Uses
1,3,6,8-Tetrabromopyrene is used as a reactant in the synthesis of pyrene-centered starburst oligofluorenes which display good film forming ability and sky blue fluroescence and used in electroluminescent devices.
Synthesis
The general procedure for the synthesis of 1,3,6,8-tetrabromopyrene from pyrene was as follows: bromine (8.75 g, 0.055 mol) was added dropwise to a solution of pyrene (2.5 g, 12.3 mmol) in nitrobenzene (50 mL) with vigorous stirring, and the temperature of the reaction was 80 °C [24]. Subsequently, the reaction mixture was heated to 120 °C and maintained at this temperature for 12 h of reaction. After completion of the reaction, the mixture was cooled to room temperature and the solid product was collected by filtration. The solid was washed with ethanol (100 mL) and then dried under vacuum to afford 1,3,6,8-tetrabromopyrene (6.04 g, 96% yield) as a light green solid with a melting point of more than 300°C (literature value: > 300°C) [21]. The results of elemental analysis were as follows: measured values C, 36.85; H, 1.23. Theoretical values for C16H6Br4 (molecular weight 517.84): C, 37.11; H, 1.17%. The compound has very low solubility in all common organic solvents and therefore 1H NMR spectra were not obtained in CDCl3.
References
[1] Organic Letters, 2007, vol. 9, # 25, p. 5215 - 5218
[2] Journal of the American Chemical Society, 2010, vol. 132, # 12, p. 4119 - 4130
[3] Organometallics, 2017, vol. 36, # 3, p. 556 - 563
[4] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 33, p. 3868 - 3877
[5] Chemistry - A European Journal, 2017, vol. 23, # 62, p. 15746 - 15758
