Journal
CHEMICAL SCIENCE
Volume 6, Issue 1, Pages 152-157Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc02380c
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Funding
- National Science Foundation [CHE-1306326]
- Natural Science Foundation of China [91227109]
- US Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-AC02-06CH11357]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1306326] Funding Source: National Science Foundation
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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 > 10(13) 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.
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