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- Title
Highly efficient synthesis of non-planar macrocycles possessing intriguing self-assembling behaviors and ethene/ethyne capture properties.
- Authors
Mao, Lijun; Hu, Yang; Tu, Qian; Jiang, Wei-Ling; Zhao, Xiao-Li; Wang, Wenjing; Yuan, Daqiang; Wen, Jin; Shi, Xueliang
- 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. The design of covalent macrocycles which show characteristic self-assembly behaviour and host-guest properties is challenging. Here, the authors demonstrate the synthesis of diphenylamine[n]arenes through a one-pot synthesis and demonstrate the π-π pi stacking of the non-planar rings as well as ethane/ethyne host-guest interactions.
- Subjects
SUPRAMOLECULAR chemistry; STACKING interactions; DIPHENYLAMINE; MACROCYCLIC compounds; SOLID solutions; AROMATIC compounds; CUCURBITURIL
- Publication
Nature Communications, 2020, Vol 11, Issue 1, pN.PAG
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-020-19677-x