(338a) Thioaminals As Degradable Cross-Links in Polymer Networks Via Exchange with Thiols

Thioaminals are a functional group where a carbon atom is bonded to one nitrogen and one sulfur atom. These groups can undergo exchange with thiols, resulting in a new thioaminal. When thioaminals are incorporated into polymer networks, the thiol-thioaminal exchange reaction allows the thioaminal to serve as a degradable link, resulting in a degradable crosslinked network. We’ve shown that polymer networks containing various thioaminal crosslinks can be degraded by reaction with a number of different thiols, and that timescale for these reactions varies with different functional groups on both thiol and thioaminal. Moving forward from that, we’re investigating the effect of varying functional groups on the equilibrium and kinetics of the thiol-thioaminal reaction through small molecule studies. Understanding the effect of different functional groups on thiol and thioaminal will allow us to apply the knowledge to thioaminal polymer networks; create networks that can be tuned to desired properties through the thioaminal functional group; and synthesize networks that can be degraded at desired rates, temperatures, and extents based on the thiol used to exchange.