Biodegradability of poly(ester-thioether)s containing chiral biomass <i>via</i> a Michael-type thiol-ene click reaction.

ABSTRACT: We prepared dianhydrosugar-based diacrylates: isosorbide bis(acrylate) (ISDA) and isomannide bis(acrylate) (IMDA) from the corresponding dianhydrosugars. Using a scandium triflate as the catalyst, the chemoselective dehydration of d-, l-, and meso-tartaric acids with 2-mercaptoethanol selectively synthesized three dithiols: l-bis(2-mercaptoethyl)tartrate (META), d-META, and meso-META. The thiol-Michael click polyaddition of ISDA or IMDA with the three dithiols proceeded in N,N-dimethylformamide (40 °C) using triethylamine as the catalyst, yielding the expected six poly(ester-thioether) diastereomers (M _n, 8.2 × 10³ to 9.2 × 10³; molecular weight distribution (M _w/M _n), 1.29-1.51). The sy

SUBMITTER: Imamura R 

PROVIDER: S-EPMC12004360 | biostudies-literature | 2025 Apr

REPOSITORIES: biostudies-literature