Insights into the self-assembly of small, organic molecules: Case study of2,4,6-trichlorophenol

Hybrid Monte Carlo and classical molecular dynamics simulations of a hydrat ed 2,4,6-trichlorophenol bilayer are presented. In line with recent freeze- fracture electron microscopy observations, the present investigation confir ms that 2,4,6-trichlorophenol can form stable, lamellar structures. Self-as sembly into a bilayer arises from strong dispersion forces that favor stack ed arrangements of the monomers, as is demonstrated by high-level quantum c hemical calculations. It also results from the subtle balance between hydro phobic and hydrophilic contributions, responsible for the preferential orie ntation of the aromatic compounds and the cohesion of the supramolecular ar rangement. Imbalance of these contributions is illustrated in the case of 2 ,6-dichlorophenol that does not yield lamellar structures.