Issue 11, 2008

Trianionic calix[4]arene monoalkoxy derivatives: synthesis, solid-state structures and self-assembly properties

Abstract

The synthesis of a series of novel tris[(carboxy)methyl]-monoalkoxy-trihydroxycalix[4]arenes is described. Treatment of the tris[(dimethylamino)methyl]-monoalkoxy-trihydroxycalix[4]arene derivatives with iodomethane, followed by sodium cyanide as a nucleophile, gave the corresponding tris[(cyano)methyl]-monoalkoxy-trihydroxycalix[4]arenes in excellent yield, and these latter compounds were converted by hydrolysis to their tris[(carboxy)methyl]-monoalkoxy derivatives. The solid-state structures of four of the intermediate tris[(cyano)methyl]-monoalkoxy-trihydroxycalix[4]arenes show inclusion of an acetonitrile guest in the ethoxy derivative and intermolecular inclusion of the hydrophobic terminal region of the alkoxy groups for longer chain lengths. The packing of both structural types show 1-D inclusion polymer behaviour. At pH values above 5.5, all the trianionic tris[(carboxy)methyl]-monoalkoxy-trihydroxycalix[4]arene derivatives showed self-assembly to yield micellar systems, for which there was a clear odd–even effect in the observed surface tensions at the critical micelle concentrations.

Graphical abstract: Trianionic calix[4]arene monoalkoxy derivatives: synthesis, solid-state structures and self-assembly properties

Supplementary files

Article information

Article type
Paper
Submitted
15 Apr 2008
Accepted
04 Jul 2008
First published
26 Aug 2008

New J. Chem., 2008,32, 1988-1998

Trianionic calix[4]arene monoalkoxy derivatives: synthesis, solid-state structures and self-assembly properties

K. Suwinska, O. Shkurenko, C. Mbemba, A. Leydier, S. Jebors, A. W. Coleman, R. Matar and P. Falson, New J. Chem., 2008, 32, 1988 DOI: 10.1039/B806342G

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