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Issue 1, 2001
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Controlled dethreading/rethreading of a scorpion-like pseudorotaxane and a related macrobicyclic self-complexing system

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Abstract

A scorpion-like pseudorotaxane (1·H2+), composed of a macrocyclic polyether containing a 1,5-dioxynaphthalene (1,5-DON) and a 1,3-dioxybenzene (1,3-DOB) electron-donor unit, the latter bearing a 4,4′-bipyridinium electron-acceptor tail, underwent threading/dethreading motions under control of (i) solvent polarity and (ii) solution acidity. Furthermore, the complexation of 1 ·H2+ with the trans-1,2-bis(1-benzyl-4-pyridinio)ethylene electron acceptor can be acid/base controlled. The spectroscopic properties of a related macrobicyclic compound 24+ (comprised of an electron-donor and an electron-acceptor macrocycle that share a benzene ring) have also been investigated. The results obtained for 24+ are consistent with the presence of intramolecular self-complexed species where the electron-donor macrocycle is threaded through the electron-acceptor one. Electrochemical experiments confirm the self-complexing structures of 1·H2+ and 24+. It seems likely that both compounds undergo decomplexation upon electrochemical stimulation.

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Publication details

The article was received on 19 Jun 2000, accepted on 26 Sep 2000 and first published on 15 Dec 2000


Article type: Paper
DOI: 10.1039/B004934O
Citation: New J. Chem., 2001,25, 25-31
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    Controlled dethreading/rethreading of a scorpion-like pseudorotaxane and a related macrobicyclic self-complexing system

    V. Balzani, P. Ceroni, A. Credi, M. Gómez-López, C. Hamers, J. Fraser Stoddart and R. Wolf, New J. Chem., 2001, 25, 25
    DOI: 10.1039/B004934O

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