 6-bromo-3-methylthieno[3,2-b]thiophene-2-carboxylic acid (YE210) were found to be the two most potent GPR35 agonists with an EC50 of 32.5 ±1.7 nM and 63.7 ±4.1 nM, respectively. Both agonists exhibited better potency than that of zaprinast, a known GPR35 agonist. DMR antagonist assays, knockdown of GPR35 with interference RNA, receptor internalization assays, and Tango β-arrestin translocation assays confirmed that the agonist activity of these ligands is specific to GPR35. The present study provides novel chemical series as a starting point for further investigations of GPR35 biology and pharmacology.
- Deng, Huayun,Hu, Haibei,He, Mingqian,Hu, Jieyu,Niu, Weijun,Ferrie, Ann M.,Fang, Ye
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experimental part
p. 7385 - 7396
(2011/12/04)
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- Thienothiophenes. Part 2. Synthesis, metallation and bromine→lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives
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Methods for the large-scale synthesis of thieno[3,2-b]thiophene [including a catalytic vapour-phase reaction (at 550°C) between 2-(2-thienyl)ethanol and carbon disulfide], its 2-carboxylic acid and its 3,6-dibromo and 2,3,5,6-tetrabromo derivatives are reported. With 2 mol equiv. of butyllithium thieno[3,2-6]thiophene gives its 2,5-dilithiated derivative and its 3,6-dibromo derivative gives the 3,6-dilithiated compound. By quenching with suitable electrophilic reagents these dilithiated compounds have been converted into various 2,5- or 3,6-disubstituted thieno[3,2-6]thiophenes, respectively. Likewise 2,3,5,6-tetrabromothieno[3,2-b]thiophene has been converted into 2,5-disubstituted 3,6-dibromothieno[3,2-b]thiophenes.
- Fuller, Lance S.,Iddon, Brian,Smith, Kevin A.
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p. 3465 - 3470
(2007/10/03)
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- Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid.
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Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) th
- Kukolja,Draheim,Graves,Hunden,Pfeil,Cooper,Ott,Counter
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p. 1896 - 1903
(2007/10/02)
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