2-Bromo-9,9'-spirobi[9H-fluorene]

Description

2-Bromo-9, 9’-spirobifluorene is a derivative of 9,9'-spirobifluorene. It is a quite useful blue light emitting material used in the organic light emitting diodes (OLEDs). It possesses high photoluminescence efficiency and good chemical stability. Moreover, It has high glass-transition temperature, excellent thermal stability and easy color tenability through introducing low band gap co-monomers.

Chemical Properties

Off-white to light yellow crystal or powder

Synthesis

Synthesis of 2-bromo-spirofluorene
2-bromo-9-hydroxy-9-(2-biphenyl)fluorene (2g) dissolved in 25 mL acetic acid (15 mol/L) containing hydrochloric acid (12 mol/L) was refluxed for about 2 h to separate out a white solid, which was recrystallized with ethanol to produce white crystals of 2-bromo-spirofluorene (1.2 g, yield 63%).
GC-MS (m/z +): 394. 1HNMR (400 MHz, CDCl3, ppm):δ7.80～7.86 (m, 3H), δ7. 70 (d, 1H),δ7.48 (m, 1H), δ7.36 ～ 7.40 (m, 3H), δ7.13 (m, 3H), δ6.84 (d, 1H), δ6.72 (m, 3H)

References

http://www.sigmaaldrich.com/catalog/product/aldrich/767735?lang=en&region=US
Tang, S., et al. "A Molecular Glass for Deep-Blue Organic Light-Emitting Diodes Comprising a 9,9′-Spirobifluorene Core and Peripheral Carbazole Groups." Advanced Functional Materials 17.15(2010):2869-2877.
Nakanotani, H., et al. "Extremely Low-Threshold Amplified Spontaneous Emission of 9,9′-Spirobifluorene Derivatives and Electroluminescence from Field-Effect Transistor Structure." Advanced Functional Materials17.14(2010):2328-2335.