Issue 4, 2010

Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry

Abstract

The supramolecular chemistry of anions provides a means to sense and manipulate anions in their many chemical and biological roles. For this purpose, Click chemistry facilitated the synthetic creation of new receptors and thus, an opportunity to aid in the recent re-examination of CH⋯anion hydrogen bonding. This tutorial review will focus on the privileged C–H hydrogen bond donor of the 1,2,3-triazole ring systems as elucidated from anion-binding studies with macrocyclic triazolophanes and other receptors. Triazolophanes are shape-persistent and planar macrocycles that direct four triazole and four phenylene CH groups into a 3.7 Å cavity. They display strong (log K(Cl) = 7), size-dependent halide binding (Cl > BrF ≫ I) and a rich set of binding equilibria. For instance, the too large iodide (4.4 Å) can be sandwiched between two pyridyl-based triazolophanes with extreme positive cooperativity. Computational studies verify the triazole's hydrogen bond strength indicating it approaches the traditional NH donors from pyrrole. These examples, those of transport, sensing (e.g., ion-selective electrodes), templation, and versatile synthesis herald the use of triazoles in anion-receptor chemistry.

Graphical abstract: Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry

Article information

Article type
Tutorial Review
Submitted
18 Sep 2009
First published
24 Feb 2010

Chem. Soc. Rev., 2010,39, 1262-1271

Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry

Y. Hua and A. H. Flood, Chem. Soc. Rev., 2010, 39, 1262 DOI: 10.1039/B818033B

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