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3,6-Dibromothieno[3,2-b]thiophene (TT36)

CAS Number 392662-65-6

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

3,6-Dibromothieno[3,2-b]thiophene (TT36) CAS 392662-65-6
Product Code B951-5g
Price $300 ex. VAT
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3,6-Dibromothieno[3,2-b]thiophene (TT36)

Widely used intermediate for further synthesis of semiconducting molecules, oligomers and conjugated polymers

3,6-Dibromothieno[3,2-b]thiophene (TT36) is a derivate of thieno[3,2-b]thiophene with bromine function groups at the 3,6-positions of the fused rings. TT36 is a widely used intermediate to build up more complex structures as semiconducting molecules, oligomers and conjugated polymers for OFETs, sensors, OLEDs and OPVs.

TT36 preparation by halogen dance reaction
TT36 preparation by halogen dance reaction

Interestingly, 3,6-dibromothieno[3,2-b]thiophene is prepared by the halogen dance reaction of 2,5-dibromothieno[3,2-b]thiophene with lithium diisopropyl amide (LDA), shown above.

3,6-Dibromothieno[3,2-b]thiophene has a good planar symmetrical structure and functional groups that can be easily modified to optimize the electronic properties. Alkylation or arylation of thieno[3,2-b]thiophene at 3.6-positions can be achieved via Negishi cross-coupling reaction by reacting 3,6-Dibromothieno[3,2-b]thiophene with RMBr (R = alkyl or aryl, M = Zn).

General Information

CAS Number 392662-65-6
Chemical Formula C6H2Br2S2
Full Name 3,6-Dibromothieno[3,2-b]thiophene
Molecular Weight 298.0 g/mol
Synonyms TT36
Classification / Family Thienothiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

3,6-Dibromothieno[3,2-b]thiophene (TT36) chemical structure, CAS 392662-65-6
3,6-Dibromothieno[3,2-b]thiophene (TT36) chemical structure, CAS 392662-65-6

Product Details

Purity >98% (1H NMR in CDCl3)
Melting Point 127.0 °C
Appearance Fluffy white/off white powder

MSDS Documentation

3,6-Dibromothieno[3,2-b]thiophen MSDS3,6-Dibromothieno[3,2-b]thiophen MSDS Sheet

Literature and Reviews

  1. Fused electron deficient semiconducting polymers for air stable electron transport, A. Onwubiko et al., Nat. Commun. 9, 416 (2018); DOI: 10.1038/s41467-018-02852-6.
  2. Thieno[3,2-b]thiophene based electrochromic polymers: experimental cum theoretical appraisal of the EDOT position, X. Zhu et al., RSC Adv., 6, 75522 (2016); DOI: 10.1039/c6ra12319h.
  3. Small Band Gap Polymers Incorporating a Strong Acceptor, Thieno[3,2-b]thiophene-2,5-dione, with P-Channel and Ambipolar Charge Transport Characteristics, I. Osaka et al., J. Mater. Chem. C, 2, 2307-2312 (2014); DOI: 10.1039/C3TC32386B.
  4. Efficient synthesis of 3,6-dialkoxythieno[3,2-b]thiophenes as precursors of electrogenerated conjugated polymers, N. Hergue et al., Org. Biomol. Chem., 9, 588–595 (2011); DOI: 10.1039/c0ob00585a.
  5. Dithienylthienothiophenebisimide, a Versatile Electron-Deficient Unit for Semiconducting Polymers, M. Saito et al., Adv. Mater., 28 (32), 6921-6925 (2016); DOI: 10.1002/adma.201601373.

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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