Bioresorbable, stereochemically defined elastomers and methods of making and using same

Abstract

In various embodiments, the present invention relates to a series of biodegradable thiol-yne elastomers that incorporate degradable C-Cdicarboxylic acid-based monomer units made using a nucleophilic thiol-yne polymerization methodology that targets high cis-content at comparable molar masses to provide excellent mechanical properties. As each C-Cdicarboxylic acid-based monomer unit contains at least two labile ester linkages, altering the stoichiometry of degradable C-Cdicarboxylic acid-based monomer unit incorporation allows the degradation rate of the material to be tuned precisely, while retaining control over the mechanical properties by maintaining the cis/trans stereochemistry of the double bonds to provide independent tuning of mechanical and degradative properties. In one or more embodiments, these degradable C-Cdicarboxylic acid-based monomers can be introduced into the thiol-yne polymerization reaction via one, or both, of the thiol and alkyne functional groups, providing additional flexibility in developing suitable polymer species.