Document Type

Article

Publication Date

4-27-2026

Department

Department of Biomedical Engineering

Abstract

Premature oxidation of catechol drastically reduces its adhesion strength and utility. This study chemically linked catechol to an imidazolium group, which functioned as an intrinsic protecting group that retarded catechol oxidation and enabled stable wet adhesion under basic conditions. Johnson–Kendall–Roberts (JKR) contact mechanical testing was performed to determine the work of adhesion (Wadh) of imidazolium-modified catechol (VIMCAT), which remained unchanged for up to 48 hours when incubated at pH 7.4. Contrastingly, Wadh values of unprotected catechol were quickly reduced by over 25% within 30 minutes. VIMCAT still retained its initial adhesion strength even after incubation at pH 9 for over 2 hours. Electron spin resonance (ESR) and ultraviolet-visible (UV-vis) spectra confirmed that VIMCAT resisted conversion to quinone under alkaline conditions. VIMCAT is intrinsically more resistant to oxidation as demonstrated by a higher anodic potential observed from the cyclic voltammetry (CV) experiment and a lower highest occupied molecular orbital (HOMO) energy level calculated using density functional theory (DFT) analysis when compared to unmodified catechol. The direct conjugation of imidazolium with catechol offers a metal-free and intrinsically stabilizing molecular design for a high-performance adhesive polymer, capable of long-term operation in alkaline environments.

Publisher's Statement

© 2026 The Author(s). Published by the Royal Society of Chemistry. Publisher’s version of record: https://doi.org/10.1039/D6LF00041J

Publication Title

RSC Applied Interfaces

Creative Commons License

Creative Commons Attribution-Noncommercial 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial 3.0 License

Version

Publisher's PDF

Download

Included in

Life Sciences Commons

Share

COinS
 
 

To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.