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CAS Number 98057-08-0

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

Product Code B1071-1g
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This intermediate is widely used for the synthesis of semiconducting molecules, oligomers and conjugated polymers.

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene (CAS number 98057-08-0) is a brominated derivative of α-terthienyl at 5,5′′-positions. 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene can be prepared via bromination 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 synthesis 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.

General Information

CAS Number 98057-08-0
Chemical Formula C12H6Br2S3
Full Name 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene
Molecular Weight 406.18 g/mol
Synonyms 2,5-Bis(5-bromothiophen-2-yl)thiophene
Classification / Family Terthiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene chemical structure
5,5′′-Dibromo-2,2′:5′,2′′-terthiophene chemical structure, CAS 98057-08-0

Product Details

Purity >98% (1H NMR in CDCl3)
Melting Point 158.0 °C
Appearance Light yellow powder/crystals

MSDS Documentation

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene MSDS5,5′′-Dibromo-2,2′:5′,2′′-terthiophene MSDS Sheet

Literature and Reviews

  1. Selective Synthesis of α-Substituted Oligothiophenes, P. Bauerle, et al., Synthesis,11, 1099-1103 (1993); DOI:10.1055/s-1993-26009.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. 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.

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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