Competitive Bonding of Amino and Hydroxyl Groups in Ethanolamine on Si(100)2×1: Temperature-Dependent X-Ray Photoemission and Thermal Desorption Studies of Nanochemistry of a Double-Chelating Agent

radi, adel h.; Leung, K. T.

doi:10.1166/mex.2011.1015

Cited by 11 publications

(7 citation statements)

References 36 publications

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“…The major difference in N 1s between the thermal reaction (Figure c) and UV photoionization (Figure d) was the emergence of the distinctive peaks for Si–N at 397.7 eV , and 400.1 eV , for the thermally reacted cyclopropylamine (Figure c). Radi et al described the behavior of ethanolamine thermally reacting with the silicon (100) surface and found that the Si–N bond also had a tendency to form Si–N–Si bridges. On the basis of this argument, we prudently fitted and assigned the peak centered at 399.1 eV as Si–N–Si bridging.…”

Section: Resultsmentioning

confidence: 99%

Grafting of Ring-Opened Cyclopropylamine Thin Films on Silicon (100) Hydride via UV Photoionization

Tung

Ching

et al. 2017

ACS Appl. Mater. Interfaces

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The grafting of cyclopropylamine onto a silicon (100) hydride (Si-H) surface via a ring-opening mechanism using UV photoionization is described here. In brief, radicals generated from the Si-H surface upon UV irradiation were found to behave in classical hydrogen abstraction theory manner by which the distal amine group was first hydrogen abstracted and the radical propagated down to the cyclopropane moiety. This subsequently liberated the strained bonds of the cyclopropane group and initiated the surface grafting process, producing a thin film approximately 10-15 nm in height. Contact angle measurements also showed that such photoionization irradiation had yielded an extremely hydrophilic surface (∼21.3°) and X-ray photoelectron spectroscopy also confirmed the coupling was through the Si-C linkage. However, when the surface underwent high-temperature hydrosilylation (>160 °C), the reaction proceeded predominantly through the nucleophilic NH group to form a Si-N linkage to the surface. This rendered the surface hydrophobic and hence suggested that the Si-H homolysis model may not be the main process. To the best of our knowledge, this was the first attempt reported in the literature to use photoionization to directly graft cyclopropylamine onto a silicon surface and in due course generate a highly rich NH-terminated surface that was found to be highly bioactive in promoting cell viability on the basis of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide studies.

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Section: Resultsmentioning

confidence: 99%

Grafting of Ring-Opened Cyclopropylamine Thin Films on Silicon (100) Hydride via UV Photoionization

Tung

Ching

et al. 2017

ACS Appl. Mater. Interfaces

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“…On the other hand, thermal-based hydrosilylation is another alternative that works at higher temperature (150-200 • C) that may ensure that water within from solvent is kept minimal to reduce the chances of oxidation. Recent models of thermal reactions do suggest that the surface reaction to form a stable Si-C linkage can proceed at lower temperatures (<150 • C) as reported by Horrock et al [4] but at these lower temperatures, hydrogenated silicon surface can also be prone to nucleophilic reactions [5,6]. Of these, surface reaction between alcohol and hydrogenated Silicon (Si-H) was well established in literature and many other reports had shown the formation of stable Si-O-C linkage towards the surface [7][8][9][10].…”

Section: Introductionmentioning

confidence: 82%

Influences of Doping and Crystal Orientation on Surface Roughening upon Alcohol Grafting onto Silicon Hydride

Tung

Khung

2017

Applied Sciences

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An alcohol bearing alkyne was thermally grafted to both p-type and n-type silicon (111) and (100) substrate of comparable doping levels and surface flatness. The surface topography as well as the surface chemistry was examined via atomic force microscopy (AFM), X-ray photoelectron spectroscopy (XPS) and water contact angle measurements. P-type silicon (111) was observed to experience roughening on the surface upon functionalization while n-type silicon (111) surfaces remained relatively unchanged. When the alcohol was grafted onto silicon (100) surface, the roughening effect was found to be even more profound for the p-type while the effects were marginal for the n-type surfaces. Both roughening effects were attributed to the differential weakening of the Si-Si backbond induced by majority carriers in p-and n-type silicon while (111) was observed to be able to resist the roughening effect better and this was explained by the notion of its denser adatom surface packing as well as the presence of surface defects.

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“…Second, the trimethoxysilyl groups of SiBr initiators could be hydrolyzed into silicon hydroxyl groups in the coating preparation condition (pH 8.5) and then condensed with the PDA hydroxyl and amino groups, as well as the neighboring silicon hydroxyl groups. − Third, the formation of Si–O–Si and Si–O–C linkages at the PDA/SiBr coating interface was supported by the broadening of the XPS high-resolution spectrum of Si 2p (Figure S3A), since the SiBr-self-cross-linked Si–O–Si bond shows a narrow peak of Si 2p at 102.5 eV. Moreover, the appearance of the N 1s new peak (N–Si) at 398 eV (Figure S3B) suggests that the silicon hydroxyl also reacted with the amino group of the PDA forming an additional cross-linking bond (N–Si) at the interface of PDA/SiBr coating . Thus, the cross-linked PDA/SiBr coating enables the formation of stable PMPC brushes.…”

Section: Resultsmentioning

confidence: 98%

“…Moreover, the appearance of the N 1s new peak (N−Si) at 398 eV (Figure S3B) suggests that the silicon hydroxyl also reacted with the amino group of the PDA forming an additional crosslinking bond (N−Si) at the interface of PDA/SiBr coating. 46 Thus, the cross-linked PDA/SiBr coating enables the formation of stable PMPC brushes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Universal Strategy for Efficient Fabrication of Blood Compatible Surfaces via Polydopamine-Assisted Surface-Initiated Activators Regenerated by Electron Transfer Atom-Transfer Radical Polymerization of Zwitterions

Qiao

et al. 2020

ACS Appl. Mater. Interfaces

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Implant and blood-contacting biomaterials are challenged by biofouling and thrombus formation at their interface. Zwitterionic polymer brush coating can achieve excellent hemocompatibility, but the preparation often involves tedious, expensive, and complicated procedures that are designed for specific substrates. Here, we report a facile and universal strategy of creating zwitterionic polymer brushes on variety of materials by polydopamine (PDA)-assisted and surface-initiated activators regenerated by electron transfer atom-transfer radical polymerization (PDA-SI-ARGET-ATRP). A PDA adhesive layer is first dipcoated on a substrate, followed by covalent immobilization of 3-trimethoxysilyl propyl 2-bromo-2-methylpropionate (SiBr, ATRP initiator) on the PDA via condensation. Meanwhile, the trimethoxysilyl group of SiBr also cross-links the PDA oligomers forming stabilized PDA/SiBr complex coating. Finally, SI-ARGET-ATRP is performed in a zwitterionic monomer solution catalyzed by the parts per million level of CuBr2 without deoxygenization. The conveniently fabricated zwitterionic polymer brush coatings are demonstrated to have stable, ultralow fouling, and extremely blood compatible and functionalizable characteristics. This facile, versatile, and universal surface modification strategy is expected to be widely applicable in various advanced biomaterials and devices.

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Competitive Bonding of Amino and Hydroxyl Groups in Ethanolamine on Si(100)2×1: Temperature-Dependent X-Ray Photoemission and Thermal Desorption Studies of Nanochemistry of a Double-Chelating Agent

Cited by 11 publications

References 36 publications

Grafting of Ring-Opened Cyclopropylamine Thin Films on Silicon (100) Hydride via UV Photoionization

Grafting of Ring-Opened Cyclopropylamine Thin Films on Silicon (100) Hydride via UV Photoionization

Influences of Doping and Crystal Orientation on Surface Roughening upon Alcohol Grafting onto Silicon Hydride

Universal Strategy for Efficient Fabrication of Blood Compatible Surfaces via Polydopamine-Assisted Surface-Initiated Activators Regenerated by Electron Transfer Atom-Transfer Radical Polymerization of Zwitterions

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