Towards hybrid silicon-organic molecular electronics: The stability of acetone on the Si(001) surface

Interaction of acetone with the Si(001) surface

“…It is also clear from the above discussion that we are not able to determine from the STM images which of these two structures are formed at room temperature, as their simulated STM appearances are very similar. Our atomic-resolution STM data clearly shows, however, that there is only one type of single-dimer adsorbate [8], and hence suggests that either the a-H cleavage, O-bonded (dissociation) structure, or the [2 + 2] cycloaddition structure is formed, but not both. Previous experimental work [6] has suggested that the one-dimer feature (S) is the [2 + 2] cycloaddition structure.…”

“…It has been argued that for the dative bond formed between a Si dimer and NH 3 , the lone pair electrons are donated to the surface and become delocalized resulting in a strong 0.84-1.15 eV dative bond [17]. Differences between the calculated binding energies of the dative bonds formed by oxygen and nitrogen have been explained by the fact that oxygen is more electronegative than nitrogen and therefore less willing to share its lone pair electrons [8]. The strength of the dative bond between an ethyl-vinyl-ketone molecule and the Si(0 0 1) surface was calculated using a one-dimer and two-dimer cluster to be 0.62 eV and 0.76 eV, respectively, [18].…”

“…Recently we have reported the results of a combined scanning tunneling microscopy (STM) and density functional theory (DFT) study of the interaction of acetone with the Si(0 0 1) surface and identified three distinct adsorbate features in the STM images [8,9]. One of these features was one-dimer wide, while the other two were two-dimers wide.…”

Acetone on silicon (001): ambiphilic molecule meets ambiphilic surface

“…The adsorption chemistry of acetone on Si(001) has been the subject of a number of experimental [14][15][16][17][18][19] and theoretical studies. [16][17][18][19][20][21][22][23] An early, comprehensive surface-science study by Armstrong et al 14 brought together a variety of experimental techniques including X-ray photoelectron spectroscopy (XPS), high-resolution electron energy loss spectroscopy (HREELS) and temperature-programmed desorption (TPD). The absence of CQO signals in the XPS and vibrational data led these authors to conclude that acetone binds to the surface in a di-s fashion.…”

Selectivity of [2+2] C＝O Cycloaddition and <em>&alpha;</em>-H Cleavage of Carbonyl Compounds on Si(100) Surface

“…For example, by attaching functional groups, such as COOH, NH2, OH, or CH3, different hydrophobic surfaces with adjustable contact properties with metals and electron conductivities could be obtained. In the past decade, the [2+2] C＝O cycloaddition reactions of carbonyl compounds with Si(100) surface have been studied extensively, and the theoretical and experimental investigations were mostly focused on acetone [2+2] C＝O clycloaddition on Ge(100) 3,19 and Si(100) [1][2][3]5,[10][11][12][19][20][21] surfaces, where the π components of C＝O double bonds reacted with semiconductor surfaces to form Si(Ge)-C and Si(Ge)-O σ-bonds. 9 Also of interest among the carbonyl compounds is aldehydes.…”