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CAS Number 67061-69-2

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Monomers

Product Code B1051-500mg
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High-quality 2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene

Widely used as intermediate for semiconducting molecules, oligomers, and conjugated polymer synthesis for the applications of OFETs and OPVs.

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene (2,6-Dibromo-DTT) is a bis-brominated derivates of thieno[3,2-b:2′,3′-d]thiophene (DTT), which have unique electronic properties due to its planar, conjugated, sulfur-rich, and highly thermally stable structure, contains three annulated thiophene rings and is one of the six isomers of DTTs. DTTs having planar and rigid structures show intense electronic absorption, good hole mobility and high stability. In particular, being closely packed, rigid and planar structures lead to better charge injection efficiency in solid state.

The synthesis of 2,6-bis(dicyanomethylene)-2,6-dihydrodithieno[3,2-b:2',3'-d]thiophene
The synthesis of 2,6-bis(dicyanomethylene)-2,6-dihydrodithieno[3,2-b:2',3'-d]thiophene

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene is synthesised by reacting thieno[3,2-b:2′,3′-d]thiophene with N-Bromosuccinimide in dimethylformamide (DMF).Treatment of 2,6-dibromodithieno(3,2-b:2',3'-d]thiophene with tetracyanoethylene oxide in 1,2-dibromoethane under reflux gives 2,6-bis(dicyanomethylene)-2,6-dihydrodithieno[3,2-b:2',3'-d]thiophene as violet deep fine crystals.

Solar cell based on polymer semiconductor 2,6-di(pyren-1-yl) dithieno[3,2-b:2',3'-d]thiophene (DDT), consisting of dithieno [3,2-b:2',3'-d]thiophene (DTT) and pyrene units, as donor and C70 as acceptor exhibits an efficient power conversion efficiency (PCE) of 3.60%.

General Information

CAS Number 67061-69-2
Chemical Formula C8H2Br2S3
Full Name 2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene
Molecular Weight 354.1 g/mol
Synonyms DTT-2Br
Classification / Family Thienothiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene chemical structure
2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene chemical structure, CAS 67061-69-2

Product Details

Purity >98% (1H NMR in CDCl3)
Melting Point 171.0 °C
Appearance Fluffy white/off white powder

MSDS Documentation

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene MSDS2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene MSDS Sheet

Literature and Reviews

  1. Novel copolymers incorporating dithieno[3,2-b:2′,3′-d]thiophene moieties for air-stable and high performance organic field-effect transistors, K. Lu et al., J. Mater. Chem., 18, 3426-3432 (2008); DOI: 10.1039/B801603H.
  2. D-π-D Chromophores based on Dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell, C. Wang et al., Tetrahedron 73 (4), 307-312 (2017); DOI: 10.1016/j.tet.2016.11.077.
  3. Improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene (DTT) and derivatives for cross coupling, J. Frey et al., Chem. Commun., 2424-2425 (2022); DOI: 10.1039/B207403F.
  4. Vacuum processable donor material based on dithieno[3,2-b:2′,3′-d]thiophene and pyrene for efficient organic solar cells, J. Kwon et al., RSC Adv., 4, 24453-24457 (2014); DOI: 10.1039/C4RA02895C.
  5. Solution-processable multicolored dithienothiophene-based conjugated polymers for electrochromic applications, W. Neo et al., Eur. Polym. J. 49 (9), 2446-2456 (2013); DOI: 10.1016/j.eurpolymj.2013.02.026.
  6. High-Performance and Stable Organic Thin-Film Transistors Based on Fused Thiophenes, Adv. Funct. Mater., 16 (3), 426-432 (2006); Y. Sun et al., DOI: 10.1002/adfm.200500547.
  7. The synthesis, characterization and flexible OFET application of three (Z)-1,2-bis(4-(tert-butyl)phenyl)ethane based copolymers, Y. Huang et al., Polym. Chem., 7, 538-545 (2016); DOI: 10.1039/C5PY01647A.
  8. Synthesis, Characterization and Field-Effect Transistor Performance of Benzoannulated Pentathienoacene Derivative, X. Qi et al., New J. Chem., 39, 1045-1050 (2015); DOI: 10.1039/C4NJ01590H.
  9. Color Fine-Tuning of Optical Materials Through Rational Design, B. Holzer et al., ChemPhysChem, 18 (5), 549-563 (2017); DOI: 10.1002/cphc.201601204.
  10. Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide, Z. Fei et al., Macromolecules, 49, 17, 6384–6393 (2016); DOI: 10.1021/acs.macromol.6b01423.

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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