Self-assembly has long been demonstrated as the authoritative strategy to engineer complex, organic nanostructures at surfaces with high fidelity. The formation of these arrays using components with solution phase host-guest recognition properties can result in stimuli-responsive and dynamic self-assemblies that extend growth away from the surface into the third dimension. We demonstrate the two-dimensional crystallization and three-dimensional stacking of novel organic macrocycles that self-assemble from solution on surfaces. The 5-fold symmetric cyanostar assembles into antiparallel rows of molecules. Anions appear to drive sandwich formation on the surface as observed with scanning tunneling microscopy (STM). Dimer stacking can also be shown without guest anions in the 3-fold symmetric tricarbazolo triazolophane, which is believed to stack on the basis of favorable electrostatic matching of the p surfaces. This work demonstrates characteristics of supramolecular self-assemblies required for extending order and function beyond the two-dimensional surface plane.

Assembly and stacking of novel macrocycles on surfaces

247th National Meeting (2014)

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