The development of synthetic methods that are both robust and efficient are of paramount importance in accessing functional small molecules, one-dimensional polymers, and higher-ordered materials. In this way, I will discuss distinct synthetic efforts in supramolecular polymerization and small-molecule methods development. I will first discuss the development of a general synthetic method to access synthetic nanotubes via acid-mediated macrocycle assembly. Protonation of basic residues within imine-linked macrocycles activates robust yet reversible electrostatic interactions leading to spontaneous nanotube formation. Despite being supported solely by non-covalent interactions, these high-aspect ratio supramolecular polymers exhibited cohesive energies stronger than C–C bonds. I will highlight how rational synthetic design first enabled nanotube formation under mild conditions via the formation of pyridinium ions, and that this process was generalized through the development of a conserved pyridine-containing diamine synthon. Utilizing this approach, nanotubes of varying shapes, channel sizes, and chemical functionalities were realized. I will conclude this portion of the seminar by discussing how this general synthetic method enabled the development of structure-property relationships within this class of materials for the first time. 
In the second half of my talk, I will discuss the development of a new family of anionic ligands for Cu-catalyzed C–heteroatom bond forming reactions. This ligand design was initially guided by DFT calculations to (1) increase the electron density on Cu, thereby increasing the rate of oxidative addition, and (2) stabilize the active anionic Cu(I) catalyst via non-covalent interactions. A significant portion of this talk will focus on how the catalysts derived from these ligands has improved the scopes of Cu-catalyzed C–N and C–O coupling reactions while concomitantly utilizing milder reaction conditions. I will also highlight how the modularity of this ligand scaffold has resulted in systematic improvements in reaction efficiency by using reaction outcomes and mechanistic insights as guides. Collectively, the results to be discussed have established a new class of anionic ligands for Cu-catalyzed C–heteroatom bond forming reactions in synthetically useful contexts.