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Product Code B941-5g
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3,3'-Dibromo-2,2'-bithiophene available to buy online

Key intermediate for the preparation of semiconducting molecules, oligothiophenes and polymers

3,3'-Dibromo-2,2'-bithiophene is an isomer to 5,5'-Dibromo-2,2'-bithiophene. It is a key intermediate for the preparation of semiconducting molecules, oligothiophenes and polymers which find applications in a variety of organic electronic and optoelectronic devices. These include organic field-effect transistors, chemical sensors, and organic solar cells.

Alkylation or arylation at 3-positions of the bithiophene not only provide either extended conjugation or improved solubility, but also give new functionality to change the electron and photophysical properties of the target materials. In addition, alkylation or arylation at 3-positions has a significant impact on the crystallinity of the target molecules to tune the morphology and the microstructure of the cast films.

Substitution of the bromines with either fluorine (F) or cyano (CN) groups makes the structure more electron deficient, which has a pounding effect on the device performance in terms of charge mobility, stability and overall OFET and OPV device efficiency.

3,3'-Dibromo-2,2'-bithiophene is also a must have building block for the synthesis of more complicated fused structures such as dithieno[3,2-b:2,3-d]pyrroles (DTP), dithieno[3,2-b:2,3-d]silole (DTS), dithieno[3,2-b:2,3-d]selenophene (DTSe), dithieno[3,2-b:2′,3′-d]germole (DTG) and 4,4′-Spiro-bis[cyclopenta[2,1-b;3,4-b′]dithiophene] (SCT).

General Information

CAS Number 51751-44-1
Chemical Formula C8H4Br2S2
Full Name 3,3'-Dibromo-2,2'-bithiophene
Molecular Weight 324.06 g/mol
Synonyms 2,2'-Bi(3-bromothiophene)
Classification / Family Bithiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

3,3'-Dibromo-2,2'-thiophene chemical structure
3,3'-Dibromo-2,2'-thiophene chemical structure, CAS 51751-44-1

Product Details

Purity >98% (1H NMR in CDCl3)
Melting Point 99 °C
Appearance White-yellowish powder

MSDS Documentation

3,3'-Dibromo-2,2'-bithiophene MSDS3,3'-Dibromo-2,2'-bithiophene MSDS Sheet

Literature and Reviews

  1. Simplified Synthetic Approach to Tetrabrominated Spiro-Cyclopentadithiophene and the Following Derivation to A-D-A Type Acceptor Molecules for Use in Polymer Solar Cells, X. Liu et al., J. Org. Chem., 87 (8), 5057–5064 (2022).
  2. Polymerization of Solid-State 2,2′-Bithiophene Thin Film or Doped in Cellulose Paper Using DBD Plasma and Its Applications in Paper-Based Electronics, K. Chen et al., ACS Appl. Polym. Mater., 2 (4), 1518–1527 (2020); DOI: 10.1021/acsapm.9b01202.
  3. Design of novel electroactive polybithiophene derivatives, K. Faid et al., Macromolecules, 26 (10), 2501–2507 (1993); DOI: 10.1021/ma00062a017.
  4. Synthesis and properties of novel bis(triarylamines) based on a 3,3'-diphenyl-2,2'-bithiophene core, K. Wong et al., Chem. Commun., 1628–1629 (2001); DOI: 10.1039/b103194p.
  5. Improved Synthesis of N-alkyl Substituted Dithieno[3,2-b:2’,3’-d]pyrroles, G. Koeckelberghs et al., Tetrahedron, 61 (3), 687-691 (2005); DOI: 10.1016/j.tet.2004.10.106.
  6. Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3%, T. Chu et al., J. Am. Chem. Soc., 133 (12), 4250–4253 (2011); DOI: 10.1021/ja200314m.

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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