Two-Dimensional Chiral Single Domain by D-Alaninol Functionalization of Cu(100)

Abstract

We report the results of chemisorption in saturating conditions of D-alaninol on Cu(100) in term of the analysis of low-energy electron diffraction and scanning tunneling microscopy data. A large two-dimensional, single domain, ordered chiral structure of quadrangular tetrameric molecular units is formed. The four molecules interact differently with the surface in the two orthogonal directions.

Transfer of chirality from adsorbed chiral molecules to the substrate highlighted by circular dichroism in angle-resolved valence photoelectron spectroscopy

“…[23][24][25][26][27] Alaninol is a small and conformationally flexible bifunctional chiral amino-alcohol belonging to a group of molecules that are important industrial precursors or intermediates for the synthesis of pharmaceutical compounds. 28 It is known that D-alaninol and L-alaninol adsorbed on Cu (100) surface form an ordered self-assembled chiral saturated monolayer.…”

“…28 It is known that D-alaninol and L-alaninol adsorbed on Cu (100) surface form an ordered self-assembled chiral saturated monolayer. [23][24][25] At room temperature (RT), The CDAD experiments were performed by using circular polarized synchrotron radiation available on the APE beamline at the ELETTRA storage ring of "Sincrotrone Trieste" (Italy). The electronic molecular states found on the lower and higher BE side of the main 3d copper electronic states were identified, respectively, as due to antibonding state (peak A) and bonding state (buried in peak B), originating mainly from the interaction of the Cu 3d states with the N 2p lone pair state of the alaninol molecule.…”

Supramolecular organization of chiral molecules on metallic surfaces: D‐alaninol on Cu(100) as a case study

“…4a. It is worth noting that this structure has a C 4 symmetry that, however, seems not to be supported by the observation of STM images obtained at monolayer coverage [5].…”

“…The practical use of such modified surfaces is made possible by the fact that a longrange ordered molecular phase is formed upon adsorption. Experimentally [5], alaninol is found to self-assemble on Cu(100) forming, at monolayer coverage, a phase composed by tetrameric units. In particular, as shown by low energy electron diffraction (LEED), its D-enantiomer arranges in a square structure represented in matricial form as (1,4|4,-1) leading to a 14 degrees clockwise rotation of the molecular phase with respect to the [011] direction of the copper surface.…”

Self-assembling of calcium salt of the new DNA base 5-carboxylcytosine

“…Indeed, self-assembly happens spontaneously and follows a twist of several processes involving interactions among molecules and the adsorption sur-face. Concerning organic and biological systems, the complexity of these systems result in an uncountable ensemble of possibili-ties, which could be consequently exploited in a large variety of applications [6][7][8][9][10][11]. In this context, there is no doubt about the importance of investigation of nucleobases and their derivatives.…”