(3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)
[CAS# 1619967-09-7]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organotin
• Name: (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)
• Synonyms: [4-fluoro-5-(3-fluoro-5-trimethylstannylthiophen-2-yl)thiophen-2-yl]-trimethylstannane
• Molecular Formula: C₁₄H₂₀F₂S₂Sn₂
• Molecular Weight: 527.86
• CAS Registry Number: 1619967-09-7
• EC Number: 834-552-6
• SMILES: C[Sn](C)(C)C1=CC(=C(S1)C2=C(C=C(S2)[Sn](C)(C)C)F)F

Properties

• Boiling Point: 410.9±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 202.3±31.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS09 Danger
• Risk Statements: H302-H310+H330-H300-H310-H330-H400-H410
• Safety Statements: P260-P262-P264-P270-P271-P273-P280-P284-P301+P316-P302+P352-P304+P340-P316-P320-P321-P330-P361+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	1	H310
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H330
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

• Transport Information: UN 3146

Discovery and Applications

(3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) is a versatile organotin compound featuring a bithiophene core functionalized with fluorine atoms and trimethylstannane groups. This compound is a critical building block in materials science, particularly for synthesizing conjugated polymers and small molecules used in optoelectronic devices such as organic photovoltaics (OPVs), organic light-emitting diodes (OLEDs), and field-effect transistors (OFETs).

The discovery of this compound is rooted in the exploration of fluorinated bithiophene derivatives for their unique electronic properties. Fluorine atoms, with their strong electronegativity, influence the electron density and energy levels of the bithiophene backbone, enhancing its semiconducting performance. Additionally, the trimethylstannane groups allow for efficient cross-coupling reactions, such as the Stille coupling, enabling the synthesis of a variety of complex π-conjugated systems.

The synthesis of (3,3'-difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) involves halogenation and subsequent stannylation of a bithiophene precursor. This method ensures high purity and functional group compatibility, making it an ideal intermediate for constructing advanced polymeric and molecular systems. The dual fluorination enhances intramolecular interactions and molecular packing, critical factors for high charge-carrier mobility in electronic applications.

In terms of application, this compound is widely utilized in the design of donor-acceptor copolymers for OPVs. Its fluorinated bithiophene unit contributes to lowering the bandgap and improving light absorption, while the trimethylstannane moiety enables straightforward integration into polymer backbones. Solar cells employing materials derived from this compound have demonstrated enhanced power conversion efficiencies due to optimized energy level alignment and charge transport properties.

Beyond photovoltaics, (3,3'-difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) is also employed in the fabrication of OLEDs, where its electron-rich structure contributes to high luminescence efficiency. In OFETs, polymers incorporating this compound exhibit excellent charge mobility and stability, essential for next-generation electronic devices. Its fluorination further provides chemical robustness, enhancing device lifespan under operational conditions.

While its applications are extensive, challenges remain in optimizing its synthetic routes to improve yield and cost efficiency. Additionally, the environmental impact of organotin compounds necessitates the development of safer processing methods and recycling strategies. Current research focuses on these areas to ensure the sustainable use of (3,3'-difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) in large-scale manufacturing.

In conclusion, (3,3'-difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) is a pivotal compound in the advancement of organic electronic materials. Its unique structural features enable the synthesis of high-performance polymers and small molecules, driving innovation in renewable energy and electronic technologies.

References

2023. Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors. Chinese Journal of Polymer Science, 41(6), 891-900.
DOI: 10.1007/s10118-023-2918-2

2019. High open-circuit voltage organic solar cells enabled by a difluorobenzoxadiazole-based conjugated polymer donor. Science China Chemistry, 62(5), 631-638.
DOI: 10.1007/s11426-018-9429-1

2017. D-A copolymers based on a pentacyclic acceptor unit and a 3,3′-difluoro-2,2′-bithiophene for solar cells. Chinese Journal of Polymer Science, 35(12), 1493-1500.
DOI: 10.1007/s10118-017-1996-4