One-Pot Synthesis of Shape-Persistent Molecular Ladders

Significance

Moore and co-workers synthesized large, shape-persistent ladder molecules in one pot using dynamic covalent chemistry. The perfectly matched polycyclic molecule can be formed in high yields via reversible imine formation followed by irreversible reduction to the amine. High molecular weight byproducts were also observed and the yield of byproducts increased with increasing ‘n’. Although the precursor m-phenylene ethynylene oligomer syntheses can be laborious, Moore and co-workers utilized an efficient solid-phase synthetic approach (E. L. Elliott et al. J. Org. Chem. 2006, 71, 5282-5290).