Issue 25, 2016
From the journal:

Chemical Communications

Rotamerism-driven large magnitude host–guest binding change in a crown ether derivatized pyridinium-phenolate series†

Emel Ay,a   Nelly Hobeika,b   Hélène Chaumeil,a   Théophile Tschamber,a   Ming Jin,c   Davy-Louis Versaced  and  Jean-Pierre Malval*b  

* Corresponding authors

a Laboratoire de Chimie Organique et Bioorganique, Université de Haute Alsace, ENSCMu, 3 rue Alfred Werner, Mulhouse, France

b Institut de Science des Matériaux de Mulhouse CNRS-UMR 7361, Université de Haute Alsace, 15 rue Jean Starcky, 680 Mulhouse, Mulhouse, France
E-mail: jean-pierre.malval@uha.fr

c School of Materials & Engineering, Tongji University, 4800 CaoAn Road, Shanghai, China

d Institut de Chimie et des Matériaux Paris-Est CNRS-UMR 7182, Paris-Est Créteil Val de Marne, 2-8 rue Henri Dunant, Thiais, France

Abstract

Two TICTOID-based pyridinium-phenolates bearing a crown ether macrocycle have been designed for the complexation of a potassium cation. The nucleophilicity of the intraannular phenolate –O− function can be strongly modulated by biaryl twisting. Such a structure/electronic transduction effect gives rise to a host–guest binding change by more than two orders of magnitude.

Graphical abstract: Rotamerism-driven large magnitude host–guest binding change in a crown ether derivatized pyridinium-phenolate series

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Article information

DOI
https://doi.org/10.1039/C6CC00684A
Article type
Communication
Submitted
23 Jan 2016
Accepted
26 Feb 2016
First published
26 Feb 2016

Chem. Commun., 2016,52, 4652-4654

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Rotamerism-driven large magnitude host–guest binding change in a crown ether derivatized pyridinium-phenolate series

E. Ay, N. Hobeika, H. Chaumeil, T. Tschamber, M. Jin, D. Versace and J. Malval, Chem. Commun., 2016, 52, 4652 DOI: 10.1039/C6CC00684A

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