Next Article in Journal
Effect of pH, Surfactant, and Temperature on Mixed-Phase Structure and Band Gap Properties of BiNbO4 Nanoparticles Prepared Using Different Routes
Next Article in Special Issue
Solvatochromism and Selective Sorption of Volatile Organic Solvents in Pyridylbenzoate Metal-Organic Frameworks
Previous Article in Journal
Acetylation of Alcohols, Amines, Phenols, Thiols under Catalyst and Solvent-Free Conditions
Open AccessCommunication

Hydroquinone-Based Anion Receptors for Redox-Switchable Chloride Binding

School of Chemistry (F11), The University of Sydney, Sydney, NSW 2006, Australia
*
Author to whom correspondence should be addressed.
Chemistry 2019, 1(1), 80-88; https://doi.org/10.3390/chemistry1010007
Received: 21 June 2019 / Revised: 8 July 2019 / Accepted: 8 July 2019 / Published: 11 July 2019
(This article belongs to the Special Issue Supramolecular Chemistry in the 3rd Millennium)
A series of chloride receptors has been synthesized containing an amide hydrogen bonding site and a hydroquinone motif. It was anticipated that oxidation of the hydroquinone unit to quinone would greatly the diminish chloride binding affinity of these receptors. A conformational switch is promoted in the quinone form through the formation of an intramolecular hydrogen bond between the amide and the quinone carbonyl, which blocks the amide binding site. The reversibility of this oxidation process highlighted the potential of these systems for use as redox-switchable receptors. 1H-NMR binding studies confirmed stronger binding capabilities of the hydroquinone form compared to the quinone; however, X-ray crystal structures of the free hydroquinone receptors revealed the presence of an analogous inhibiting intramolecular hydrogen bond in this state of the receptor. Binding studies also revealed interesting and contrasting trends in chloride affinity when comparing the two switch states, which is dictated by a secondary interaction in the binding mode between the amide carbonyl and the hydroquinone/quinone couple. Additionally, the electrochemical properties of the systems have been explored using cyclic voltammetry and it was observed that the reduction potential of the system was directly related to the expected strength of the internal hydrogen bond. View Full-Text
Keywords: anion binding; chloride receptor; switchable system; hydroquinone; redox switch anion binding; chloride receptor; switchable system; hydroquinone; redox switch
Show Figures

Graphical abstract

MDPI and ACS Style

McNaughton, D.A.; Fu, X.; Lewis, W.; D’Alessandro, D.M.; Gale, P.A. Hydroquinone-Based Anion Receptors for Redox-Switchable Chloride Binding. Chemistry 2019, 1, 80-88.

Show more citation formats Show less citations formats

Article Access Map by Country/Region

1
Back to TopTop