A Diels-Alder/Retro Diels-Alder approach for controlling hybridization of aromatic oligoamide foldamers into multiple helices

Self-assembly of secondary structural elements represent an intriguing approach for non-covalent synthesis that can potentially offer greater selectivity and orthogonality than existing methods. To this end, the ability of aromatic oligamide foldamers to hybridize into multiple helices can be seen as a powerful tool for the formation of discrete molecular cages or even networks. Still, the spontaneity of this process complicates synthetic aspects of the incorporation of multi-helical segments into larger scaffolds. In this poster we describe the synthesis of a series of diazaiptycene based aromatic monomers via Diels-Alder reaction and show that their incorporation into longer oligomers leads to structural distortions that prevent aggregation between multiple strands. Importantly the use of a TAD (triazoledione) group as dienophile opens a way to the control the oligomer topology via a Diels-Alder / retro Diels-Alder strategy and the use of thermal stimulus to trigger double helix formation. Perspectives for using this approach for the design and synthesis of larger molecular architectures formed via double helix driven self-assembly are also discussed