Extremely strong tubular stacking of aromatic oligoamide macrocycles

Kline, Mark A.; Wei, Xiaoxi; Horner, Ian J.; Liu, Rui; Chen, Shuang; Chen, Si; Yung, Ka Yi; Yamato, Kazuhiro; Cai, Zhonghou; Bright, Frank V.; Zeng, Xiao Cheng; Gong, Bing

doi:10.1039/C4SC02380C

Title: Extremely strong tubular stacking of aromatic oligoamide macrocycles

Journal Article · Thu Jan 01 00:00:00 EST 2015 · Chemical Science

DOI:https://doi.org/10.1039/C4SC02380C· OSTI ID:1214393

Kline, Mark A. ^[1]; Wei, Xiaoxi ^[1]; Horner, Ian J. ^[1]; Liu, Rui ^[1]; Chen, Shuang ^[2]; Chen, Si ^[3]; Yung, Ka Yi ^[1]; Yamato, Kazuhiro ^[1]; Cai, Zhonghou ^[3]; Bright, Frank V. ^[1]; Zeng, Xiao Cheng ^[2]; Gong, Bing ^[4]

State Univ. of New York (SUNY), Buffalo NY (United States)
Univ. of Nebraska, Lincoln, NE (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)
State Univ. of New York (SUNY), Buffalo NY (United States); Beijing Normal Univ. (China)

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. Furthermore, 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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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1214393

Alternate ID(s):: OSTI ID: 1251158

Journal Information:: Chemical Science, Vol. 6, Issue 1; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 26 works

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