The control of molecular structures at the nanoscale
plays a critical
role in the development of materials and applications. The adsorption
of a polyheteroaromatic molecule with hydrogen bond donor and acceptor
sites integrated in the conjugated structure itself, namely, benzodi-7-azaindole
(BDAI), has been studied on Au(111). Intermolecular hydrogen
bonding determines the formation of highly organized linear structures
where surface chirality, resulting from the 2D confinement of the
centrosymmetric molecules, is observed. Moreover, the structural features
of theBDAImolecule lead to the formation of two differentiated
arrangements with extended brick-wall and herringbone packing. A comprehensive
experimental study that combines scanning tunneling microscopy, high-resolution
X-ray photoelectron spectroscopy, near-edge X-ray absorption fine
structure spectroscopy, and density functional theory theoretical
calculations has been performed to fully characterize the 2D hydrogen-bonded
domains and the on-surface thermal stability of the physisorbed material.