9,9-Dioctyl-2,7-dibromofluorene

Order Code: B331
MSDS sheet

Price

(excluding Taxes)

£38.00


General Information

CAS number 198964-46-4
Chemical formula C29H40Br2
Molecular weight 548.44 g/mol
Synonyms
  • 2,7-Dibromo-9,9-dioctyl-9H-fluorene
  • 2,7-Dibromo-9,9-dioctylfluorene
  • 2,7-Dibromo-9,9-di-n-octylfluorene
Classification / Family

Fluorene, Halogenated fluorene, Organic materials, Semiconductor Synthesis, Low band gap polymers, OFETs, Organic Photovoltaics, Polymer Solar Cells, Polymer light-emitting diodes

 

Product Details

Purity 98%
Melting point

 
59-63 °C

Color White crystyals/solid

 

Chemical Structure

Chemical structure of 9,9-Dioctyl-2,7-dibromofluorene. CAS number: 198964-46-4, Chemical formula C29H40Br2.

Applications

9,9-Dioctyl-2,7-dibromofluorene can be used for the synthesis of polymer semiconductors, engaging either Suzuki coupling or Stille coupling reactions.

Alkyl-substituted polyfluorenes have emerged as a very attractive class of conjugated polymers, especially for display applications. This is due to their pure blue and efficient electroluminescence, coupled with a high charge-carrier mobility and good processability.

Their unique molecular structure, joined biphenyl at 9-postion for a maximum pi-conjugation and planar structure, and also their excellent optical and electronic properties altogether have brought semiconducting polyfluorenes to the focus of scientific and industrial interest. Polyfluorenes are known as semiconducting materials used for light emitting diodes, organic photovoltaics and interface layer materials for organic electronics. By reacting with 9,9-Dioctylfluorene-2,7-diboronic acid bis(pinacol) ester in toluene, it yields PFO (F8).

Synthesis of PCPDTBT from benzothiadiazole boronic ester
Synthesis of PFO (F8) from 9,9-Dioctylfluorene-2,7-diboronic acid bis(pinacol) ester and 9,9-Dioctyl-2,7-dibromofluorene in toluene with Et4NOH as the base and Pd(OAc)2/(o-tolyl)3P as the catalyst engaging Suzuki coupling reaction.

 

NMR Charaterisation

 

1H NMR dibromo-dioctylfluorene in CDCl3
H NMR spectrum of 9,9-Dioctyl-2,7-dibromofluorene in CDCl3: Instrument AVIIIHD400 (view full version)

 

Literature and Reviews

  1. Synthesis and Spectroscopy of Poly(9,9-dioctylfluorene-2,7-diyl-co-2,8-dihexyldibenzothiophene-S,S-dioxide-3,7-diyl)s: Solution-Processable, Deep-Blue Emitters with a High Triplet Energy, K. Kamtekar et al., Macromolecules, 43 (10), 4481–4488 (2010).
  2. Synthesis and electroluminescence properties of fluorene–anthracene based copolymers for blue and white emitting diodes, H. Song et al., J. Industr. and Eng. Chem., 17, 352–357 (2011).
  3. Enhanced Efficiency of Polyfluorene Derivatives: Organic–Inorganic Hybrid Polymer Light-Emitting Diodes, J. LEE et al., J. Poly. Sci.: Part A: Poly. Chem., 9, 2943 (2006).
  4. Dioctylfluorene-thiophene based conjugated copolymers for bulk heterojunction solar cells and enhanced power conversion efficiency via methanol treatment, H-Y. Chuang et al., Polym. Int.(2015); DOI 10.1002/pi.4979.