Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers

Abstract

Accessing cyclic carbonate monomers on a large scale is critical for the development of any new carbonate-based materials platform. The synthesis of carbonate monomers can be a challenging and tedious endeavor requiring multiple synthetic steps and purifications. To address this, we report a drastically improved process for the synthesis of carbonate monomers via a two-step route that avoids the use of hazardous triphosgene or chloroformate reagents. This process enables rapid access to a broad array of functional groups on the carbonate monomer and the monomers generated from the procedure can readily be polymerized via ring-opening polymerization.

Effects of Hydrophobicity on Antimicrobial Activity, Selectivity, and Functional Mechanism of Guanidinium‐Functionalized Polymers

“…The experimental procedures and NMR characterization are provided in the Supporting Information. [ 24,37,38 ]…”

“…The experimental procedures and NMR characterization are provided in the Supporting Information. [24,37,38] Synthesis of Boc-Protected Guanidinium-Functionalized Random Co-Polymers (Scheme 1): The Boc-protected guanidinium-functionalized random co-polymers were synthesized according to the previously published protocol. [28] Briefly, the synthesis of P1′ is given as a representative example.…”

Elucidating the anticancer activities of guanidinium-functionalized amphiphilic random copolymers by varying the structure and composition in the hydrophobic monomer

“…The concomitant loss of MeSH as the by-product afforded boc-protected guanylated alcohol. Subsequently, the desired guanidinium-functionalized monomer was efficiently accessed through acid promoted cyclisation of bis-MPA and the boc-protected guanylated alcohol 42 . On the other hand, the hydrophobic monomers M1-M5 were readily synthesized from bis-MPA and the respective alcohol of interest, followed by cyclisation using ethyl chloroformate under nitrogen (Scheme 1 ) 45 .…”

“…The cyclic carbonate monomers were synthesized according to a previously published protocol and the brief description of the experimental procedures can be found in the supplementary information 29 , 40 , 42 .…”

Broad‐Spectrum Antiviral Peptides and Polymers

“…Technical advances in synthetic methods seem to have rapidly progressed in the last decade to help overcome this barrier. [208][209][210] The study of the pharmacokinetics of polymers is challenging due to polydispersity in molecular weight. Isotopic labelling may provide a solution.…”