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Usage

Uses

Used in Organic Synthesis:
3,4-Dibromo-2,5-bis(trimethylsilyl)thiophene is utilized as a building block in organic synthesis for the production of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries.
Used as a Protecting Group in Organic Chemistry:
In the realm of organic chemistry, 3,4-Dibromo-2,5-bis(trimethylsilyl)thiophene is employed as a protecting group. This role is crucial for selective manipulation of functional groups within molecules, enabling chemists to carry out reactions with precision and control, which is essential for the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
3,4-Dibromo-2,5-bis(trimethylsilyl)thiophene is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique properties allow for the development of new drugs with potential therapeutic benefits.
Used in Material Science:
3,4-Dibromo-2,5-bis(trimethylsilyl)thiophene is also utilized in material science for the development of new materials with specific properties. Its ability to be modified and incorporated into various structures makes it a valuable component in the creation of advanced materials for diverse applications.
Used in Research and Development:
3,4-Dibromo-2,5-bis(trimethylsilyl)thiophene is employed in research and development settings to explore new chemical reactions and mechanisms. Its unique structure provides a platform for studying novel chemical pathways and understanding the fundamental principles of organic chemistry.

Upstream product

• 3141-27-3 2,5-dibromothiophen 
• 75-77-4 chloro-trimethyl-silane 
• 3141-26-2 3,4-dibromothiophene 
• 3958-03-0 Tetrabromothiophene 
• 112051-54-4 3,5-dibromo-2-(trimethylsilyl)thiophene 

Downstream Products

• 347838-12-4 3,4-difluorothiophene-2,5-diyl-bis(trimethylsilane) 
• 17906-71-7 2,5-bis(trimethylsilyl)thiophene 

Relevant academic research and scientific papers

Utilizing Difluorinated Thiophene Units to Improve the Performance of Polymer Solar Cells

While there are numerous approaches to functionalize conjugated polymers for organic solar cells (OSCs), one widely adopted approach is fluorination. Of the many different locations for fluorination, one of the least studied is the conjugated linker which connects the donor and acceptor moieties; further, all existing reports primarily explore monofluorinated thiophene units. Herein, we synthesize and compare two conjugated polymers, HTAZ and DFT-HTAZ, which have different thiophene linkers. In HTAZ, a bare thiophene unit connects the donor and acceptor moieties, while DFT-HTAZ utilizes difluorinated thiophene (DFT) linkers. These polymers serve as the model system to explore the impact of DFT units in OSCs; additionally, this is the first publication to investigate polymers containing DFT units paired with non-fullerene acceptors. Compared to HTAZ, the incorporation of the DFT units maintained the optical properties while lowering the energy levels by a0.4 eV, which allowed for a much improved Voc value of a1 V. Importantly, when compared with the appropriate non-fullerene acceptor, DFT-HTAZ:ITIC-Th1 blends reached an efficiency of a10%, which is nearly 3× that of the nonfluorinated HTAZ. As most OSC polymers have thiophene linkers, using DFT units could serve as a proficient method to increase OSC performance in many polymer systems, especially those that do not have locations for functionalization on the acceptor moiety.

Synthesis and characterization of perfluorinated arylenevinylene polymers

Fully fluorinated arylenevinylene polymers have been synthesized via a methodology based on the Stille cross-coupling reaction and characterized by FTIR spectroscopy and MALDI-TOF mass spectrometry. Investigation of thin film properties by cyclic voltammetry and ellipsometry shows that complete substitution of hydrogen atoms with fluorine atoms on the conjugated backbone of the poly(arylenevinylene)s results in a strong increase of the band gap.

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.

Simple organic donors based on halogenated oligothiophenes for all small molecule solar cells with efficiency over 11%

Recent work has emphasized the pivotal role of halogen substituents in the development of polymer donors or small-molecule (SM) acceptors for efficient bulk-heterojunction (BHJ) solar cells. However, the application of-F or-Cl substitutions in the design of SM donors is yet to receive similar considerations. In this contribution, we report a set of oligothiophene derivatives (2F7T and 2Cl7T) with halogenation at the central thienyl moiety. Such halogenation is shown to induce a sufficient increase in ionization potential (IP; i.e. deeper HOMO) to modify the electron-donating and-transporting characteristics of the molecules. When combined with a low-bandgap SM acceptor (Y6), the devices with 2Cl7T achieved power conversion efficiencies (PCEs) of up to ca. 11.5% (vs. ca. 2.5% for non-halogenated donor DRCN7T based devices), representing the best photovoltaic performance of oligothiophene donors.

Isoindigo-3,4-Difluorothiophene Polymer Acceptors Yield “All-Polymer” Bulk-Heterojunction Solar Cells with over 7 % Efficiency

Poly(isoindigo-alt-3,4-difluorothiophene) (PIID[2F]T) analogues used as “polymer acceptors” in bulk-heterojunction (BHJ) solar cells achieve >7 % efficiency when used in conjunction with the polymer donor PBFTAZ (model system; copolymer of benzo[1,2-b:4,5

Thieno[3,4-c]pyrrole-4,6-dione-3,4-difluorothiophene Polymer Acceptors for Efficient All-Polymer Bulk Heterojunction Solar Cells

Branched-alkyl-substituted poly(thieno[3,4-c]pyrrole-4,6-dione-alt-3,4-difluorothiophene) (PTPD[2F]T) can be used as a polymer acceptor in bulk heterojunction (BHJ) solar cells with a low-band-gap polymer donor (PCE10) commonly used with fullerenes. The “all-polymer” BHJ devices made with PTPD[2F]T achieve efficiencies of up to 4.4 %. While, to date, most efficient polymer acceptors are based on perylenediimide or naphthalenediimide motifs, our study of PTPD[2F]T polymers shows that linear, all-thiophene systems with adequately substituted main chains can also be conducive to efficient BHJ solar cells with polymer donors.

Influence of backbone fluorination in regioregular poly(3-alkyl-4-fluoro)thiophenes

We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylhexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation of a single regioisomer as a result of the pronounced directing effect of the fluorine group. Polymerization of the resulting species affords highly regioregular poly(3-alkyl-4-fluoro)thiophenes. Comparison of their properties to those of the analogous non-fluorinated polymers shows that backbone fluorination leads to an increase in the polymer ionization potential without a significant change in optical band gap. Fluorination also results in an enhanced tendency to aggregate in solution, which is ascribed to a more co-planar backbone on the basis of Raman and DFT calculations. Average charge carrier mobilities in field-effect transistors are found to increase by up to a factor of 5 for the fluorinated polymers.

The efficient synthesis of dithieno [3,4-b:3',4'-d] thiophene

The efficient synthesis of dithieno[3,4-b:3',4'-d]thiophene was improved by the introduction of TMS groups in four synthetic steps including TMS protection, sulfidation, intramolecular cyclization, and TMS removal. The total yield is 55-63% with 3,4-dibro

Regioselective palladium(0)-catalyzed cross-coupling reactions and metal-halide exchange reactions of tetrabromothiophene: Optimization, scope and limitations

The Suzuki reaction of tetrabromothiophene with arylboronic acids provides a regioselective approach to various 5-aryl-2,3,4-tribromothiophenes, symmetrical 2,5-diaryl-3,4-dibromothiophenes, and tetraarylthiophenes. Unsymmetrical 2,5-diaryl-3,4-dibromo thiophenes are prepared by Suzuki reaction of 5-aryl-2,3,4-tribromothiophenes. Tetraarylthiophenes containing two different types of aryl groups are obtained by Suzuki reactions of 2,5-diaryl-3,4- dibromothiophenes. During the optimization of the conditions of each individual reaction, the solvent, the catalyst and the temperature play an important role. In several cases, classical conditions.

Organic compound having functional groups different in elimination reactivity at both terminals, organic thin film, organic device and method of producing the same

Provided are a single monomolecular film uniform in film thickness and highly ordered in molecule alignment and its multilayer film, an organic compound allowing production of such films at high reproducibility, an organic device superior in electroconductive properties and a method of producing the same. An organic compound represented by Formula: Si(A1)(A2)(A3)-B—Si(A4)(A5)(A6) (A1 to A6 each represent a hydrogen atom, a halogen atom, an alkoxy group or an alkyl group and satisfy the relationship in elimination reactivity of: A1 to A3>A4 to A6; and B represents a bivalent organic group), an organic thin film using the compound, and an organic device having the thin film; A method of producing an organic thin film and organic device, comprising a step of forming a single monomolecular film by allowing the silyl group having A1 to A3 in the organic compound to react with the substrate surface; a step of removing unreacted organic compounds by using a non-aqueous solvent; and a step of forming an additional monomolecular film of the organic compound by using the unreacted silyl groups present on the film surface side of the monomolecular film obtained as the sites for adsorption reaction.