Issue 3, 2016

One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy

Abstract

The construction and efficient synthesis of hetero[n]rotaxanes with high structural complexity are always attractive challenges. Herein, we demonstrate a facile one-pot preparation of a hetero[4]rotaxane, by employing a self-sorting strategy, which contains an interpenetrated dibenzo-24-crown-8 (DB24C8) based [c2]daisy chain structure and is ended with a benzo-21-crown-7 (B21C7) based rotaxane at each side. The key to the design involved encoding the selective threading using a steric hindrance-related “language”, where highly selective self-assemblies occurred in a three-component self-sorting process, which included the threading of a benzylalkylammonium into a B21C7 and interpenetrated dimerized formation of a DB24C8 based [c2]daisy chain simultaneously; the precise pre-assembled system resulted in the efficient synthesis of hetero[4]rotaxane with a high-level of structural complexity under the “CuAAC” reaction.

Graphical abstract: One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Dec 2015
Accepted
12 Jan 2016
First published
12 Jan 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 1696-1701

One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy

X. Fu, Q. Zhang, S. Rao, D. Qu and H. Tian, Chem. Sci., 2016, 7, 1696 DOI: 10.1039/C5SC04844C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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