Hierarchical assembly provides a route to complex architectures when using building blocks with recognition elements that are strong and structurally well-defined. For this purpose, shape-persistent macrocycles offer distinct advantages: the recognition elements encoded into their rigid inner and outer surfaces are reliably retained and displayed. Tricarbazole (tricarb) macrocycles are exemplary. These macrocycles possess electropositive cavities for anions, hydrogen bonding motifs for complementary contacts, and have large π-faces for stacking. Building on this macrocycle framework, we utilize a step-wise synthesis to program peripheral alkyl units and other functional groups in order to probe their impact on the two-dimensional, ordered tricarb assemblies. This 2D assembly was investigated at the solution-surface interface using scanning tunneling microscopy. The work presented here demonstrates the power granted by sequence-specific syntheses in the study and control of self-assembly on surfaces.

Leveraging a step-wise, sequence-specific synthesis of shape-persistent macrocycles to control hierarchical self-assembly on surfaces

2019 Spring National Meeting

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