OC1C=CC=C(O)C=1.ClC[Si](CCl)(C)O[Si](C)(C)C.C([O-])([O-])=O.[K+].[K+].[N+]([C:29]1[CH:30]=[C:31]([C:37]#[N:38])[C:32](=[CH:35][CH:36]=1)[C:33]#[N:34])([O-])=O.Cl>O.CS(C)=O>[C:37](#[N:38])[C:31]1[C:32](=[CH:35][CH:36]=[CH:29][CH:30]=1)[C:33]#[N:34]To a 2000 mL, three-necked flask fitted with a thermometer and a nitrogen inlet were added 1,3-dihydroxybenzene (48.2 g, 0.438 mol), bis(chloromethyl)tetramethyl disiloxane (50.1 g, 0.217 mol), powdered anhydrous K2CO3 (150 g, 1.09 mol), and dimethylsulfoxide (DMSO) (1000 mL). The resulting mixture was degassed with nitrogen at ambient temperature and heated at 90° C. under a nitrogen atmosphere for 8-16 hr. The mixture was cooled to 50° C. At this time, 4-nitrophthalonitrile (76.1 g, 0.440 mol) was added in one portion and the reaction mixture was heated at 80° C. for 6-8 hr. The mixture was allowed to cool to ambient temperature and poured into 1000 mL of distilled water. The mixture was made acidic by the addition of 6 M aqueous HCl and the resin was extracted out of the water layer by toluene (200 mL). The toluene extracts were washed 3 times with 500 mL of distilled water and the toluene extracts were dried using magnesium sulfate. Removal of the toluene resulted in an amber oil, which was dried at 80° C. under vacuum. The 2:1 oligomeric phthalonitrile was isolated as an amber glassy solid (131 g, 95%). 1H-NMR [CDCl3]: λ 7.70 (m, aromatic-HR), 7.69 (m, aromatic-HR), 7.35 (m, aromatic-HR), 7.10 (m, aromatic-HR), 6.98 (m, aromatic-HR), 6.88 (m, aromatic-HR), 3.73 (m, aliphatic-HR), 3.46 (m, aliphatic-HR), 0.22 (s, Si—CH3), 0.06 (s, Si—CH3).
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