pH-Tolerant Wet Adhesion of Catechol Analogs

George D Degen; Syeda Tajin Ahmed; Parker R Stow; Alison Butler; Roberto C Andresen Eguiluz

doi:10.1021/acsami.4c01740

pH-Tolerant Wet Adhesion of Catechol Analogs

ACS Appl Mater Interfaces. 2024 May 1;16(17):22689-22695. doi: 10.1021/acsami.4c01740. Epub 2024 Apr 15.

Authors

George D Degen¹, Syeda Tajin Ahmed², Parker R Stow³, Alison Butler³, Roberto C Andresen Eguiluz^{2

4}

Affiliations

¹ Department of Chemical Engineering, University of California, Santa Barbara, California 93106, United States.
² Department of Materials Science and Engineering, University of California, Merced, California 95344, United States.
³ Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
⁴ Health Sciences Research Institute, University of California, Merced, California 95344, United States.

Abstract

The need for improved wet adhesives has driven research on mussel-inspired materials incorporating dihydroxyphenylalanine (DOPA) and related analogs of the parent catechol, but their susceptibility to oxidation limits practical application of these functionalities. Here, we investigate the molecular-level adhesion of the catechol analogs dihydroxybenzamide (DHB) and hydroxypyridinone (HOPO) as a function of pH. We find that the molecular structure of the catechol analogs influences their susceptibility to oxidation in alkaline conditions, with HOPO emerging as a particularly promising candidate for pH-tolerant adhesives for diverse environmental conditions.

Keywords: DOPA; HOPO; mussel-inspired; pH tolerant adhesive; surface forces apparatus; surface primers; wet adhesion.