Poly(ethylene glycol) (PEG) is the most important representative of the class of aliphatic polyether due to its outstanding properties. Its high aqueous solubility is unique among the polyether, which are usually not water-soluble. PEG exhibits a low immunogenicity, antigenicity and toxicity. It is the gold standard of biocompatible polymers in medical, pharmaceutical and cosmetic applications. Diverse surfaces, drugs or biomolecules can be modified by covalent attachment of PEG chains, which is known as “PEGylation”. This strategy improves the biomedical and pharmaceutical properties of drugs. Some “PEGylated” pharmaceuticals are already approved by the American Food and Drug Administration (FDA). The drawback of PEG for some applications is the low number of functional groups of the polymer. To achieve multifunctionality, ethylene oxide can be copolymerized with various functional epoxides, leading to multifunctional PEG. In recent years, PEG with catechol termini have been used to impart antifouling properties to surfaces, to fabricate composite materials and to stabilize nanoparticles. PEG modified with catechol moieties can form supramolecular polymer networks in the presence of iron ions. In this work we present the synthesis of a novel catechol-containing monomer safrole oxide (SFO). SFO is obtained in a one-step reactions and enables the incorporation of surface-active catechol moieties into a variety of hydrophilic and biocompatible polyether architectures by copolymerization. Via cleavage of the protecting groups, the polymer-attached catechol functionalities are liberated and available for surface attachment or metal complexation. SFO has been copolymerized with ethylene oxide using the monomer activating technique. This method enables the copolymerization with a variety of comonomers and therefore the incorporation of divers functional groups, which could not be introduced via the well-established classical approach of the AROP.

Safrole Oxide (SFO): A novel functional epoxide monomer for the introduction of Catechol moieties into multifunctional Poly(ethylene glycol) via monomer activated technique

253rd National Meeting (2017)

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