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.

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

The unique molecular structure, the joined biphenyl at 9-postion for a maximum pi-conjugation and planar structure, and also the excellent optical and electronic properties, have brought semiconducting polyfluorenes in 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
1H 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.