2,7-Dibromofluorene

Description

2,7-Dibromofluorene is a halogenated polycyclic aromatic compound and its vapour pressure has been measured using the Knudsen effusion method.

Chemical Properties

white to off-white crystalline powder

Uses

2,7-Dibromofluorene is used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It is also used in the synthesis of conjugated polymer, poly[9,9-bis(6-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays, in the preparation of blue photoluminescent unsymmetrically substituted polyfluorene and in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9-position of the fluorene ring, such as: 9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene, 9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene, 9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene.

Uses

2,7-Dibromofluorene was used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It may be used in the synthesis of conjugated polymer, poly[9,9′-bis(6′′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays. It was used in the preparartion of blue photoluminescent unsymmetrically substituted polyfluorene. It was also used in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9′-position of the fluorene ring, such as:
9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene
9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene
9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene

Uses

2,7-Dibromofluorene was used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It may be used in the synthesis of conjugated polymer, poly[9,9′-bis(6′′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays. It was used in the preparartion of blue photoluminescent unsymmetrically substituted polyfluorene. It was also used in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9′-position of the fluorene ring, such as:

• 9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene
• 9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene
• 9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene

Synthesis

86-73-7

16433-88-8

General procedure for the synthesis of 2,7-dibromofluorene from fluorene: Fluorene (1.5 g, 9.0 mmol) was dissolved in carbon tetrachloride (80 mL), followed by the addition of 30 g of copper(II) bromide loaded on aluminum oxide. The reaction mixture was stirred under reflux conditions for 5 hours. Upon completion of the reaction, the solution was cooled to room temperature, filtered to remove solid impurities, and the filter cake was washed with carbon tetrachloride (50 mL). The combined organic phases were dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give 2.87 g (98% yield) of 2,7-dibromofluorene as a yellow solid. Recrystallization by ethyl acetate/hexane (5:95, v/v) mixed solvent gave pure 2,7-dibromofluorene as light yellow crystals.

References

[1] Tetrahedron, 2003, vol. 59, # 17, p. 3131 - 3156
[2] Dyes and Pigments, 2015, vol. 113, p. 682 - 691
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 22, p. 4071 - 4075
[4] Chemistry Letters, 2013, vol. 42, # 11, p. 1355 - 1357
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443