9,9-Dihexyl-2,7-dibromofluorene Chemical Properties

Melting point:

67-71 °C(lit.)

Boiling point:

0°C

Density 

1.274±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C25H32Br2/c1-3-5-7-9-15-25(16-10-8-6-4-2)23-17-19(26)11-13-21(23)22-14-12-20(27)18-24(22)25/h11-14,17-18H,3-10,15-16H2,1-2H3

InChIKey

OXFFIMLCSVJMHA-UHFFFAOYSA-N

SMILES

C1(CCCCCC)(CCCCCC)C2=C(C=CC(Br)=C2)C2=C1C=C(Br)C=C2

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29039990

9,9-Dihexyl-2,7-dibromofluorene Usage And Synthesis

Chemical Properties

White to brown crystal or powder

Uses

It finds its application as an intermediate for polymeric light-emitting diodes and as an OLED material because of their pure blue emission and efficient electroluminescence coupled with a high charge-carrier mobility and good process ability.

General Description

Intermediate for polymeric light-emitting diodes.

Synthesis

General procedure for the synthesis of 9,9-dihexyl-2,7-dibromofluorene from 2,7-dibromofluorene and 1-bromohexane: 2,7-dibromofluorene (1.5 g), and triethylbenzylammonium chloride (0.009 g) were suspended in 30 mL of dimethylsulfoxide in a triple-necked flask. 1.5 mL of 50 wt% aqueous sodium hydroxide solution was slowly added dropwise and the reaction was carried out for 30 min followed by the addition of 1.59 g of 1-bromohexane dropwise. The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, it was extracted with ether. The organic phase was sequentially washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the resulting crude product was recrystallized from aqueous ethanol to give orange needle-like crystals of 2,7-dibromo-9,9-dihexylfluorene (1.96 g) in 86% yield.

References

[1] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2714 - 2717
[2] Macromolecules, 2003, vol. 36, # 19, p. 6995 - 7003
[3] Chemical Communications, 2008, # 32, p. 3765 - 3767
[4] Macromolecules, 2003, vol. 36, # 19, p. 6970 - 6975
[5] Tetrahedron Letters, 2007, vol. 48, # 1, p. 89 - 93

9,9-Dihexyl-2,7-dibromofluorene(189367-54-2)Related Product Information

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