Reaction Steps
To a magnetically stirred solution of 2,7-dibromofluorene 1 (2.00 g, 6.17 mmol) and semi-perfluoroalkyl iodide 4 (9.72 g, 15.4 mmol) in toluene (12 cm3) were added 50% (w/w) NaOH aqueous solution (24 g) and Bu4NBr (0.20 g, 0.62 mmol). The mixture was then heated to 80° C. After the reaction was stirred overnight under N2 atmosphere, it was allowed to cool to ambient temperature and quenched by the addition of water (150 cm3). The product was extracted with hexanes (150 cm3). The organic layer was then washed with water (150 cm3), dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel, hexanes) and then recrystallized from hexanes (40 cm3) twice to give the dibromofluorene 6 as colorless crystals (5.91 g, 72%); mp 82-83° C. (hexanes); (Found: C, 37.4; H, 2.1. C41H30Br2F34 requires C, 37.1; H, 2.3%); IR (KBr) νmax: 2932, 2855, 1600, 1448, 1371, 1329, 1245, 1208, 1150, 1054, 1017, 980, 954, 810, 705 cm−1; 1H NMR (500 MHz, CDCl3, δ) 7.55 (d, J=8 Hz, 2H, Ar—H), 7.49 (dd, J=1.5, 8 Hz, 2H, Ar—H), 7.46 (d, J=1.5 Hz, 2H, Ar—H), 2.00-1.90 (m, 8H, 2×ArCCH2 and 2×CH2CF2), 1.47-1.41 (m, 4H, 2×CH2CH2CF2), 1.20-1.09 (m, 8H, 2×ArCCH2CH2CH2 and 2×CH2CH2CH2CF2), 0.65-0.59 ppm (m, 4H, 2×ArCCH2CH2); 13C NMR (126 MHz, CDCl3, δ) 152.1, 139.1, 130.3, 126.0, 121.6, 121.2, 55.5, 40.0, 30.7 (t, J=22 Hz), 29.4, 28.7, 23.5, 20.0 ppm; m/z (ESI) 1328.0 [M+. C4H30Br2F34: requires M, 1328.01].
