Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 1, Issue 21, Pages 3851-3856Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b306727k
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A [3] rotaxane 2subset of1(2) consisting of an anionic phenylene ethynylene dumbbell 2(4-) threaded through two cationic cyclophanes 1(2+) has been prepared using aqueous Glaser coupling. Stern-Volmer analysis of the fluorescence quenching using three different electron-acceptors (methyl viologen 13(2+), dipropyl-4,4'-bipyridinium disulfonate 14 and anthraquinone-2,6-disulfonate 15(2-)) shows that the threaded cyclophanes inhibit electron-transfer from the excited state of the dumbbell by steric shielding, and by electrostatic shielding in the case of methyl viologen.
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