Adsorption of nitrogen-containing aromatic molecules on Si(1 1 1)-7 × 7

Huang, Huan; Huang, Jing Yan; Wang, Zhong Hai; Ning, Yuesheng; Feng, Tao; Zhang, Yong Ping; Cai, Ying Hui; Tang, Hai Hua; Xu, Guo Qin

doi:10.1016/j.susc.2006.12.070

Cited by 14 publications

(13 citation statements)

References 31 publications

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“…Two recent publications describe in detail the chemistry of cyclic heteroaromatic hydrocarbons on Si(111)-7×7. Huang et al report a logical extension of the work of this group on nitrogen-containing aromatics applying HREELS, XPS, and DFT calculations to understand the chemistry of pyrimidine and triazine, where both molecules form Si-C and Si-N σ -linkages to the surface [474]. The work of Tao and Bernasek uses HREELS to examine a very complex and highly temperaturedependent chemistry of five-member aromatic ring molecules containing two different heteroatoms [475].…”

Section: Note Added In Proofmentioning

confidence: 99%

Chemical manipulation of multifunctional hydrocarbons on silicon surfaces

Leftwich

Teplyakov

2007

Surface Science Reports

123

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Section: Note Added In Proofmentioning

confidence: 99%

Chemical manipulation of multifunctional hydrocarbons on silicon surfaces

Leftwich

Teplyakov

2007

Surface Science Reports

123

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“…For pyrimidine on the silicon surface, there is one report of butterflylike structures on Si(111), but no report on Si(100) to our best knowledge. 25 However, there is one report on Ge(100), in which well-defined zig-zag lines based on the NN-CRB structures are observed by scanning tunneling microscopy (STM). 26 For s-triazine, there is one report each on Si(111) 25 and Si(100).…”

Section: Introductionmentioning

confidence: 99%

“…25 However, there is one report on Ge(100), in which well-defined zig-zag lines based on the NN-CRB structures are observed by scanning tunneling microscopy (STM). 26 For s-triazine, there is one report each on Si(111) 25 and Si(100). 27 On Si(111), butterfly-like structures are observed, similar to those in the case of pyrimidine.…”

Section: Introductionmentioning

confidence: 99%

Pyrimidine and s-triazine as structural motifs for ordered adsorption on Si(100): a first principles study

Liu

2015

Phys. Chem. Chem. Phys.

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The chemisorption of pyrimidine and s-triazine, two aromatic molecules with N atoms in the aromatic ring, is studied by first principles calculations to examine not only the chemisorption energy, but also the reaction barriers and the cooperative effects. Among the reaction paths at low coverage, the formation of a cross-bridge structure with two N-Si dative bonds is almost barrierless and should be dominant at low temperature. At higher coverage and low temperature, these cross-row structures should produce an ordered zig-zag pattern, even though it is not the energetically most stable arrangement. Upon heating, the zig-zag pattern could be transformed into lines along dimer rows. These two molecules also provide structural motifs that could facilitate the formation of ordered adsorption structures on Si(100). By symmetry, the complexity of tight-bridge structures could be greatly reduced, while the X-C-X motif, with X being an electronegative atom, could provide the building blocks for cross-row bridges.

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“…From the many molecules studied for adsorption on group 14 semiconductors, heteroaromatic molecules have gained much interest, covering a wide range of functional groups. − The interest in these molecules comes from a desire to understand the role of aromaticity on surface reactions, which can serve as the guiding principle for surface modification. ,, …”

Section: Introductionmentioning

confidence: 99%

“…17−25 The interest in these molecules comes from a desire to understand the role of aromaticity on surface reactions, which can serve as the guiding principle for surface modification. 18,26,27 In this study, we report on the adsorption of homobifunctional pyrazine on the Ge(100)-2×1 surface. Pyrazine (C 4 H 4 N 2 ) is a six-membered ring molecule with two nitrogen atoms in the para position (see Figure 1).…”

Section: ■ Introductionmentioning

confidence: 99%

Effect of Heteroaromaticity on Adsorption of Pyrazine on the Ge(100)-2×1 Surface

et al. 2020

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The reaction of pyrazine with the Ge(100)-2×1 surface has been investigated by X-ray photoelectron spectroscopy (XPS) and density functional theory calculations. Results show that pyrazine reacts with the surface through both the nitrogen and carbon atoms of the ring to form N-dative bonds and cycloaddition products, respectively. These products are assigned based on calculated electron core level binding and adsorption energies, as well as experimental XPS results. We find that the product distribution changes as a function of coverage and temperature, and in all cases, both dative bonded and cycloaddition products are present. A temperature dependence analysis shows evidence of molecular desorption as well as changes in the product distribution. We found that the number of nitrogen dative bonds is maximized at low temperature through kinetic trapping, while carbon cycloaddition products are promoted with increasing thermal energy. Coverage dependence analysis shows that as the surface becomes crowded, most of the reactions occur through the nitrogen moiety. The nature of surface-adsorbate bonding is revealed by natural population analysis and energy decomposition analysis. We find strong evidence for the dative bond character from molecule to surface donation of the nitrogen lone pairs and surface to molecule back-donation from Ge–Gesubsurface bonds. A loss of aromaticity is found for the structure with two dative bonds. The reaction to the cycloaddition product shows signatures of an inverse electron-demand Diels–Alder reaction.

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Adsorption of nitrogen-containing aromatic molecules on Si(1 1 1)-7 × 7

Cited by 14 publications

References 31 publications

Chemical manipulation of multifunctional hydrocarbons on silicon surfaces

Chemical manipulation of multifunctional hydrocarbons on silicon surfaces

Pyrimidine and s-triazine as structural motifs for ordered adsorption on Si(100): a first principles study

Effect of Heteroaromaticity on Adsorption of Pyrazine on the Ge(100)-2×1 Surface

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