Extremely strong tubular stacking of aromatic oligoamide macrocycles

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Abstract

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 Kdimer > 1013 M-1 in CHCl3), 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. This journal is

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Kline, M. A., Wei, X., Horner, I. J., Liu, R., Chen, S., Chen, S., … Gong, B. (2015). Extremely strong tubular stacking of aromatic oligoamide macrocycles. Chemical Science, 6(1), 152–157. https://doi.org/10.1039/c4sc02380c

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