Vinylimidazole

Example 11

The synthesis of Monomer 5 was carried out according to Scheme 10 below.

[Figure (not displayed)]

A solution of 1,8 bis (bromomethyl) anthracene (Aldrich 5 mmol) and vinylimidazole (Aldrich, 5 mmol) in acetonitrile (Merck, 25 ml) was refluxed over night. To prevent polymerisation, a spatula tip of sulphur was added to the reaction mixture. After cooling to room temperature, the solvent was evaporated to dryness under vacuum. The resulting solid was then redissolved in ethanol and precipitated out with the addition of diethyl ether, to afford the desire product as a solid.

Example 6

The synthesis of Monomer 2 was carried out according to Scheme 5 below.

[Figure (not displayed)]

A solution of 1,3-bis(bromomethyl)benzene (Aldrich, 2 g, 7.56 mmol) and vinylimidazole (Aldrich, 1.4 ml, 15.04 mmol) in acetonitrile (Merck, 60 ml) was refluxed over night. To prevent polymerisation, a spatula tip of sulphur was added to the reaction mixture. After cooling to room temperature, the solvent was evaporated to dryness under vacuum. The resulting solid was then redissolved in ethanol and precipitated out with the addition of diethyl ether, to afford the desire product (2.41 g) as a solid (72%).

¹H NMR (400 MHz, DMSO) δ 5.42-5.45 (m, 2H), 5.43, 5.45, 5.45, 5.52 (s, 4H), 5.99-6.04 (m, 2H), 7.33-7.39 (m, 2H), 7.50 (s, 3H), 7.68 (s, 1H), 8.01 (s, 2H), 8.29 (s, 2H), 9.80 (S, 2H);

¹³C NMR (101 MHz, DMSO) δ 51.84, 108.89, 119.45, 123.31, 128.80, 128.86, 128.96, 129.70, 135.10, 135.62.

Calculated C, 47.81%, H, 4.46%, N, 12.39%; found C, 46.08%, H, 4.96%, N, 12.28%.