The general procedure for the synthesis of 2-bromo-9,10-bis(2-naphthalenyl)anthracene from 2-bromo-9,10-bis(2-naphthalenyl)anthracene-9,10-diol was as follows: compound 109 (2-bromonaphthalene, 11.0 g, 53.1 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL) under nitrogen protection. The solution was cooled to -78 °C in a cooling bath, followed by the slow addition of tert-butyl lithium (47.0 mL, 1.7 M pentane solution). The reaction mixture was stirred for about 1 hour while maintaining -78 °C, followed by the addition of compound 104 (6.31 g, 22.0 mmol). The cooling bath was removed and the reaction mixture was allowed to warm up to room temperature and stirring was continued for about 3 hours. Upon completion of the reaction, the reaction was quenched by addition of aqueous ammonium chloride to the mixture and extracted with dichloromethane. The organic phases were combined, dried with magnesium sulfate and concentrated under reduced pressure to give the crude product. The crude product was dissolved in ether, crystallization was induced by the addition of petroleum ether, and the solid was collected by filtration after stirring for several hours and dried under vacuum to give dinaphthalenyl glycol (11.2 g, 93% yield). Next, dinaphthyl glycol (11.2 g, 20.5 mmol) was suspended in acetic acid (600 mL) under nitrogen protection and potassium iodide (34.2 g, 206 mmol) and sodium hypophosphite hydrate (36.0 g, 340 mmol) were added sequentially. The reaction mixture was heated and stirred at reflux for about 3 hours. After completion of the reaction, it was cooled to room temperature, filtered, the solid was washed with water and methanol, and dried under vacuum to give the light yellow target compound 109 (2-bromo-9,10-bis(2-naphthyl)anthracene, 10.1 g, 96% yield).
