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Usage

Uses

Used in Organic Synthesis:
2,5-Bis(trimethylsilyl)thiophene is used as a reagent for the incorporation of thiophene rings into different molecules, which is crucial for the synthesis of complex organic compounds with specific properties.
Used in Protective Group Chemistry:
In the field of organic chemistry, 2,5-Bis(trimethylsilyl)thiophene serves as a protective group for reactive functional groups, allowing chemists to selectively modify certain positions within a molecule without affecting others, which is essential for the synthesis of intricate molecular structures.
Used in Electronic Devices:
2,5-Bis(trimethylsilyl)thiophene is utilized in the preparation of functional materials for electronic devices, capitalizing on the unique electronic properties of thiophene-containing compounds to enhance device performance.
Used in Materials Science:
2,5-BIS(TRIMETHYLSILYL)THIOPHENE is also applied in materials science for the development of materials with distinctive optical properties, leveraging the thiophene ring's characteristics to create innovative materials for various applications.
Used in the Preparation of Conductive Polymers:
2,5-Bis(trimethylsilyl)thiophene is used as a monomer in the synthesis of conductive polymers, which are essential in the fabrication of organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs), due to their ability to facilitate charge transport and improve device efficiency.

Upstream product

• 188290-36-0 thiophene 
• 75-77-4 chloro-trimethyl-silane 
• 3141-27-3 2,5-dibromothiophen 
• 63762-35-6 2,5-dilithiothiophene 
• 93041-07-7 3-Bromo-2,5-bis(trimethylsilyl)thiophene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 146434-35-7 2,5-bis(trimethylsilyl)thiophene-S-oxide 
• 1066-54-2 trimethylsilylacetylene 
• 112051-54-4 3,5-dibromo-2-(trimethylsilyl)thiophene 
• 234773-49-0 (Z,Z)-1,4-bis(thiocyanato)-1,4-bis(trimethylsilyl)-1,3-butadiene 
• 259109-99-4 Bernsteinsaeure-bis-(trimethylsilyl)-ester 
• 175658-90-9 3,4-dibromo-2,5-bis(trimethylsilanyl)thiophene 
• 87495-58-7 3,8-bis(trimethylsilyl)-1,2,5,6-tetrathiacyclooctane 
• 87495-56-5 1-trimethylsilyl-2,3,4,5,6-pentathiacycloheptane 

Downstream Products

• 3141-27-3 2,5-dibromothiophen 
• 1445-78-9 2,5-Diphenyl-thiophene 
• 1412912-69-6 1-(5-trimethylsilylthien-2-yl)-2,3,4,5-tetraphenylborole 
• 18245-28-8 2-(trimethylsilyl)thiophene 
• 23395-56-4 5-chloro-2-trimethylsilylthiophene 
• 130789-01-4 5-chloro-2-phenylselenothiophene 
• 130789-02-5 2-phenylseleno-5-trimethylsilylthiophene 
• 18246-28-1 2-bromo-5-trimethylsilylthiophene 
• 130789-03-6 2-bromo-5-phenylselenothiophene 
• 94800-55-2 2-(phenylselenenyl)thiophene 

Relevant academic research and scientific papers

Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers

Conjugated organoboranes have emerged as attractive hybrid materials for optoelectronic applications. Herein, a highly efficient, environmentally benign catalytic B-C bond formation method is presented that uses organosilicon compounds, dibromoboranes, and the metal-free organocatalyst Me3SiNTf2. This Si/B exchange approach has been successfully applied to the synthesis of arylborane molecules 4a-c, oligomers 8a,b, and polymers 8a′,b′. Photophysical investigations, supported by TD-DFT calculations, reveal highly effective π-conjugation in thienyl- and furylborane species; the latter are also highly emissive.

SILYLATION OF AROMATIC HETEROCYCLES BY DISILANES USING POTASSIUM ALKOXIDE CATALYSTS

The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates, said system consisting essentially of a mixture of (a) at least one organodisilane and (b) at least alkoxide base, preferably a potassium alkoxide base, and said methods comprising contacting a quantity of the organic substrate with a mixture consisting essentially of (a) at least one organodisilane and (b) at least one alkoxide base, preferably a potassium alkoxide, under conditions sufficient to silylate the heteroaromatic substrate.

CYCLOHEXADIENE FULLERENE DERIVATIVES

The invention relates to novel fullerene derivatives, to methods for their preparation and educts or intermediates used therein, to mixtures and formulations containing them, to the use of the fullerene derivatives, mixtures and formulations as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising, or being prepared from, these fullerene derivatives, mixtures or formulations.

Synthesis of thiophene 1,1-dioxides and tuning their optoelectronic properties

A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1

Photochemistry of thiophene-S-oxide derivatives

Photolysis of substituted thiophene-S-oxides in solution results in the formation of either the corresponding thiophene or furan, in addition to uncharacterized materials. No good rationalization is available for the choice of which pathway may predominat

Synthesis of new silylated sulfur-containing heterocycles through thionation of bis(acylsilanes)

The thionation of bis(acylsilanes) with spacers of variable size with hexamethyldisilathiane under cobalt(II) chloride or trimethylsilyl triflate catalysis affords 2,5-bis(trialkylsilyl)-thiophenes, 2,6-bis(trialkylsilyl)-4H- thiopyrans and 2,7-bis(trialkylsilyl)-4,5-dihydrothiepine generally along with a minor amount of the corresponding oxo analogue. The synthesis of both symmetrical and unsymmetrical bis(trialkylsilyl) derivatives was achieved.

Regiospecific silylation of 2,5-dibromothiophene: A reinvestigation

Lithiation of 2,5-dibromothiophene by LDA with ensuing silylation proceeds regiospecifically in accordance with the halogen dance mechanism to yield 3,5-dibromo-2-trimethylsilylthiophene or 3,4-dibromo-2,5-bis(trimethylsilyl)thiophene depending on the ratio of reagents. The outcome of the reaction was confirmed by further chemical transformations of the latter compound to 2,5-bis(trimethylsilyl)thiophene and 2,5-bis(trimethylsilyl)thiophene-1,1-dioxide. The structures of the compounds obtained were determined by 1H, 13C and 29Si NMR, and X-ray analysis in the case of a sulfone.

Synthesis, properties, oxidation, and electrochemistry of 1,2- dichalcogenins

Syntheses are presented of the 1,2-dichalcogenins: 1,2-dithiin, 1,2- diselenin, and 2-selenathiin, both substituted and unsubstituted. 1,2-Dithiin and 1,2-diselenin are prepared by reaction of PhCH2XNa (X = S or Se) with 1,4-bis(trimethylsilyl)-1,3-butadiyne followed by reductive cleavage and oxidation. 2-Selenathiin is similarly prepared using a mixture of PhCH2SeNa and PhCH2SNa. Reaction of titanacyclopentadienes with (SCN)2 or (SeCN)2 followed by bis(thiocyanate) or bis(selenocyanate) cyclization affords substituted 1,2-dithiins or 1,2-diselenins, respectively. With S2Cl2, 1,2- dithiins are directly formed from titanacyclopentadienes. Oxidation of 1,2- dithiins and 1,2-diselenins gives the corresponding 1-oxide and, with 1,2- dithiins and excess oxidant, 1,1-dioxides; oxidation of 2-selenathiin gives the 2-oxide. Electrochemical oxidation of 1,2-dichalcogenins, which have a twisted geometry, affords planar radical cations by an EC mechanism. One- electron AlCl3 oxidation of 3,6-diphenyl-1,2-dithiin gives the corresponding radical cation, characterized by EPR spectroscopy. Theoretical calculations result in a flattened structure for the 1,2-dithiin radical cation and a fully planar structure for the 1,2-diselenin radical cation. The 77Se NMR chemical shifts of 1,2-diselenin are characteristically high-field-shifted with respect to open chain diselenides in good agreement with results of GIAO-DFT calculations based on MP2 and DFT optimum geometries.

Perfluorophenylation of aromatic and heteroaromatic compounds with pentafluorobenzenesulfonyl chloride catalyzed by a ruthenium (ii) phosphine complex

The reactions of pentafluorobenzenesulfonyl chloride with benzene and thiophene derivatives in the presence of a ruthenium(II) catalyst proceeded at 240°C, with extrusion of sulfur dioxide and hydrogen chloride, to give the corresponding perfluorophenylated compounds.