Bis[2-(diphenylphosphino)phenyl] ether oxide

Description

DPEPO, with steric ortho-substituted diphenylphosphine oxide (DPPO) groups, is one of the most popular large band-gap materials used to host blue TADF-based OLEDs.

Uses

Bis[2-((oxo)diphenylphosphino)phenyl]ether (CAS# 808142-23-6), also known as DPEPO, is a fluorescent compound often incorporated into OLED materials.

Synthesis

General procedure for the synthesis of bis[2-((oxo)diphenylphosphino)phenyl] ether from bis(2-diphenylphosphino)phenyl ether: compound 8 (5.0 g, 9.3 mmol) was dissolved in 100 mL of dichloromethane, and 30% hydrogen peroxide solution (4.0 mL, 186 mmol) was added slowly and dropwise under the cooling of an ice bath. The reaction mixture was stirred under ice bath conditions for 4 hours. After completion of the reaction, the reaction was quenched with distilled water and extracted three times with dichloromethane. The organic layers were combined, dried with anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting solid was purified by hexane reprecipitation to afford compound 9 (white powder, 5.0 g, 94% yield). IR (ATR) analysis showed characteristic peaks at 1183 cm^-1 (strong absorption, P=O) and 1070-1226 cm^-1 (strong absorption, C-O-C).1H NMR (300 MHz, CDCl3, 25°C) δ 7.06- 7.71 (m, 26H, Ar), 6.02-6.07 (m, 2H, Ar) ppm.31P NMR (200 MHz, CDCl3, 25°C) δ 26.41 (2P) ppm.FAB-MS (m/z) = 571 [M + H]+.

References

[1] Chemistry - A European Journal, 2011, vol. 17, # 2, p. 521 - 528
[2] Patent: EP2471799, 2012, A1. Location in patent: Page/Page column 16
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2014, vol. 69, # 2, p. 239 - 247
[4] Chemistry - A European Journal, 2013, vol. 19, # 1, p. 141 - 154
[5] Patent: JP2018/35101, 2018, A. Location in patent: Paragraph 0086; 0087