Functionalized diene monomers and polymerized functionalized diene monomers including 2-cyanomethyl-1,3-butadiene, 2-acetoxymethyl-buta-1,3-diene, dimethyl-(2-methylene-but-3-enyl)-amine, 2-dimethylaminomethyl-1,3-butadiene, 2-di-n-propylaminomethyl-1,3-butadiene, 3-methylene-pent-4-enoic acid, 3-methylene-pent-4-enoic acid ethyl ester, bis-2,3-[N,N-diethylaminomethyl]-1,3-butadiene, ethyl-5,6-dimethylenedecanediote, and cyano- 5,6-dimethylenedecanediote. Methods for synthesizing such functionalized diene monomers and polymers are also provided.