A strategy for constructing anti-adhesion surfaces based on interfacial thiol–ene photoclick chemistry between DOPA derivatives with a catechol anchor group and zwitterionic betaine macromolecules

Abstract

A novel route to construct stable and durable anti-adhesion surfaces was explored via a combination of the excellent anti-adhesion performance of zwitterionic betaine macromolecules with the strong adhesion of DOPA or its derivatives to various substrates. The zwitterionic betaine macromolecules bearing a thiol group poly(DMAPMAPS-co-BAC) and a DOPA derivative DMA containing a catechol anchor group and a double bond were first designed and synthesized. The poly(DMAPMAPS-co-BAC)-grafted surfaces were then fabricated via the interfacial thiol–ene photoclick reaction between poly(DMAPMAPS-co-BAC) and DMA anchored onto substrate (i.e., Glass slides and flat PET sheets) surfaces. The chemical formation of each layer on the surfaces was confirmed by XPS and ATR-FTIR analyses. Their morphologies and wettability were characterized. The results indicate that, compared with the original surfaces, the modified surfaces possess an increased nanoscale roughness; the WCA and OCA values on the modified Glass/PET surfaces can reach 10°/12° and 156°/162°, respectively, showing their strong hydrophilicity and excellent underwater superoleophobicity. The anti-oil-fouling and antifogging properties were investigated and the anti-bacterial adhesion properties were evaluated by bacterial adhesion tests using E. coli and S. aureus as test bacteria, respectively. The results show that the modified surfaces possess obvious anti-oil-fouling and antifogging properties and a strong ability to resist bacterial adhesion with a long term stability. It suggests that such a facile yet universal strategy based on interfacial thiol–ene photoclick chemistry could offer an effective solution to the poor stability of anti-adhesion surfaces modified with ultralow-adherent zwitterionic betaine macromolecules, and could be applicable to a wide variety of substrates.