ZnII-induced conformational control of amphiphilic cavitands in Langmuir monolayers

Markus Frei; Federica Marotti; François Diederich

doi:10.1039/B405331A

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Zn^II-induced conformational control of amphiphilic cavitands in Langmuir monolayers†

Markus Frei,^a Federica Marotti^a and François Diederich*^a

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* Corresponding authors

^a Laboratorium für Organische Chemie, ETH-Hönggerberg, CH-8093 Zürich, Switzerland
E-mail: diederich@org.chem.ethz.ch
Fax: +41 1 632 1109
Tel: +41 1 632 2992

Abstract

The reversible switching from the C_4v-symmetric vase to the C_2v-symmetric kite conformation of an amphiphilic resorcin[4]arene cavitand was induced by Zn^II ion coordination. Langmuir monolayers were obtained of both conformers with the area per molecule increasing dramatically from 120 Å² for the vase to 270 Å² for the kite form. ¹H NMR spectroscopy in chloroform solution supports the formation of a stoichiometric kite-cavitand˙(Zn^II)₂ complex, with the metal ions coordinating to pairs of neighbouring quinoxaline N-atoms.

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Supplementary files

Characterization of 1 and 2; protocol of Langmuir experiments performed on the water subphase at different pH; Job plot analysis. DOC (103K)

Article information

DOI: https://doi.org/10.1039/B405331A
Article type: Communication
Submitted: 08 Apr 2004
Accepted: 06 May 2004
First published: 18 May 2004

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Chem. Commun., 2004, 1362-1363

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Zn^II-induced conformational control of amphiphilic cavitands in Langmuir monolayers

M. Frei, F. Marotti and F. Diederich, Chem. Commun., 2004, 1362 DOI: 10.1039/B405331A

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