Extremely strong tubular stacking of aromatic oligoamide macrocycles
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| Authors: | Mark A Kline Xiaoxi Wei Ian J Horner Rui Liu Shuang Chen Si Chen Ka Yi Yung Kazuhiro Yamato Zhonghou Cai Frank V Bright Xiao Cheng Zeng Bing Gong |
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| Institution: | a Department of Chemistry , the State University of New York at Buffalo , Buffalo , New York , USA 14260 . Email: ; http://www.chemistry.buffalo.edu/people/faculty/gong/ ;b Department of Chemistry , University of Nebraska-Lincoln , Lincoln , Nebraska 68588 , USA ;c X-ray Science Division , Argonne National Laboratory , 9700 South Cass Avenue , Argonne , IL 60439 , USA ;d College of Chemistry , Beijing Normal University , Beijing 100875 , China |
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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 K
dimer > 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. |
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