Abstract
A [3]rotaxane 2⊂12 consisting of an anionic phenylene ethynylene dumbbell 24− threaded through two cationic cyclophanes 12+ has been prepared using aqueous Glaser coupling. Stern–Volmer analysis of the fluorescence quenching using three different electron-acceptors (methyl viologen 132+, dipropyl-4,4′-bipyridinium disulfonate 14 and anthraquinone-2,6-disulfonate 152−) 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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