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Sulfur-containing amide-based [2]rotaxanes and molecular shuttles
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Altieri, Andrea, Aucagne, Vincent, Carrillo, Romen, Clarkson, Guy J., D'Souza, Daniel M., Dunnett, Jennifer A., Leigh, David A. and Mullen, Kathleen M.. (2011) Sulfur-containing amide-based [2]rotaxanes and molecular shuttles. Chemical Science, Vol.2 (No.10). pp. 1922-1928. ISSN 2041-6520
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Official URL: http://dx.doi.org/10.1039/c1sc00335f
Abstract
We report on the synthesis, structure and properties of [2]rotaxanes prepared by the assembly of benzylic amide macrocycles around a series of amide and sulfide-/sulfoxide-/sulfone-containing threads. The efficacy of rotaxane formation is related to the hydrogen bond accepting properties of the various sulfur-containing functional groups in the thread, with the highest yields (up to 63% with a rigid vinyl spacer in the template site) obtained for sulfoxide rotaxanes. X-Ray crystallography of a sulfoxide rotaxane, 5, shows that the macrocycle adopts a highly symmetrical chair-like conformation in the solid state, with short hydrogen bonds between the macrocycle isophthalamide NH-protons and the amide carbonyl and sulfoxide S-O of the thread. In contrast, in the X-ray crystal structures of the analogous sulfide (4) and sulfone (6) rotaxanes, the macrocycle adopts boat-like conformations with long intercomponent NH center dot center dot center dot O=SO and NH center dot center dot center dot S hydrogen bonds (in addition to several intercomponent amide-amide hydrogen bonds). Taking advantage of the different hydrogen bonding modes of the sulfur-based functional groups, a switchable molecular shuttle was prepared in which the oxidation level of sulfur determines the position of the macrocycle on the thread.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Library of Congress Subject Headings (LCSH): | Sulfur, Rotaxanes, Amides, Macrocyclic compounds, Hydrogen bonding |
| Journal or Publication Title: | Chemical Science |
| Publisher: | Royal Society of Chemistry |
| ISSN: | 2041-6520 |
| Date: | 2011 |
| Volume: | Vol.2 |
| Number: | No.10 |
| Page Range: | pp. 1922-1928 |
| Identification Number: | 10.1039/c1sc00335f |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| Funder: | European Research Council (ERC), Engineering and Physical Sciences Research Council (EPSRC), Deutsche Akademie der Naturforscher Leopoldina (DANL), Peter und Traudl Engelhorn-Stiftung (PTES), Fundación Ramón Areces (FRA) |
| Grant number: | LPD 9901/8-166 (DANL) |
| URI: | http://wrap.warwick.ac.uk/id/eprint/38468 |
Data sourced from Thomson Reuters' Web of Knowledge
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