Sodium hydride → HCID 86688389, compound

Participants

Reaction Steps

Postfunctionalization of P1. To the solution of 37 mg (0.047 mmol) of P1 dissolved in 3 mL of anhydrous THF was added 0.9 mg (0.037 mmol) of NaH (60% in mineral oil) and stirred for half an hour under nitrogen atmosphere. Then to the mixture a solution of 20 mg (0.048 mmol) 4-(((8-bromooctyl)oxy)methyl)-2,2′-bi(1,3-dithiolylidene)/propargyl bromide in 0.2 mL of anhydrous THF was added followed by the addition of DBU (2 μL) in catalytic amount. The mixture was stirred for 48 h under nitrogen atmosphere. The reaction mixture was poured then into 100 mL water and extracted 3-4 times from 40 mL methylene chloride. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield red solid. The solid was then dissolved in CHCl3, and reprecipitated in methanol 3-4 times. The polymer was then purified by washing it with hexane and methanol, followed by reprecipitating it again in methanol. The solid hence obtained was then dried under vacuum for 24 h. P2: Yield: 66%. Mn=11857, Mw/Mn=2.2. 1H NMR (400 MHz, CDCl3): δ 0.79 (b, 6H), 0.96-1.55 (b, 52H), 2.34 (b, 2H), 2.58 (b, 2H), 3.18 (b, 2H), 3.25 (b, 2H), 3.76 (b, 2H), 3.88 (b, 2H), 5.81 (b, 1H), 5.94 (b, 2H), 6.69-6.95 (b, 7H). P3: Yield: 80%. Mn=12228, Mw/Mn=2.41. 1H NMR (400 MHz, CDCl3): δ 0.87 (b, 6H), 1.26-1.69 (b, 40H), 2.51 (b, 1H), 2.77 (b, 4H), 4.28 (b, 2H), 4.70 (b, 2H), 7.07 (b, 4H), 7.14 (b, 3H).

Provenance & Evidence