Adsorption, ordering, and chemistry of nitrobenzene on Si(100)-2×1

Bocharov, Semyon; Teplyakov, Andrew V.

doi:10.1016/j.susc.2004.09.044

Cited by 29 publications

(51 citation statements)

References 58 publications

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“…In this case, thermal chemistry was used to pattern the surface by initial attachment of a removable placeholder molecule, ethylene, supplemented by further exposure to strongly binding nitrobenzene; 86,146,147 however, it is possible to form mixed functionalities of the surface by co-adsorbing other molecules and further studies in this direction are needed. This opportunity may result in the ability to combine different functionalities in a specific desired surface pattern.…”

Section: Iii3 Recent Developments In Designing Reaction Schemes On Si...mentioning

confidence: 99%

Reactivity of selectively terminated single crystal silicon surfaces

Perrine

Teplyakov

2010

Chem. Soc. Rev.

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As the cornerstone of multiple practical applications, silicon single crystal surfaces have attracted the interest of scientific and engineering communities for several decades. The most recent advances employ the surfaces precovered with a specific functionality to extend into the realm of organic and metal-organic films with well-defined interfaces, to protect the surfaces from oxidation and other contaminations, and to build the components of present and future molecular electronics and sensing devices. This critical review will focus on the reactivity of the selectively terminated Si(100) and Si(111) surfaces. The hydrogen and halogen-terminated surfaces are the most widely used and most heavily reviewed previously, thus only a brief summary will be given here with the emphasis of the most recent thermal approaches to functionalization of hydrogen-terminated silicon. The silicon surfaces precovered with NH(x) functionality are emerging as a very likely candidate both for the production of sharp interfaces and for coadsorption, co-assembly, and potential molecular templating of patterns on single crystalline surfaces. A brief overview of recent advances in achieving control over the hydroxyl-termination of silicon will be given. Some future directions for further development of chemistry, reactivity, and assembly on these surfaces, as well as potential applications, are highlighted in the last section (152 references).

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Section: Iii3 Recent Developments In Designing Reaction Schemes On Si...mentioning

confidence: 99%

Reactivity of selectively terminated single crystal silicon surfaces

Perrine

Teplyakov

2010

Chem. Soc. Rev.

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“…Nitrobenzene (PhNO 2 ) has been predicted to react with the Si(100)-2×1 surface via a 1,3-dipolar cycloaddition to form a five-member Si-O-C-O-Si ring as shown in Fig. 3.8 [225,226]. Similar to simpler molecules, nitromethane and nitroethane, that were studied both theoretically and experimentally [164,[227][228][229], nitrobenzene was proposed to easily form this initial adduct and this first reaction step was to be followed by a series of steps leading to the migration of both oxygen atoms into the silicon backbond.…”

Section: Functionalized Aromaticsmentioning

confidence: 99%

“…[226], experimental studies of nitrobenzene, suggest that at monolayer coverages, the apparent barrier for this transformation may be as high as 40.8 kJ/mol [225], thus making it difficult to observe the structures proposed. This work also considered addition of the nitrobenzene molecule to the two neighboring silicon dimers but this process was found to be much less likely than addition to a single dimer.…”

Section: Functionalized Aromaticsmentioning

confidence: 99%

“…This result suggests that upon chemisorption, all the nitrogen atoms exist in a chemically indistinguishable Although the previous two examples demonstrated a very high degree of selectivity of a functional group with respect to a phenyl ring and suggested the possibility of using aromatic linkers as somewhat non-reactive entities in silicon surface modification, they both suffer from the fact that further surface transformations are possible for both the adducts of nitrobenzene and phenyl isothiocyanate. Nitrobenzene has demonstrated an extraordinary thermal stability once oxygen atoms are migrated into the silicon backbond [225]. In fact, the silicon sample prepared by exposure of a clean Si(100)-2×1 surface to nitrobenzene in UHV conditions could be taken into ambient conditions and studied ex situ producing exactly the same spectroscopic signature as the in situ prepared sample.…”

Section: Functionalized Aromaticsmentioning

confidence: 99%

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Chemical manipulation of multifunctional hydrocarbons on silicon surfaces

Leftwich

Teplyakov

2007

Surface Science Reports

123

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“…Moreover, the monofunctional analogues of 4nitrophenol, namely phenol and nitrobenzene, have been shown to readily react with group 14 (100)-2 × 1 surfaces. Phenol undergoes O-H dissociative adsorption to form an H adatom and phenoxy adsorbate [35,36], and nitrobenzene reacts via 1,3-dipolar cycloaddition [37,38].…”

Section: Introductionmentioning

confidence: 99%

Adsorption of heterobifunctional 4-nitrophenol on the Ge(100)-2 × 1 surface

2016

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We report the adsorption chemistry of a heterobifunctional molecule, 4-nitrophenol, on the Ge(100)-2 × 1 surface. X-ray photoelectron and infrared spectroscopy experiments and density functional theory calculations were used to determine the adsorption products. The results show that 4-nitrophenol reacts with the Ge surface through either one or both of the-OH or-NO 2 functionalities. It was found that the fraction of dually and singly tethered adsorbates varies according to reaction conditions: namely, singly tethered adsorbates are favored at higher adsorbate coverages and lower adsorption temperatures. These variations are explained by a two-step adsorption mechanism for 4-nitrophenol, in which geometrical limitations of the adsorbates on the surface affect the product distribution.

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Adsorption, ordering, and chemistry of nitrobenzene on Si(100)-2×1

Cited by 29 publications

References 58 publications

Reactivity of selectively terminated single crystal silicon surfaces

Reactivity of selectively terminated single crystal silicon surfaces

Chemical manipulation of multifunctional hydrocarbons on silicon surfaces

Adsorption of heterobifunctional 4-nitrophenol on the Ge(100)-2 × 1 surface

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