In summary, we have synthesized a boroxole-based styrenicmonomer that can be polymerized by the RAFT method. Thecontrolled polymerization of the boroxole-based monomer 1with a PEG-based chain-transfer agent allowed us to synthesizewell-defined monosaccharide-responsive block copolymers. Byutilizing the sugar-responsive disassembly of polymersomes ofPEG-b-PBOx in aqueous solution at neutral pH, we havedemonstrated the monosaccharide-triggered disassembly ofpolymersomes to release encapsulated cargo molecules such asFITC-labeled insulin under physiologically relevant pHconditions. Encapsulated insulin was released from thepolymersomes only in response to the presence of mono-saccharides that bind to boroxole moieties. The boroxole-containing polymers and block copolymers reported here mayfind applications in the development of sensors and drugdelivery systems designed for glucose-related human diseasessuch as diabetes. We are currently working on designing newself-assembling boronic acid-containing block copolymers toimprove the binding efficiency and selectivity toward glucose23under physiological conditions.