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Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,5-dibromothiophene 1,1-dioxide is used as a building block in the synthesis of pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new drugs and pesticides.
Used in Organic Electronics Industry:
2,5-dibromothiophene 1,1-dioxide is used in the production of organic electronic materials, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells. Its electronic properties contribute to the performance and efficiency of these devices.
Used in Organic Semiconductors:
2,5-dibromothiophene 1,1-dioxide has been investigated for its potential use in organic semiconductors. Its electronic properties and stability make it a promising candidate for applications in organic field-effect transistors and other semiconductor devices.
Used as a Corrosion Inhibitor in Metal Surfaces:
2,5-dibromothiophene 1,1-dioxide has also been studied for its potential as a corrosion inhibitor in metal surfaces. Its ability to form protective layers on metal surfaces can help prevent corrosion and extend the lifespan of metal components in various industries.

Upstream product

• 3141-27-3 2,5-dibromothiophen 
• 143810-36-0 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide 

Relevant academic research and scientific papers

Stimuli-responsive azulene-based conjugated oligomers with polyaniline-like properties

Novel azulene building blocks, prepared via the cycloaddition of thiophene-S,S-dioxides and fulvenes, allow for incorporation of the seven-membered ring of the azulene nucleus directly into the backbone of conjugated materials. This unique mode of incorporation gives remarkably stable, stimuli-responsive materials upon exposure to acid. This simple doping/dedoping strategy provides for effective optical band gap control and on/off fluorescence switching, reminiscent of polyaniline.

Molecular length dictates the nature of charge carriers in single-molecule junctions of oxidized oligothiophenes

To develop advanced materials for electronic devices, it is of utmost importance to design organic building blocks with tunable functionality and to study their properties at the molecular level. For organic electronic and photovoltaic applications, the ability to vary the nature of charge carriers and so create either electron donors or acceptors is critical. Here we demonstrate that charge carriers in single-molecule junctions can be tuned within a family of molecules that contain electron-deficient thiophene-1,1-dioxide (TDO) building blocks. Oligomers of TDO were designed to increase electron affinity and maintain delocalized frontier orbitals while significantly decreasing the transport gap. Through thermopower measurements we show that the dominant charge carriers change from holes to electrons as the number of TDO units is increased. This results in a unique system in which the charge carrier depends on the backbone length, and provides a new means to tune p- and n-type transport in organic materials.

A facile route to thiophene-1,1-dioxides bearing electron-withdrawing groups

No commonly available synthetic method for thiophene-1,1-dioxides with strong EWGs has been described to date. Trifluoroperacetic acid in acetonitrile in the absence of water is shown to oxidise thiophenes, including examples possessing an electron-withdrawing group such as sulfonyl or alkoxycarbonyl. An easy and ready for scale-up procedure is developed, some formerly unknown thiophene-1,1-dioxides are obtained.

Push-pull thiophene-based small molecules with donor and acceptor units of varying strength for photovoltaic application: Beyond P3HT and PCBM

Here is reported an expedient synthesis implementing enabling technologies of a family of thiophene-based heptamers alternating electron donor (D) and acceptor (A) units in a D-A′-D-A-D-A′-D sequence. The nature of the peripheral A groups (benzothiadiazole vs. thienopyrrole-dione vs. thiophene-S,S-dioxide) and the strength of the donor units (alkyl vs. thioalkyl substituted thiophene ring) have been varied to finely tune the chemical-physical properties of the D-A oligomers, to affect the packing arrangement in the solid-state as well as to enhance the photovoltaic performances. The optoelectronic properties of all compounds have been studied by means of optical spectroscopy, electrochemistry, and density functional theory calculations. Electrochemical measurements and Kelvin probe force microscopy (KPFM) predicted a bifunctional behaviour for these oligomers, suggesting the possibility of using them as donor materials when blended with PCBM, and as acceptor materials when coupled with P3HT. Investigation of their photovoltaic properties confirmed this unusual characteristic, and it is shown that the performance can be tuned by the different substitution pattern. Furthermore, thanks to their ambivalent character, binary non-fullerene small-molecule organic solar cells with negligible values of HOMO and LUMO offsets were also fabricated, resulting in PCEs ranging between 2.54-3.96%. This journal is

A novel method for the oxidation of thiophenes. Synthesis of thiophene 1,1-dioxides containing electron-withdrawing substituents

A novel method for the synthesis of thiophene 1,1-dioxides by oxidation of substituted thiophenes with trifluoroperoxyacetic acid was developed. The effect of the solvent nature on the course of the reaction was studied and optimum conditions for the oxid

Oxidation of Sulfur-Containing Compounds with HOF-CH3CN

The HOF-CH3CN complex, easily prepared by passing F2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. All types of sulfides have been oxidized to sulfones in excellent yields, in a few minutes at room temperature. The reaction proceeds through the formation of sulfoxides which at low temperatures of around -75°C could be isolated in good yields. It was demonstrated through a reaction with thianthrene 5-oxide (20) that HOF·CH3CN is strongly electrophilic in nature. Sulfides with an electron-depleted sulfur atom such as perfluoroalkyl or aryl sulfides, which could not be well oxidized by any other method, were also efficiently converted to the corresponding sulfones in minutes. Thiophenes are generally hard to oxidize to the corresponding S-dioxides since the conditions required by the orthodox oxidants encourage consecutive typical ene and diene reactions. HOF·CH3CN requires short reaction times and low temperatures, thus enabling the isolation of thiophene dioxides, some of which could not be made by any other way. It seems that apart from unprotected amines, other functional groups such as aromatic rings, ketones, hydroxyls, and ethers do not interfere, since the sulfur atom reacts considerably faster.

A Novel Oxidation of Thiophenes using HOF*MeCN

The complex, HOF*MeCN made directly by bubbling fluorine through aqueous MeCN, oxidizes various types of thiophenes to the corresponding S,S-dioxides, including ones which could not be oxidized by any other method.

PREPARATION OF 2,5-DISILYLATED THIOPHENE DERIVATIVES AND THEIR CONVERSION TO 2,5-DIHALO DERIVATIVES

2,5-Disilylated thiophenes were prepared and readily oxidized with m-chloroperbenzoic acid (m-CPBA) to give the corresponding 1,1-dioxides.The thiophene dioxide was converted to 2,5-dihalogenothiophene dioxides with halogenating agents.

AN EXTREMELY EFFICIENT SYNTHESIS OF THIOPHENE 1,1-DIOXIDES. OXIDATION OF THIOPHENE DERIVATIVES WITH DIMETHYLDIOXIRANE

Dimethyldioxirane was found to oxidize electron-rich thiophene derivatives, including sterically hindered thiophenophanes, to the corresponding thiophene 1,1 dioxides in excellent yields.Electron-withdrawing groups on a thiophene ring substantially retard