4.8 Article

Optical Distinction between Slow and Fast Translational Motion in Degenerate Molecular Shuttles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 22, Pages 6136-6141

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201612549

Keywords

co-conformations; molecular shuttles; optical switches; rotaxanes; supramolecular chemistry

Funding

  1. NSERC of Canada
  2. International Center for Diffraction Data

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A series of six [2] rotaxane molecular shuttles was designed which contain an axle with a benzo-bis(imidazole) core (in either a neutral or dicationic form) and a single 24-membered, crown ether wheel (24C6, B24C6, or DMB24C6), and the shuttling rates of the ring along the axle were determined. The charged versions showed much slower shuttling rates as a result of the increase in noncovalent interactions between the axle and wheel. The [2] rotaxane with a B24C6 wheel shows a difference in fluorescence between the charged and neutral species, while the [2] rotaxane with a DMB24C6 wheel exhibits a difference in color between the charged and neutral compounds. These changes in optical properties can be attributed to the structural differences in the co-conformations of the [2] rotaxane as they adapt to the changes in acid/base chemistry. This allowed the relative rate of the translational motion of a molecular shuttle to be determined by observation of a simple optical probe.

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