347838-12-4

Basic information

• Product Name: 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene
• Synonyms: 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene
• CAS NO: 347838-12-4
• Molecular Formula: C10H18F2SSi2
• Molecular Weight: 264.48
• Product Categories: Functional Materials;Reagents for Conducting Polymer Research;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Thiophene Derivatives (for Conduting Polymer Research)
• Mol File: 347838-12-4.mol

Chemical Properties

• Boiling Point: 98 °C / 8mmHg
• Flash Point: 72.037°C
• Appearance: /
• Density: 1.021g/cm³
• Vapor Pressure: 0.586mmHg at 25°C
• Refractive Index: 1.4720-1.4770
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene(347838-12-4)
• EPA Substance Registry System: 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene(347838-12-4)

Safety Data

• Hazardous Substances Data: 347838-12-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene is used as a building block for the synthesis of various organic compounds and materials. Its unique structure and properties make it a valuable component in the development of new organic molecules for research and industrial applications.
Used in Organic Semiconductors:
In the field of organic semiconductors, 3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene is utilized for its potential applications in the development of materials for electronic devices. Its unique structure contributes to the performance and properties of these semiconductors, making it a promising candidate for further exploration and use.
Used in Electronic Devices:
3,4-Difluoro-2,5-bis(trimethylsilyl)thiophene is used as a component in the development of materials for electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells. Its incorporation into these devices can enhance their performance and efficiency, making it a valuable asset in the advancement of electronic technology.
Used in Research and Development:
This chemical compound is also utilized in research and development efforts, where its unique properties and potential applications are further explored and understood. This contributes to the advancement of knowledge in the field of organic synthesis and the development of new materials and technologies.

InChI:InChI=1/C10H18F2SSi2/c1-14(2,3)9-7(11)8(12)10(13-9)15(4,5)6/h1-6H3

Upstream product

• 175658-90-9 3,4-dibromo-2,5-bis(trimethylsilanyl)thiophene 

Downstream Products

• 347838-15-7 2,5-dibromo-3,4-difluorothiophene 

Relevant articles and documents

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.

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.

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.

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.