The design and synthesis of dynamic, responsive polymeric materials for various applications stands as one of the fastest developing areas of research over the past several decades. Recently, we demonstrated the robustness, rapid dynamics, and small kinetic penalties of the thiol/thioester exchange in organic media for various polymeric architectures.<br/>Here we present the synthesis of thiolactone appended thymidine and deoxycytidine monomers which engage in robust ring opening polymerizations (ROP). These polymers were found to give high conversions and low polydispersities. Moreover, the thiol-end group was found to be quantitatively functionalized via the thiol-Michael reaction to add water solubilizing groups or fluorescent tags. As each repeat unit is separated by a thioester functional group, dynamic behavior of the polymer is feasible via the thiol-thioester exchange, which is demonstrated here by the complete depolymerization/reorganization of the polymers and the blending of two polymers of different molecular weight and/or chemical composition.<br/>Finally, as our polymeric material shares many structural, spatial, and stereochemical similarities with DNA, we have shown binding of this unnatural polymer to native strands of DNA. This work constitutes the first step towards a platform which we hope will culminate in the routine synthesis of functional sequence controlled polymers via dynamic template directed synthesis. Synthesis, polymerizations and the dynamic behavior of the resulting polymers will be presented.

Dynamic, responsive DNA-like polymers

256th National Meeting (2018)

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