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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.

A new class of biodegradable polyester dendrons which are orthogonally functionalizable have been synthesized and their multifunctionality has been demonstrated. The surface of these dendrons were appended with alkyne groups that can undergo efficient Huisgen type “click” cycloaddition reaction, while their focal point consists of a reactive maleimide group that can undergo facile conjugation with thiol containing molecules. Multiarm poly(ethylene glycol) polymer with a maleimide-based reactive focal point was synthesized using such a dendron. Solubilization of a hydrophobic dye, BODIPY-SH, in aqueous solution via conjugation to these reactive multiarm PEGs demonstrate possible applications of such dendrons to design water-soluble scaffolds for drug delivery.

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