Chemisorption of catechol on gibbsite, boehmite, and noncrystalline alumina surfaces

McBride, Murray B.; Wesselink, L.G.

doi:10.1021/es00171a014

Cited by 137 publications

(124 citation statements)

References 13 publications

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“…Charged lysine plays a subtle but indispensable role in evicting hydrated surface cations from aluminosilicates (Maier et al, 2015). On mica, for example, hydrated K + sits over alumina sites, thereby blocking them from being coordinated by the catecholate moiety of Dopa (McBride and Wesselink, 1988). By removing these cations, lysine enables Dopa surface binding.…”

Section: Adhesive Chemistry At Acidic Phmentioning

confidence: 99%

“…On metal oxides such as alumina (McBride and Wesselink, 1988), titania (Bahri et al, 2011;Vega-Arroyo et al, 2005) and iron oxide surfaces, catechol (Dopa) binding is pH dependent, progressing from bidentate H-bonding to bidentate-binuclear coordinative bonding (Fig. 6A); that is, two H-bonds per catechol at pH ∼3, to one H-bond and one coordination bond at pH ∼5, and finally to two coordination bonds at pH ∼8 (Li et al, 2010;Bahri et al, 2011;Mian et al, 2014).…”

Section: Catechol-based Experimentsmentioning

confidence: 99%

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Mussel adhesion – essential footwork

Waite

2017

Journal of Experimental Biology

528

744

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Robust adhesion to wet, salt-encrusted, corroded and slimy surfaces has been an essential adaptation in the life histories of sessile marine organisms for hundreds of millions of years, but it remains a major impasse for technology. Mussel adhesion has served as one of many model systems providing a fundamental understanding of what is required for attachment to wet surfaces. Most polymer engineers have focused on the use of 3,4-dihydroxyphenyl-L-alanine (Dopa), a peculiar but abundant catecholic amino acid in mussel adhesive proteins. The premise of this Review is that although Dopa does have the potential for diverse cohesive and adhesive interactions, these will be difficult to achieve in synthetic homologs without a deeper knowledge of mussel biology; that is, how, at different length and time scales, mussels regulate the reactivity of their adhesive proteins. To deposit adhesive proteins onto target surfaces, the mussel foot creates an insulated reaction chamber with extreme reaction conditions such as low pH, low ionic strength and high reducing poise. These conditions enable adhesive proteins to undergo controlled fluid-fluid phase separation, surface adsorption and spreading, microstructure formation and, finally, solidification.

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Section: Adhesive Chemistry At Acidic Phmentioning

confidence: 99%

Section: Catechol-based Experimentsmentioning

confidence: 99%

Mussel adhesion – essential footwork

Waite

2017

Journal of Experimental Biology

528

744

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“…They react with inorganic materials, such as metal ions or metal oxide surfaces, creatings trong yet reversible bidentate coordination bonds ( Figure 3A,r eactions 1a nd 3). [9,22] In the byssal threads,t he coordination capability is used to form the protective and selfhealing Fe III -cross-linkedc oating; [16] however,t he chemistry can be easily expanded to include other hard metal ions using the hard/soft acid/base principle.…”

Section: The Promiscuous Nature Of Catecholsmentioning

confidence: 99%

Mussel‐Inspired Materials: Self‐Healing through Coordination Chemistry

Krogsgaard¹,

Nue²,

Birkedal³

2015

Chemistry A European J

283

240

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Improved understanding of the underwater attachment strategy of the blue mussels and other marine organisms has inspired researchers to find new routes to advanced materials. Mussels use polyphenols, such as the catechol-containing amino acid 3,4-dihydroxyphenylalanine (DOPA), to attach to surfaces. Catechols and their analogues can undergo both oxidative covalent cross-linking under alkaline conditions and take part in coordination chemistry. The former has resulted in the widespread use of polydopamine and related materials. The latter is emerging as a tool to make self-healing materials due to the reversible nature of coordination bonds. We review how mussel-inspired materials have been made with a focus on the less developed use of metal coordination and illustrate how this chemistry can be widely to make self-healing materials.

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“…Moreover, catechols can form stable complexes with various di-and trivalent metal ions especially iron [12]. And ortho-diphenolic compounds adsorb on metal oxides more strongly than other diphenols and phenols [14]. In addition, iron based materials are a predominant class of heterogeneous catalysts due to their abundance in nature and the reactivity in redox reactions.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous Fenton oxidation of catechol and 4-chlorocatechol catalyzed by nano-Fe3O4: Role of the interface

Yang

Men

et al. 2014

Chemical Engineering Journal

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h i g h l i g h t sCatechol or 4-chlorocatechol was removed within 3 h in nano-Fe 3 O 4 /H 2 O 2 system. 4-Chlorocatechol was removed faster than catechol, with a minor mineralization. The oxidation of (chloro-)catechols obeyed Eley-Rideal mechanism. Carboxyl acids and ethers or dimers were generated and also adsorbed on nano-Fe 3 O 4 . a r t i c l e i n f o /g. Almost all the catechol or 4-chlorocatechol was oxidized within 3 h after the addition of H 2 O 2 , while about only 10% of the parent compounds adsorbed onto nano-Fe 3 O 4 without H 2 O 2 . And the oxidation curves followed the pseudo-second order kinetic model. 4-Chlorocatechol was oxidized faster than catechol, but with only 40% of mineralization. The contribution of homogeneous reaction induced by the leaching iron was limited. The surface generated reactive oxygen species were Å OH and HO Å 2 =O ÅÀ 2 , which were further reacted to generate oxygen-centered radicals in both systems, and carbon-centered radicals only in catechol system. In-situ flow-cell ATR-FTIR spectroscopy further confirmed that the adsorbed catechol or 4-chlorocatechol remained on the nano-Fe 3 O 4 surface, indicating an EleyRideal mechanism. Meanwhile, the generated carboxyl acids and some intermediates like ethers or dimers were also adsorbed. Accordingly, schematic diagrams of oxidation mechanisms of catechol and 4-chlorocatechol in nano-Fe 3 O 4 /H 2 O 2 system were proposed.

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Chemisorption of catechol on gibbsite, boehmite, and noncrystalline alumina surfaces

Cited by 137 publications

References 13 publications

Mussel adhesion – essential footwork

Mussel adhesion – essential footwork

Mussel‐Inspired Materials: Self‐Healing through Coordination Chemistry

Heterogeneous Fenton oxidation of catechol and 4-chlorocatechol catalyzed by nano-Fe3O4: Role of the interface

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