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Dalton Trans. 2009 Sep 14;(34):6751-8. doi: 10.1039/b907289f. Epub 2009 Jul 15.

The Cu(II) complex of a C-lipophilized 13aneN4 macrocycle with an additional protonable amino group as micellar anion receptor.

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Institut de Chimie Moléculaire de l'Université de Bourgogne, UMR CNRS 5260, Université de Bourgogne, 9 avenue Alain Savary, 21078, Dijon, France.


Three 13aneN4 macrocyclic ligands have been prepared bearing a -CH(2)NHR side arm (R = H, n-C(5)H(11), n-C(10)H(21)) on a carbon atom. When Cu(2+) is complexed in the macrocyclic ring, the amino group of the side arm undergoes an acid-base protonation equilibrium but it is not able to coordinate apically the metal cation even when it is deprotonated. The Cu(2+) complex with the ligand bearing the longest appended aliphatic chain is fully confined inside Triton X-100 micelles, and its ability to bind and sequestrate a series of anions inside micelles has been studied at two different pH values, i.e. both with protonated and neutral side-arm amino group. The favourable role played by the protonated amino group in the side arm has been demonstrated.

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