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Issue 26, 2013
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Redox control of molecular motions in bipyridinium appended calixarenes

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Abstract

A series of redox-responsive architectures featuring two bipyridinium units introduced onto the lower rim of a calixarene skeleton has been synthesized. The redox-triggered intramolecular dimerization of the reduced bipyridiniums has been investigated by electrochemistry, spectroelectrochemistry and by theoretical chemistry. The spectroscopic signature of the intramolecular dimers was found to evolve significantly with the size of the alkyl linker introduced between the calixarene skeleton and the bipyridinium units. On account of experimental data supported by theoretical calculations, these differences have been attributed to the extent of the orbital overlap in the π-dimerized species, involving either four or only two of the pyridine rings of the bipyridinium radical cations stacked in eclipsed or staggered conformations, respectively.

Graphical abstract: Redox control of molecular motions in bipyridinium appended calixarenes

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Publication details

The article was received on 18 Feb 2013, accepted on 02 May 2013 and first published on 02 May 2013


Article type: Paper
DOI: 10.1039/C3OB40356D
Citation: Org. Biomol. Chem., 2013,11, 4383-4389
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    Redox control of molecular motions in bipyridinium appended calixarenes

    A. Iordache, R. Kannappan, E. Métay, M. Duclos, S. Pellet-Rostaing, M. Lemaire, A. Milet, E. Saint-Aman and C. Bucher, Org. Biomol. Chem., 2013, 11, 4383
    DOI: 10.1039/C3OB40356D

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