Expanding the aqueous-based redox-facilitated self-polymerization chemistry of catecholamines to 5,6-dihydroxy-1H-benzimidazole and its 2-substituted derivatives

Fan, Ka Wai; Peterson, Matthew B.; Ellersdorfer, Peter; Granville, Anthony M.

doi:10.1039/c5ra25590b

Cited by 11 publications

(10 citation statements)

References 65 publications

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“…In the case of catecholamines, this is partially attributed to cyclized indolic compounds that contribute to stronger π–π interactions in the coating . Nonetheless, synthetic eumelanin, constructed from cyclized 5,6‐dihydroxyindole (DHI), and coatings made from closely related N ‐heterocyclic catechol derivatives, do not adhere as strongly as when uncyclized primary amines are available in other catecholamine coatings . Also, modified dopamine derivatives with the amine converted to a quaternary ammonium or amide groups still attach readily to surfaces through their catechol group, but do not form polymeric materials that can exploit concerted adhesion.…”

Section: Catecholamine Polymers: Chemistry and Structurementioning

confidence: 99%

“…Generally, synthetic DHI materials do not form as durably adhesive coatings as those formed from compounds with available primary amines . Closely chemically related to the DHI intermediate are 5,6‐dihydroxy‐1H‐indazole and 5,6‐dihydroxy‐1H‐ benzimidazole that are both able to react and aggregate onto surfaces in a similar fashion to dopamine, though again resulting in less durable coatings . Coatings from both the compounds can be stabilized by copolymerization with dopamine and when 5,6‐dihydroxy‐1H‐indazole was copolymerized with dopamine (1:3 molar ratio), it polymerized rapidly and with coating thickness on a silica surface plateauing at ≈125 nm after 15 h …”

Section: Catecholamine Polymers: Chemistry and Structurementioning

confidence: 99%

See 1 more Smart Citation

Versatile Surface Modification Using Polydopamine and Related Polycatecholamines: Chemistry, Structure, and Applications

Barclay

Hegab

Clarke

et al. 2017

Adv Materials Inter

292

223

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Almost ten years ago, Lee et al. [13] formulated a universal adhesive coating based on observation of the strong attachment by mussels through their byssal threads to virtually all types of inorganic and organic surfaces. The amino acid compositions of the mussel foot proteins that generate the attachment are rich in catechol and amine groups. [13][14][15] These groups associate under marine conditions, forming strong covalent and noncovalent interactions with substrates. [13] This led to the idea that both catechol and amine groups were crucial in forming robust, wide spectrum adhesive nanolayers [16,17] and consequently dopamine was conceived as a powerful building block for spontaneous deposition of thin polymer films. The dopamine monomer is deposited onto unadulterated surfaces through self-assembly and oxidative cross-linking from mild pH aqueous solution in a rapid reaction. This results in a durable, nanoscale, conformal, and hydrophilic coating that can be readily modified to introduce specific surface chemistries for a particular application. [18][19][20][21][22] These bioinspired, polydopamine materials are chemically and structurally indistinguishable from eumelanins found in the human body, [23,24] providing excellent biocompatibility. Additionally, polydopamine has broad electromagnetic absorption and excellent photothermal energy conversion [25] as well as having ionic-electronic hybrid conductivity. [26] Along with the excellent coating performance, these properties provide a vast array of potential applications for polydopamine materials.In this article, we explain what is known about polydopamine and related catecholamine coatings; their formation, the adhesion mechanism, and their physicochemical properties and we also review the applications of these materials (Figure 1). Since 2011, there have been a number of reviews on this subject matter, including general reviews on the physicochemical properties of polydopamine coatings [11,20,[27][28][29] and their applications. [20,27,30] There are also a number of more specific reviews on the chemical synthesis and modulation of polycatecholamine coatings, [31] the biomedical applications of these coatings, [8,[32][33][34] their electronic properties, [26,35] the use of polydopamine to make films at fluid interfaces, [36] in hierarchically constructed particles, [33] and capsules, [30] exploitation of polycatecholamine coatings in membrane filtration, [37] polydopamine-derived carbon materials, [38] and the use of coordination chemistry in catechol-based materials. [39] Nonetheless, this area of research is growing so rapidly [25,27] that many recent Polydopamine and related polycatecholamines can be easily deposited onto almost any surface from mild, aqueous solution. This results in durable, nanoscale coatings that exhibit high biocompatibility and have useful chemical and electronic properties. Additionally, these materials can be readily chemically and physically modified, and consequently, they are used extensively for surface modification. This ...

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Section: Catecholamine Polymers: Chemistry and Structurementioning

confidence: 99%

Section: Catecholamine Polymers: Chemistry and Structurementioning

confidence: 99%

Versatile Surface Modification Using Polydopamine and Related Polycatecholamines: Chemistry, Structure, and Applications

Barclay

Hegab

Clarke

et al. 2017

Adv Materials Inter

292

223

View full text Add to dashboard Cite

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“…1,2-Dimethoxy-4,5-dinitrobenzene [2] 1,2-Dimethoxybenzene (11.08 g, 80.19 mmol, 1.0 equiv) was added dropwise into conc. HNO3 (100 mL, 65%) at 0 o C, after addition, the mixture was left to stir at 80 o C. After 2 h, the mixture was cooled down to 0 o C, and the resulting precipitate was washed with distilled water until neutral to give the desired compound as a yellow needle crystal (15.39 g, 67.45 mmol, 84%).…”

Section: Supplementary Informationmentioning

confidence: 99%

“…), concentrated under reduced pressure, to which formic acid (98%, 100 mL) was added, and the mixture was left to stir at 100 o C. After 16 h, the mixture was concentrated under reduced pressure, water (50 mL) added, and the solution was basified with solid K2CO3. The precipitate was collected, washed with water and dried to give the desired compound as a colorless solid (7.00 g, 39.3 mmol, 91% [2] 5,6-Dimethoxy-1H-benzo [d]imidazole (7.79 g, 43.7 mmol, 1.0 equiv) was added into HBr (48%, 50 mL), and the mixture was left to stir at 120 o C. After 4 h, the mixture was cooled down to 0 o C, and the precipitate was collected, washed with petroleum ether to give the desired compound as a colorless solid (4.59 g, 30.6 mmol, 70%). 1 H NMR (400 MHz, DMSO) δ 9.75 (s, 2H), 9.25 (s, 1H), 7.12 (s, 2H).…”

Section: Supplementary Informationmentioning

confidence: 99%

Fused Hybrid Linkers for Metal–Organic Frameworks-Derived Bifunctional Oxygen Electrocatalysts

Alam¹,

Ping²,

Bhadoria³

et al. 2020

Meet. Abstr.

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Preparation of electrocatalysts often relies on the use of multiple starting materials-inorganic salts or organometallic precursors, nanostructured carbon supports, organic additives, dopants and carbonization under modifying atmospheres (e.g. NH 3 or H 2)-with the examples of electrocatalysts arising from a single precursor being much less common. Herein, we have surveyed a series of heterobivalent scaffolds to identify an iron/benzimidazole-based metal-organic framework as a uniform starting material. By merging the catechol and imidazole units together, we get direct entry into a highly efficient bifunctional oxygen electrocatalyst, which alleviates the need for additional dopants and modifying conditions (ORR: E on = 1.01 V, E 1/2 = 0.87 V vs. RHE in 0.1 M KOH; OER: 1.60 V @10 mA cm-2 in 0.1 M KOH; ∆E = 0.73 V). We demonstrate that by fine-tuning the chemical nature of an organic linker, one is able modulate the electrochemical properties of a single precursor-derived electrocatalyst material. File list (2) download file view on ChemRxiv Ping et al_v2.pdf (1.09 MiB) download file view on ChemRxiv Ping_et_al_SI_v2.pdf (2.83 MiB)

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“…Hollow polymer particles (capsules) represent a specific category of polymer particles that can be accessed via a variety of synthetic routes, with applications in areas, for example, cosmetics, food applications, and drug delivery . Examples of synthetic routes to polymer capsules include miniemulsion/suspension polymerization approaches based on phase separation, techniques based on growing a polymer shell from the interior or exterior of miniemulsion droplets, as well as the use of sacrificial templates . In general, it remains challenging to prepare polymer capsules of specific size and shell thickness with well‐defined particle size distribution.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of polydopamine capsules via SPG membrane emulsion templating: Tuning of capsule size

Zhai

Ishizuka

Stenzel

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

Self Cite

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Monodisperse polydopamine capsules with thin shells are synthesized by dopamine polymerization using toluene emulsion droplets as templates. Aqueous emulsions of monodisperse toluene droplets stabilized by the anionic surfactant sodium dodecyl sulfate are prepared by use of Shirasu porous glass membrane emulsification. This approach allows convenient tuning of the polydopamine capsule size via the membrane emulsification pore size, as exemplified by providing access to well‐defined capsules with diameters in the submicron – micron‐size range.

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Expanding the aqueous-based redox-facilitated self-polymerization chemistry of catecholamines to 5,6-dihydroxy-1H-benzimidazole and its 2-substituted derivatives

Abstract: Redox-facilitated self-polymerization can be performed with 5,6-dihydroxy-1H-benzimidazole to generate materials analogous to polydopamine, proving the possibility to expand the catecholamine-based chemistry to N-heterocyclic catechol derivatives.

Cited by 11 publications

References 65 publications

Versatile Surface Modification Using Polydopamine and Related Polycatecholamines: Chemistry, Structure, and Applications

Versatile Surface Modification Using Polydopamine and Related Polycatecholamines: Chemistry, Structure, and Applications

Fused Hybrid Linkers for Metal–Organic Frameworks-Derived Bifunctional Oxygen Electrocatalysts

Synthesis of polydopamine capsules via SPG membrane emulsion templating: Tuning of capsule size

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