Chemical recycling to monomers (CRMs) of A−B−A block copolymers is governed by the chemical structure andthereby the thermodynamic behavior of different block constitu-ents. Here, we show how a thermodynamic toolkit based on acyclic monomer structure and solvent properties can be utilized inthe design of recyclable A−B−A block copolymers with varyingmaterial properties. By combining four cyclic monomers lactide, ε-decalactone, 2,2-diethyltrimethylene carbonate, and trimethylenecarbonate, three different block copolymers were created, suitablefor different CRM scenarios. The chemical structure of the softmidblock (ε-decalactone or trimethylene carbonate) appeared tohave a critical impact both on the ring-closing depolymerizationbehavior and mechanical properties, where changing from apolyester to a polycarbonate soft block increased Young’s modulus from 14 to 200 MPa. Hence, this work demonstrates thecomplexity as well as the opportunities in the design of macromolecular structures for a circular economy.