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Product Code B1381-500mg
Price $313 ex. VAT

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A fluorinated brominated bithiophene intermediate

Readily available for the synthesis of semiconducting small molecules, oligomers, and polymers in application of OLEDs, OFETs and OPVs


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

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated bithiophene building block

For semiconductors, OLEDs, and solar cells

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High purity 1619967-08-6

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

5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene chemical structure, 1619967-08-6
5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene (2T2F-2Br), CAS 1619967-08-6

Product Details

Purity >98% (1H NMR)
Melting Point N/A
Appearance White powder

MSDS Documentation

4,4'-dibromo-2,2'-dinitrobiphenyl5,5'-Dibromo-3,3'-difluoro-2,2'-bithiophene MSDS Sheet

Literature and Reviews

  1. Fluorination of Polythiophene Derivatives for High Performance Organic Photovoltaics, J. Jo et al., Chem. Mater., 26 (14), 4214–4220 2014); DOI: 10.1021/cm502229k.
  2. 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.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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