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Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization

The formation of cysteinyldopa as biogenic connectivity in proteins is used to inspire a chemical pathway toward mussel‐adhesive mimics. The mussel‐inspired polymerization (MIPoly) exploits the chemically diverse family of bisphenol monomers that is oxidizable with 2‐iodoxybenzoic acid to give bisqu...

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Detalles Bibliográficos
Autores principales: Krüger, Jana M., Börner, Hans G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7985868/
https://www.ncbi.nlm.nih.gov/pubmed/33507605
http://dx.doi.org/10.1002/anie.202015833
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author Krüger, Jana M.
Börner, Hans G.
author_facet Krüger, Jana M.
Börner, Hans G.
author_sort Krüger, Jana M.
collection PubMed
description The formation of cysteinyldopa as biogenic connectivity in proteins is used to inspire a chemical pathway toward mussel‐adhesive mimics. The mussel‐inspired polymerization (MIPoly) exploits the chemically diverse family of bisphenol monomers that is oxidizable with 2‐iodoxybenzoic acid to give bisquinones. Those react at room temperature with dithiols in Michael‐type polyadditions, which leads to polymers with thiol–catechol connectivities (TCC). A set of TCC polymers proved adhesive behavior even on challenging poly(propylene) substrates, where they compete with commercial epoxy resins in dry adhesive strength. MIPoly promises facile scale up and exhibits high modularity to tailor adhesives, as proven on a small library where one candidate showed wet adhesion on aluminum substrates in both water and sea water models.
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spelling pubmed-79858682021-03-25 Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization Krüger, Jana M. Börner, Hans G. Angew Chem Int Ed Engl Communications The formation of cysteinyldopa as biogenic connectivity in proteins is used to inspire a chemical pathway toward mussel‐adhesive mimics. The mussel‐inspired polymerization (MIPoly) exploits the chemically diverse family of bisphenol monomers that is oxidizable with 2‐iodoxybenzoic acid to give bisquinones. Those react at room temperature with dithiols in Michael‐type polyadditions, which leads to polymers with thiol–catechol connectivities (TCC). A set of TCC polymers proved adhesive behavior even on challenging poly(propylene) substrates, where they compete with commercial epoxy resins in dry adhesive strength. MIPoly promises facile scale up and exhibits high modularity to tailor adhesives, as proven on a small library where one candidate showed wet adhesion on aluminum substrates in both water and sea water models. John Wiley and Sons Inc. 2021-02-12 2021-03-15 /pmc/articles/PMC7985868/ /pubmed/33507605 http://dx.doi.org/10.1002/anie.202015833 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Krüger, Jana M.
Börner, Hans G.
Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
title Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
title_full Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
title_fullStr Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
title_full_unstemmed Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
title_short Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
title_sort accessing the next generation of synthetic mussel‐glue polymers via mussel‐inspired polymerization
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7985868/
https://www.ncbi.nlm.nih.gov/pubmed/33507605
http://dx.doi.org/10.1002/anie.202015833
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