Langmuir, Vol.35, No.4, 870-874, 2019
Observations of Gradual Chiral Self-Recognition of Adsorbed Aromatic Compound
The self-assembly of two-dimensional chiral 1H,5H-benzo(1,2-d:4,5-d')bistriazole (H(2)bbta) on a Ag(110) surface was investigated by ultra-high-vacuum scanning tunneling microscopy. The gradual formation of ordered structures by H(2)bbta molecules with the same chirality recognizing each other was observed as the annealing temperature was increased from 300 to 333 K. When the sample was annealed at 355 K, the homochiral structures were converted to coexisting structures containing lambda-H(2)bbta and delta-H(2)bbta in a ratio of 6:1. Density functional theory (DFT) calculations revealed that thermally driven and intermolecular interactions induced chiral self-recognition to form enantiomorphous H(2)bbta structures in which N-H center dot center dot center dot N hydrogen bonds and C-H center dot center dot center dot N hydrogen bonds are the main attractive forces.