This intermediate is widely used for the synthesis of semiconducting molecules, oligomers and conjugated polymers.
5,5′′-Dibromo-2,2′:5′,2′′-terthiophene is a brominated derivateive of α-terthienyl at 5,5′′-positions. 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene can be prepared via bromonation with N-bromosuccinimide in N,N-dimethylformamide (DMF).
5,5′′-Dibromo-2,2′:5′,2′′-terthiophene is a useful building block for the further synthesis of small molecules, oligomers and conjugated semiconducting polymers. Pyrene end-capped thiophene oligomer 5,5′′-di(pyren-1-yl)-2,2′:5′,2′′-terthiophene prepared from one step sythesis from 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene show great potential as semiconducting materials for OTFTs and OSCs. Devices based on 5,5′′-di(pyren-1-yl)-2,2′:5′,2′′-terthiophene exhibited a field effect mobility of 0.11 cm2 V−1 s−1. Naphthyl end-capped oligothiophenes are also good candidates for high-performance organic electronic devices. Methoxy-functionalized 5,5′′-bis-(6-methoxynaphth-2-yl)-2:2′,5′:2′′-terthiophene (MONaT3) substantially increases the crystallization into aligned fibers.
|Molecular weight||406.18 g/mol|
|Classification / Family||Terthiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Purity||>98% (1H NMR in CDCl3)|
|Melting point||158.0 °C|
|Appearance||Light yellow powder/crystals|
Literature and Reviews
- Selective Synthesis of α-Substituted Oligothiophenes, P. Bauerle, et al., Synthesis,11, 1099-1103 (1993); DOI:10.1055/s-1993-26009.
- Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5′-Bis(dicyanomethylene)-5,5′-dihydro-Δ2,2′-bithiophene and Related Compounds, Y. Koji et al., Bull. Chem. Soc. Jpn., 62 (5), 1539-1546 (1989); DOI: 10.1246/bcsj.62.1539.
- Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives, P. Liu et al., Tetrahedron 60 (24), 5259-5264 (2004); DOI: 10.1016/j.tet.2004.04.029.
- Two-photon induced emissive thiophene donor–acceptor systems as molecular probes for in vitro bio-imaging: synthesis, crystal structure, and spectroscopic properties, C. Chow, RSC Adv., 3, 18835-18843 (2013); DOI: 10.1039/C3RA42914H.
- Conformation modification of terthiophene during the on-surface synthesis of pure polythiophene, L. Liu et al., Nanoscale, 12, 18096-18105 (2020); DOI: 10.1039/D0NR04529B.
- Substrate steered crystallization of naphthyl end-capped oligothiophenes into nanofibers: the influence of methoxy-functionalization, F. Balzer et al., Phys. Chem. Chem. Phys., 16, 5747-5754 (2014); DOI: 10.1039/C3CP53881H.
- Pyrene end-capped oligothiophene derivatives for organic thin-film transistors and organic solar cells, J. Kwon et al., New J. Chem., 36, 1813-1818 (2012); DOI: 10.1039/C2NJ40348J.
- A novel method for the bromination of thiophenes, P. Arsenyan et al., Tetrahedron Lett., 51, 205–208 (2010); DOI: 10.1016/j.tetlet.2009.10.133.
- Synthesis and Characterization of Diperfluorooctyl-Substituted Phenylene-Thiophene Oligomers as n-Type Semiconductors. Molecular Structure-Film Microstructure-Mobility Relationships, Organic Field-Effect Transistors, and Transistor Nonvolatile Memory Elements, A. Facchetti et al., Chem. Mater., 16, 4715-4727 (2004); DOI: 10.1021/cm0495008.
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