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Solvent Effect on Host–Guest Two-Dimensional Self-Assembly Mediated by Halogen Bonding

Host–guest self-assemblies of methyl 5-bromo-2-(hexadecyloxy)benzoate (host) and 1-bromohexadecane (guest) molecules were investigated at the liquid/solid interface by scanning tunneling microscopy. Polar solvent (1-octanoic acid) and nonpolar solvents (1-phenyloctane, n-pentadecane, n-tetradecane, and n-decane) were selected to study the solvent effect on the self-assembly of the host–guest system. It is observed that the host–guest system self-assembles into different morphologies at low concentrations due to the solvent adsorption. Only a linear structure can be obtained at high concentration in different kinds of solvents. In particular, the different self-assembled patterns obtained at low concentration will eventually transform to the same linear structure. Owing to the participation of guest molecules, a strong Br···O═C halogen bond is formed between host and guest molecules, further leading to the occurrence of physisorbed monolayers and structural transition. The density functional theory calcula...