Access to Highly Functional and Polymerizable Carbonate-Drug Conjugates

We here report the synthesis of two types of six-membered cyclic carbonate monomers equipped with various drug molecules through ester linkages. The target compounds can be isolated in good yields and feature diagnostic IR and ¹³C NMR spectroscopic fingerprints in line with their proposed connectivities. As a potential application, we investigated their ring-opening polymerization (ROP), showing that the nature of the cyclic carbonate is crucial towards macromolecular carbonate formation. The functionalized polycarbonates have molecular weights of up to 10 kg/mol, controllable functionality and a variable drug-to-carbonate ratio. This work demonstrates the adaptive synthesis of new types of functionalized six-membered cyclic carbonates with potential as precursors to polycarbonate-drug type macromolecules.