Synthesis of Functional Polymer Particles from Morita–Baylis–Hillman Polymerization

Functional synthetic polymers are frequently explored for their use in the biomedical field. To fulfill the stringent demands of biodegradability and compatibility, the materials need to be versatile and tunable. Post‐modification is often considered challenging for well‐known degradable materials like poly(lactic acid) because of their chemical inertness. In this work a procedure is proposed to produce densely functionalized polymer particles using oligomeric precursors synthesized via the Morita–Baylis–Hillman reaction. This allows for a variety of post‐modification reactions to serve bio‐conjugation or tuning of the material properties. The particles are subjected to basic media and found to be degradable. Furthermore, cytotoxicity tests confirm good biocompatibility. Finally, as a proof of concept to demonstrate the versatility of the particles, post‐modification reactions are carried out through the formation of imines. Densely functionalized polymer particles are produced using Morita–Baylis–Hillman (MBH) precursor oligomers in combination with thiol‐ene Michael additions. The resulting MBH particles are found to be degradable, display good biocompatibility based on cytotoxicity assays, and are readily modifiable via imine formation with amines on the surface.