Replacing amine by azide: dopamine azide polymerization triggered by sodium periodate

Szukowska, Monika; Popenda, Łukasz; Coy, Emerson; Filip, Claudiu; Grajewski, Jakub; Kempiński, Mateusz; Kim, Yeonho; Mrówczyński, Radosław

doi:10.1039/d2py00293k

Cited by 8 publications

(7 citation statements)

References 49 publications

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“…Polydopamine (PDA) is a nature-inspired polymer that gained exceptional attention in chemistry due to its unique adhesive properties and multiple surface functionalization ability . A relatively simple synthesis can produce various forms of this material or its analogues, − that is, directly deposited coatings, , functional nanoparticles, − or free-standing films from the air/water interface. − The latter is particularly interesting due to the self-assembly of PDA macromolecules at the interface, leading to high-quality nanometric-thin polymer films that can be transferred to various functional substrates …”

Section: Introductionmentioning

confidence: 99%

Control of Intermolecular Interactions toward the Production of Free-Standing Interfacial Polydopamine Films

Szewczyk

Babačić

Krysztofik

et al. 2023

ACS Appl. Mater. Interfaces

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Aggregation of the polydopamine (PDA) molecular building blocks at the air/water interface leads to obtaining large surface nanometric-thin films. This mechanism follows two possible pathways, namely, covalent or non-covalent self-assembly, which result in a different degree of structure order and, consequently, different structural properties. Control of this mechanism could be vital for applications that require true self-support PDA free-standing films, for example, electrochemical sensing or membrane technology. Here, we are considering the impact of boric acid (BA) and Cu2+ ions on the mentioned mechanism exclusively for the free-standing films from the air/water interface. We have employed and refined our own spectroscopic reflectometry method to achieve an exceptionally high real-time control over the thickness growth. It turned out that BA and Cu2+ ions significantly impact the film growth process. Reduction of the nanoparticles size and their number was examined via UV–vis spectroscopy and transmission electron microscopy, showing a colossal reduction in the mean diameter of nanoparticles in the case of BA and a moderate reduction in the case of Cu2+. This modification is leading to significant enhancement of the process efficiency through moderation of the topological properties of the films, as revealed by atomic force microscopy. Next, applying infrared, Raman, and X-ray photoelectron spectroscopy, we presented small amounts of metal (B or Cu) in the final structure of PDA and simultaneously their vital role in the oxidation mechanism and cross-linking through covalent or non-covalent bonds. Therefore, we revealed the possibility of synthesizing films via the expected self-assembly mechanism which has hitherto been out of control. Moreover, modification of mechanical properties toward exceptionally elastic films through the BA-assisted synthesis pathway was shown by achieving Young’s modulus value up to 24.1 ± 5.6 and 18.3 ± 6.4 GPa, using nanoindentation and Brillouin light scattering, respectively.

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Section: Introductionmentioning

confidence: 99%

Control of Intermolecular Interactions toward the Production of Free-Standing Interfacial Polydopamine Films

Szewczyk

Babačić

Krysztofik

et al. 2023

ACS Appl. Mater. Interfaces

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“…Recently, Mrówczyński et al [11] . have shown that the polymerization of dopamine azide can only be achieved under highly oxidizing conditions (NaIO 4 ), producing polymers soluble in organic solvents.…”

Section: Resultsmentioning

confidence: 99%

Highly Functionalized SWCNTs with a Dopamine Derivative as a Support for Pd Nanoparticles: A Recyclable Catalyst for the Reduction of Nitro Compounds and the Heck Reaction

Campisciano

Valentino

Alfieri

et al. 2023

Chemistry A European J

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Single‐walled carbon nanotubes (SWCNTs) were functionalized with a dopamine derivative in which the amine group was converted to azide (dopamine azide). The direct reaction of SWCNTs and dopamine azide in o‐dichlorobenzene at high temperature (160 °C) led to very highly functionalized CNTs (≈60 wt%). Surprisingly, despite this high degree of functionalization, Raman spectroscopy detected a low disruption of the π‐network of the carbonaceous support. This finding was justified by the rehybridization from sp3 to sp2 of the sidewall carbon atoms of CNTs involved in the functionalization process. Further characterization by means of different techniques such as X‐ray photoelectron spectroscopy (XPS) analysis and transmission electron microscopy (TEM) allowed to shed some light on the chemical composition and morphology of the obtained material. Moreover, the estimation of the total content of phenolic units and their reducing potential after CNTs functionalization was also assessed using Folin and Ciocalteu and 2,2‐diphenyl‐1‐picryl hydrazide (DPPH) assays. The functionalization of CNTs was exploited to immobilize palladium(II) species that were subsequently reduced with NaBH4 leading to the formation of Pd nanoparticles (NPs). The so obtained hybrid material was used as a recyclable heterogeneous catalyst for the reduction of nitro compounds and the Heck reaction.

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“…The poly(dopazide) films are much rougher than the PDA films obtained after an identical deposition time. [ 78 ]…”

Section: Pda Deposition From Solution At Solid/liquid Interfacesmentioning

confidence: 99%

Experimental Methods to Get Polydopamine Films: A Comparative Review on the Synthesis Methods, the Films’ Composition and Properties

Ball

Hirtzel

Leks

et al. 2023

Macromol. Rapid Commun.

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In 2007, polydopamine (PDA) films were shown to be formed spontaneously on the surface of all known classes of materials by simply dipping those substrates in an aerated dopamine solution at pH = 8.5 in the presence of Tris(hydroxymethyl) amino methane buffer. This universal deposition method has raised a burst of interest in surface science, owing not only to the universality of this water based one pot deposition method but also to the ease of secondary modifications. Since then, PDA films and particles are shown to have applications in energy conversion, water remediation systems, and last but not least in bioscience. The deposition of PDA films from aerated dopamine solutions is however a slow and inefficient process at ambient temperature with most of the formed material being lost as a precipitate. This incited to explore the possibility to get PDA and related films based on other catecholamines, using other oxidants than dissolved oxygen and other deposition methods. Those alternatives to get PDA and related films are reviewed and compared in this paper. It will appear that many more investigations are required to get better insights in the relationships between the preparation method of PDA and the properties of the obtained coatings.

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Replacing amine by azide: dopamine azide polymerization triggered by sodium periodate

Abstract: Polydopamine (PDA) have been widely described for a range of biomedical and surface engineering applications. However the structure of PDA remains elusive due to the insoluble nature of the polymer....

Cited by 8 publications

References 49 publications

Control of Intermolecular Interactions toward the Production of Free-Standing Interfacial Polydopamine Films

Control of Intermolecular Interactions toward the Production of Free-Standing Interfacial Polydopamine Films

Highly Functionalized SWCNTs with a Dopamine Derivative as a Support for Pd Nanoparticles: A Recyclable Catalyst for the Reduction of Nitro Compounds and the Heck Reaction

Experimental Methods to Get Polydopamine Films: A Comparative Review on the Synthesis Methods, the Films’ Composition and Properties

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