Title: Controlling the Position of Functional Groups at the Liquid/Solid Interface: Impact of Molecular Symmetry and Chirality
Authors: De Cat, Inge ×
Gobbo, Cristian
Van Averbeke, Bernard
Lazzaroni, Roberto
De Feyter, Steven
Van Esch, Jan #
Issue Date: Dec-2011
Publisher: American Chemical Society
Series Title: Journal of the American Chemical Society vol:133 issue:51 pages:20942-20950
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.
ISSN: 0002-7863
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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