1619967-09-7

Basic information

• Product Name: (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)
• Synonyms: (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane);Stannane, 1,1'-(3,3'-difluoro[2,2'-bithiophene]-5,5'-diyl)bis[1,1,1-trimethyl-
• CAS NO: 1619967-09-7
• Molecular Formula: C14H20F2S2Sn2
• Molecular Weight: 527.8554064
• Mol File: 1619967-09-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 410.9±55.0 °C(Predicted)
• Appearance: /
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)(CAS DataBase Reference)
• NIST Chemistry Reference: (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)(1619967-09-7)
• EPA Substance Registry System: (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)(1619967-09-7)

Safety Data

• Hazardous Substances Data: 1619967-09-7(Hazardous Substances Data)

Usage

Description

(3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane), also known as 3,3'-Difluoro-5,5'-bis(trimethylstannyl)-2,2'-bithiophene, is an organostannane compound that features a bithiophene core with fluorine atoms at the 3,3'-positions and trimethylstannyl groups at the 5,5'-positions. (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) is characterized by its potential applications in the field of organic electronics due to its unique structural properties.

Uses

Used in Organic Electronics:
(3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) is used as a synthetic building block for the development of small molecules or polymer semiconductors in organic electronic applications. Its incorporation into these materials can enhance their electronic properties, making them suitable for use in various devices such as organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and organic light-emitting diodes (OLEDs).
Used in the Synthesis of P(NDI2OD-T2F):
Specifically, (3,3'-Difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) is utilized in the synthesis of a particular polymer semiconductor known as P(NDI2OD-T2F). This polymer is of interest due to its potential performance in organic electronic devices, and the compound in question plays a crucial role in its formation, contributing to the overall properties and performance of the resulting material.

Upstream product

• 1066-45-1 trimethyltin(IV)chloride 
• 207742-50-5 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene 
• 1619967-08-6 5,5'-bisbromo-3,3'-difluoro-2,2'-bithiophene 

Relevant articles and documents

Preparation method of 5, 5-bis(trimethylstannyl)-3, 3-difluoro-2, 2-bithiophene

The invention discloses a preparation method of 5, 5-bis(trimethylstannyl)-3, 3-difluoro-2, 2-bithiophene. The method comprises the following steps: S1: synthesizing 3, 3-difluoro-2, 2-bithiophene; and S2: performing synthesis of 5, 5-bis(trimethylstannyl)-3, 3-difluoro-2, 2-bithiophene: adding the 3, 3-difluoro-2, 2-bithiophene obtained in S1 into a reaction vessel, performing dissolving with anhydrous tetrahydrofuran, performing cooling to 42-38 DEG C, dropwise adding butyl lithium, performing reacting at low temperature for 25-35 minutes, naturally performing heating to room temperature, performing reacting for 0.8-1.2 hours, performing cooling to -42-38 DEG C, and dropwise adding a tetrahydrofuran solution of trimethyltin chloride; and naturally performing heating to room temperature,reacting for 2-5 hours, and performing washing and crystallizing to obtain a white flaky target object 5, 5-bis(trimethylstannyl)-3, 3-difluoro-2, 2-bithiophene. According to the method, cheaper 3, 3-dibromo-2, 2-bithiophene is used as a starting raw material, the process route is relatively short, the reaction yield of each step is very high, and the overall yield can reach 75-80%.

Fluorination of polythiophene derivatives for high performance organic photovoltaics

For the purpose of examining the tuning of photophysical property by fluorine atom substitution, fluorinated and nonfluorinated poly(3,4- dialkylterthiophenes) (PDATs) were synthesized, and their photovoltaic properties were compared. Fluorinated PDATs exhibit a deeper highest occupied molecular orbital energy level than nonfluorinated ones, leading to higher open-circuit voltage in organic solar cells and also enhanced molecular ordering as evidenced by a vibronic shoulder in UV-vis spectra, π-π scattering in GIWAXS, and a well-developed fibril structure in TEM, which contributes to efficient charge transport. As a result, the fluorine substitution increases the power conversion efficiency by 20% to 250% as compared with nonfluorinated PDATs.