5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene
CAS Number 1619967-08-6
Chemistry Building Blocks, Dibromo Monomers, Fluorinated Building Blocks, Heterocyclic Building Blocks, Materials, Monomers
A fluorinated brominated bithiophene intermediate
Readily available for the synthesis of semiconducting small molecules, oligomers, and polymers in application of OLEDs, OFETs and OPVs
Specifications | MSDS | Literature and Reviews
5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene (2T2F-2Br), CAS number 1619967-08-6, is a double fluorinated brominated bithiophene. The bromo groups at 5,5'-positions enable the intermediate to be further coupled to form C-C bonds via either Suzuki or Stille coupling reactions for the synthesis of more complex conjugated structures, i.e., semiconducting small molecules, oligomers and polymers in application of organic field effect transistors and polymer solar cells. Fluorine atoms on the thiophene rings are electron poor thus down-shift the highest occupied molecular orbital (HOMO) energy level and increasing charge mobility of the targeted polymer donors. Planar structure in the solid state can also be promoted by fluorination in the backbone of the structure via the interaction of the fluoro and sulfur atoms (F⋅⋅⋅S).
Indeed, fluorinated poly(3,4-dialkylterthiophenes) (F-PDATs) exhibited a deeper HOMO energy level than the nonfluorinated PDATs, leading to higher open-circuit voltage in organic solar cells with enhanced molecular ordering in films, showing by a vibronic shoulder peak in UV–Vis spectrum of F-PDATs [1].
Multiple functional groups
For facile synthesis
Fluorinated bithiophene building block
For semiconductors, OLEDs, and solar cells
Worldwide shipping
Quick and reliable shipping
High purity
>98% High purity
General Information
| CAS Number | 1619967-08-6 |
| Chemical Formula | C8H2Br2F2S2 |
| Full Name | 5,5'-Dibromo-3,3'-difluoro-2,2'-bithiophene |
| Molecular Weight | 360.04 g/mol |
| Synonyms |
2T2F-2Br, 5-Bromo-2-(5-bromo-3-fluorothiophen-2-yl)-3-fluorothiophene |
| Classification / Family | Bithiophene derivatives, Fluorinated building blocks, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics |
Chemical Structure
Product Details
| Purity | >98% (1H NMR) |
| Melting Point | N/A |
| Appearance | White powder |
MSDS Documentation
5,5'-Dibromo-3,3'-difluoro-2,2'-bithiophene MSDS Sheet
Literature and Reviews
-
Fluorination of Polythiophene Derivatives for High Performance Organic Photovoltaics, J. Jo et al., Chem. Mater., 26 (14), 4214–4220 2014); DOI: 10.1021/cm502229k.
- Implication of Fluorine Atom on Electronic Properties, Ordering Structures, and Photovoltaic Performance in Naphthobisthiadiazole-Based Semiconducting Polymers, K. Kawashima et al., J. Am. Chem. Soc., 138 (32), 10265–10275 (2016); DOI: 10.1021/jacs.6b05418.