Two- and three-tiered stacked architectures by covalent assembly

Fengfeng Ren, Kody J. Day, and C. Scott Hartley*
Angew. Chem., Int. Ed. 2016, 55, 8620–8623
[Published version]


Simple discotic cores functionalized with reactive arms have been assembled into two- and three-tiered covalent stacks through imine formation. The targets are obtained in good yields, but competing formation of misassembled byproducts highlights some of the challenges inherent to the thermodynamically controlled assembly of rigid, compact, three-dimensional architectures. The structures comprise a central stack of arenes surrounded by a triple helix of interconnected arms. The racemization rate is strongly dependent on the number of tiers, suggesting cooperative conformational coupling in these multi-tiered structures.