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Pure Appl. Chem., 2003, Vol. 75, No. 8, pp. 1055-1060

Photoinduced dynamics in hydrogen-bonded rotaxanes

Albert M. Brouwer1*, Sandro M. Fazio1, Céline Frochot1, Francesco G. Gatti2, David A. Leigh2*, Jenny K. Y. Wong2 and George W. H. Wurpel1

1 University of Amsterdam, Institute of Molecular Chemistry, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
2 School of Chemistry, University of Edinburgh, The King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK

Abstract: Two classes of rotaxanes are described in which photoinduced processes modulate a large-amplitude motion. In the first type, E–Z-isomerization of a fumaric diamide unit to a maleic diamide leads to a substantial weakening of the hydrogen bonds between the diamide and the macrocyclic ring that surrounds it. As a result, the rate of the pirouetting motion is increased approximately by six orders of magnitude. In the second type, intermolecular photoinduced electron transfer is used to induce a reversible shuttling motion on a time scale of microseconds. Medium effects on the rate of shuttling are presented.