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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 practical application of these functionalities is limited by their susceptibility to oxidation. 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.
Supplementary materials
Title
Resilient wet adhesion of catechol analogs
Description
S1. Synthetic methods for Tren(Lys-3,4-DHB)3 and Tren(Lys-1,2-HOPO)3
Scheme S1. Synthetic scheme for Tren(Lys-3,4-DHB)3 and Tren(Lys-1,2-HOPO)3
Methods S1. Synthetic methods for Tren(Lys-3,4-DHB)3 and Tren(Lys-1,2-HOPO)3
Figure S1. 1H NMR of Tren(Lys-3,4-DHB)3
Figure S2. 13C NMR of Tren(Lys-3,4-DHB)3
Figure S3. 1H-13C HMBC NMR of Tren(Lys-3,4-DHB)3
Table S1. NMR data for Tren(Lys-3,4-DHB)3
Figure S4. 1H NMR of Tren(Lys-1,2-HOPO)3
Figure S5. 13C NMR of Tren(Lys-1,2-HOPO)3
Figure S6. 1H-13C HMBC NMR of Tren(Lys-1,2-HOPO)3
Table S2. NMR data for Tren(Lys-1,2-HOPO)3
Figure S7. Reversibility of the adhesion of Tren(Lys-1,2-HOPO)3
Figure S8. Reversibility of the adhesion of Tren(Lys-3,4-DHB)3
Figure S9. Adhesion of mica surfaces in buffer
Figure S10. Adhesion and film thickness of Tren(Lys-1,2-HOPO)3 vs deposition concentration
Table S3. pKa values of selected compounds and functional groups.
Table S4. Average deprotonation fraction and total charge of Tren(Lys-2,3-DHB)3 at pH 3, 7, and 10.
Figure S11. Adhesion measurements of Tren(Lys-2,3-DHB)3 and Tren(Lys-3,4-DHB)3 deposited after incubation at pH 10.
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