This intermediate is widely used for the synthesis of semiconducting molecules, oligomers and conjugated polymers and more fused aromatic rings.
3,3′,5,5′-Tetrabromo-2,2′-bithiophene has a structure of two thiophenes joined at 2,2'-positions and each is brominated with two bromides at 3,5-positions. This tetra-brominated compound adds fuctions for further polymerisaiton, cyclisation to form polymers or to add conjugation to the bithiophene unit to form fused rings.
3,3′,5,5′-Tetrabromo-2,2′-bithiophene has been used for the synthesis of dithieno[3,2-b:2′,3′-d]pyrrole, dithieno[3,2-b:2,3-d]silole and their derivatives. Bromides at 3,3'-positions give rise to obtaining fused rings for higher degree of conjugation and flat structures. Polymerization of 3,3′,5,5′-tetrabromo-2,2′-bithiophene and ethynylbenzene monomers via the palladium-catalyzed Sonogashira–Hagihara crosscoupling reaction gives microporous polymers that show ultrahigh absorption performance for iodine vapour with an uptake of up to 345 wt%. Homopolymer poly(N-(2-octyldodecyl)-2,2′-bithiophene-3,3′-dicarboximide), derived from 3,3′,5,5′-tetrabromo-2,2′-bithiophene, exhibits n-channel FET activity and its films exhibit a very high degree of crystallinity and an electron mobility > 0.01 cm2 V-1 s-1 with a current on−off ratio of 107.
3,3′,5,5′-Tetrabromo-2,2′-bithiophene can be obtained by direct bromination of 2,2'-bithiophene with bromine in chloroform and acetic acid. N-Bromosuccinimide (NBS) can also be used as the oxidising agent to replace bromine for the synthesis. By refluxing 3,3′,5,5′-Tetrabromo-2,2′-bithiophene with zinc in hydrogenchloride and acetic acid, it gives 3,3'-dibromobithiophene.
|Molecular weight||481.85 g/mol|
|Classification / Family||Bithiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Purity||>98% (1H NMR in CDCl3)|
|Melting point||144.0 °C|
|Appearance||Light yellow to white/off white powder/crystals|
Literature and Reviews
- Synthesis and Properties of Alternating Copolymers Based on 4H-Cyclopenta[2,1-b:3,4-b']dithiophene and 4H-Dithieno[3,2-b:2',3'-d]silol, F. Drozdov et al., Polym. Sci. Ser. B 61, 56–76 (2019); DOI: 10.1134/S1560090419010032.
- Novel thiophene-bearing conjugated microporous polymer honeycomb-like porous spheres with ultrahigh iodine uptake, F. Ren et al., Chem. Commun., 52, 9797-9800 (2016); DOI: 10.1039/c6cc05188j.
- Two-photon absorption chromophores with a tunable [2,2']bithiophene core, C. Chou et al., Tetrahedron, 62, 8467–8473 (2006); DOI: 10.1016/j.tet.2006.06.085.
- Dithiophene-Fused Oxadiborepins and Azadiborepins: A New Class of Highly Fluorescent Heteroaromatics, M. Crumbach et al., Angew. Chem. Int. Ed., 60, 9290 – 9295 (2021); DOI: 10.1002/anie.202100295.
- Photovoltaic-Active Dithienosilole-Containing Polymers, L. Liao et al., Macromolecules, 40, 9406-9412 (2007); DOI: 10.1021/ma071825x.
- Dialkylthienosilole and N-alkyldithienopyrrole-based copolymers: Synthesis, characterization, and photophysical study, A. El-Shehawy et al., J Phys Org Chem., e4063 (2020); DOI: 10.1002/poc.4063.
- Extended conjugated mesogens: synthesis and mesomorphic properties of H-shaped mesogens based on 3,3ʹ,5,5ʹ-tetrasubstituted 2,2ʹ-bithiophene with oligo(1,4-phenyleneethynylene) arms, T. Yatabe et al., Liq. Cryst., 43 (10), 1375-1389 (2016); DOI: 10.1080/02678292.2016.1175674.
- Synthesis, Structures, and Electronic Properties of Dithienosiloles Bearing Bulky Aryl Groups: Conjugation between a π-Electron System and “Perpendicular” Aryl Groups, A. Tsurusaki et al., Asian J. Org. Chem., 6 (6), 737-745 (2016); DOI: 10.1002/ajoc.201700058.
- n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors, J. Letizia et al., J. Am. Chem. Soc., 130, 30, 9679–9694 (2008); DOI: 10.1021/ja710815a.
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