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
• Article Data: 12

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

General description

Thieno(3,2-b)thiophene (TT) is an electron rich conjugated polymer that has a quinoidal structure with a narrow band gap. It facilitates a strong intermolecular networking.

Application

Thieno[3,2-b]thiophene may be used as conjugated side chains in the synthesis of donor-acceptor copolymers. It finds potential applications in the enhancement of power conversion efficiency (PCE) for organic solar cells.

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).

Description

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).

Chemical Properties

White to yellow Solid

Uses

TT may be used as conjugated side chains in the synthesis of donor-acceptor copolymers. It finds potential applications in the enhancement of power conversion efficiency (PCE) for organic solar cells.

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

Upstream product

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

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 
• 201004-10-6 2,5-bis(methylthio)thieno[3,2-b]thiophene 
• 1723-27-9 thieno[3,2-b]thiophene-2-carboxylic acid 
• 139896-65-4 2,5-bis[2-(trimethylsilyl)ethynyl]thieno[3,2-b]thiophene 
• 31486-86-9 thieno[3,2-b]thiophene-2-carbaldehyde 
• 1155850-87-5 C₂₀H₁₂O₂S₂ 
• 1004784-50-2 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-thieno-[3,2-b]-thiophen-2-yl 
• 1396173-85-5 2,5-bis(methylsulfinyl)-3,6-diphenylthieno[3,2-b]thiophene 
• 1381839-80-0 2,5-bis(methylthio)-3,6-diphenylthieno[3,2-b]thiophene 
• 1420071-64-2 6,6,12,12-tetrakis(4-hexylphenyl)-6,12-dihydro-dithieno[2,3-d:2',3'-d]-s-indaceno[1,2-b:5,6-b']dithiophene 
• 1420071-65-3 3,9-bis(trimethylstannyl)-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene 
• 924894-85-9 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1,3,2-dioxaborolane 

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.

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)

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.