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Title: Extremely strong tubular stacking of aromatic oligoamide macrocycles

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. 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.

Authors:
 [1];  [1];  [1];  [1];  [2];  [3];  [1];  [1];  [3];  [1];  [2];  [4]
+ Show Author Affiliations
  1. State Univ. of New York (SUNY), Buffalo NY (United States)
  2. Univ. of Nebraska, Lincoln, NE (United States)
  3. Argonne National Lab. (ANL), Argonne, IL (United States)
  4. State Univ. of New York (SUNY), Buffalo NY (United States); Beijing Normal Univ. (China)
Publication Date:
Research Org.:
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1214393
Alternate Identifier(s):
OSTI ID: 1251158
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 6; Journal Issue: 1; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

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, and Gong, Bing. Extremely strong tubular stacking of aromatic oligoamide macrocycles. United States: N. p., 2015. Web. doi:10.1039/C4SC02380C.
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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. Extremely strong tubular stacking of aromatic oligoamide macrocycles. United States. https://doi.org/10.1039/C4SC02380C
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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, and Gong, Bing. Thu . "Extremely strong tubular stacking of aromatic oligoamide macrocycles". United States. https://doi.org/10.1039/C4SC02380C. https://www.osti.gov/servlets/purl/1214393.
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@article{osti_1214393,
title = {Extremely strong tubular stacking of aromatic oligoamide macrocycles},
author = {Kline, Mark A. and Wei, Xiaoxi and Horner, Ian J. and Liu, Rui and Chen, Shuang and Chen, Si and Yung, Ka Yi and Yamato, Kazuhiro and Cai, Zhonghou and Bright, Frank V. and Zeng, Xiao Cheng and Gong, Bing},
abstractNote = {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.},
doi = {10.1039/C4SC02380C},
journal = {Chemical Science},
number = 1,
volume = 6,
place = {United States},
year = {Thu Jan 01 00:00:00 EST 2015},
month = {Thu Jan 01 00:00:00 EST 2015}
}
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