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2,2'-bithiophene-5-carbonitrile

2,2'-bithiophene-5-carbonitrile
Product Code B311
Price $375.00 ex. VAT
$ USD

2,2'-bithiophene-5-carbonitrile, high-purity monomer

For the synthesis of semiconducting materials used in organic electronic devices

2,2'-bithiophene-5-carbonitrile is the intermediate used for the synthesis of 3,6-bis[5-(2,2'-bithiophene)]pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione which can be further modified to form oligomers or polymers used for organic electronic devices.

2,2'-bithiophene unit is electron-rich, and thus a good building block for the synthesis of semiconducting materials that are used for organic electronic devices. Embedded in the polymer backbones, 2,2'-bithiophene unit is proven to promote cystallinity to form small domains in bulk heterojunction solar cells [4].

Synthesis of 3,6-bis[5-(2,2'-bithiophene)]pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
Synthesis of 3,6-bis[5-(2,2'-bithiophene)]pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

General Information

CAS Number 16278-99-2
Chemical Formula C9H5NS2
Molecular Weight 191.27 g/mol
Synonyms
  • 5-(2-thienyl)thiophene-2-carbonitrile
  • 5-cyano-2,2'-bithiophene
Classification / Family Thiophene, Bithiophene, Heterocyclic five-membered ring, Organic materials, Semiconductor synthesis, Building blocks

Chemical Structure

Chemical structure of 2,2-bithiophene-5-carbonitrile, CAS 16278-99-2
Chemical structure of 2,2-bithiophene-5-carbonitrile, CAS 16278-99-2

Product Details

Purity >98%
Melting Point 74 °C - 75 °C
Appearance White powder/crystals

NMR Characterisation

1H NMR bithiophene-5-carbonitrile in CDCl3
1H NMR spectrum of 2,2’-bithiophene-5-carbonitrile in CDCl3: Instrument AVIIIHD400 (view full version).

MSDS Documentation

2,2'-bithiophene-5-carbonitrile MSDS2,2'-bithiophene-5-carbonitrile MSDS sheet

Literature and Reviews

  1. Effect of substituents on redox, spectroscopic and structural properties of conjugated diaryltetrazines—a combined experimental and theoretical study, E. Kurach et al., Phys. Chem. Chem. Phys., 13, 2690–2700 (2011).
  2. Dicationic phenyl-2,2′-bichalcophenes and analogues as antiprotozoal agents, M. A. Ismail et al.,  Bioorg. Med. Chem. 19, 978–984 (2011).
  3. Compromise between conjugation length and charge-transfer in nonlinear optical h5 -monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands: Synthesis, electrochemical studies and first hyperpolarizabilities, M. H. Garcia et al., J. Organometallic Chem., 692, 3027–3041 (2007).
  4. Fluorene-Based Co-polymer with High Hole Mobility and Device Performance in Bulk Heterojunction Organic Solar Cells, D. Watters et al., Macromol. Rapid Commun. , 34, 1157−1162 (2013).

To the best of our knowledge the information provided here is accurate. However, Ossila assume no liability for the accuracy of this page. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. All products are for laboratory and research and development use only, and may not be used for any other purpose including health care, pharmaceuticals, cosmetics, food or commercial applications.

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