Potassium Carbonate → 2,2'-(5-(8-bromodibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)

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A mixture of 2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole) (3.00 g, 5.10 mmol), 2,8-dibromodibenzo[b,d]furan (1.83 g, 5.61 mmol), tetrakis(triphenylphosphine) palladium(0) (0.30 g, 0.26 mmol), potassium carbonate (2.11 g, 15.30 mmol), 1,4-dioxane (90.00 mL), and water (18.00 mL) was degassed with bubbling argon for 50 min. The reaction mixture was then heated to 80° C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with ethyl acetate in dichloromethane as the eluent. The product fractions were then dried and the product was collected to yield Compound 14 (2.00 g, 56%). Confirmed by LCMS (APCI): calculated for C44H27BrN4O (M+H): 707. Found: 707.

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