title: Controlling the position of functional groups at the liquid/solid interface: impact of molecular symmetry and chirality.
abstract: With the aim of controlling the position of functional groups in a substrate-supported monolayer, a new family of functionalized linear alkyl chains was designed and synthesized, aided by molecular mechanics and dynamics simulations of its two-dimensional self-assembly on graphite. The self-assembly of these amino functionalized diamides at the liquid/solid interface was investigated with scanning tunneling microscopy. Intermolecular hydrogen-bonding interactions involving amides, combined with the effect of molecular symmetry and chirality, were found to guide the self-assembly. Control of the relative position and orientation of the amine groups was achieved, in the case of enantiopure compounds. Interestingly, racemates led to both racemic conglomerate and solid solution formation, with a concomitant loss of positional and orientational control of the amino groups as a result.
authors: Department of Chemistry, Division of Molecular Imaging and Photonics, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
authors: Inge
authors: I
authors: De Cat
authors: Cristian
authors: C
authors: Gobbo
authors: Bernard
authors: B
authors: Van Averbeke
authors: Roberto
authors: R
authors: Lazzaroni
authors: Steven
authors: S
authors: De Feyter
authors: Jan
authors: J
authors: van Esch