Extremely strong tubular stacking of aromatic oligoamide macrocycles

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 C Zeng, Bing Gong

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 > 10 13 M -1 in CHCl 3 ), 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

Original languageEnglish (US)
Pages (from-to)152-157
Number of pages6
JournalChemical Science
Volume6
Issue number1
DOIs
StatePublished - Jan 1 2015

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Binding energy
Dimers
Agglomeration
Ions
X ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

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 C; Gong, Bing.

In: Chemical Science, Vol. 6, No. 1, 01.01.2015, p. 152-157.

Research output: Contribution to journalArticle

Kline, MA, Wei, X, Horner, IJ, Liu, R, Chen, S, Chen, S, Yung, KY, Yamato, K, Cai, Z, Bright, FV, Zeng, XC & Gong, B 2015, 'Extremely strong tubular stacking of aromatic oligoamide macrocycles', Chemical Science, vol. 6, no. 1, pp. 152-157. https://doi.org/10.1039/c4sc02380c
Kline MA, Wei X, Horner IJ, Liu R, Chen S, Chen S et al. Extremely strong tubular stacking of aromatic oligoamide macrocycles. Chemical Science. 2015 Jan 1;6(1):152-157. https://doi.org/10.1039/c4sc02380c
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 C ; Gong, Bing. / Extremely strong tubular stacking of aromatic oligoamide macrocycles. In: Chemical Science. 2015 ; Vol. 6, No. 1. pp. 152-157.
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