2,7-Dibromocarbazole

Order Code: B251

Price

(excluding Taxes)

£109.00


General Information

CAS number
136630-39-2
Chemical formula C12H7Br2N
Molecular weight 325.0 g/mol
Synonyms 2,7-Dibromo-9H-carbazole
Classification / Family

Monomers, Building blocks, Carbazoles, Halogenated heterocycles, Chemical synthesis for Low band gap polymers

Intermediates for OFETs, OLED, Organic Photovoltaics, Polymer Solar Cells


Product Details

Purity

>99%

Melting point

226-230°C

Color Off White powder

Chemical Structure

2,7-dibromocarbazole
Chemical structure of 2,7-dibromocarbazole
CAS number 136630-39-2; Chemical formula C12H7Br2N

Applications

2,7-dibromocarbazole, also known as 2,7-dibromo-9H-carbazole, is a building block for the synthesis of small molecules of carbazole series or carbazole back-boned polymers in the application of OFETs, OLEDs, PLEDs and OPVs.

Carbazole derivatives, small molecules or poly(2,7-carbazole)s, have been one of the most popular candidates for the application of organic electronics due to their well-known good electron-donating abilities and chemical stability comparing with fluorene units. Also, the functional group on the 9-position makes them chemically available to be easily adjustable to different aromatic or alkyl chains to allow solubility for devices film morphology or even further tuning the energy levels of such compounds.

One of the most popular products made available from 2,7-dibromocarbazole is PCDTBT, a well-known polymer semiconductor used for polymer solar cells. A good example for adjusting the solubility of the carbazole compounds by using 2,7-dibromocarbazole as the starting materials is the synthesis of 2,7-dibromo-9-heptadecanylcarbazole.

 

synthesis of dibromo-9-heptadecanylcarbazole using dibromocarbazole as starting material
Synthesis of 2,7-dibromo-9-heptadecanylcarbazole using 2,7-dibromocarbazole as starting material

NMR Charaterisation

 

1H NMR of 2-7-dibromocarbazole in CDCl3
1H NMR spectrum of 2,7-Dibromo-9H-carbazole in CDCl3 (view full version)

Literature and Reviews

  1. Solution-processed blue phosphorescent OLEDs with carbazole-based polymeric host materials, F. Dumur et al., Org. Electronics 25, 21–30 (2015)
  2. Synthesis, Characterization, and Use as Emissive Layer of White Organic Light Emitting Diodes of the Highly Isotactic Poly(N-pentenyl-carbazole), A. Botta et al., poly. Composites, 1110-1117 (2015)
  3. A low bandgap carbazole based small molecule for organic solar cells, M. Li, et al., Org. Electronics 24, 89-95 (2015)
  4. Thioalkyl-Substituted Benzothiadiazole Acceptors: Copolymerization with Carbazole Affords Polymers with Large Stokes Shifts and High Solar Cell Voltages, A. Casey et al., Macromolecules 47, 2279−2288 (2014)
  5. Pendant group effects on the optical and electrical properties of carbazole-diketopyrrolopyrrole copolymers, O. Kwon et al., J. Mater. Chem. A, 1, 7118-7124 (2013)
  6. Morphology control in polycarbazole based bulk heterojunction solar cells and its impact on device performance, T-Y. Chu et al., Appl. Phys. Lett. 98, 253301 (2011)
  7. Largely Enhanced Efficiency with a PFN/Al Bilayer Cathode in High Efficiency Bulk Heterojunction Photovoltaic Cells with a Low Bandgap Polycarbazole Donor, Z. He., et al., Adv. Mater., 23, 3086–3089 (2011)
  8. Poly(2,7-carbazole)s: Structure-Property Relationships, N. Blouin et al., Acc. Chem. Res., 41 (9), 1110–1119 (2008)