201004-08-2

Basic information

• Product Name: Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester
• Synonyms: Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester;ethyl thieno[3,2-b]thiophene-5-carboxylate
• CAS NO: 201004-08-2
• Molecular Formula: C₉H₈O₂S₂
• Molecular Weight: 212.28862
• Mol File: 201004-08-2.mol

Chemical Properties

• Boiling Point: 318.8±22.0 °C(Predicted)
• Appearance: /
• Density: 1.352±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester(201004-08-2)
• EPA Substance Registry System: Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester(201004-08-2)

Safety Data

• Hazardous Substances Data: 201004-08-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester is used as a precursor in the synthesis of organic semiconductors for its potential to contribute to the development of electronic devices. Its unique structure and properties make it a valuable component in the creation of materials with specific electronic characteristics, such as conductivity and stability.
Used in Organic Synthesis:
As an ester derivative, Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester is utilized as a reagent in various organic synthesis processes. Its ester functional group allows for a range of chemical reactions, making it a versatile building block in the synthesis of more complex organic molecules.
Used in Research and Development:
In the field of organic chemistry and materials science, Thieno[3,2-b]thiophene-2-carboxylic acid ethyl ester is employed as a subject of study for its potential applications and to understand its chemical behavior. Researchers explore its properties and interactions to innovate new uses and improve existing technologies in related industries.

Upstream product

• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 623-51-8 ethyl 2-sulfanylacetate 

Downstream Products

• 1356621-59-4 C₂₂H₂F₁₀S₄ 
• 1219808-50-0 C₂₂H₁₂S₄ 
• 469912-82-1 trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane 
• 124638-53-5 tetrabromo-thieno[3,2-b]thiophene 
• 1620070-13-4 C₃₁H₃₂N₄O₅S₂ 
• 1620074-61-4 C₂₆H₂₃N₃O₄S₂ 
• 1185221-51-5 2,5-di(5-phenylthiophen-2-yl)thieno[3,2-b]thiophene 
• 21210-90-2 2,5-di-thiophen-2-yl-thieno[3,2-b]thiophene 
• 1422279-59-1 C₂₈H₁₄F₆S₄ 
• 1185221-50-4 2,5-bis(5-(4-dodecylphenyl)thiophen-2-yl)thieno[3,2-b]thiophene 
• 1219036-84-6 (2Z)-1-(9-ethyl-9H-carbazol-2-yl)-3-hydroxy-3-thieno[3,2-b]thiophen-2-ylprop-2-en-1-one 
• 201004-10-6 2,5-bis(methylthio)thieno[3,2-b]thiophene 
• 1723-27-9 thieno[3,2-b]thiophene-2-carboxylic acid 

Relevant articles and documents

Enhanced electrochromic performances of Polythieno[3,2-b]thiophene with multicolor conversion via embedding EDOT segment

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.

A new alkyl substituted and method for the synthesis of polythiophene

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.

Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors

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

Conjugated polymer for organic thin-film transistor comprising of Quinoxaline and Thieno[3,2-b]thiophene

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)

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

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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

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.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX

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Versatile α,ω-disubstituted tetrathienoacene semiconductors for high performance organic thin-film transistors

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

Synthesis and characterization of new thieno[3,2-b]thiophene derivatives

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.

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

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.