Stereo-selective binding of chlorobenzene on Si(111)-7×7

Cao, Yi; Deng, Jing; Xu, Guo Qin

doi:10.1063/1.481032

Cited by 53 publications

(102 citation statements)

References 23 publications

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“…For chlorobenzene and toluene there are several possible configurations dependent on the location of the chlorine or methyl group with respect to the carbon-silicon bonds. Theoretical and experimental results indicate that the lowest energy state is a 2-5 di-σ configuration [19,20]. In our experiments we are insensitive to this fine detail and only record the presence of a molecule at an adatom site.…”

Section: Methodsmentioning

confidence: 99%

“…black spots) in STM [14,15]. Each molecule forms a pair of covalent bonds to two silicon atoms, one to a silicon adatom and one to a silicon restatom, so called di-σ bonding [20]. There are therefore four distinct binding configurations of aromatic molecules on the Si(1 1 1)-7×7 surface related to the type of adatom that the molecule binds to: faulted corner (FC), faulted middle (FM), unfaulted corner (UC) and unfaulted middle (UM).…”

Section: Methodsmentioning

confidence: 99%

“…filled states image displaying the STM signature of the two distinct halves of the unit cell-the faulted half of the unit cell images more brightly than the unfaulted. The adsorption of chlorobenzene, benzene and toluene on the Si(1 1 1)-7×7 surface has been actively studied by many experimental and theoretical techniques [14][15][16][17][18][19][20][21]. These aromatic molecules chemisorb on the Si(1 1 1)-7×7 surface at room temperature and are imaged as 'missing' Si adatom features (i.e.…”

Section: Methodsmentioning

confidence: 99%

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Mapping the site-specific potential energy landscape for chemisorbed and physisorbed aromatic molecules on the Si(1 1 1)-7 × 7 surface by time-lapse STM

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Sakulsermsuk

Palmer

et al. 2014

J. Phys.: Condens. Matter

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View the article online for updates and enhancements. AbstractWe present a scanning tunnelling microscope study of site-specific thermal displacement (desorption or diffusion) of benzene, toluene, and chlorobenzene molecules on the Si(1 1 1)-7×7 surface. Through time-lapse STM imaging and automated image analysis we probe both the chemisorbed and the physisorbed states of these molecules. For the chemisorption to physisorption transition there are distinct site-specific variations in the measured rates, however their kinetic origin is ambiguous. There is also significant variation in the competing rates out of the physisorbed state into chemisorption at the various surface sites, which we attribute to differences in site-specific Arrhenius pre-factors. A prediction of the outcome of the competing rates and pre-factors for benzene over three hours matches experiment.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Mapping the site-specific potential energy landscape for chemisorbed and physisorbed aromatic molecules on the Si(1 1 1)-7 × 7 surface by time-lapse STM

Lock

Sakulsermsuk

Palmer

et al. 2014

J. Phys.: Condens. Matter

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“…Previous work in this area mainly involves some unsaturated hydrocarbons containing unpolarized covalent bonds of CvC or CwC, including typical ethylene, 5,6 acetylene, [7][8][9] five-membered heterocyclic aromatics, [10][11][12][13] benzene, 14,15 aniline, 16 and chlorobenzene. 17, 18 These studies demonstrate that the adjacent adatom-rest atom pair can act as a ''diradical'' to react with unsaturated functional groups of organic molecules.…”

Section: Introductionmentioning

confidence: 99%

Selective attachment of benzonitrile on Si(111)-7×7: Configuration, selectivity, and mechanism

Tao

Wang²,

Chen³

et al. 2002

Phys. Rev. B

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The cycloaddition of benzonitrile with Si͑111͒-7ϫ7 has been investigated as a model system for understanding the interaction of conjugated -electron systems with Si͑111͒-7ϫ7 using high-resolution electron energy loss spectroscopy, x-ray photoelectron spectroscopy ͑XPS͒, ultraviolet photoelectron spectroscopy, scanningtunneling microscopy ͑STM͒, and density-functional-theory calculation ͑perturbative Beck-Perdew functional in conjugation with a basis set of DN**͒. Vibrational features of chemisorbed benzonitrile unambiguously demonstrate that the cyano group directly interacts with Si surface dangling bonds, evidenced in the disappearance of CwN stretching mode around 2256 cm Ϫ1 coupled with the appearance of CvN stretching mode at 1623 cm Ϫ1 and the retention of all vibrational signatures of phenyl ring. XPS shows that both C 1s and N 1s core levels of the cyano groups display large down-shifts by 2.5 and 1.5 eV, respectively, after chemisorption. A smaller down-shift of ϳ0.8 eV is observed for the C 1s core level of phenyl group due to the weaker inductive effect of the formed CvN groups in chemisorbed benzonitrile than that of CwN groups in physisorbed molecules. Compared with physisorbed molecules, the photoemission from CN orbitals of chemisorbed benzonitrile is significantly reduced, suggesting the direct involvement of CN in the surface binding. These experimental results show that the covalent attachment of benzonitrile on Si͑111͒-7ϫ7 occurs in a selective manner through the ͑2ϩ2͒ cycloaddition between the cyano group and the adjacent adatom-rest atom pair. The cycloadduct formed contains an intact phenyl ring protruding into vacuum, retaining aromaticity. This functionalized Si surface may serve as a substrate for further modification or act as an intermediate for fabrication of multilayer organic thin films or materials syntheses in vacuum.

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“…This bonding configuration has been proposed as a stable configuration in other halobenzene adsorption systems on Si(111)-7×7 surface. 1,11,12) For the type A molecule, we consider weak bondings like physisorption in which surface flat benzene ring is capping an adatom, 13,14) or a single halogen atom is attaching to a Si atom.…”

Section: Adsorption Of Phi On Si(111)-(7×7)mentioning

confidence: 99%

Surface Chemical Reaction Enhanced by Adsorbate-Electron Interaction

Shahed

Matsuhashi

Sainoo

et al. 2009

Journal of The Surface Science Society of Japan

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We have observed two type of bonding configuration of Iodobenzene (C6H5I) molecule upon room temperature adsorption on the Si (111) -7×7 surface and investigated an effect of Adsorbate-Electron interaction on a bonding configuration change of the Iodobenzene molecules on the Si(111)-7×7 surface using scanning tunneling microscope (STM). With the direct-current heating, a conversion rate of the bonding configuration as a function of the lattice temperature, K(Tl), has been determined. The plot of ln(K(T)) vs. T shows a deviation from a Arrhenius straight line, which suggests that the current accelerates the molecule's reaction by heating the adsorbate preferentially above the lattice temperature. Though tunneling current induced chemical reaction has been reported, we believe this is the first report of a direct observation that the interaction between an adsorbate and lattice current causes a chemical reaction.

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Stereo-selective binding of chlorobenzene on Si(111)-7×7

Cited by 53 publications

References 23 publications

Mapping the site-specific potential energy landscape for chemisorbed and physisorbed aromatic molecules on the Si(1 1 1)-7 × 7 surface by time-lapse STM

Mapping the site-specific potential energy landscape for chemisorbed and physisorbed aromatic molecules on the Si(1 1 1)-7 × 7 surface by time-lapse STM

Selective attachment of benzonitrile on Si(111)-7×7: Configuration, selectivity, and mechanism

Surface Chemical Reaction Enhanced by Adsorbate-Electron Interaction

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