Reaction of Alkenes with Hydrogen-Terminated and Photooxidized Silicon Surfaces. A Comparison of Thermal and Photochemical Processes

Mischki, T.; Donkers, Robert L.; Eves, Brian J.; Lopinski, Gregory P.; Wayner, Danial D. M.

doi:10.1021/la060797t

Cited by 42 publications

(65 citation statements)

References 32 publications

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“…24, 32 We recently reported on the reaction of oxidized silicon surfaces with alkenes, observing signals in the X-ray photoemission spectrum corresponding to oxidized hydrocarbon. 27 In this study the thermal reaction of 1-decene with oxidized silicon surfaces was found to be consistent with Markovnikoff addition of the alkene to the silanol at lower temperature (80°Ca n d∼35°C in the Rayonet photoreactor) and antiMarkovnikoff at higher temperature (150°C). The X-ray photoemission spectrum of the high-temperature reaction showed evidence for the presence of carboxylic acid groups, indicating that the organic material had been oxidized.…”

Section: Resultssupporting

confidence: 71%

Evidence for Initiation of Thermal Reactions of Alkenes with Hydrogen-Terminated Silicon by Surface-Catalyzed Thermal Decomposition of the Reactant

2009

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New insights into the mechanism of thermal reactions of alkenes with hydrogen terminated silicon are presented. Scanning tunneling microscopy (STM) imaging at the early stages of the reaction of 1-decene with H/Si(111) at 150 °C confirm this reaction occurs via a propagating radical chain mechanism. In addition, evidence is presented for an initiation mechanism involving degradation of hydrocarbon molecules catalyzed by the silanol surface of Schlenk tubes commonly used in carrying out these reactions. Hydrogen-terminated silicon surfaces are found to be unstable in the “inert” solvent dodecane when heated at 150 °C in a Pyrex Schlenk tube. By contrast, the surfaces were significantly more stable at the same temperature when reactions were carried out in Teflon (polytetrafluoroethylene or PTFE). The thermal reaction of decene with H/Si(111) was found to proceed more rapidly in Pyrex than in PTFE, consistent with an impurity-based initiation mechanism.

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Section: Resultssupporting

confidence: 71%

Evidence for Initiation of Thermal Reactions of Alkenes with Hydrogen-Terminated Silicon by Surface-Catalyzed Thermal Decomposition of the Reactant

2009

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“…The mechanism was further delineated by studying the wavelength dependence of this photochemical reaction. It had been reported before by Wayner and co‐workers that 300 nm irradiation of SiO x in the presence of 1‐decene yielded a static water contact angle of 59° 135. Irradiation with wavelengths greater than 275 nm of fused silica in the presence of 1‐hexadecene also yielded only 60°.…”

Section: Alkenes and Alkynesmentioning

confidence: 80%

Covalent Surface Modification of Oxide Surfaces

Scheres²,

et al. 2014

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The modification of surfaces by the deposition of a robust overlayer provides an excellent handle with which to tune the properties of a bulk substrate to those of interest. Such control over the surface properties becomes increasingly important with the continuing efforts at down-sizing the active components in optoelectronic devices, and the corresponding increase in the surface area/volume ratio. Relevant properties to tune include the degree to which a surface is wetted by water or oil. Analogously, for biosensing applications there is an increasing interest in so-called "romantic surfaces": surfaces that repel all biological entities, apart from one, to which it binds strongly. Such systems require both long lasting and highly specific tuning of the surface properties. This Review presents one approach to obtain robust surface modifications of the surface of oxides, namely the covalent attachment of monolayers.

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“…Cycloaddition [139][140][141][142][143] Condensation [144,145] Silanization with chlorosilanes and trichlorosilanes with azanes [146][147][148] Arylation [149] Hydrosilation [138,[150][151][152][153][154] Phosphonation [155][156][157] Reaction with metal organic reagents/Grignard route [158][159][160] Electrochemical deposition See Figure 5 in section 1.3 of this review [161,162] Brought to you by | University of New Orleans Authenticated Download Date | 5/29/15 4:06 PM for the study of monolayers. In 1917 Irving Langmuir [166] developed the theoretical and experimental fundamentals that lead to the birth of a new method for the fabrication of ordered monomolecular films on a liquid surface, which are also known as Langmuir films.…”

Section: Reaction Referencementioning

confidence: 99%

Nanofabrication techniques of highly organized monolayers sandwiched between two electrodes for molecular electronics

2014

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Molecular electronics [1,2] is a promising field of research based on the idea that a single molecule or two dimensional assemblies of molecules (monomolecular films) can work as wires, switches, rectifiers, etc. Molecules are the smallest functional units and therefore it is expected that the use of molecules will permit to catch up with the limits of miniaturization (MM: more Moore), with an increase in device density by a factor of several orders of magnitude compared to today's state of the art. At the same time due to quantum effects novel and remarkable properties of organic and organometallic compounds at the nanoscale devices will result in increased performance (MtM: more than Moore) together with the appearance of new functions not possible with conventional semiconductors, and also cheaper devices due to the non-dependence of expensive materials used today in CMOS (complementary metal-oxide semiconductor) technology such as hafnium oxide. Nowadays, the number of research groups from different disciplines of science contributing to molecular electronics is gradually growing, and this field is becoming of great scientific and technological interest [1,3-8]. Since the seminal work of Aviram and Ratner in 1974 who firstly suggested that a single molecule could function as a rectifier [9], molecules have been experimentally demonstrated to work as switches, molecular wires or rectifiers, and a new field of opportunities is opened due to the understanding of electron transport through single entities or assemblies of molecules and expansion towards work on molecular spintronics, vibronic effects, excitation of the molecular junction with polarized light, quantum interference and decoherence, molecular chirality, molecular stretching and distortion as well as work on thermoelectric response in molecular junctions.Abstract: It is expected that molecular electronics, i.e., the use of molecules as critical functional elements in electronic devices, will lead in the near future to an industrial exploitable novel technology, which will open new routes to high value-added electronic products. However, despite the enormous advances in this field several scientific and technological challenges should be surmounted before molecular electronics can be implemented in the market. Among these challenges are the fabrication of reliable, robust and uniform contacts between molecules and electrodes, the deposition of the second (top) contact electrode, and development of assembly strategies for precise placement of molecular materials within device structures. This review covers advances in nanofabrication techniques used for the assembly of monomolecular films onto conducting or semiconducting substrates as well as recent methods developed for the deposition of the top contact electrode highlighting the advantages and limitations of the several approaches used in the literature. This contribution also aims to define areas of outstanding challenges in the nanofabrication of monomolecular layers sandwiched between two electro...

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Reaction of Alkenes with Hydrogen-Terminated and Photooxidized Silicon Surfaces. A Comparison of Thermal and Photochemical Processes

Cited by 42 publications

References 32 publications

Evidence for Initiation of Thermal Reactions of Alkenes with Hydrogen-Terminated Silicon by Surface-Catalyzed Thermal Decomposition of the Reactant

Evidence for Initiation of Thermal Reactions of Alkenes with Hydrogen-Terminated Silicon by Surface-Catalyzed Thermal Decomposition of the Reactant

Covalent Surface Modification of Oxide Surfaces

Nanofabrication techniques of highly organized monolayers sandwiched between two electrodes for molecular electronics

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