In various embodiments, the present invention relates to a series of anti-fouling zwitterionic biodegradable thiol-yne elastomers that incorporate degradable C4-C14 dicarboxylic 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 and zwitterionic side chains that provide anti fouling properties. As each C4-C14 dicarboxylic acid-based monomer unit contains at least two labile ester linkages, altering the stoichiometry of degradable C4-C14 dicarboxylic 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.