1723-27-9

Basic information

• Product Name: THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID
• Synonyms: THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID;BUTTPARK 145\50-55;thieno[3,2-b]thiophene-5-carboxylic acid;Thieno[3,2-b]thiophene-2-carboxylic Acid
• CAS NO: 1723-27-9
• Molecular Formula: C₇H₄O₂S₂
• Molecular Weight: 184.24
• Product Categories: Carboxylic Acids;Thiophenes & Benzothiophenes;Carboxylic Acids;Fused Ring Systems;Thiophenes & Benzothiophenes
• Mol File: 1723-27-9.mol

Chemical Properties

• Melting Point: 225-227
• Boiling Point: 386.7 °C at 760 mmHg
• Flash Point: 187.6 °C
• Appearance: /
• Density: 1.601 g/cm³
• Vapor Pressure: 1.14E-06mmHg at 25°C
• Refractive Index: 1.769
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.40±0.30(Predicted)
• CAS DataBase Reference: THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID(1723-27-9)
• EPA Substance Registry System: THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID(1723-27-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-37/39-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 1723-27-9(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID is used as a reactant for the synthesis of versatile α,ω-disubstituted tetratienoacene semiconductors. These semiconductors are crucial for the development of high-performance organic thin-film transistors (OTFTs), which are essential components in modern electronic devices such as displays, sensors, and flexible electronics.
The application reason for THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID in this context is its ability to contribute to the formation of semiconductors with enhanced electronic properties, such as high charge carrier mobility and improved stability. These properties are vital for the performance and reliability of organic thin-film transistors, making THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID a valuable compound in the electronics industry.

InChI:InChI=1/C7H4O2S2/c8-7(9)6-3-5-4(11-6)1-2-10-5/h1-3H,(H,8,9)

Upstream product

• 251-41-2 thieno[3,2-b]thiophene 
• 124-38-9 carbon dioxide 
• 98800-10-3 methyl thieno<3,2-b>thiophene-2-carboxylate 
• 31486-86-9 thieno[3,2-b]thiophene-2-carbaldehyde 
• 6319-47-7 5-(2'-thiophenemethylene)rhodamine 
• 98-03-3 thiophene-2-carbaldehyde 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 121-69-7 N,N-dimethyl-aniline 
• 201004-08-2 ethyl thieno[3,2,-b]thiophene-2-carboxylate 
• 98778-43-9 3-(2-thienyl)-2-sulfanylpropenoic acid 
• 39131-69-6 1-thieno[3,2-b]thiophen-2-yl-ethanone 

Downstream Products

• 124638-53-5 tetrabromo-thieno[3,2-b]thiophene 
• 25121-88-4 2,3,5-tribromothieno[3,2-b]thiophene 
• 201004-10-6 2,5-bis(methylthio)thieno[3,2-b]thiophene 
• 31486-86-9 thieno[3,2-b]thiophene-2-carbaldehyde 
• 469912-82-1 trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane 
• 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 
• 1219808-50-0 C₂₂H₁₂S₄ 
• 1356621-59-4 C₂₂H₂F₁₀S₄ 
• 1273308-35-2 C₂₇H₁₈ClNO₅S₃ 
• 1273308-28-3 2-(4-chlorophenyl)-4-(thiopheno[2,3-d]thiophen-2-ylcarbonylamino)thiophene-3-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.

Small isomeric push-pull chromophores based on thienothiophenes with tunable optical (non)linearities

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.

HETEROCYCLIC COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

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

Discovery of Potent and Orally Bioavailable GPR40 Full Agonists Bearing Thiophen-2-ylpropanoic Acid Scaffold

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.

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)

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.

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