251-41-2

Basic information

• Product Name: Thieno[3,2-b]thiophene
• Synonyms: THIENO[3,2-B]THIOPHENE;1,4-DITHIAPENTALENE;1,4-THIOPHTHENE;BUTTPARK 145\50-51;1,4-Dithiapentalene 1,4-Thiophthene;4-Dithiapentalene 1,4-Thiophthene;Thieno[3,2-b]thiophen;Thieno[3,2-b]thiophene 1,4-Dithiapentalene
• CAS NO: 251-41-2
• Molecular Formula: C₆H₄S₂
• Molecular Weight: 140.23
• Product Categories: Electronic Chemicals;Fused Ring Systems;Heterocycle-oher series
• Mol File: 251-41-2.mol

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 71 °C / 1mmHg
• Flash Point: 98℃
• Appearance: /
• Density: 1.367 g/cm³
• Vapor Pressure: 0.144mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: Thieno[3,2-b]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[3,2-b]thiophene(251-41-2)
• EPA Substance Registry System: Thieno[3,2-b]thiophene(251-41-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 251-41-2(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Solar Cells:
Thieno[3,2-b]thiophene is used as conjugated side chains in the synthesis of donor-acceptor copolymers for organic solar cells. Its application aims to enhance the power conversion efficiency (PCE) of these solar cells by leveraging its electron-rich conjugated polymer properties and strong intermolecular networking.
2. Used in Organic Field-Effect Transistors (OFETs):
Thieno[3,2-b]thiophene serves as an intermediate for the synthesis of small molecules and polymers in the application of organic field-effect transistors. Its unique structure and properties contribute to the development of high-performance OFETs.
3. Used in Organic Photovoltaic Devices (OPV):
Thieno[3,2-b]thiophene is also utilized as an intermediate in the synthesis of materials for organic photovoltaic devices. Its electron-rich nature and quinoidal structure play a crucial role in improving the efficiency and performance of these devices.

Classification

Thiophene, Fused thiophene, Dithiapentalene, Heterocylic aromatics, Five-membered ring, Semiconductor synthesis intermediates, Low band gap polymers OFETs, Organic Photovoltaics, Polymer solar cells

preparation

Thieno[3,2-b]thiophene, also known as thienothiophene (TT), is a heterocyclic compound. It belongs to the family of fused thiopehenes and is widely used as an intermediate for the synthesis of small molecules and polymers in the application of organic field-effect transistors (OFETs) and organic photovoltaic devices (OPV). Fused thiophenes are more electron-rich and more structurally rigid, with extended π-conjugation so they are good candidates for adjusting the band gap of the organic polymer semiconducting materials, i.e. Poly[2,5-bis(3-hexadecylthiophen-2-yl)thieno[3,2-b]thiophene] (also known as PBTTT).

InChI:InChI=1/C6H4S2/c1-3-7-6-2-4-8-5(1)6/h1-4H

Upstream product

• 96-43-5 2-thienyl chloride 
• 110-81-6 Diethyl disulfide 
• 51639-98-6 ethyldisulfanyl 
• 352-93-2 diethyl sulphide 
• 3600-24-6 diethyltrisulfane 
• 75-08-1 ethanethiol 
• 6911-35-9 2-ethylthiophene 
• 250-84-0 thieno[2,3-b]thiophene 
• 25121-88-4 2,3,5-tribromothieno[3,2-b]thiophene 
• 74-86-2 acetylene 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 52-90-4 L-Cysteine 
• 50-81-7 ascorbic acid 

Downstream Products

• 25121-87-3 2,5-dibromothieno[3,2-b]thiophene 
• 124638-53-5 tetrabromo-thieno[3,2-b]thiophene 
• 937187-29-6 2,5-diiodothieno[3,2-b]thiophene 
• 35022-09-4 2-phenylthieno<3,2-b>thiophene 
• 37882-75-0 2,5-Thieno<3,2-b>thiophendicarbaldehyd 
• 25121-88-4 2,3,5-tribromothieno[3,2-b]thiophene 
• 201004-10-6 2,5-bis(methylthio)thieno[3,2-b]thiophene 
• 1723-27-9 thieno[3,2-b]thiophene-2-carboxylic acid 
• 648430-73-3 α,α-bis(thieno[3,2-b]thiophene) 
• 139896-65-4 2,5-bis[2-(trimethylsilyl)ethynyl]thieno[3,2-b]thiophene 

Relevant articles and documents

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.

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.

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.

Preparation of 4,7-dibromobenzo[b]thiophene as a versatile building block and synthetic application to a bis(ethynylthienyl)oligoarene system

Benzo[b]thiophene, 4,7-dibromobenzo[b]thiophene, thieno[3,2-b]thiophene, and 3-bromothieno[3,2-b]thiophene were prepared by AuCl-catalyzed cyclization of (t-butylsulfanyl)(ethynyl)benzenes or (t-butylsulfanyl)(ethynyl)thiophenes. Several reactions of 4,7-dibromobenzo[b]thiophene were investigated, including metallation and cross coupling reactions.

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.

Aroma compounds generated from thermal reaction of l-ascorbic acid with l-cysteine

The reaction of l-ascorbic acid with l-cysteine in heated aqueous solution (141 ± 1 °C) at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.00) for 2 h, resulted in the formation of a complex mixture of aroma volatiles. The volatile compounds generated were analysed by SPME-GC-MS. The results gave 43 aroma compounds. The reaction between l-ascorbic acid and l-cysteine led mainly to the formation of alicyclic sulphur compounds, thiophenes, thienothiophenes, thiophenones, thiazoles and pyrazines, most of which contain sulphur. Many of these volatiles had meaty flavour. The origin of many of the compounds was explained. The studies showed that thienothiophenes and thienones were formed mainly at acidic pH. In contrast, higher pH values could promote the production of thiophenes, thiazoles and pyrazines.

Thienothiophenes. Part 2. Synthesis, metallation and bromine→lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives

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.

High-Temperature Organic Synthesis. XLIV. Reaction of 2-Chlorothiophene with the System Dialkyl Disulfide-Acetylene

A convenient procedure is proposed for simultaneous preparation of thiophene and thienothiophene from readily accessible reactants by thermolysis of 2-chlorothiophene in the system diethyl disulfide-acetylene at 500-700 deg C.Thiophene results mainly from the reaction of acetylene with vinylthio radicals generated by thermal decomposition of diethyl disulfide.Thienothiophene is formed by reaction of acetylene with 2-thienylthio radicals generated by reaction of 2-chlorothiophene with hydrogen sulfide which is a product of thermal decomposition of diethyl disulfide.A mixture of lower dialkyl disulfides (disulfide oil) can be used instead of diethyl disulfide.