Issue 70, 2017

Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly

Abstract

This feature article summarises recent contributions of the authors in the area of anion-induced supramolecular self-assembly. It is based on the chemistry of a set of tetracationic imidazolium macrocycles, specifically the so-called ‘Texas-sized’ molecular box, cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,4-dimethylenebenzene) (14+), and its congeners, cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,2-dimethylenebenzene) (24+), cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,3-dimethylenebenzene) (34+), and cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](2,6-dimethylenepyridine) (44+). These systems collectively have been demonstrated as being versatile building blocks that interact with organic carboxylate or sulfonate anions, as well as substrates (e.g., neutral molecules or metal cations). Most work to date has been carried out with 14+, a system that has been found to support the construction of a number of stimuli responsive self-assembled ensembles. This macrocycle and others of the ‘Texas-sized’ box family also show the potential to react as carbene precursors and to undergo post-synthetic modification (PSM) to produce new functional macrocycles, such as trans- and cis-cyclo[2]((Z)-N-(2-((6-(1H-imidazol-1-yl)pyridin-2-yl)amino)vinyl)formamide)[2](1,4-bismethylbenzene) (52+ and 62+, respectively). On the basis of the work reviewed in this Feature article, we propose that the imidazolium macrocycles 14+44+ can be considered as useful tools for the construction of ensembles with environmentally responsive features, including control over self-assembly and an ability to undergo precursor-specific PSM.

Graphical abstract: Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly

Article information

Article type
Feature Article
Submitted
20 lip 2017
Accepted
25 srp 2017
First published
25 srp 2017

Chem. Commun., 2017,53, 9684-9696

Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly

Y. Yang, J. L. Sessler and H. Gong, Chem. Commun., 2017, 53, 9684 DOI: 10.1039/C7CC04661H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements