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As the third-generation rigid macrocycles evolved from progenitor 1 , cyclic aromatic oligoamides 3 , with a backbone of reduced constraint, exhibit extremely strong stacking with an astoundingly high affinity (estimated lower limit of K  dimer &gt; 10 13 M -1 in CHCl 3 ), which leads to dispersed tubular stacks that undergo further assembly in solution. Computational study reveals a very large binding energy (-49.77 kcal mol -1 ) and indicates highly cooperative local dipole interactions that account for the observed strength and directionality for the stacking of 3 . In the solid-state, X-ray diffraction (XRD) confirms that the aggregation of 3 results in well-aligned tubular stacks. The persistent tubular assemblies of 3 , with their non-deformable sub-nm pore, are expected to possess many interesting functions. One such function, transmembrane ion transport, is observed for 3 .

Extremely strong tubular stacking of aromatic oligoamide macrocycles