Highly efficient synthesis of non-planar macrocycles possessing intriguing self-assembling behaviors and ethene/ethyne capture properties

Lijun Mao, Yang Hu, Qian Tu, Wei-Ling Jiang, Xiao-Li Zhao, Wenjing Wang, Daqiang Yuan, Jin Wen and Xueliang Shi ()
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Lijun Mao: East China Normal University
Yang Hu: East China Normal University
Qian Tu: East China Normal University
Wei-Ling Jiang: East China Normal University
Xiao-Li Zhao: East China Normal University
Wenjing Wang: Chinese Academy of Sciences
Daqiang Yuan: Chinese Academy of Sciences
Jin Wen: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic
Xueliang Shi: East China Normal University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract It has been a challenging topic and perpetual task to design and synthesize covalent macrocycles with characteristic self-assembling behaviors and excellent host-guest properties in supramolecular chemistry. Herein, we present a family of macrocyclic diphenylamine[n]arenes (DPA[n]s, n = 3–7) consisting of methyldiphenylamine units through a facile one-pot synthesis strategy. Unlike many other reported macrocyclic arenes, the resultant non-planar DPA[n]s feature intrinsic π-π stacking interactions, interesting self-assembling behaviors and ethene/ethyne capture properties. Specifically, strong multiple intermolecular edge-to-face aromatic interactions in DPA[3] have been systematically investigated both in solid and solution states. The intriguing findings on the intermolecular edge-to-face stacking interaction mode in the macrocycle would further highlight the importance of noncovalent π-π interaction in supramolecular self-assembly. This study will also shed light on the macrocyclic and supramolecular chemistry and, we expect, will provide a direction for design and synthesis of covalent macrocycles in this area.

Date: 2020
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DOI: 10.1038/s41467-020-19677-x

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