Azobisisobutyronitrile → 3-Hydroxy-1-adamantyl acrylate

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Reaction Steps

To a 100 mL roundbottom flask, 2-methyl-2-(trifluoromethylsulfonamido)propyl methacrylate (2,2-diMe-EATf-MA) (1.0 g, 3.5 mmol, 0.15 eq.), 1-ethylcyclopentyl methacrylate (ECPMA) (1.9 g, 10.4 mmol, 0.45 eq.), 3-hydroxyadamantyl methacrylate (HADMA) (2.18 g, 9.2 mmol, 0.40 eq.), 2,2′-azobis(2-methylpropionitrile) (AIBN) (151 mg, 0.04 eq.), and methyl ethyl ketone (10 mL) were added. A reflux condenser with a rubber septum was added and the oxygen was removed from the solution by three sequential pump-backfill cycles using nitrogen while stirring vigorously. The reaction flask was placed under nitrogen and transferred to an oil bath to reflux overnight. Upon completion, the reaction flask was cooled to room temperature and the polymer precipitated into a 30-fold excess of methanol. The polymer was isolated using a medium porosity ceramic fitted Buchner funnel. The white polymer was redissolved into a minimal amount of methyl ethyl ketone and the precipitation process repeated one time. Upon final isolation on the Buchner funnel, the polymer was washed 1 time with methanol. The polymer was dried in vacuo at 80° C. overnight. The polymer was allowed to cool to room temperature under vacuum prior to determining the yield. The final composition was 17:42:41 as determined by inverse-gated 13C NMR using Cr(acac)3 as a relaxation agent in acetone-d6. Yield: 4.3 g (84%). Mn: 6750 g/mol. PDI: 2.43. Tg: >Tdecomp.

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