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Synfacts 2011(9): 0961-0961  
DOI: 10.1055/s-0030-1261019
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Rotaxanes under the Spotlight: A Metal-Free Synthesis

Contributor(s): Timothy M. Swager, Sébastien Rochat
S.-Y. Hsueh, J.-L. Ko, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu*
National Taiwan University, Taipei, National Chung Hsing University and China Medical University, Taichung, Taiwan
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Mechanically interlocked structures are eagerly sought after for their potential uses in molecular machinery. Here, the macrocycle 1 and the axle 2 associate in solution to form the pseudo-rotaxane 3. Upon irradiation of 3, photochemical extrusion of SO2 results in a shrinking of the macrocycle, forming rotaxane 4. Owing to the reduced size of the macrocyclic cavity, 4 cannot dissociate and the interlocked structure is stabilized, as confirmed by ¹H NMR and X-ray diffraction data.