124638-53-5

Basic information

• Product Name: TETRABROMO-THIENO[3,2-B]THIOPHENE
• Synonyms: TETRABROMO-THIENO[3,2-B]THIOPHENE;2,3,5,6-TetrabroMothieno[3,2-b]thiophene;Perbromothieno[3,2-b]thiophene;Thieno[3,2-b]thiophene,2,3,5,6-tetrabromo-.;2,3,5,6-Tetrabromothieno[3,2-b]thiophene
• CAS NO: 124638-53-5
• Molecular Formula: C₆Br₄S₂
• Molecular Weight: 455.81
• Mol File: 124638-53-5.mol

Chemical Properties

• Melting Point: 232.0 to 236.0 °C
• Boiling Point: 443.2°C at 760 mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 2.725g/cm³
• Vapor Pressure: 1.23E-07mmHg at 25°C
• Refractive Index: 1.801
• CAS DataBase Reference: TETRABROMO-THIENO[3,2-B]THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRABROMO-THIENO[3,2-B]THIOPHENE(124638-53-5)
• EPA Substance Registry System: TETRABROMO-THIENO[3,2-B]THIOPHENE(124638-53-5)

Safety Data

• Hazardous Substances Data: 124638-53-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TETRABROMO-THIENO[3,2-B]THIOPHENE is used as a key intermediate in the synthesis of various organic compounds. Its reactivity, stemming from the bromine atoms and the thiophene rings, makes it a valuable building block for creating complex molecules with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Materials Science:
In the field of materials science, TETRABROMO-THIENO[3,2-B]THIOPHENE is employed as a component in the development of novel materials with specific properties. The heavy and polar nature of the compound can contribute to the creation of materials with tailored characteristics, such as improved thermal stability, enhanced electrical conductivity, or specific optical properties, depending on the intended application.
Used in Research Applications:
TETRABROMO-THIENO[3,2-B]THIOPHENE is utilized as a research chemical in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studies aimed at understanding the fundamental aspects of chemical reactions, exploring new synthetic routes, or investigating the potential of the compound in various applications, such as catalysis or the development of new materials with specific functionalities.

InChI:InChI=1/C6Br4S2/c7-1-3-4(12-5(1)9)2(8)6(10)11-3

Upstream product

• 251-41-2 thieno[3,2-b]thiophene 
• 1723-27-9 thieno[3,2-b]thiophene-2-carboxylic acid 
• 25121-88-4 2,3,5-tribromothieno[3,2-b]thiophene 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 201004-08-2 ethyl thieno[3,2,-b]thiophene-2-carboxylate 

Downstream Products

• 201004-20-8 3,6-dibromo-2,5-bis(6-methylcyclohex-1-enyl)thieno<3,2-b>thiophene 
• 1356621-59-4 C₂₂H₂F₁₀S₄ 
• 1219808-50-0 C₂₂H₁₂S₄ 
• 35093-32-4 2,3,5,6-tetraphenylthieno[3,2-b]thiophene 

Relevant articles and documents

Novel Electron Acceptors Bearing a Heteroquinonoid System. II. Synthesis and Conductive Complexes of 2,5-Bis(dicyanomethylene)-2,5-dihydrothienothiophene, 2,6-Bis(dicyanomethylene)-2,6-dihydrothienothiophene, and Their Derivatives

Novel heteroquinoid compounds as potential electron acceptors, 2,5-bis(dicyanomethylene)-2,5-dihydrothienothiophene (4a), 3,6-dibromo derivative, 2,6-bis(dicyanomethylene)-2,6-dihydrothienothiophene, 3,5-dibromo derivative, and 4,4-dioxide were synthesized by the action of tetracyanoethylene oxide or by a Pd(0)-catalyzed substitution reaction with sodium dicyanomethanide on the corresponding α,α'-dihalo-substituted fused thiophenes.They show effectively diminished on-site Coulomb repulsion owing to the extensive conjugation, and most of their molecular complexes with various electron donors exhibit very high electrical conductivies up to metallic region.In addition, X-ray crystallographic analysis of the complex of 4a with bis(ethylenedithio)tetrathiafulvalene has elucidated that sulfur atoms embedded in 4a molecule are capable of inducing a significant intermolecular interaction, forming a sheet-like network structure.

Hexathienoacene: Synthesis, characterization, and thin-film transistors

A new linear six thiophene-fused system of hexathienoacene (HTA) has been synthesized, which has also been compared with pentathienoacene (PTA) in terms of optical, electrochemical, and charge-transfer properties of organic semiconductors. The highest mobility of 0.06 cm2 V-1 s-1 with a current on/off ratio of 105 on n-octadecyltrichlorosilane (OTS)-treated SiO2/Si substrates has been achieved.

Tetrasubstituted Thieno[3,2- b]thiophenes as Hole-Transporting Materials for Perovskite Solar Cells

Three hole-transporting materials (HTMs) were prepared following a straightforward synthetic route by cross-linking arylamine-based ligands with a simple thieno[3,2-b]thiophene (TbT) core. The novel HTMs were fully characterized with standard techniques t

Molecular design of benzothienobenzothiophene-cored columnar mesogens: Facile synthesis, mesomorphism, and charge carrier mobility

Benzothienobenzothiophene (BTBT) liquid-crystalline semiconductors are arousing a lot of interest due to their long-range ordered, self-organizational abilities and high-charge carrier transport properties. In this work, we report the design and the straightforward synthesis of a homologous series of compounds containing the BTBT substructure by the successive Suzuki cross-coupling and FeCl3 oxidative Scholl cyclodehydrogenation reaction. Target π-conjugated aromatic, H-shaped sanidic mesogens self-organize into a classical hexagonal columnar mesophase over wide temperature ranges as deduced from polarized optical microscopy (POM), differential scanning calorimetry (DSC), and small-angle X-ray scattering (SAXS) investigations. UV/Vis absorption and photoluminescence spectra, measured in both solution and films, revealed strong photoluminescence with high quantum yields. The charge carrier mobility measured by the time-of-flight (TOF) technique showed a balanced ambipolar hole and electron mobility in the range of 10-3 cm2 V-1 s-1 between 100 and 230 °C in the mesophase. These BTBT-based columnar liquid crystals may represent attractive candidates to be incorporated within one-dimensional organic optoelectronic devices.

Thiophene or furan derivative and organic light emitting device using the derivative

The invention discloses a thiophene or furan derivative and an organic light emitting device using the derivative, and belongs to the technical field of organic optoelectronic materials. Thiophene and [3, 2-b] thiophene, furan and [3, 2-b] furan, or thiophene and [3, 2-b] thiophene 1, 1, 4, 4-tetroxide is adopted as a main structure in the derivative, the molecular weight of materials, pi conjugacy and eletrophilicity, charge transfer capacity, photochromism and the like can be adjusted by changing the linking method of a donor, meanwhile the problem that current carriers of a unipolar luminescent material are not balanced can be effectively solved, and thus the thiophene or furan derivative has high luminescence property, electronic transmission performance, membrane stability, thermostability and triplet state energy. The organic light emitting device prepared from the thiophene or furan derivative has the advantages of being excellent in electron chemistry performance and thermostability, long in service life and the like, and has a high luminescence efficiency even on the condition of a low starting voltage.

Stereoscopic structure organic semiconductor material and monomer preparation method

The invention discloses a stereoscopic structure organic semiconductor material and a monomer preparation method. The structural formula of monomer of the stereoscopic structure organic semiconductor material is shown in the instruction. The preparation method is simple, a butterfly monomeric compound is obtained and has four different polymerization sites, so that the compound polymerized at different sites can be obtained under different polymerization conditions, and different types of stereoscopic polymer organic semiconductor materials are obtained. Thiophene or EDOT (ethylenedioxy thiophene) derivatives are added to a mother nucleus, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels of the material are further adjusted, the excellent organic semiconductor material is obtained, the preparation process is simple and convenient, product cost is greatly reduced, and a foundation is provided for application.

BIS-THIENOBENZOTHIENOTHIOPHENE COMPOUNDS AND PROCESS FOR THEIR PREPARATION

The present invention relates to bis-thienobenzothienothiophene compounds and a process for their preparation. More in particular, the present invention relates to a new angular bis-thienobenzothienothiophene compound and the process for its preparation wherein said process comprises reacting at least one dihalogenated dithiophene compound with at least one terminal alkyne and the subsequent double annulation reaction. Said bis-thienobenzothienothiophene compounds can be appropriately functionalized and polymerized to produce electron donor compounds that can be advantageously used in the construction of photovoltaic devices or semiconductor polymers. Furthermore, said bis-thienobenzothienothiophene compounds, after functionalization, may be advantageously used as spectral converters in luminescent solar concentrators.

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.

High-performance organic field-effect transistors based on single-crystalline microribbons of a two-dimensional fused heteroarene semiconductor

A novel two-dimensional organic semiconductor material [1]benzothieno[3,2-b][1]benzothieno[2,1-b:3,4-b′:6,5-b″:7,8-b]tetra(benzothiophene) (BTBTTBT) which largely extends the scope of the π-conjugated framework of heteroarene through "H" configuration was synthesized and its thermal, optical and electrochemical properties were investigated. This 2D molecule enables the easy growth of single-crystalline microribbons by the physical vapor transport method, which were evidenced by XRD, SEM and TEM. The single-crystalline OFET devices were fabricated based on the individual BTBTTBT microribbon and the remarkable high mobility of 17.9 cm2 V-1 s-1 and on/off ratios of over 107 could be achieved.

Synthesis, crystal structure, and polymerization of butterfly-shaped thieno[3,2-b]thiophene oligomers

A series of new butterfly-shaped thieno[3,2-b]thiophene oligomers with phenyl and thiophene units were synthesized through Suzuki coupling and Stille coupling reactions. The optical and thermal properties of these materials can be tuned by varying both su