Original Research ARTICLE
Pillararene based rotaxane systems with redox-responsive host-guest property: design, synthesis and the key role of chain length
- 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 pillararenes based MIMs have been investigated a lot recent years, pillararene based rotaxanes are very limited. In this report, we synthesized a series of amide-linked pillararene-based rotaxanes with ferrocene unit as the stopper. Under the catalysis of HOBT/EDCL, the mono-amido-functionalized pillararenes were amidated with ferrocene carboxylic acid to constructed ferrocene-based rotaxanes, respectively. The structure of the rotaxanes were characterized by 1H NMR, 13C NMR, 2D NMR, mass spectroscopy and single-crystal X-ray structural determination. In the experiment, the monofunctionalized pillararene 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 pillararene-based rotaxanes perform electrochemically reversible property. Based on this nature, we hope these pillararene-based 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.
Mx. Yong Yao, Nantong University, Nantong, China, email@example.com
Prof. Tingting Chen, Nantong University, Nantong, China, firstname.lastname@example.org
Prof. Chaoguo Yan, Yangzhou University, Yangzhou, 225009, Jiangsu Province, China, email@example.com