Halogen-Atom-SubstitutedDOPA with Enhanced Wet Adhesionand Antioxidization Ability

3,4-Dihydroxyphenylalanine (DOPA) has inspired the development of artificial adhesives, but efforts to enhance its adhesion strength and durability continue to evolve. However, it is tough work to improve DOPA wet adhesion by chemically decorating DOPA itself, despite the potential benefit of a concise and high-quality adhesion unit. Here, we synthesized a series of DOPA substituents by introducing different electron-withdrawing groups at the ortho position of the phenyl ring. This modification allowed us to effectively control the adhesion and antioxidation properties of DOPA. Combining atomic force microscopy (AFM)-based single-molecule force spectroscopy (SFMS) and cyclic voltammetry, we comprehensively investigated DOPA’s antioxidation and adhesion capabilities. We found that adding a chlorine or bromine atom to the catechol ring significantly increases the DOPA wet adhesion strength. Additionally, halogen-substituted DOPA exhibited greater stability than dopamine in liquid solutions. Notably, chlorine-substituted DOPA maintained a strong adhesion ability even in salt water, offering potential benefits for bioadhesive applications.

Publication Details

Journal
Figshare
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.biomac.4c01338.s001
Primary Topic
Genetic and Environmental Crop Studies
Type
article
Field-Weighted Citation Impact
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article

Halogen-Atom-SubstitutedDOPA with Enhanced Wet Adhesionand Antioxidization Ability

Figshare
Genetic and Environmental Crop Studies
article

Halogen-Atom-SubstitutedDOPA with Enhanced Wet Adhesionand Antioxidization Ability

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Abstract

3,4-Dihydroxyphenylalanine (DOPA) has inspired the development of artificial adhesives, but efforts to enhance its adhesion strength and durability continue to evolve. However, it is tough work to improve DOPA wet adhesion by chemically decorating DOPA itself, despite the potential benefit of a concise and high-quality adhesion unit. Here, we synthesized a series of DOPA substituents by introducing different electron-withdrawing groups at the ortho position of the phenyl ring. This modification allowed us to effectively control the adhesion and antioxidation properties of DOPA. Combining atomic force microscopy (AFM)-based single-molecule force spectroscopy (SFMS) and cyclic voltammetry, we comprehensively investigated DOPA’s antioxidation and adhesion capabilities. We found that adding a chlorine or bromine atom to the catechol ring significantly increases the DOPA wet adhesion strength. Additionally, halogen-substituted DOPA exhibited greater stability than dopamine in liquid solutions. Notably, chlorine-substituted DOPA maintained a strong adhesion ability even in salt water, offering potential benefits for bioadhesive applications.

Figshare
Openalex Percentile: Top 42%
Genetic and Environmental Crop Studies
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Halogen-Atom-SubstitutedDOPA with Enhanced Wet Adhesionand Antioxidization Ability · Figshare (2025) | TGRS Research Map | TGRS