SYNTHESIS AND MODIFICATION OF AN EPOXIDE-CONTAINING POLYMER PREPARED USING RING OPENING METATHESIS POLYMERIZATION (ROMP)

Epoxides, also known as oxiranes, are highly strained three-membered, cyclic ethers that can readily undergo ring-opening reactions with a variety of nucleophiles. Furthermore, these reactions can be used to modify the properties of epoxide-containing polymers and to synthesize a wide range of functionalized polymers. Epoxide containing polymers (EPs) have been widely used as starting materials and as intermediates in the synthesis of various functional materials. However, polymers that contain epoxide groups can be synthesized with controlled molecular weights and polydispersities (Ð). In this study, cyclooctene and 9-oxabicyclo [6.1.0] non-4-ene monomers are used to prepare EPs using ROMP conditions with Grubbs 2nd generation initiator. Post-polymerization modification (PPM) reactions are important tools to tailor a polymer’s properties and performance for various applications. Therefore, the focus of this project is aimed at the synthesis of EP’s, using ROMP, that can undergo PPM reactions to provide polymers decorated with functionalities that include azides, hydroxyls, thiols, esters, silanes, amines, and others. In particular, the conversion of these epoxides to azidohydrins is an important step for the efficient synthesis of functionalized molecules and materials using the copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction, the prototypical “Click reaction”. Notably, epoxide polymers containing azides (EP-N3) can act as a common platform linking various functional groups and would be an effective route to synthesize polymers without any by-products. In thio-bromo click reactions, the advantages of this reaction include the mild reaction conditions, high efficiency, and selectivity use as a tool for the v post-polymerization modification of materials derived from ROMP. Consistent with our expectations, the modified copolymers will provide an effective and facile route to synthesize PPM copolymers.