Design and synthesis of novel "orthogonally" functionalizable maleimide-based styrenic copolymers.

Macromolecular rapid communications (2012-04-21)
Idil Ipek Yilmaz, Mehmet Arslan, Amitav Sanyal

Polymers containing maleimide groups on their side chains have been synthesized by utilization of a novel styrenic monomer containing a masked-maleimide unit. AIBN initiated free radical polymerization and reverse addition-fragmentation chain transfer (RAFT) polymerization was utilized for synthesis of copolymers containing masked maleimide groups as side chains. The maleimide groups were unmasked via the retro Diels-Alder reaction. Orthogonally functionalizable copolymers were obtained by copolymerization of the maleimide-based monomer with other reactive monomers to yield copolymers that are reactive towards thiol- and amine-containing molecules, or two different thiol-containing molecules sequentially via the nucleophilic thiol-ene and the free-radical thiol-ene "click" reactions.

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2,2′-Azobis(2-methylpropionitrile) solution, 0.2 M in toluene
Azobisisobutyronitrile, 12 wt. % in acetone
2,2′-Azobis(2-methylpropionitrile), recrystallized from methanol, 99%