Widely used intermediate for 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.
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).
|Molecular weight||298.0 g/mol|
|Classification / Family||Thienothiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Purity||>98% (1H NMR in CDCl3)|
|Melting point||127.0 °C|
|Appearance||Fluffy white/off white powder|
Literature and Reviews
- 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.
- 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.
- 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.
- 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.
- 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.
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