Dioctylamine → 4,4'-Bis-dioctylaminostilbene

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An oven dried 3-necked flask was fitted with a reflux condenser and purged with nitrogen. Into the flask was placed 4,4′-dibromostilbene (1.0 g, 2.96 mmol) (synthesized by the general Wittig procedure described above), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (13.5 mg, 0.0148 mmol), o-tolylphosphine (13,5 mg, 0.044 mmol), and sodium t-butoxide (711 mg, 7.4 mmol) in 6 mL dry toluene. Dioctylamine (1.608 g, 6.65 mmol) was then added and the reaction mixture was stirred for 48 hours at 80° C. under nitrogen balloon atmosphere. The crude product was then adsorbed onto silica gel and purified via flash chromatography with gradual elutions from 98/2 to 95/5 (hexanes:ethyl acetate). 1H NMR (d6-acetone) δ 0.89 (m, 12H), 1.20-1.70 (m, 24H), 3.34 (t, J=7.51 Hz, 8H), 6.66 (d, J=8.75 Hz, 4H), 6.83 (s, 2H), 7.32 (d, J=8.62 Hz, 4H).

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