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. doi:10.1039/c1sc00335f ISSN 2041-6520.

Research output not available from this repository.

Request-a-Copy directly from author or use local Library Get it For Me service.

Request Changes to record.

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, Engineering and Medicine > 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
Official Date:	2011
Dates:	Date Event 2011 Published
Volume:	Vol.2
Number:	No.10
Page Range:	pp. 1922-1928
DOI:	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)

Data sourced from Thomson Reuters' Web of Knowledge

Request changes or add full text files to a record

Repository staff actions (login required)

View Item