2,2'-bithiophene-5-carbonitrile

Order Code: B311
MSDS sheet

Price

(excluding Taxes)

£99.00


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

 

Product Details

Purity >98%
Melting point 74-75°C
Color White powder/crystals

 

Chemical Structure

Chemical structure of 2,2-bithiophene-5-carbonitrile
CAS number 16278-99-2; Chemical formula C9H5NS2.

 

Applications

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.

 

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).

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).