Mechanisms of a Cyclobutane-Fused Lactone Hydrolysis in Alkaline and Acidic Conditions

Searching for functional polyesters with stability and degradability is important due to their potential applications in biomedical supplies, biomass fuel, and environmental protection. Recently, a cyclobutane-fused lactone (CBL) polymer was experimentally found to have superior stability and controllable degradability through hydrolysis reactions after activation by mechanical force. In order to provide a theoretical basis for developing new functional degradable polyesters, in this work, we performed a detailed quantum chemical study of the alkaline and acidic hydrolysis of CBL using dispersion-corrected density functional theory (DFT-D3) and mixed implicit/explicit solvent models. Various possible hydrolysis mechanisms were found: BAC2 and BAL2 in the alkaline condition and AAC2, AAL2, and AAL1 in the acidic condition. Our calculations indicated that CBL favors the BAC2 and AAC2 mechanisms in alkaline and acidic conditions, respectively. In addition, we found that incorporating explicit water solvent molecules is highly necessary because of their strong hydrogen-bonding with reactant/intermediate/product molecules.

Protecting-Group-Free Synthesis of Thiol-Functionalized Degradable Polyesters

Thiol-functionalized degradable polyesters have significant applications in nanoscience and polymer chemistry due to the combination of the biodegradability and biocompatibility of polyesters, and the special chemical and physical properties of...

Consequences of isolated critical monomer sequence errors for the hydrolysis behaviors of sequenced degradable polyesters

Despite the known sensitivity to sequence mutations of biological polymers, little is known about the effects of errors in sequenced synthetic copolymers.

Reversible networks of degradable polyesters containing weak covalent bonds

The synthesis of reversible polyester networks based mainly on the Diels–Alder chemistry, alkene [2 + 2] cycloaddition or transesterification reactions and studies of their reversibility and its consequences are reviewed.

Hydrophilic and degradable polyesters based on l-aspartic acid with antibacterial properties for potential application in hernia repair

A polyester hernia patch has received extensive attention in mesh hernia repair.