  2-Oxazoline monomers can undergo cationic ring-opening polymerizations if certain criteria are met, in particular the absence of certain functional groups: Only non-nucleophilic functional groups do not inherently disturb the polymerization. Hence, XH groups such as alcohols, amines and thiols must either be protected during the polymerization or be introduced in polymeranalogous fashion. Click reactions are a set of key reactions for the post-synthetic strategy due to their high yield, and as such the UV-induced thiol-ene reaction plays a prominent role: 2-Oxazoline monomers bearing unsaturated double bonds can be easily synthesized from compounds from renewable resources such as undecenoic acid, and be reacted with (commercially available) thiols. While non-conjugated double bonds do not interfere with the polymerization itself, these click reactions can be applied to the monomers and polymers, respectively, ranging from the derivation of 2-oxazoline monomers and poly(2-oxazoline)s with functional groups as well as the crosslinking of the corresponding (co-)polymers.

Models, light, and click: Functionalization of 2-oxazoline monomers and poly(2-oxazoline)s by thiol-ene click reactions

248th National Meeting (2014)

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