Even with state of the art adhesive systems the adhesion on water wetted surfaces or under water offers still technological challenges. In nature, different maritime creatures, like for instance mussels, solved this problem during evolutionary adaptation. One of the key factors for the impressive wet adhesion capabilities of blue mussels (<i>Mytilus Edulis</i>) is L-3,4-dihydroxyphenylalanine (L-Dopa). This amino acid derivative contributes to adhesion and cohesion due to a rich follow-up chemistry including ion complex formation, nucleophilic trapping and radical dimerization. Recently a mussel-inspired polymerization pathway was described that enabled the tyrosinase activated polymerization of Tyr/Cys bearing peptides by generating cysteinyldopa connectivities. In the present study, the bottleneck of enzyme availability was overcome. Straightforward access to tailor made backbone structures can be achieved by using peptide AB-monomers bearing L-Dopa and a free thiol of a cysteine residue as starting point. After chemical activation of the monomer, polymerization takes place via Michael-type addition. Nucleophilic attack of free thiol functionalities to quinones lead to polymers with adhesive thiol-catechol-connectivities (TCCs) in the backbone (Figrue 1). The artificial mussel glue polymers proved versatile adhesiveness on various substrates even under seawater model conditions and generated coatings with exceptional stability against rinsing with hypersaline solutions.

Mussel-inspired polymerization: Expanding chemical and sequential spaces of artificial mussel glue polymers by a chemically activated pathway

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.