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.
Balzani, V., Ceroni, P., Credi, A., Gomez-Lopez, M., Hamers, C., Stoddart, J.F., et al. (2001). Controlled dethreading/rethreading of a scorpion-like pseudorotaxane and a related macrobicyclic self-complexing system. NEW JOURNAL OF CHEMISTRY, 25(1), 25-31 [10.1039/b004934o].
Controlled dethreading/rethreading of a scorpion-like pseudorotaxane and a related macrobicyclic self-complexing system
Balzani V.;Ceroni P.;Credi A.;
2001
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
