Self-healing capabilities have been observed in byssal threads of ocean mussels. These self-healing properties arise from the covalent bond interactions between the molecule histidine and a transition metal creating a coordinated network. While this self-healing capability has been studied to better understand the coordination mechanism, it has not been applied to polymer chemistry yet. This project focuses on the synthesis of self-healing polymer networks using thiol-ene chemistry, and the effect that thiol-to-ene ratio and transition metals have on the properties of the overall network. Using ethane-1,2-dithiol, and vinyl imidazole in varying ratios two monomers were synthesized for the creation of self-healing networks: a fully modified imidazole monomer (FMIM) and single modified imidazole monomer (SMIM). Full conversions of both the FMIM and SMIM monomers were confirmed using proton NMR spectroscopy. Metallic salts were added to synthesize the coordinated self-healing networks, with a noticeable difference in viscosity between the resultant gels. The Gaussian 16 system was used to simulate one fragment of a SMIM metal coordinated network and run to collect computational data on the molecules. IR spectroscopy and bond relaxation simulations were used to further examine why the viscosities of the two synthesized gels differ and better understand the binding affinity of the individual metal salts within the network to gain insight into the fundamental self-healing properties.

Synthesis, polymerization, and characterization of self-healing thiol-ene networks

ACS Spring Meeting 2021

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