Covalent bonding of thiophenes to Si(111) by a halogenation/thienylation route1Issued as NRCC Publ. No. 40854.1

He, J.; Patitsas, S. N.; Preston, K. F.; Wolkow, Robert A.; Wayner, Danial D. M.

doi:10.1016/s0009-2614(98)00128-6

Cited by 65 publications

(97 citation statements)

References 27 publications

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“…Figure 1 shows the O 1s, N 1s, C 1s, and S 2s spectra of cysteine films as a function of exposure time, with their corresponding peak positions and assignments of the fitted features given in Tables S1 and S2 (Supporting Information). It should be noted that because the S 2p spectrum partially overlaps with one of the plasmon peaks of Si located at ∼168.0 eV (Supporting Information, Figure S2), 25 we have chosen S 2s for the present work. At very low exposures of 5−15 s, the N 1s spectra (Figure 1b) show only one peak at 398.7 ± 0.1 eV, attributed to a N−Si bond, which indicates that cysteine undergoes N−H dissociative adsorption on Si(111)7×7.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Biofunctionalization of Si(111)7×7 by “Renewable” l-Cysteine Transitional Layer

et al. 2014

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Surface functionalization of an inorganic surface with bio-organic molecules is often aimed at creating a "permanent" bio-organic surface with receptor functional groups. We show here that L-cysteine can be used to transform a highly reactive Si(111)7×7 surface to not just a permanent bio-organic surface but also a semipermanent (or renewable) and a temporary bio-organic surfaces by manipulating the exposure. In the early growth stage, the strong bonding between the first cysteine adlayer and the Si substrate through Si-N or Si-S linkages in unidentate or bidentate arrangement provides permanent biofunctionalization by this interfacial layer. This interfacial layer can be used to build a transitional layer (second adlayer) mediated by interlayer vertical hydrogen bonding between an amino group and a carboxylic acid group. Further exposure of cysteine eventually leads to a zwitterionic multilayer film involving electrostatic interactions between cation (-NH3(+)) and anion moieties (-COO(-)). The interlayer hydrogen bonding therefore provides temporary trapping of bio-organic molecules as the second transitional layer that is stable up to 175 °C. This transitional layer can be easily removed by annealing above this temperature and then regenerated with the same molecular layer or a different one by "renewing" the interlayer hydrogen bonds. We also illustrate coverage-dependent adsorption structures of cysteine, from bidentate to unidentate attachments and to self-assembled multimers, involving formation of intralayer horizontal N···H-O hydrogen bonds, by combining our X-ray photoemission data with the local density-of-state images obtained by scanning tunnelling microscopy.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Biofunctionalization of Si(111)7×7 by “Renewable” l-Cysteine Transitional Layer

et al. 2014

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“…8,9 We have used a similar approach to covalently attach thiophenes to the Si(111) surface. 10 In this case, surfaces were brominated by reaction with N-bromosuccinimide or bromotrichloromethane using radical initiating conditions followed by reaction with 2-thienyllithium or the bi-and terthiophene analogues. While it may be too early to generalize, it appears that the surface chemistry of Si(111)-H closely parallels molecular organosilane chemistry.…”

Section: Introductionmentioning

confidence: 99%

New Synthetic Routes to Alkyl Monolayers on the Si(111) Surface¹

et al. 1999

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Two new methods for the formation of Si−C monolayers from reactions with Si(111)−H are reported. Besides the photochemical method previously reported by Chidsey, Lewis acid-catalyzed hydrosilylation of alkenes and direct reaction of alkylmagnesium bromide produce a surface with similar chemical composition. These processes are demonstrated and compared using reactions of a C10 precursor. The surfaces are chemically stable and can be stored for several weeks without measurable deterioration. The availability of a variety of synthetic approaches leading to the same chemical product is key to the development of flexible surface synthetic strategies. It is expected that these approaches will underpin the development of stepwise solid-phase-like syntheses of more complex organic/bioorganic species on these surfaces.

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“…[14,15] Another commonly used method for chlorination in the liquid phase involves heating the SiÀH surfaces with PCl 5 at about 80 ± 100 8C in the presence of benzoyl peroxide as the radical initiator. [12] Herein, we report on a very simple and novel method for the functionalization of H-terminated porous and crystalline silicon surfaces with alcohols in a solution phase, using CHI 3 as the in situ iodinating agent. [12] Herein, we report on a very simple and novel method for the functionalization of H-terminated porous and crystalline silicon surfaces with alcohols in a solution phase, using CHI 3 as the in situ iodinating agent.…”

Section: Surface Functionalization Of H-terminated Silicon Surfaces Wmentioning

confidence: 99%

“…and I . [12] The chemical selectivity of atomic iodine over atomic chlorine has been observed during the gas ± solid reaction of ICl with a Si(111) ± (7 Â 7) surface, and it was proposed that the selectivity was due to the higher polarizability of I . [18] The CHI 2 .…”

Section: Surface Functionalization Of H-terminated Silicon Surfaces Wmentioning

confidence: 99%

Surface Functionalization of H-Terminated Silicon Surfaces with Alcohols Using Iodoform as an In Situ Iodinating Agent

Joy¹,

Mandler²

2002

ChemPhysChem

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Covalent bonding of thiophenes to Si(111) by a halogenation/thienylation route1Issued as NRCC Publ. No. 40854.1

Cited by 65 publications

References 27 publications

Biofunctionalization of Si(111)7×7 by “Renewable” l-Cysteine Transitional Layer

Biofunctionalization of Si(111)7×7 by “Renewable” l-Cysteine Transitional Layer

New Synthetic Routes to Alkyl Monolayers on the Si(111) Surface¹

Surface Functionalization of H-Terminated Silicon Surfaces with Alcohols Using Iodoform as an In Situ Iodinating Agent

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Covalent bonding of thiophenes to Si(111) by a halogenation/thienylation route1Issued as NRCC Publ. No. 40854.1

Cited by 65 publications

References 27 publications

Biofunctionalization of Si(111)7×7 by “Renewable” l-Cysteine Transitional Layer

Biofunctionalization of Si(111)7×7 by “Renewable” l-Cysteine Transitional Layer

New Synthetic Routes to Alkyl Monolayers on the Si(111) Surface1

Surface Functionalization of H-Terminated Silicon Surfaces with Alcohols Using Iodoform as an In Situ Iodinating Agent

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Resources

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New Synthetic Routes to Alkyl Monolayers on the Si(111) Surface¹