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Original Research ARTICLE Provisionally accepted The full-text will be published soon. Notify me

Front. Chem. | doi: 10.3389/fchem.2019.00508

Pillar[5]arene based [1]rotaxane systems with redox-responsive host-guest property: design, synthesis and the key role of chain length

 Yong Yao1*, Runmiao Zhang1, 2, Chenwei Wang1, Renhua Long1, Tingting Chen1* and Chaoguo Yan2*
  • 1Nantong University, China
  • 2Yangzhou University, China

Pillar[n]arenes are a new type of macrocyclic compounds, which were first reported in 2008 by Ogoshi. They not only have cylindrical, symmetrical and rigid structures, but also have many advantages, including easy functionalization and rich host-guest properties. On the other hand, mechanically interlocked molecules (MIMs) exist extensively in nature which have been artificially synthesized and widely applied in the fields of nanotechnology and biology. Although pillar[5]arenes based MIMs have been investigated a lot recent years, pillar[5]arene based [1]rotaxanes are very limited. In this report, we synthesized a series of amide-linked pillar[5]arene-based [1]rotaxanes with ferrocene unit as the stopper. Under the catalysis of HOBT/EDCL, the mono-amido-functionalized pillar[5]arenes were amidated with ferrocene carboxylic acid to constructed ferrocene-based [1]rotaxanes, respectively. The structure of the [1]rotaxanes were characterized by 1H NMR, 13C NMR, 2D NMR, mass spectroscopy and single-crystal X-ray structural determination. In the experiment, the monofunctionalized pillar[5]arene we synthesized with a self-inclusion property, which forming a pseudo-rotaxane, the key role is the length of the imine chain in this process, formed a rotaxane through amidation of ferrocene dicarboxylic acid which acting as a plug. In addition, due to the ferrocene units, the pillar[5]arene-based [1]rotaxanes perform electrochemically reversible property. Based on this nature, we hope these pillar[5]arene-based [1]rotaxanes can be applied in battery devices in future.

Keywords: Pillar[n]arenes, Rotaxanes, electrochemically reversible, Single-crystal X-ray, Ferrocene

Received: 05 May 2019; Accepted: 02 Jul 2019.

Edited by:

De-Xian Wang, Institute of Chemistry (CAS), China

Reviewed by:

Tangxin Xiao, Changzhou University, China
Xiao-Yu Hu, Nanjing University of Aeronautics and Astronautics, China
Haibo Yang, East China Normal University, China  

Copyright: © 2019 Yao, Zhang, Wang, Long, Chen and Yan. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence:
Mx. Yong Yao, Nantong University, Nantong, China, yaoyong1986@ntu.edu.cn
Prof. Tingting Chen, Nantong University, Nantong, China, ttchen1980@126.com
Prof. Chaoguo Yan, Yangzhou University, Yangzhou, 225009, Jiangsu Province, China, cgyan@yzu.edu.cn