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Issue 23, 2013
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Argentivorous molecules with two kinds of aromatic side-arms: intramolecular competition between side-arms

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Abstract

Three tetra-armed cyclens with two kinds of side-arms, 3′,5′-difluorobenzyl/4′-methylbenzyl, 3′,5′-difluorobenzyl/1′-naphthylmethyl, and 3′,5′-difluorobenzyl/9′-anthrylmethyl groups, were prepared by reductive amination of 1,7-bis(3′,5′-difluorobenzyl)-1,4,7,10-tetraazacyclododecane and the corresponding aromatic aldehydes in the presence of NaBH(OAc)3. The X-ray structures of the Ag+ complexes and Ag+-ion-induced 1H NMR spectral changes suggest that (i) the chemical shift changes of the protons at the 2′- and 6′-positions in the 3′,5′-difluorobenzyl/4′-methylbenzyl side-arms are dependent on the electron density on the adjacent substituted benzenes, and (ii) in the tetra-armed cyclens with 3′,5′-difluorobenzyl/1′-naphthylmethyl and 3′,5′-difluorobenzyl/9′-anthrylmethyl groups as side-arms, electron-rich aromatic rings preferentially cover the Ag+ ions incorporated into the ligand cavities, and 3′,5′-difluorobenzyl groups do not participate in the Ag+ interactions. The log K values were estimated using Ag+-ion-induced UV-vis spectral changes.

Graphical abstract: Argentivorous molecules with two kinds of aromatic side-arms: intramolecular competition between side-arms

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Publication details

The article was received on 04 Jan 2013, accepted on 06 Feb 2013 and first published on 07 Feb 2013


Article type: Paper
DOI: 10.1039/C3DT00034F
Dalton Trans., 2013,42, 8212-8217

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    Argentivorous molecules with two kinds of aromatic side-arms: intramolecular competition between side-arms

    Y. Habata, Y. Oyama, M. Ikeda and S. Kuwahara, Dalton Trans., 2013, 42, 8212
    DOI: 10.1039/C3DT00034F

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